Heart UK

Lenny's Podcast: Product | Career | Growth

Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.

Lenny Rachitsky

Ian Silber is the head of product design at OpenAI, where he has led the design of ChatGPT, Codex, and all of OpenAI’s product experience for the past three years. Before OpenAI, he was at Artifact, the AI-powered news app built by the founders of Instagram. Prior to that, he spent eight years at Instagram, where he worked on products including Reels. Ian is one of the most consequential designers working in AI today, and he takes us inside how OpenAI designs ChatGPT, Codex, and the future of how we will interact with AI.In our in-depth conversation, we discuss:1. Why Ian believes this is the best time in history to be a product designer2. Why engineers 10x’d with AI but design teams haven’t3. What OpenAI looks for when hiring designers4. “Just do less”: Ian’s counterintuitive advice to his designers5. The future of ChatGPT as a super app6. Where humans still win: user understanding, invention, and point of view—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and moreMercury—Radically different banking, now with Command—Where to find Ian Silber:• X: https://x.com/iansilber• LinkedIn: https://www.linkedin.com/in/iansilber• Website: https://iansilber.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Ian Silber(02:14) Why designers in general feel anxious about AI(09:01) What makes specific designers thrive in the AI era(13:41) Why Ian says it’s the best time in history to be a designer(17:13) How product roles are converging(22:24) Can AI design great products?(23:54) Where human judgment still matters(27:34) What Ian looks for when hiring designers(30:20) Why systems thinking matters(32:53) Balancing speed and craft(38:05) Designing for vastly different audiences(41:57) Solving the blank-box problem(43:31) How ChatGPT is evolving beyond chat(46:07) The vision for Codex(49:07) What Ian wishes he knew on day one(51:40) Why humility matters in AI(53:41) Advice for designers who are feeling overwhelmed(55:16) AI corner(57:43) Failure corner(01:00:45) Lightning round and final thoughts(01:05:52) Lessons from Groupon—Referenced:• OpenAI: https://openai.com• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• 3 Spiderman Pointing meme template: https://www.kapwing.com/explore/3-spiderman-pointing-meme-template• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape• Notion: https://www.notion.com• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead• Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• ChatGPT Work: https://openai.com/chatgpt-work• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Please Stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna• Maybe Happy Ending: https://www.maybehappyending.com• The Invite: https://www.imdb.com/title/tt14173636• Rivian: https://rivian.com• Waymo: https://waymo.com• Groupon: https://www.groupon.com• How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital): https://www.lennysnewsletter.com/p/how-a-vc-and-a-tech-founder-used• Andrew Mason on X: https://x.com/andrewmason• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom• Sam Altman on X: https://x.com/sama—Recommended book:• The Design of Everyday Things: https://www.amazon.com/dp/0465050654—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber

Adam Ward is the Head of Talent at Cursor, one of the fastest-growing developer tools in history. Before joining Cursor, he founded Growth by Design, an independent recruiting and talent strategy firm that helped build teams at the most ambitious AI and technology companies in the world. Adam has spent more than 20 years building elite, high-talent-density teams across the industry and is widely regarded as one of the most effective and creative recruiters in tech.In our in-depth conversation, we discuss:1. Inside today’s “tale of two cities” talent market2. Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires3. Adam’s three-step playbook: scoping, mapping, and relentless pursuit4. The worst question to ask when sourcing great talent5. The rise of the forward deployed engineer—and how to become one6. The biggest mistake founders make when hiring their first recruiter—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and moreMercury—Radically different banking, now with Command—Where to find Adam Ward• X: https://x.com/wardadamp• LinkedIn: https://www.linkedin.com/in/adampward—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction(03:01) The state of the hiring market(06:41) What roles are trending up and what roles are trending down(11:25) The three-step hiring framework that changes everything(21:58) Getting the right people to actually respond(25:42) Keeping talent a top priority(29:16) Inside Cursor’s recruiting operation(32:19) How to relentlessly pursue top talent(35:42) “Caring is free”(38:33) The conversation most companies underestimate(39:19) Rethinking the atomic unit of a search(40:12) Other recruiting tactics(45:04) What the on-site is really for(49:35) The importance of work trials(53:10) The offer stage(57:53) Negotiations and comp(01:01:50) The details that actually close the deal(01:07:23) What it’s like working with an exec team who values recruiting(01:09:42) Talent density(01:11:18) The first recruiting hire most founders get wrong(01:15:00) Building incredible teams(01:18:12) The time between offer and acceptance(01:19:48) What’s next for the recruiting function(01:21:00) Lightning round—Referenced:• Cursor: https://cursor.com• Trilogy: https://trilogy.com• Brie Wolfson on LinkedIn: https://www.linkedin.com/in/brie-wolfson-17758724• Inside Cursor: https://colossus.com/article/inside-cursor• SpaceX: https://www.spacex.com• Joe Gebbia’s website: https://joegebbia.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• The Pitt on HBO Max: https://www.hbomax.com/shows/pitt-2024/e6e7bad9-d48d-4434-b334-7c651ffc4bdf• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f• Granola: https://www.granola.ai• Wispr Flow: https://wisprflow.ai• 11 products I love, free for a year—the biggest Product Pass expansion in 2 years: https://www.lennysnewsletter.com/p/productpass-summer2026launch• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working• The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham—Recommended books:• Emotional Intelligence: Why It Can Matter More Than IQ: https://www.amazon.com/dp/055338371X• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100• Scaling People: Tactics for Management and Company Building: https://press.stripe.com/scaling-people—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor

Tom Verrilli is the chief product officer at Whatnot, a live shopping platform that’s become the fastest-growing U.S. marketplace business in history, with over $8 billion in GMV. Before joining Whatnot, Tom was CPO at Twitch and director of product growth at Twitter (during one of the most turbulent periods in the company’s history).In our in-depth conversation, we discuss:1. Why Whatnot’s product team was founded on the premise “we regret that product management exists”2. How AI is reshaping the PM role3. What Tom looks for when hiring PMs4. The shift toward senior ICs doing the work5. How AI has transformed data science at Whatnot6. Tom’s “play the accordion” mental model7. Why “hire great people and get out of their way” fails8. His biggest lessons from his time at Twitter—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and moreMercury—Radically different banking, now with Command—Episode transcript: https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Tom Verrilli:• X: https://x.com/tdrobbo• LinkedIn: https://www.linkedin.com/in/tom-robertson-042—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction(02:40) “We regret that product management exists”: what it means and why(08:30) When specialization makes sense, and when it doesn’t(15:20) How Whatnot structures its PM org(17:28) What 31,832 PM applications revealed about the function(19:40) How to develop systems thinking(22:10) The shift to senior ICs doing IC work(32:26) Advice for PMs struggling in today’s market(35:22) How AI has transformed work at Whatnot(41:14) The data scientist problem(42:48) Which roles are trending up and down(44:48) What the product team of the future looks like(46:29) Why core PM skills are the most durable in an AI world(49:23) How to get the most out of the people you hire(53:32) Navigating the CPO-founder relationship(57:34) Advice for aspiring CPO’s(59:16) How to know when to stand firm and when to step back(01:01:38) Play the accordion: balancing strategic vision with fast iteration(01:06:35) Agentic commerce vs. live commerce(01:09:46) Lessons from Twitter(01:13:07) Failure corner(01:15:45) Lightning round and final thoughts—Referenced:• Whatnot: https://www.whatnot.com• Building, and Whatnot: https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc• Twitch: https://www.twitch.tv• Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future• Peter Bailis on LinkedIn: https://www.linkedin.com/in/pbailis• Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Ben Kus on LinkedIn: https://www.linkedin.com/in/benkus• Henry Shi on LinkedIn: https://www.linkedin.com/in/henrythe9th• Hex Threads: https://hex.tech/product/threads• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine• Logan Head on LinkedIn: https://www.linkedin.com/in/logan-head• Emmett Shear on LinkedIn: https://www.linkedin.com/in/emmettshear• Kara Swisher on X: https://x.com/karaswisher• Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY• Star City on AppleTV+: https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7• Service NSW Mobile App: https://www.service.nsw.gov.au/services/service-nsw-mobile-app• Rudyard Kipling: https://en.wikipedia.org/wiki/Rudyard_Kipling• E-fish.com: https://www.e-fish.com—Recommended books:• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/dp/0062273205• The Purpose Driven Church: Every Church Is Big in God’s Eyes: https://www.amazon.com/dp/0310201063• Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase.In our in-depth conversation, we discuss:1. What Anthropic’s early days were like2. The inflection points that turned Anthropic from an underdog into the fastest-growing company in history3. How exactly Claude got so good at coding4. The eval-driven development loop her team is pioneering5. How to find joy in AI when everything is moving this fast6. Why Claude’s willingness to push back is key to its success7. Where human judgment remains irreplaceable—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and moreMercury—Radically different banking, now with Command—Episode transcript: https://www.lennysnewsletter.com/p/anthropics-first-technical-pm-on—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Dianne Penn:• LinkedIn: linkedin.com/in/dianne-na-penn—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction(02:31) Early Anthropic days(08:55) Big milestones(13:50) Inside the exponential(20:02) Token maxing(23:30) Anthropic Labs and the incubation model(27:30) How the research role works(31:35) How to become a top researcher(35:18) Frontier model safeguards(39:38) Hiring in the AI era(44:16) Building an eval set(47:48) Evals vs PRDs(49:55) The importance of hands-on leadership(52:46) Finding joy in AI(58:10) How Dianne uses Claude(01:01:05) Avoiding overreliance on AI(01:03:50) The constitution that makes Claude better(01:07:11) AI writing and verification(01:11:40) Where human brains will continue to be valuable(01:14:10) Navigating AI with kids(01:16:26) Alignment, the future of the PM role, and burnout(01:21:54) Lightning round and final thoughts—Referenced:• Anthropic: https://www.anthropic.com• Golden Gate Claude: https://www.anthropic.com/news/golden-gate-claude• Dario Amodei’s website: https://darioamodei.com• Scaling Laws and Interpretability of Learning from Repeated Data: https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data• Tokenmaxxing: How Top Builders Use AI To Do The Work Of 400 Engineers: https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers• Garry Tan on X: https://x.com/garrytan• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Introducing Labs: https://www.anthropic.com/news/introducing-anthropic-labs• Louis CK | about airplane Wi Fi: https://www.youtube.com/watch?v=me4BZBsHwZs• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering• The Anthropic Hive Mind: https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b• How to build a company that withstands any era | Eric Ries, Lean Startup author: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands• Fallout on Prime Video: https://www.amazon.com/dp/B0CN4GGGQ2• Fallout (video game): https://fallout.bethesda.net• Claude Tag: https://www.anthropic.com/news/introducing-claude-tag—Recommended books:• Crucial Conversations: Tools for Talking When Stakes Are High: https://www.amazon.com/dp/0071771328• How to Raise an Adult: Break Free of the Overparenting Trap and Prepare Your Kid for Success: https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779• Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great: https://www.amazon.com/dp/B0FWZZBPZB—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn

Elizabeth Stone is the Chief Product and Technology Officer (CPTO) at Netflix, where she oversees Engineering, Product, and Design. Since her first appearance on the podcast two years ago—which remained my second-most-popular episode for more than a year—she has expanded her role to lead product, in addition to engineering. Before Netflix, Elizabeth was VP of Science at Lyft, Chief Operating Officer at Nuna, an economist at Analysis Group, and a trader at Merrill Lynch.In our in-depth conversation, we discuss:1. Why “systems thinking” is now the most important skill she looks for2. How to manage the flood of AI-generated output without losing quality or signal3. How Netflix thinks about AI fluency as a universal expectation rather than a level-specific skill4. What “excellence as an operating system” means—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyMercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign—Episode transcript: https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Elizabeth Stone:• LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction(02:25) AI and role confusion: the storming phase before the forming phase(07:36) How roles have changed in the past two and a half years(11:55) Will functions survive? The case for craft specialism(13:26) What Netflix is hiring more of—and less of(17:22) Why systems thinking is the rising skill across every function(20:20) Is the design process dead?(22:08) Skills trending down(28:33) AI fluency and Netflix’s career ladder overlay(31:00) AI use cases beyond coding(35:12) Netflix’s AI history(38:36) Excellence as an operating system(41:11) The pillars of the excellence OS(46:41) The keeper’s test—and why it’s mostly a positive conversation(50:21) Attracting top talent in the age of frontier AI labs(52:54) Junior talent, craft mastery, and the mentorship question(56:25) Where engineering goes in 5 to 10 years(59:45) The future of entertainment: beyond film and TV(1:02:18) AI in Hollywood: Netflix’s creator-enablement position(1:06:15) Lightning round and final thoughts—Referenced:• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead• Claude Code: https://www.anthropic.com/product/claude-code• Claude Cowork: https://www.anthropic.com/product/claude-cowork• Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it• Innovation for Filmmaking, By Filmmakers: Why InterPositive Is Joining Netflix: https://about.netflix.com/en/news/why-interpositive-is-joining-netflix• InterPositive: https://weareinterpositive.com• Netflix Prize: https://en.wikipedia.org/wiki/Netflix_Prize• Quarterback on Netflix: https://www.netflix.com/title/81482895• The Bill Simmons Podcast on Netflix: https://www.netflix.com/title/82186214• Spencer Pratt on Instagram: https://www.instagram.com/spencerpratt• Salman Rushdie’s Substack: https://salmanrushdie.substack.com• Remarkably Bright Creatures on Netflix: https://www.netflix.com/title/81911351• Eight Sleep: https://www.eightsleep.com• Tour de France: https://www.letour.fr/en—Recommended books:• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• Into Thin Air: A Personal Account of the Mt. Everest Disaster: https://www.amazon.com/Into-Thin-Air-Personal-Disaster/dp/0385494785• Liar’s Poker: https://www.amazon.com/Liars-Poker-Norton-Paperback-Michael/dp/039333869X—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO)

Noam Segal is a longtime research leader across Airbnb, Meta, Twitter, Zapier, Intercom, and Figma, a certified coach, AI builder, and my community research lead. Together, we run the annual Tech Worker Sentiment Survey, now in its second year and one of the largest of its kind: a quantitative study of how people in tech actually feel about their jobs, AI, burnout, and the future of their careers. This year’s survey captured responses from thousands of workers across product, engineering, design, research, marketing, data, and sales, and the results are striking.In our in-depth conversation, we discuss:1. Why AI has split the tech workforce almost exactly in half—one half that’s thriving, another that’s shaken2. The four emotional archetypes defining tech workers right now (the Energized, the Conflicted, the Disoriented, and the Resentful)3. Why burnout has jumped an alarming 11 points in a single year4. Why nobody in tech would recommend their job to someone entering the industry today5. The #1 fear in tech right now (it’s not job loss to AI)6. Why managers are the single biggest lever for employee well-being7. Concrete advice for what employees and leaders can do right now—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyMercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign—Episode transcript: https://www.lennysnewsletter.com/p/how-tech-workers-actually-feel-about—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Noam Segal:• X: https://x.com/noamseg• LinkedIn: https://www.linkedin.com/in/noamsegal—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Noam Segal(02:34) About the survey: methodology and scope(06:04) The core finding: AI has split the tech workforce in half(13:03) The AI identity stance(14:40) The four archetypes: Energized, Conflicted, Disoriented, Resentful(19:35) Burnout is surging (and why shipping faster is making it worse)(22:53) A glimmer of hope(24:55) Layoff worries(29:15) The career recommendation NPS score(36:45) The ladder metaphor: rungs disappearing beneath our feet(45:14) AI is making us faster, not better(52:53) The #1 fear: being squeezed to do more for the same pay(55:55) The emotional landscape and “smiling exhaustion”(01:01:02) Designers and researchers: the most negative group two years running(01:06:27) Who’s happiest(01:12:18) Managers: the single biggest lever on well-being(01:18:47) The industry is “chaotic”(01:24:53) What employees and leaders can do right now(01:31:32) AI guilt and closing thoughts—Referenced:• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026• How tech’s most resilient workers handle burnout: https://www.lennysnewsletter.com/p/how-techs-most-resilient-workers• Please stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp• NPS Is The Worst: https://www.npsistheworst.com• The Terminator: https://www.imdb.com/title/tt0088247• Skynet: https://terminator.fandom.com/wiki/Skynet• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu• Devin: https://devin.ai• An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union• Redeploying Fable 5: https://www.anthropic.com/news/redeploying-fable-5• Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble• Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennysnewsletter.com/p/inside-linear-building-with-taste• Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennysnewsletter.com/p/building-beautiful-products-with• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape• Elon Musk: ‘Chances are we’re all living in a simulation’: https://www.theguardian.com/technology/2016/jun/02/elon-musk-tesla-space-x-paypal-hyperloop-simulation—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How tech workers actually feel about AI in 2026 | Annual AI sentiment survey (Noam Segal)

Adam Mosseri is the Head of Instagram, where he oversees an app used by over 3 billion people. He also leads the team building Threads. Adam has run Instagram for longer than its founders did, after taking over from Kevin Systrom and Mike Krieger in 2018. A designer by training, he spent over 15 years at Meta, starting as a designer on Facebook’s mobile app, rising to lead Facebook’s News Feed, and eventually chosen to lead Instagram. During his tenure, Instagram’s user base has more than tripled.In our in-depth conversation, we discuss:1. How the canonical product team structure is changing in 2026, from baker’s-dozen specialist teams to lean pods of four to six generalists2. The rise of the “product staff” role—a blending of PM, design, data science, and research into one generalist operator3. Why Adam is bullish on designers even as functional boundaries dissolve, and which roles are most at risk4. What the Instagram algorithm knows about you, and why it’s only now catching up to what people assumed it knew years ago5. Why the rise of AI-generated content is a tailwind for Instagram, and how the company is thinking about creator identity in a synthetic-content world6. The two biggest product failures of Adam’s career—Facebook Home and the first version of Reels—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyMercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign—Episode transcript: https://www.lennysnewsletter.com/p/adam-mosseri-ai-is-a-tailwind-for—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Adam Mosseri:• X: https://x.com/mosseri• LinkedIn: linkedin.com/in/mosseri• Instagram: https://www.instagram.com/mosseri• Threads: https://www.threads.com/@mosseri—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Adam Mosseri(02:09) How product teams are changing inside Meta(05:48) Blurring roles and career anxiety(14:01) Hiring traits that matter now(16:48) How AI is resetting who succeeds at work(19:38) How Meta thinks about token spend and AI costs(23:23) Where human judgment still matters(25:56) Why AI is not automatically great at strategy(30:36) Why great product leaders are curators(34:23) What Instagram’s algorithm actually knows about you(38:08) Why chronological feeds often disappoint users(40:56) Why AI content may be a tailwind for Instagram(43:42) The future of AI and human content in the feed(48:00) What Adam admires about other social platforms(52:05) How he handles public criticism(56:31) Lessons from the Instagram feed redesign backlash(01:00:21) Adam’s biggest failure: Instagram on iPad(01:03:03) His approach to kids, screens, and social media(01:06:56) What Adam wants listeners to remember—Referenced:• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering• Claude Code: https://www.anthropic.com/product/claude-code• Claude Cowork: https://www.anthropic.com/product/claude-cowork• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens• A rational conversation on where AI is actually going | Benedict Evans: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Mythos: https://www.anthropic.com/claude/mythos• Fable: https://www.anthropic.com/claude/fable• Pluralistic: The Reverse-Centaur’s Guide to Criticizing AI: https://pluralistic.net/2025/12/05/pop-that-bubble• Plastic Dream Sequence on Instagram: https://www.instagram.com/plasticdreamsequence• TikTok: https://www.tiktok.com• Facebook–Cambridge Analytica data scandal: https://en.wikipedia.org/wiki/Facebook%E2%80%93Cambridge_Analytica_data_scandal• Facebook Home: https://en.wikipedia.org/wiki/Facebook_Home—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Adam Mosseri: AI is a tailwind for authenticity

Andrew Ambrosino leads development of the Codex desktop app at OpenAI. Nearly 100% of OpenAI employees—not just engineers—now use Codex weekly. A lifelong builder with a background spanning engineering, design, product management, and founding companies, he is now responsible for turning the Codex desktop experience into what he calls “the best desktop app that has ever existed, full stop.”In our in-depth conversation, we discuss:1. Why AI has completely flipped the product development process2. What “taste” really means as a professional skill, and why it is emerging as the most valuable capability in an AI-first workplace3. Why Andrew believes the Codex app would have failed if they launched it last November (vs. in February)4. The “zone defense” model for how product managers at OpenAI operate when everyone can build anything5. How roles are collapsed on Andrew’s team, and why eliminating the concept of roles entirely is a big mistake6. How Andrew uses Codex to run his own workflows7. The vision for a home base that coordinates work across ChatGPT, Codex, and the tools people already use.—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and moreMercury—Radically different banking, now with Command—Episode transcript: https://www.lennysnewsletter.com/p/openais-codex-lead-on-the-new-shape—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Andrew Ambrosino:• X: https://x.com/ajambrosino• LinkedIn: https://www.linkedin.com/in/ajambrosino• Website: https://ambrosino.io—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Andrew Ambrosino(02:30) How AI is changing the shape of product work(06:32) When to use documents vs. prototypes(10:25) What “taste” actually means(12:06) Why AI is still bad at design(16:18) Is the design process really dead?(21:35) What the design process looks like on the Codex team(23:41) Are product functions disappearing?(27:22) Team structure(30:12) IC vs. management(31:37) Planning roadmaps(35:16) Building features that don’t work yet(38:13) The ambition problem: when you’re too AGI-pilled(39:17) The latest frontier: loops and autonomous development(52:05) How Andrew uses Codex to automate his entire job(46:52) The power of computer use and browser automation(49:10) Will we run all our SaaS apps inside Codex?(52:05) The future vision for Codex(57:20) The videographer who built a Premiere Pro extension with Codex(59:30) Failure corner(1:01:50) Lightning round(1:07:03) BTS: How our producer uses Codex for editing—References:  https://www.lennysnewsletter.com/p/openais-codex-lead-on-the-new-shape—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

OpenAI Codex lead on the new shape of product work | Andrew Ambrosino

Fiona Fung leads the teams behind Claude Code and Cowork at Anthropic (overseeing Boris Cherny and the entire engineering and PM team). Before Anthropic, she spent 11 years at Microsoft building Visual Studio and TypeScript and then moved to Meta, where she started Facebook Marketplace (now generating over $100 billion in GMV annually), worked on Meta’s first smart glasses and AR glasses, and led infrastructure, growth, integrity, and safety teams at Instagram. She’s been an engineer for over 25 years and has a unique perspective on how the role of building software is changing.In our in-depth conversation, we discuss:1. What she’s learned about running a team that’s shipping 8x more code than before2. Which roles AI will transform next3. Specific ways her team uses AI4. How Claude “routines” have changed how she operates as a manager5. The context-switching problem no one has solved yet6. The biggest unsolved problem in AI7. What keeps her up at night—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyMercury—Radically different banking, now with Command: https://mercury.com/—Where to find Fiona Fung:• LinkedIn: linkedin.com/in/fionafung—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Fiona Fung(02:31) How the engineering role has transformed over 25 years(09:28) What an AI-pilled software team looks like in 2026(12:26) Using Claude to manage and review team output(14:40) The evolution of code review and verification(16:55) Who to hire: creative builders and deep systems experts(18:18) The shift to ambitious thinking(19:40) The growth mindset required to thrive in AI-native teams(25:52) Helping small businesses adopt AI tools(31:46) How Anthropic spots latent demand and builds for it(35:08) The next frontier: asynchronous work with AI routines(38:06) Agency and accountability in AI-native teams(39:40) The vibe shift from token-maxing to ROI measurement(44:24) The “bad vs. sad” quality framework(49:34) Why all managers start as ICs at Anthropic(55:24) Preventing skill atrophy(58:43) Managing context switching with 20 AI agents running(1:00:08) How PM and data science roles are transforming(1:03:40) The importance of dogfooding and using your own product(1:08:36) Outstanding questions(1:12:48) The future of engineering jobs and education(1:17:59) What keeps Fiona up at night: team culture at scale(1:22:53) From six-month roadmaps to JIT (just-in-time) monthly planning(1:27:03) Lightning round—References: https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams)

Mark Pincus founded Zynga—the company behind Words With Friends, FarmVille, and Zynga Poker—and has arguably created more hit consumer products than anyone in history. At Zynga, eight of 10 major game launches became massive hits, reaching over a billion players. Over the past five years, Mark has been synthesizing everything he’s learned about building successful consumer products and turning it into a book, Life at the Speed of Play, which comes out on June 23. This is the first interview he’s done about the book.In our in-depth conversation, we discuss:1. His “Proven, Better, New” framework: copy what’s proven, make it better so that 10 out of 10 people say “f*ck yes, I’ll use this”—then add something new2. Why being less ambitious is the path to the most ambitious ideas3. His rule of thumb that your instincts are right 95% of the time, but your ideas are wrong 75% of the time4. “Kill hope before hope kills you”5. How to raise kids in the age of AI—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and moreVanta—Automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/the-common-pattern-behind-successful—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Mark Pincus:• X: https://x.com/markpinc• LinkedIn: https://www.linkedin.com/in/markpincus• Website: https://www.lifeatthespeedofplay.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Mark Pincus(02:46) The Proven Better New framework overview(07:29) Earning the right to innovate(08:30) What “better” really means(12:03) Quick summary of the framework(12:40) Examples of the framework in action(13:30) How to use proven correctly on your platform(15:13) The moral arbitrage of copying(23:55) Be less ambitious(28:25) The Bolt.new story and staying humble(33:15) Kill hope before hope kills you(37:00) Using AI as a failure machine(40:08) Why Zynga’s games succeeded (it wasn’t virality)(48:36) The future of consumer social apps(57:05) How to know if your product is a B+(1:01:25) Distribution in the age of AI(1:15:39) Make everyone a CEO(1:18:18) Stay close to the metal(1:21:35) Why Mark says micromanagement is beautiful(1:23:35) The expert witness(1:25:05) The number one job of a CEO is to be right(1:26:35) What Mark is teaching his five kids(1:35:14) Mark’s “why”(1:37:08) Mark’s new book: Life at The Speed of Play—Referenced:• Tribe.net: https://en.wikipedia.org/wiki/Tribe.net• Zynga: https://www.zynga.com• Sid Meier: https://en.wikipedia.org/wiki/Sid_Meier• Electronic Arts: https://www.ea.com• CityVille: https://en.wikipedia.org/wiki/CityVille• Words With Friends: https://wordswithfriends.com/• Scrabble: https://playscrabble.com• Reddit: https://www.reddit.com• TED Radio Hour, MIT Media Lab founder, 1984 TED talk.: https://www.ted.com/talks/nicholas_negroponte_5_predictions_from_1984• Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel• FarmVille: https://en.wikipedia.org/wiki/FarmVille• Craig Newmark: https://en.wikipedia.org/wiki/Craig_Newmark• How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor): https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier• Angry Birds: https://www.angrybirds.com/• OMGPop: https://en.wikipedia.org/wiki/OMGPop• Draw Something: https://en.wikipedia.org/wiki/Draw_Something• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong• Jason Citron on X: https://x.com/jasoncitron• Stanislav Vishnevskiy on LinkedIn: https://www.linkedin.com/in/svishnevskiy• Jeff Bezos on X: https://x.com/JeffBezos• Andy Jassy on X: https://x.com/ajassy• Niantic: https://nianticlabs.com• Pokémon Go: https://pokemongo.com• Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon—Recommended book:• Life at the Speed of Play: Launch Products People Love!: https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ref=tmm_hrd_swatch_0—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The hidden pattern behind successful products | Mark Pincus (founder of Zynga)

Tony Fadell created the iPod, co-created the iPhone, and founded Nest (which he sold to Google for $3.2 billion). He’s co-authored over 300 patents, was part of the legendary team at General Magic, and wrote one of the most important and inspiring books for builders, called Build.In our in-depth conversation, we discuss:1. The heated internal debates about whether the iPhone should have a physical keyboard2. Why opinion-based decisions are essential for v1 products3. Why marketing matters as much as the product itself, and how the iPod almost failed4. Why voice will eventually become the primary interface with AI5. Why cognitive surrender to AI is the biggest risk facing product builders today—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/father-of-the-ipod-and-iphone-on—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Tony Fadell:• X: https://x.com/tfadell• LinkedIn: https://www.linkedin.com/in/tonyfadell• Website: https://www.buildc.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Tony Fadell(02:23) The Blackberry vs. iPhone keyboard debate(07:50) Micromanaging vs. kind lies: what great products actually need(15:57) The Nest thermostat and smoke alarm story(21:22) How to decide what’s worth building: pain plus new technology(27:36) The three-generation rule: why nothing works the first time(34:20) The full customer journey: why marketing defines your product(40:53) The power of storytelling and the press-release-first approach(48:37) The evolution of product management and the builder role(50:27) Why AI-generated code creates brittle, unmaintainable products(58:00) Storytelling techniques(1:05:45) The next iPhone(1:13:15) Hardware is back(1:17:01) What Tony is most excited about(1:21:38) Working with Tony(1:25:36) Ethics, morals, and the responsibility of product builders(1:32:40) How to connect with Tony and Build Collective—References: https://www.lennysnewsletter.com/p/father-of-the-ipod-and-iphone-on—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era | Tony Fadell

Benedict Evans is an independent analyst and former partner at Andreessen Horowitz, where he spent years as their in-house “thinker” tracking the most important technology trends. For the past six years, he’s been publishing deeply researched presentations on where tech is heading, most recently focused on AI’s transformation of the economy. His work is read by founders, investors, and operators trying to make sense of a noisy field. His most controversial opinion: AI is as big a deal as the internet or mobile—and only as big.In our in-depth conversation, we discuss:1. Why we’re in “1997” for AI—early, exciting, and deeply uncertain about what comes next2. Where value will actually accrue in the AI stack3. The anti-AI backlash, and where it may lead4. The surprising boom in consulting and professional services at AI companies5. Why distribution is becoming the ultimate moat as software gets easier to build6. Why the right question about your job isn’t “What percent can AI do?” but “Is this a task or a job?”7. Why things will probably be okay—and what you need to do to prepare—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Benedict Evans:• LinkedIn: https://www.linkedin.com/in/benedictevans• Newsletter: https://www.ben-evans.com/newsletter• Website: https://www.ben-evans.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Benedict Evans(02:19) What people aren’t pricing in about AI’s impact(06:24) Why we’re in the 1997 moment of AI(09:44) The unexpected boom in professional services and consultants(17:44) Why distribution is becoming the ultimate moat(23:17) The coming job transformation: what’s real vs. panic(27:33) Why AGI definitions keep shifting(38:11) Where value will accrue: models vs. applications(42:55) Distribution wars: Google, Meta, Apple, and OpenAI(48:12) The anti-AI sentiment and backlash(53:11) How to raise kids in an AI future(58:27) What jobs to steer toward or away from(59:20) The question nobody’s asking about AI(1:06:25) How to be successful in this coming future(1:08:43) AI corner(1:11:43) Lightning round—Referenced: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

A rational conversation on where AI is actually going | Benedict Evans

Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models.Dan’s predictions:1. The future of work will happen inside Codex or Claude Code.2. Every company will have one “super-agent” inside their Slack that every employee talks to regularly.3. SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.”4. SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins.5. PMs will thrive in the AI era.6. Full-stack designers will become superheroes.7. The AI job apocalypse is not happening.8. Forward deployed engineer is the new most essential role.9. CLIs are over.10. Automation is a lie.11. We will read way more AI-generated writing and we will like it.12. We’ll be building software for humans and agents to use together.—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Dan Shipper:• X: https://x.com/danshipper• LinkedIn: https://www.linkedin.com/in/danshipper/• Podcast: https://every.to/podcast• Website: https://danshipper.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Dan Shipper(02:56) Dan’s unique position living in the AI future(09:17) How the way we work will change in the coming year(16:39) The case for general agents(18:08) Codex and Claude Code as the new operating system for work(25:39) How Cursor fits in(27:42) How this changes what SaaS companies should build(31:13) Why CLI is already over(33:34) Two agents are better than one(36:22) Why Dan is bullish on SaaS stocks(39:01) Why automation doesn’t reduce human work(47:00) The value of human-written code(48:36) Quick recap(50:15) How work is changing(56:17) Why data scientists are drowning in bad analysis(58:24) Which product/tech roles are least changed by AI(1:02:17) We will read way more AI-generated writing and we will like it(1:08:28) Why product managers will dominate the AI era(1:11:05) Full-stack designers are the other big winners(1:13:11) The AI job apocalypse won’t happen(1:16:00) How to “ride the models” to stay relevant(1:21:02) Final predictions and advice(1:25:24) Lightning round—References: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The AI paradox: More automation, more humans, more work | Dan Shipper

Caitlin Kalinowski was most recently at OpenAI helping build their robotics and hardware teams from scratch. Prior to that, she was head of AR glasses and VR hardware at Meta, where she led the teams building every generation of the Quest, Rift, and Orion, and was Meta’s first consumer electronics hire. Before this, she was  technical lead on MacBook Air and Mac Pro at Apple, and helped engineer the original unibody MacBook Pro. She’s designed and engineered some of the hardest and most beloved consumer hardware products in history and is now focused on the next frontier: robotics.In our in-depth conversation, we discuss:1. VR—what happened?2. The coming memory price shock and why she’s telling startups to pre-buy now3. How the technologies built for VR became the foundation of modern warfare4. Why humanoid robots are still just prototypes, and what’s actually gating mass deployment5. Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman6. Why she left OpenAI—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/why-were-at-the-beginning-of-the—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Caitlin Kalinowski:• X: https://x.com/kalinowski007• LinkedIn: https://www.linkedin.com/in/ckalinowski• Website: https://www.caitlinkalinowski.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/In this episode, we cover:(00:00) Introduction to Caitlin Kalinowski(02:32) Why VR didn’t take off despite incredible hardware(04:55) The future of AR glasses and physical AI(08:45) Why robotics and hardware are suddenly hot(13:33) Why humanoid robots aren’t ready yet(16:13) Supply chain bottlenecks threatening robotics(17:31) Why magnets and actuators are critical dependencies(20:51) The geopolitical implications of hardware supply chains(24:48) AI safety concerns with physical robots(26:50) Apple’s approach to hardware excellence(30:10) Building a hardware program from scratch at Meta(31:39) The Quest 2 cost reduction story(33:07) Critical principles for hardware development(39:58) The MacBook Air manila envelope moment(41:01) The butterfly keyboard situation(41:43) Lessons from Apple on customer feedback(44:46) The memory price crisis coming for hardware(49:31) How many components go into a robot(52:53) When to use off-the-shelf vs. custom components(55:02) How AI is changing hardware engineering(1:00:27) Why humanoids aren’t the answer for most use cases(1:03:05) When robots will build other robots(1:06:23) What makes a robot feel human and connected(1:09:15) Robots in the home(1:12:00) What the next five years look like(1:15:38) Why she left OpenAI(1:18:09) How to hire exceptional hardware teams(1:23:42) Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman(1:27:27) Failure corner(1:32:33) Lightning round—References: https://www.lennysnewsletter.com/p/why-were-at-the-beginning-of-the—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)

Eric Ries is the author of The Lean Startup, a book that reshaped how a generation of founders think about building companies. His new book, Incorruptible, explains how successful companies are destroyed by failing to protect what makes them valuable, and how to change it.In our in-depth conversation, we discuss:1. Why 80% of venture-backed founders are ousted within three years of going public2. The governance structures that protect companies like Anthropic, Costco, and Novo Nordisk3. The simple legal filing that takes two pages and could save your company4. Financial gravity: why successful companies predictably get corrupted into mediocrity5. Why mission-aligned companies like Anthropic reap major benefits from protecting their mission through governance6. Why success won’t protect you—it instead makes you a bigger target—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Eric Ries:• X: https://x.com/ericries• LinkedIn: https://www.linkedin.com/in/eries• Website: https://www.incorruptible.co• Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://news.theleanstartup.com/• Podcast:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ https://ericriesshow.com• YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Eric Ries(02:26) Introducing Incorruptible(06:26) Protecting what you’ve built(11:35) Why founders get ousted(14:58) Too early, too late(19:32) The blueprint: ethos plus integrity(20:49) Novo Nordisk’s 100-year governance fortress(26:41) The Vectura Group and Philip Morris(33:16) The “harder is easier” principle(37:22) Cloudflare’s mission emergence story(42:43) Groupon’s email frequency death spiral(45:37) How to define your purpose(51:09) Mission-driven vs. mission-hopeful companies(54:46) Integrity: structural and personal(57:47) Shareholder primacy: the 40-year-old “natural law”(01:00:04) Public benefit corporations: the easiest protection(01:04:24) Downsides and objections(01:06:08) The Anthropic example: fastest-growing company ever(01:08:39) The torchbearers in every organization(01:10:37) The culture bank: deposits and withdrawals(01:12:28) OpenAI and Anthropic governance(01:16:21) Mission guardians explained(01:18:29) Spiritual holding companies(01:21:53) The founder control trap(01:25:25) Three things to do this week(01:30:10) AI alignment and human alignment(01:34:00) Conway’s law: org charts in architecture(01:37:31) Book resources and farewell—References: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How to build a company that withstands any era | Eric Ries, Lean Startup author

Max Schoening is head of product at Notion, where he’s been especially effective at getting designers and PMs to ship code, prototype in the terminal, and launch extremely successful AI products. He was previously a PM at Google, ran design at Heroku, was VP of Design (and a part-time engineer) at GitHub, and is a two-time founder. He’s one of the most AI-forward product leaders out there and one of the deepest thinkers on how AI changes how we build and use software.We discuss:1. What’s most worked in getting designers and PMs to embrace AI2. Why agency—not skills—is the thing that separates people who thrive from those who fall behind3. How the first 10% of every project is now “free,” and what that means for product development4. Max’s “tiny core” theory of great products: iPhone multitouch, the GitHub pull request, Notion blocks, Dropbox’s menu bar icon5. Why the SaaSpocalypse is overstated6. Why the amount of software has exploded but the quality hasn’t, and why that gap creates opportunity—Brought to you by:WorkOS—Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Max Schoening:• X: https://x.com/mschoening• LinkedIn: https://www.linkedin.com/in/max-schoening• Website: https://max.dev—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Max Schoening(01:55) The origin story of designers coding at Notion(06:30) How much designers and PMs are shipping today(08:24) The balance between shipping code and strategic work(10:32) Why agency will help you thrive in the AI era(11:49) Examples of high agency at Notion(13:52) What we might lose as roles merge(15:56) Advice for developing agency(17:42) Malleable software explained(20:43) The Dieter Rams video and design philosophy(24:00) The SaaS apocalypse debate(28:25) How product building has changed in the past two years(30:27) What’s next in how we build products(34:16) Token spend and ROI conversations(37:39) Getting people to change how they work(39:04) Max’s AI stack(41:41) Which roles AI will transform next(44:26) When companies will start caring about ROI(48:38) Why Notion AI is so successful(51:47) How to ship more quickly while maintaining quality(56:40) Building taste through iterations(1:00:09) What matters most in building successful products(1:05:06) Using the jobs-to-be-done framework(1:07:28) Hot take on universal basic income(1:09:26) What Max would do with AGI(1:10:53) Contrarian corner(1:13:14) Failure corner(1:16:20) Advice for young people in Silicon Valley(1:19:20) Lightning round and final thoughts—Referenced: https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)

Evan Spiegel, the co-founder and CEO of Snap, is one of the very few people in the world who has successfully built and scaled a lasting consumer social product. Snapchat has nearly 1 billion MAUs, and Evan and his team invented some of the most important consumer products and features, including Stories, AR glasses, swipe-based navigation, the camera as the primary UX, and a lot more.In our in-depth conversation, we discuss:1. Why distribution is now the biggest challenge for creating a consumer technology business2. How Snap innovates at scale with a 9-to-12-person design team: no titles, no hierarchy, hundreds of ideas reviewed weekly with the CEO3. Why a pure software business is no longer a moat, and what actually creates durable competitive advantages today4. How AI is changing the way designers work and why they’re now shipping code5. Why every major Snap feature was copied and how that forced the company to work differently6. Evan’s prediction that humanity’s comfort with AI will be a bigger bottleneck than the technology itself7. This year’s crucible moment for Snap—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Evan Spiegel:• X: https://x.com/evanspiegel• Snapchat: https://www.snapchat.com/@evan• LinkedIn: https://www.linkedin.com/in/evan-spiegel• Website: https://www.spiegelfamilyfund.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Evan Spiegel(02:28) Why consumer social products are so hard to build(04:31) How Snapchat cracked distribution with close friends, not network size(05:50) Why distribution is the new moat in the AI era(08:39) Snapchat’s innovation track record (and why software isn’t a moat)(11:39) Why Snap is betting on two of the hardest businesses: consumer social and hardware(16:00) Specs use cases(17:56) The innovation process(21:34) The velocity of design work at Snapchat(25:07) Why Evan says you must talk to customers(26:06) The origin story of Stories(28:25) How screenshot detection saved early Snapchat(31:03) Why they waited to hire PMs—and what role they play now(34:41) How AI is shifting the designer-PM-engineer triad(36:10) Design as an intentional bottleneck for product cohesion(37:24) Why staying close to customers matters for any leader(39:39) What Evan looks for when hiring designers(41:57) How to develop young design talent(44:16) Designers shipping code with AI—and the guardrails needed at scale(47:20) Using jobs-to-be-done to organize AI transformation(48:50) How the CEO job has changed over 15 years(51:30) Learning to communicate(54:08) Why this year is Snapchat’s “crucible moment”(56:22) Being the “middle child” in tech(57:51) Screen-time philosophy with four kids (ages 2 to 15)(1:01:08) AI Corner(1:04:02) Contrarian Corner(1:06:04) Lightning round and final thoughts—References: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel

Cat Wu is Head of Product for Claude Code and Cowork at Anthropic, building one of the most important AI products of this generation. Before joining Anthropic, Cat spent years as an engineer and briefly worked in VC. Today, she’s interviewing hundreds of product managers who are trying to break into AI—and seeing firsthand what separates those who thrive from those who fall behind.We discuss:1. How Anthropic’s shipping cadence went from months to weeks to days2. The emerging skills PMs need to develop right now3. Why you need to build products that don’t yet fully work, so you’re ready when the next model closes the gap4. Cat’s most underrated AI skill: asking the model to introspect on its own mistakes5. Why Claude’s personality is core to its success6. Why Anthropic’s mission alignment eliminates the friction that slows most large organizations7. Why “just do things” is the most important principle for working at AI-native companies—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVanta—Automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Cat Wu:• X: https://x.com/_catwu• LinkedIn: linkedin.com/in/cat-wu• Newsletter: https://catwu.substack.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Cat Wu(01:29) Working with Boris Cherny(04:29) What Anthropic looks for when hiring PMs(06:18) How to help your teams move fast(08:58) How PRDs and roadmaps have evolved at Anthropic(10:28) The Mythos model and Anthropic’s shipping velocity(11:54) What happened with the Claude Code source code leak(12:53) Integrating with OpenClaw(14:19) How the PM team is structured at Anthropic(15:42) How engineer and PM roles are merging(17:54) Why product taste is the most valuable skill(20:10) Where human brains will continue to be useful(22:23) How to stay sane in constant chaos(24:16) What gets sacrificed when you ship so fast(27:47) The /powerup command(28:32) Why Anthropic has been so successful(32:28) When to use Claude Code vs. Desktop vs. Cowork(35:58) Tips for getting started with Cowork(38:44) Demo: Using Cowork to build slide decks overnight(41:48) Cat’s PM tech stack and internal tools(46:47) Which teams use the most tokens(51:15) The emerging skills PMs need for AI companies(55:00) Why building evals is underappreciated(58:44) Why Claude’s character and personality matter so much(1:00:44) How new models force product changes(1:05:11) The vision for Claude Code and Cowork(1:07:22) Advice for thriving in an AI-driven world(1:09:18) Why 95% automation isn’t good enough(1:11:58) Build apps you use every day, not prototypes(1:13:41) The divide between AI skeptics and believers(1:15:19) Lightning round—Referenced: https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)

Nikhyl Singhal is the founder of The Skip, a community for senior product leaders; a former product exec at Meta, Google, and Credit Karma; and a many-time founder. He’s also one of the most honest, unfiltered voices on what’s actually happening in product management right now.In our in-depth conversation, we discuss:1. Why the next two years will be the most chaotic period in product management history2. Why half of current product managers are at risk, and what separates those who’ll do well3. Why you need to find your “moments of joy” with AI4. The “smiling exhaustion” he’s seeing across the product community5. The psychological barriers that prevent people from reinventing themselves6. Why your resume’s fancy logos matter less than ever, and what matters now7. His prediction that companies will shed 30,000 people and rehire 8,000—all AI-first—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVanta—Automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Nikhyl Singhal:• LinkedIn: https://www.linkedin.com/in/nikhyl• X: https://x.com/nikhyl• Podcast & Newsletter: https://skip.show• Skip Community: https://skip.community• Skip Coach: https://skip.coach• Skip.help: https://skip.help—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nikhyl Singhal(02:25) The big picture: what’s changing for product managers(10:00) Are product leaders doing better than 2-3 years ago?(11:44) What will change in the next couple of years(14:23) How companies are changing the way they build products(15:51) What “judgment” really means for PMs(17:46) Why there won’t be any more bad software(20:25) The skills you need to be effective today(23:31) Why there are more PM roles than ever(24:27) The builder versus information-mover divide(30:14) The non-builder problem(30:53) Should PMs code?(34:15) Why experienced leaders still matter(35:44) The diversity setback nobody’s talking about(37:21) Why your brand doesn’t matter as much anymore(39:54) How valued skills are flipping upside down(40:49) Why change is so hard for humans(43:53) The “equal disappointment” algorithm(46:39) You must cross the threshold(48:37) This chaos will settle(53:19) Finding your moment of joy(58:50) Nikhyl’s AI stack and what he’s building(1:00:53) The obsolescence mindset(1:05:24) Specific advice for PMs right now(1:08:58) The four jobs that will exist in the future(1:11:59) Why alignment is changing (but not disappearing)(1:15:40) How engineering is changing even more than PM(1:17:04) The surprising design plateau(1:18:49) Finding optimism in the chaos(1:21:12) Lightning round—Referenced:• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career• COBOL: https://en.wikipedia.org/wiki/COBOL• United Airlines: https://www.united.com• State of the product job market in early 2026: https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9• Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run• Demis Hassabis on X: https://x.com/demishassabis• Sam Altman on X: https://x.com/sama• Dario Amodei on X: https://x.com/DarioAmodei• Cross on Prime Video: https://www.amazon.com/Cross-Season-1/dp/B0D6X7ZZHC• Jack Ryan on Prime Video: https://www.amazon.com/Tom-Clancys-Jack-Ryan/dp/B0CNDCMN8R• 24 on Prime Video: https://www.amazon.com/24-Season-1/dp/B000HPF85A• Claude Code: https://code.claude.com• Codex: https://chatgpt.com/codex• Lovable: https://lovable.dev• Sonos: https://www.sonos.com• “There are only four jobs” on X: https://x.com/yrechtman/status/2039012253341495462• Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f• Lioness on Paramount+: https://www.paramountplus.com/shows/lioness• Tesla: https://www.tesla.com• Albert Einstein’s quote: https://www.goodreads.com/quotes/115696-genius-is-1-talent-and-99-percent-hard-work—Recommended books:• James: https://www.amazon.com/James-Novel-Percival-Everett/dp/0385550367• The Adventures of Huckleberry Finn: https://www.amazon.com/Adventures-Huckleberry-Finn-Unabridged-Uncensored/dp/195483943X—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)

Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad).In our in-depth conversation, Keith shares:1. The barrels vs. ammunition hiring framework (and how to spot barrels)2. Why talking to customers is actively harmful for consumer products3. How to identify undiscovered talent4. Why the PM role is dying5. The three traits of the best-performing companies right now6. The specific interview question he asks every senior candidate7. Why CMOs (not engineers) are becoming the #1 consumer of tokens—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVanta—automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/hard-truths-about-building-in-the-ai-era—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Keith Rabois:• X: https://x.com/rabois• LinkedIn: linkedin.com/in/keith• Website: https://www.khoslaventures.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Keith Rabois(01:59) Why Keith hasn’t used a computer since 2010(04:52) The team you build is the company you build(07:40) How Keith learned to identify talent at PayPal(10:05) Tactics for getting better at hiring(15:31) The barrels vs. ammunition framework(18:52) What makes someone a barrel(22:36) How to attract the best talent(26:18) Building companies on undiscovered talent(27:53) Why better performance requires more pressure(32:36) Career advice in the age of AI(35:14) The future of the product triad(41:03) Why design and code are merging(49:35) What practicing law taught Keith about entrepreneurship(51:22) Contrarian takes on customer feedback(1:02:33) Identifying great AI opportunities(1:05:13) Advice for evaluating statrups (1:12:36) Criticizing in public vs. private(1:15:05) Failure corner(1:17:29) Lightning round—Referenced:• Square: https://squareup.com• Jack Dorsey on X: https://x.com/jack• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens• Simon Willison’s Weblog: https://simonwillison.net• Vinod Khosla on X: https://x.com/vkhosla• Peter Thiel on X: https://x.com/peterthiel• Max Levchin on X: https://x.com/mlevchin• David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks• Tony Xu on X: https://x.com/t_xu• David Sze on X: https://x.com/davidsze• Faire: https://www.faire.com• Max Rhodes on X: https://x.com/MaxRhodesOK• Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson• Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois• Lattice: https://lattice.com• Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights• Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs)• Eric Glyman on X: https://x.com/eglyman• Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html• Opendoor: https://www.opendoor.com• The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q• Lovable: https://lovable.dev• The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Jeremy Stoppelman on X: https://x.com/jeremys• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead• Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol• Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms• Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway• William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare• Evan Moore on X: https://x.com/evancharles• Andrew Mason on X: https://x.com/andrewmason• Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941• The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early• David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden• Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred• Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000• Jon Chu on X: https://x.com/jonchu• Kanu Gulati on X: https://x.com/KanuGulati• Rogo: https://rogo.ai• Profound: https://www.tryprofound.com• Basis: https://www.getbasis.ai• Spellbook: https://www.spellbook.legal• Roelof Botha on X: https://x.com/roelofbotha• Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742• Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp• Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4• Eight Sleep: https://www.eightsleep.com• “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224—Recommended books:• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012• The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666• The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year.In our in-depth discussion, Amol shares:1. How Amol landed his role by cold emailing Anthropic’s CPO Mike Krieger2. How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”)3. Why the ratio of PMs to engineers might need to flip (more PMs than engineers) as AI makes engineers exponentially more productive4. Why activation is the single highest-leverage growth problem in AI5. Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams)6. How he uses Cowork to detect team misalignment in Slack7. How the company’s focus on AI coding created a research flywheel that accelerated their models—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVanta—Automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Amol Avasare:• X: https://x.com/TheAmolAvasare• LinkedIn: https://www.linkedin.com/in/amolavasare—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Amol and Anthropic’s growth(03:15) The story of cold emailing Mike Krieger to get the job(08:28) What it’s like leading growth at the fastest-growing company ever(10:46) What the growth team actually does at Anthropic(12:16) The concept of “success disasters”(13:55) Why activation is the biggest challenge in AI products(18:05) Improving Mercury’s onboarding experience(20:57) The importance of adding the right kind of friction(25:10) Anthropic’s org structure(27:06) Why Anthropic focuses on big bets over micro-optimizations(33:34) Automating growth experiments with Claude (CASH)(38:20) How AI is starting to identify what experiments to run(41:07) The future of PM, engineering, and design roles(47:19) Why you might need more PMs as engineers get more productive(51:13) How Amol uses AI to prototype ideas and skip PRDs(58:10) Amol’s morning routine: AI analyzes 20 to 25 charts automatically(1:03:31) Getting coaching from an AI version of your manager(1:06:27) How Anthropic’s focus on coding and B2B drove their success(1:12:10) Balancing growth with AI safety as a core mission(1:18:09) Advice for thriving in an AI-first future(1:22:53) Anthropic’s culture and the “notebook channels” on Slack(1:35:12) Failure corner: Shutting down his startup after raising money(1:38:25) The traumatic brain injury that changed everything(1:46:49) Lightning round—References: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare

Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwide. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—and he’s been documenting everything he learns in real time on his blog, SimonWillison.net.In our in-depth conversation, Simon shares:1. Why November 2025 was the inflection point when AI coding agents crossed from “mostly works” to “actually works”2. How Simon writes 95% of his code from his phone now and why he’s mentally exhausted by 11 a.m.3. Why mid-career engineers (not juniors) are most at risk right now4. The three agentic engineering patterns Simon uses daily (red/green TDD, templates, hoarding)5. The next leap: the “dark factory” pattern where nobody writes or reviews code and AI does its own QA6. Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster7. Why the pelican riding a bicycle became the unofficial benchmark for AI model quality—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVanta—automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Simon Willison:• X: https://x.com/simonw• LinkedIn: https://www.linkedin.com/in/simonwillison• Website: https://simonwillison.net• Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Simon Willison(02:40) The November 2025 inflection point(08:01) What’s possible now with AI coding(10:42) Vibe coding vs. agentic engineering(13:57) The dark-factory pattern(20:41) Where bottlenecks have shifted(23:36) Where human brains will continue to be valuable(25:32) Defending of software engineers(29:12) Why experienced engineers get better results(30:48) Advice for avoiding the permanent underclass(33:52) Leaning into AI to amplify your skills(35:12) Why Simon says he’s working harder than ever(37:23) The market for pre-2022 human-written code(40:01) Prediction: 50% of engineers writing 95% AI code by the end of 2026(44:34) The impact of cheap code(48:27) Simon’s AI stack(54:08) Using AI for research(55:12) The pelican-riding-a-bicycle benchmark(59:01) The inherent ridiculousness of AI(1:00:52) Hoarding things you know how to do(1:08:21) Red/green TDD pattern for better AI code(1:14:43) Starting projects with good templates(1:16:31) The lethal trifecta and prompt injection(1:21:53) Why 97% effectiveness is a failing grade(1:25:19) The normalization of deviance(1:28:32) OpenClaw: the security nightmare everyone is looking past(1:34:22) What’s next for Simon(1:36:47) Zero-deliverable consulting(1:38:05) Good news about Kakapo parrots—References: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison

Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life.We discuss:1. The exact step-by-step process to install and set up OpenClaw (it’s easier than you think)2. How to avoid the biggest OpenClaw mistakes (don’t install it on your main computer)3. Actual use cases that have changed Claire’s life (e.g. family scheduling, inbound sales, podcast prep, and course management)4. Why multiple specialized agents beat one general-purpose agent5. The security risks everyone worries about—and how to handle them6. Browser limitations, memory issues, and practical workarounds—Brought to you by:Mercury—Radically different bankingOmni—AI analytics your customers can trustOrkes—The enterprise platform for reliable applications and agentic workflows—Where to find Claire Vo:• X: https://x.com/clairevo• LinkedIn: https://www.linkedin.com/in/clairevo• Podcast: https://www.youtube.com/@howiaipodcast• Website: https://clairevo.com• ChatPRD: https://www.chatprd.ai—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Claire and OpenClaw(08:00) The journey from OpenClaw skeptic to believer(11:50) What OpenClaw actually does that’s useful(13:35) OpenClaw vs. other AI agent products(17:05) How to actually install OpenClaw: the basics(18:49) Setting up like you’d onboard a real assistant(20:41) Security and privacy considerations(24:53) Live demo: Installing OpenClaw step-by-step(28:47) Setting up Q: an agent for her kids’ homework(34:08) Understanding “soul,” “identity,” and “memory”(40:40) The unlock: multiple agents, not just one(45:02) How to run multiple agents on one machine(47:28) Jesse Genet’s homeschooling use case(49:58) Real examples and use cases(56:41) Finn, Claire’s family agent(1:00:05) Sage the Course Bot(1:02:15) Common issues and workarounds(1:08:08) The Exa/Perplexity web search workaround(1:09:29) Memory management and context overload(1:12:09) Pro tip: Screen sharing to manage Mac Minis(1:14:18) Using Google Workspace for agent collaboration(1:16:24) What makes OpenClaw special(1:20:15) The “yappers API” and ramble mode(1:22:04) Using Claude Code as your OpenClaw brain surgeon(1:25:16) Bringing management skills to AI agents(1:29:32) Why this matters(1:32:37) Lightning round and final thoughts—Referenced:• OpenClaw: https://openclaw.ai• Claude Cowork: https://claude.com/product/cowork• Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics• Peter Steinberger on LinkedIn: https://www.linkedin.com/in/steipete• Telegram: https://telegram.org• WhatsApp: https://www.whatsapp.com• Fin: https://fin.ai• Why OpenClaw feels alive even though it’s not (this AI has a heartbeat but not a brain): https://x.com/clairevo/status/2017741569521271175• 5 OpenClaw agents run my home, finances, and code | Jesse Genet: https://www.youtube.com/watch?v=96Vl8s3EQhk• Executive Playbook for AI in Engineering, Product, and Design: https://maven.com/clairevo/ai-native-epd-org• Zach Davis on LinkedIn: https://www.linkedin.com/in/zach-m-davis/• ChatGPT Atlas: https://chatgpt.com/atlas• Perplexity Comet: https://www.perplexity.ai/comet• Browser (OpenClaw-managed): https://docs.openclaw.ai/tools/browser• Buffer: https://buffer.com• Brave: https://brave.com/search/api/• Exa: https://exa.ai• Hilary Gridley on X: https://x.com/yourgirlhils• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.youtube.com/watch?v=xDMkkOC-EhI• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang• How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter• Age of Attraction on Netflix: https://www.netflix.com/title/81779095• Oura Ring: https://ouraring.com/• Eight Sleep: https://www.eightsleep.com• Hoopsalytics: https://hoopsalytics.com• DJI Osmo smartphone gimbal: https://www.amazon.com/DJI-Stabilizer-Tracking-Extension-Stabilization/dp/B0FJ2L67HJ?ref_=ast_sto_dp• Silent basketball: https://www.amazon.com/Rzkipdy-Silent-Basketball-Size-27-5/dp/B0FHFSQWPP/ref=sr_1_9• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom—Recommended books:• Treasure Island: https://www.amazon.com/Treasure-Island-Robert-Louis-Stevenson/dp/1505297400• Alice’s Adventures in Wonderland: https://www.amazon.com/Alices-Adventures-Wonderland-Illustrated-Illustrations/dp/991673268X• Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

From skeptic to true believer: How OpenClaw changed my life | Claire Vo

Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process.We discuss:1. Why great ideas often don’t get buy-in2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much3. Why executives are usually optimizing for a global maximum while you are often optimizing locally4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?”5. Why you should go in to learn, not to convince6. Why showing only one option is a mistake7. Why AI will make influence more important, not less—Brought to you by:Omni—AI analytics your customers can trustLovable—Build apps by simply chatting with AIVanta—Automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jessica Fain:• LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jessica Fain(03:53) Why influence is the highest-leverage skill in product(04:47) Why great ideas fail without executive buy-in(06:00) How executives actually think(09:05) The fundamentals: context-setting, communication, and empathy(10:22) Stop pitching for approval—start co-creating with execs(12:59) Influence vs. politics (and why people get it wrong)(15:44) How to disagree with execs without losing trust(17:20) Going in to learn, not to convince(19:08) How to present ideas(26:05) The Minto-style approach and tailoring your communication to each exec(28:22) Why Jessica doesn’t like the question “What’s top of mind for you?”(30:24) Understanding incentives to unlock buy-in(32:10) Aligning product work with company strategy(35:10) Quick summary(37:31) Disarming the executive(40:49) Speed matters: why fast follow-up builds momentum(43:32) How to run high-impact meetings (the 60-second rule)(47:00) Why influencing execs is part of your job(49:15) Asking for more resources and thinking in 10x bets(52:23) What to do when your idea gets rejected(54:18) Clarifying information(56:50) How to build trust and make ideas stick(58:30) Shrinking big ideas into experiments(01:02:27) Common mistakes people make when influencing leaders(01:06:00) How to grow into your next role(01:09:32) How AI is changing influence and product work(01:17:55) Using AI to simulate exec feedback and improve pitches(01:21:15) Protecting our brains from overwhelm(01:22:44) Lightning round and final thoughts—Referenced:• Box: https://www.box.com• Slack: https://slack.com• Brightwheel: https://mybrightwheel.com• Webflow: https://webflow.com• April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood• Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua• Atlassian: https://www.atlassian.com• Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid• Calendly: https://calendly.com• Glassdoor: https://www.glassdoor.co.in/index.htm• The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai• Ethan Eismann on X: https://x.com/eeismann• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield• Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank• Checkr: https://checkr.com• Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl• Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan• How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief• Barbara Minto’s website: https://www.barbaraminto.com• How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD• Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2• Casa: https://getcasa.com• Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix• Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles)—Recommended books:• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927• Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061• A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)

Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes.We discuss:1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump2. Why Jacob sees 40% average movement when negotiations are run well3. When negotiation actually starts (hint: it’s much earlier than you think)4. Why information + timing create power5. The biggest mistakes people make when negotiating6. How to navigate the important “What’s your comp expectation?” question without anchoring too low7. Why the best interviews feel more like discovery calls than interrogations—Brought to you by:Orkes—The enterprise platform for reliable applications and agentic workflowsMercury—Radically different bankingOmni—AI analytics your customers can trust—Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jacob Warwick:• Substack: https://www.execsandthecity.com• YouTube: https://www.youtube.com/@ExecsandtheCity• Website: https://www.thinkwarwick.com• Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jacob Warwick(04:12) How much comp people leave on the table(07:52) Why you shouldn’t feel greedy asking for more(09:45) What founders should know about negotiation(13:03) How Jacob works behind the scenes(15:35) The biggest mistakes people make when negotiating(19:30) Home-field advantage and controlling the conversation(23:02) The step-by-step approach to negotiating an offer(30:17) Jacob’s passion and why these tips don’t work on kids(32:04) Who should speak first about compensation(35:36) Understanding power(39:52) Breaking out of salary bands by focusing on pain points(45:45) Brief summary(47:20) Selling the vacation: How to visualize success(50:07) Controlling the narrative and planting seeds(59:01) Jacob’s role as hype man(01:01:05) Positioning yourself like a product(01:02:49) Making the process frictionless for hiring managers(01:06:20) Flipping the interview to extract information(01:12:17) Five tactical tips for negotiating comp(01:21:45) What to do when negotiations fall apart(01:25:05) Why negotiation is different for every individual(01:28:55) Why outcomes aren’t predetermined(01:32:52) Wild Hollywood negotiation stories(01:37:35) The first step you should take after getting an offer(01:40:30) Jacob’s personal mission(01:44:42) Lightning round and final thoughts—Referenced:• The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating• Sam Altman on X: https://x.com/sama• Tom Brady on X: https://x.com/TomBrady• Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8• Salesforce: https://www.salesforce.com• Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts• Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon• Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that• Chris Voss on X: https://x.com/fbinegotiator• Werewolf: https://playwerewolf.co• Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion• How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy• ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation• Marvel: https://www.marvel.com• Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030• Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0• Minuscule: https://www.youtube.com/user/Minuscule• Claude Cowork: https://claude.com/product/cowork• Macrofactor: https://macrofactor.com• Whoop: https://www.whoop.com• Gemini: https://gemini.google.com/app• The Cody Dieruf Foundation: https://breathinisbelievin.org• Cystic Fibrosis Foundation: https://www.cff.org—Recommended books:• Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941• Influence: The Psychology of Persuasion: https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X• You Can Negotiate Anything: How to Get What You Want: https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229• Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal: https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)

People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it.We discuss:1. The collection of moments that led me to what I do now2. When I added a paywall, and how I knew it was working3. The hidden treadmill behind shipping a newsletter post and podcast episode every week4. The most stressful moments I’ve had in business and in life5. How I think about stress, consistency, and keeping the business small—Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyMetaview—The AI platform for recruiting: https://metaview.ai/lennyDX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Michelle Rial:• X: https://x.com/TheRialMichelle• LinkedIn: https://www.linkedin.com/in/michellerial• Website: https://www.michellerial.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction and role reversal(04:06) What would Lenny be doing without the newsletter?(07:20) The moments that led to starting the newsletter(09:58) Does Lenny still enjoy the work?(12:42) Stress management and misophonia(14:00) The psychedelic trip that changed everything(15:45) Online happiness course and baseline optimization(17:30) Thunder round: Lenny’s misophonia worst sounds(20:20) What makes Michelle’s charts so shareable(23:55) Where chart ideas come from (and why meditation helps)(26:59) Where does “Lenny” come from?(28:54) Being recognized in public(31:24) Early projects(36:30) Michelle and Lenny’s yin and yang(37:49) Missing office culture (but not really)(39:37) Lenny’s face blindness(40:47) The $100M fraud attack story(42:50) Michelle’s childbirth emergency(47:22) Michelle’s creative process(51:58) Lenny’s favorite children’s books(54:00) Product management lessons in parenting(55:31) Defining product management in five words(58:23) Why Michelle pivoted to children’s books(01:01:30) The power of iteration and real experience—Resources and episode mentions: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. To hear more, visit www.lennysnewsletter.com

How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky

Qasar Younis is the co-founder and CEO of Applied Intuition, a $15 billion AI company that adds intelligence to cars, tractors, planes, submarines, and other vehicles—essentially, Tesla or Waymo without the hardware. He was previously COO of Y Combinator, started his career as an engineer at GM and Bosch, and was born on a farm in Pakistan.We discuss:1. Why the biggest AI revolution will play out in mining, farming, construction, and trucking over the next 5 to 10 years, not in software2. Why Qasar intentionally stayed under the radar for nearly a decade while building Applied Intuition, and why most founders shouldn’t do that3. The truth about China’s AI capabilities and why comparisons to American companies are fundamentally flawed4. The company values that drive Applied Intuition: speed above everything, laugh a lot, half the work is follow-up, never disappoint the customer5. The biggest lessons from Qasar’s stint as YC’s COO, including that the most successful companies show traction very early6. How reading old books is the best way to build taste—Brought to you by:Omni—AI analytics your customers can trustVanta—Automate compliance. Simplify security.Lovable—Build apps by simply chatting with AI—Episode transcript: https://www.lennysnewsletter.com/p/the-most-successful-ai-company-youve-never-heard-of—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Qasar Younis:• X: https://x.com/qasar• LinkedIn: https://www.linkedin.com/in/qasar• Website: https://qy.co• Reading list: https://qy.co/books—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Qasar and Applied Intuition(04:01) The optimistic vision: How AI will create abundance(08:49) Why anxiety about AI comes from misunderstanding—and how to fight fear with knowledge(12:58) The market sell-off explained(16:31) Self-driving cars: Why 30,000 annual deaths prove we need autonomy now(20:22) The spectrum of physical AI(28:00) How AI is coming just in time(33:26) Why comparing Chinese AI companies to American AI companies is a category error(39:12) Why Qasar finally joined Twitter after staying silent for a decade(45:08) Why successful companies almost always show early signs of traction(50:40) Applied Intuition’s core values(56:00) Why the company cleans its own office—and never spent a dollar of raised capital(58:50) Quasar’s reading philosophy(01:06:14) How to operationalize listening to naysayers(01:12:53) The importance of decisiveness(01:14:55) Removing emotions from decisions(01:19:02) Why most Silicon Valley CEOs don’t have great taste—and how to develop it—Referenced:• Applied Intuition: https://www.appliedintuition.com• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Elad Gil’s website: https://eladgil.com• Bosch: https://www.bosch.com• Berkshire Hathaway: https://www.berkshirehathaway.com• Naval Ravikant on X: https://x.com/naval• Y Combinator: https://www.ycombinator.com• Waymo: https://waymo.com/• Tesla: https://www.tesla.com• DeepSeek: https://www.deepseek.com• Rivian: https://rivian.com• Crate & Barrel: https://www.crateandbarrel.com• OpenClaw: https://openclaw.ai• Sam Altman on X: https://x.com/sama• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig• What Steve Jobs really meant when he said ‘Good artists copy; great artists steal’: https://www.cnet.com/tech/tech-industry/what-steve-jobs-really-meant-when-he-said-good-artists-copy-great-artists-steal• 7 quotes on the power of reading from Charlie Munger: https://www.neil.blog/articles/7-quotes-power-reading-charlie-munger• Andreessen Horowitz: https://a16z.com• John Doerr on LinkedIn: https://www.linkedin.com/in/john-doerr-03248211• Gandhi’s quote: https://www.azquotes.com/author/5308-Mahatma_Gandhi/tag/truth#google_vignette• Steve Ballmer on X: https://x.com/Steven_Ballmer• General Motors: https://www.gm.com—Recommended books:• House of Huawei: The Secret History of China’s Most Powerful Company: https://www.amazon.com/House-Huawei-History-Powerful-Company/dp/0593544633• Maintenance: Of Everything, Part One: https://press.stripe.com/maintenance-part-one• The Autobiography of Malcolm X: As Told to Alex Haley: https://www.amazon.com/Autobiography-Malcolm-Told-Alex-Haley/dp/0345350685• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916• Made in America: https://www.amazon.com/Sam-Walton-Made-America/dp/0553562835• My American Journey: https://www.amazon.com/American-Journey-Autobiography-Colin-Powell/dp/0679432965• Guns, Germs, and Steel: The Fates of Human Societies: https://www.amazon.com/Guns-Germs-Steel-Fates-Societies/dp/0393317552• Collapse: How Societies Choose to Fail or Succeed: https://www.amazon.com/Collapse-Societies-Choose-Succeed-Revised/dp/0143117009• SPQR: A History of Ancient Rome: https://www.amazon.com/SPQR-History-Ancient-Mary-Beard/dp/0871404230• A World Appears: A Journey into Consciousness: https://www.amazon.com/World-Appears-Journey-into-Consciousness/dp/198488199X—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The most successful AI company you’ve never heard of | Qasar Younis

Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square, and Shopify.—We discuss:1. Why the classic discovery → mock → iterate design process is becoming obsolete2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack3. Whether AI will eventually surpass humans in taste and judgment4. Why Jenny left a director role at Figma to return to IC work at Anthropic5. The three archetypes Jenny is hiring for now6. Why chatbot interfaces may be more durable than most people expect—Brought to you by:Mercury—Radically different banking: https://mercury.com/?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q1_brand_campaignOrkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/Omni—AI analytics your customers can trust: https://omni.co/lenny—Episode transcript: https://www.lennysnewsletter.com/p/the-design-process-is-dead—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jenny Wen:• X: https://x.com/jenny_wen• LinkedIn: https://www.linkedin.com/in/jennywen• Substack: https://jennywen.substack.com• Website: https://jennywen.ca—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jenny Wen(04:23) Why the traditional design process is dead(06:33) The two new types of design work(10:00) How widespread this shift will be(13:00) Day-to-day life as a designer at Anthropic(18:45) Jenny’s AI stack(20:03) Why Figma still matters for exploration(22:25) Advice for working with engineers(24:19) How to maintain craft, quality, and trust in the AI era(27:35) Will AI ever have “taste”?(31:38) The future of chatbot interfaces(35:33) Moving from director back to IC(41:00) The 10-day build of Claude Cowork(46:06) Hiring: the three archetypes(50:44) Advice for new and senior designers(54:42) The value of “low leverage” tasks for managers(57:52) Why the best teams roast each other(01:01:45) The legibility framework(01:07:22) Lightning round and final thoughts—Referenced:• Figma: https://www.figma.com• Anthropic: https://www.anthropic.com• v0: https://v0.app• Navigating a Design Career with Jenny Wen | Figma at Waterloo: https://www.youtube.com/watch?v=OHcBPMh2ivk• Claude Cowork: https://claude.com/product/cowork• Use Claude Code in VS Code: https://code.claude.com/docs/en/vs-code• Claude Code in Slack: https://code.claude.com/docs/en/slack• Lex Fridman’s website: https://lexfridman.com• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens• OpenClaw: https://openclaw.ai• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Socratica: https://www.socratica.info• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Evan Tana’s ‘legibility matrix’ on X: https://x.com/evantana/status/1927404374252269667• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early• Palantir: https://www.palantir.com• Stripe: https://stripe.com• Linear: https://linear.app• Notion: https://www.notion.com• Julie Zhuo’s website: https://www.juliezhuo.com• Sentimental Value: https://www.imdb.com/title/tt27714581• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD• Noah Wyle: https://en.wikipedia.org/wiki/Noah_Wyle• ER on Prime Video: https://www.amazon.com/gp/video/detail/B0FWZSDYRP• Retro: https://retro.app• Granola: https://www.granola.ai—Recommended books:• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394480767• Insomniac City: New York, Oliver Sacks, and Me: https://www.amazon.com/Insomniac-City-New-York-Oliver/dp/162040494X—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)

Jeetu Patel is the president and chief product officer at Cisco, where he leads a team of 30,000 people and is playing a central role in the massive AI infrastructure buildout happening right now. Previously, he spent five years as CPO at Box and 17 years running his own startup. Recently Jeetu organized an AI summit featuring industry leaders like Jensen Huang, Sam Altman, Marc Andreessen, and Fei-Fei Li.We discuss:1. How Cisco went AI-first across 90,000 employees2. His six-part framework for building great companies: timing, market, team, product, brand, distribution3. Why he says he couldn’t have done this job without AI4. His “right to win” strategic framework5. His communication framework for preventing “packet loss” across an organization6. Why he flips “praise in public, criticize in private” and does the exact opposite7. The important communication lesson his mother taught him—Brought to you by:Sentry—Code breaks, fix it faster: https://sentry.io/lennyFramer—Build better websites faster: https://framer.com/lennySamsara—Saving lives with AI built for physical operations: https://samsara.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jeetu Patel:• X: https://x.com/jpatel41• LinkedIn: https://www.linkedin.com/in/jeetupatel• Website: https://blogs.cisco.com/author/jeetupatel—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction and welcome(04:15) Insights from Cisco’s Al summit(08:45) Transforming Cisco into an Al-first company(15:33) What Cisco actually does in the Al infrastructure stack(19:09) The future of Al(24:36) Raising kids in the AI era(29:46) “Permission to play” framework(36:50) Lessons from great CEOs(42:02) Leading at scale(50:54) Why Jeetu inverts the ‘praise in public, criticize in private’ rule(57:45) Surrounding yourself with good human beings(58:35) Lessons from loss(01:03:21) Career advice: platforms, hunger, and preparation(01:10:21) The six-part framework for building great companies(01:19:05) Lightning round and final thoughts—Resources and episode mentions: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

AI is critical for humanity’s survival: Cisco president on the AI revolution | Jeetu Patel

Boris Cherny is the creator and head of Claude Code at Anthropic. What began as a simple terminal-based prototype just a year ago has transformed the role of software engineering and is increasingly transforming all professional work.We discuss:1. How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month2. The counterintuitive product principles that drove Claude Code’s success3. Why Boris believes coding is “solved”4. The latent demand that shaped Claude Code and Cowork5. Practical tips for getting the most out of Claude Code and Cowork6. How underfunding teams and giving them unlimited tokens leads to better AI products7. Why Boris briefly left Anthropic for Cursor, then returned after just two weeks8. Three principles Boris shares with every new team member—Brought to you by:DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lennySentry—Code breaks, fix it faster: https://sentry.io/lennyMetaview—The AI platform for recruiting: https://metaview.ai/lenny—Episode transcript: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Boris Cherny:• X: https://x.com/bcherny• LinkedIn: https://www.linkedin.com/in/bcherny• Website: https://borischerny.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Boris and Claude Code(03:45) Why Boris briefly left Anthropic for Cursor (and what brought him back)(05:35) One year of Claude Code(08:41) The origin story of Claude Code(13:29) How fast AI is transforming software development(15:01) The importance of experimentation in AI innovation(16:17) Boris’s current coding workflow (100% AI-written)(17:32) The next frontier(22:24) The downside of rapid innovation (24:02) Principles for the Claude Code team(26:48) Why you should give engineers unlimited tokens(27:55) Will coding skills still matter in the future?(32:15) The printing press analogy for AI’s impact(36:01) Which roles will AI transform next?(40:41) Tips for succeeding in the AI era(44:37) Poll: Which roles are enjoying their jobs more with AI(46:32) The principle of latent demand in product development(51:53) How Cowork was built in just 10 days(54:04) The three layers of AI safety at Anthropic(59:35) Anxiety when AI agents aren’t working(01:02:25) Boris’s Ukrainian roots(01:03:21) Advice for building AI products(01:08:38) Pro tips for using Claude Code effectively(01:11:16) Thoughts on Codex(01:12:13) Boris’s post-AGI plans(01:14:02) Lightning round and final thoughts—References: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Head of Claude Code: What happens after coding is solved | Boris Cherny

Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach.We discuss:1. His LOCKS framework for evaluating founders2. Why you should build your team like the 2004 Red Sox3. Why hiring “spicy” candidates beats consensus picks4. Why enterprise sales will be the last white-collar job AI replaces5. Some of my favorite “Halliganisms”—Brought to you by:Sentry—Code breaks, fix it faster: http://sentry.io/lennyDatadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Brian Halligan• X: https://x.com/bhalligan• LinkedIn: linkedin.com/in/brianhalligan• Delphi: https://www.delphi.ai/bhalligan• Podcast: https://sequoiacap.com/series/long-strange-trip—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Brian Halligan(03:56) The perpetual state of constructive dissatisfaction(05:25) Coaching CEOs(07:49) The art of interviewing and hiring(11:21) Getting the most out of reference calls(13:10) Homegrown talent vs. big company hires(16:31) Traits of successful CEOs(19:40) Brian’s LOCKS framework for evaluating founders(21:34) Are great CEO’s born or made?(23:41) Giving effective feedback(25:54) The future of go-to-market strategies(31:56) Understanding forward deployed engineers(34:17) How the CEO role has evolved over the last 20 years(38:10) Halliganisms(01:01:18) The CEO’s role in scaling a company(01:02:41) Lightning round and final thoughts—Referenced:• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria• HubSpot: https://www.hubspot.com• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• McKinsey & Company: https://www.mckinsey.com• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392• OpenClaw: https://openclaw.ai• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159• Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin• Glassdoor: https://www.glassdoor.com• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution• Delphi: https://www.delphi.ai• Sonos: https://www.sonos.com• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan• The Boston Red Sox: https://www.mlb.com/redsox—Recommended book:• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

Sherwin Wu leads engineering for OpenAI’s API platform, where roughly 95% of engineers use Codex, often working with fleets of 10 to 20 parallel AI agents.We discuss:1. What OpenAI did to cut code review times from 10-15 minutes to 2-3 minutes2. How AI is changing the role of managers3. Why the productivity gap between AI power users and everyone else is widening4. Why “models will eat your scaffolding for breakfast”5. Why the next 12 to 24 months are a rare window where engineers can leap ahead before the role fully transforms—Brought to you by:DX—The developer intelligence platform designed by leading researchersSentry—Code breaks, fix it fasterDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Episode transcript: https://www.lennysnewsletter.com/p/engineers-are-becoming-sorcerers—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Sherwin Wu:• X: https://x.com/sherwinwu• LinkedIn: https://www.linkedin.com/in/sherwinwu1—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Sherwin Wu(03:10) AI’s role in coding at OpenAI(06:53) The future of software engineering with AI(12:26) The stress of managing agents(15:07) Codex and code review automation(19:29) The changing role of engineering managers(24:14) The one-person billion-dollar startup(31:40) Management lessons(37:28) Challenges and best practices in AI deployment(43:56) Hot takes on AI and customer feedback(48:57) Building for future AI capabilities(50:16) Where models are headed in the next 18 months(53:35) Business process automation(57:22) OpenAI’s ecosystem and platform strategy(01:00:50) OpenAI’s mission and global impact(01:05:21) Building on OpenAI’s API and tools(01:08:16) Lightning round and final thoughts—Referenced:• Codex: https://openai.com/codex• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• OpenClaw: https://openclaw.ai• The creator of Clawd: “I ship code I don’t read”: https://newsletter.pragmaticengineer.com/p/the-creator-of-clawd-i-ship-code• The Sorcerer’s Apprentice: https://en.wikipedia.org/wiki/The_Sorcerer%27s_Apprentice_(Dukas)• Quora: https://www.quora.com• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Sarah Friar on LinkedIn: https://www.linkedin.com/in/sarah-friar• Sam Altman on X: https://x.com/sama• Nicolas Bustamante’s “LLMs Eat Scaffolding for Breakfast” post on X: https://x.com/nicbstme/status/2015795605524901957• The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html• Overton window: https://en.wikipedia.org/wiki/Overton_window• Developers can now submit apps to ChatGPT: https://openai.com/index/developers-can-now-submit-apps-to-chatgpt• Responses: https://platform.openai.com/docs/api-reference/responses• Agents SDK: https://platform.openai.com/docs/guides/agents-sdk• AgentKit: https://openai.com/index/introducing-agentkit• Ubiquiti: https://ui.com• Jujutsu Kaisen on Crunchyroll: https://www.crunchyroll.com/series/GRDV0019R/jujutsu-kaisen?srsltid=AfmBOoqvfzKQ6SZOgzyJwNQ43eceaJTQA2nUxTQfjA1Ko4OxlpUoBNRB• eero: https://eero.com• Opendoor: https://www.opendoor.com—Recommended books:• Structure and Interpretation of Computer Programs: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871• The Mythical Man-Month: Essays on Software Engineering: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959• There Is No Antimemetics Division: A Novel: https://www.amazon.com/There-No-Antimemetics-Division-Novel/dp/0593983750• Breakneck: China’s Quest to Engineer the Future: https://www.amazon.com/Breakneck-Chinas-Quest-Engineer-Future/dp/1324106034• Apple in China: The Capture of the World’s Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

“Engineers are becoming sorcerers” | The future of software development with OpenAI’s Sherwin Wu

Lazar Jovanovic is a full-time professional vibe coder at Lovable. His job is to build both internal tools and customer-facing products purely using AI, while not having a coding background. In this conversation, he breaks down the tactics, workflows, and framework that let him ship production-quality products using only AI.We discuss:1. Why having no coding background can be an advantage when building with AI2. Why most of your time should go to planning and chat mode, not prompting3. What to do when you get stuck: his 4x4 debugging workflow4. The PRD and Markdown file system that keeps AI agents aligned across complex builds5. Why kicking off four or five parallel prototypes is the best way to clarify your thinking6. Why design skills and taste are going to be the most important skills in the future7. His “genie and three wishes” mental model for making the most of AI’s limitations8. How product, engineering, and design roles are converging—and what that means for your career—Brought to you by:Strella—The AI-powered customer research platform: https://strella.io/lennySamsara—Saving lives with AI built for physical operations: https://samsara.com/lennyWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Lazar Jovanovic:• X: https://x.com/lakikentaki• LinkedIn: https://www.linkedin.com/in/lazar-jovanovic• YouTube: https://www.youtube.com/@50in50challenge• Starter Story course: https://build.starterstory.com/build/ai-build-accelerator?via=lazar (code LAZAR15 for 15% off)—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Lazar and professional vibe coding(04:53) What a professional vibe coder actually does day-to-day(09:26) Why non-technical backgrounds can be an advantage(12:24) The importance of self-awareness(14:42) His “genie and three wishes” mental model(17:43) Developing taste and judgment in the age of AI(21:46) The parallel project approach for better outcomes(29:30) Creating dynamic context windows with PRDs(36:56) Why elite vibe coders focus on planning, not coding(44:43) Creating MD files to guide AI development(50:57) Why prototyping still matters(56:50) Why “good enough” is no longer good enough(01:00:53) The future of engineering in an AI world(01:05:14) What to do when you get stuck: his 4x4 debugging workflow(01:14:27) Helping agents learn from their mistakes(01:15:35) Why watching agent output is more important than code(01:19:08) The incredible pace of AI development(01:22:55) Why emotional intelligence will become more valuable(01:28:30) How to become a professional vibe coder(01:30:10) Why building in public is the fastest path to opportunities(01:37:03) Final thoughts on focusing on quality over tech stack—Referenced:• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna• Lovable: https://lovable.dev• Lovable + Shopify: https://lovable.dev/shopify• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Mobbin: https://mobbin.com• Dribbble: https://dribbble.com• 21st.dev: https://21st.dev• Lovable base prompt generator: https://building-advisor.lovable.app/• Lovable PRD generator: https://chatgpt.com/g/g-67e1e85fbeac8191a69b95c6d5c42ef6-lovable-prd-generator• Felix Haas’s newsletter: https://designplusai.com• Bauhaus: https://en.wikipedia.org/wiki/Bauhaus• Glassmorphism: https://www.figma.com/community/plugin/1197106608665398190/glassmorphism• UI style guide: http://uistyle.lovable.app• Cloudflare: https://www.cloudflare.com• Ben Tossell on X: https://x.com/bentossell• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Peter Thiel says AI will be ‘worse’ for math nerds than for writers: https://www.businessinsider.com/peter-thiel-ai-worse-for-math-professionals-than-writers-2024-4• Andrej Karpathy on X: https://x.com/karpathy• The 100-person AI lab that became Anthropic and Google’s secret weapon | Edwin Chen (Surge AI): https://www.lennysnewsletter.com/p/surge-ai-edwin-chen• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody• Slumdog Millionaire: https://www.imdb.com/title/tt1010048—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder)

Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside, and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dynamics can make you more effective in every relationship.We discuss:1. Why repair—not perfection—defines strong leadership2. Why you need to connect before you correct to build cooperation and trust3. The “most generous interpretation” framework for handling difficult behaviors4. How to correctly set boundaries (vs. making requests)5. The power of “I believe you, and I believe in you”6. What it looks like to be a “sturdy” leader—Brought to you by:Merge—Fast, secure integrations for your products and agents: https://merge.dev/lennyMetaview—The AI platform for recruiting: https://metaview.ai/lennyFramer—Builder better websites faster: https://framer.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/dr-becky-on-the-surprising-overlap—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Dr. Becky Kennedy:• X: https://x.com/GoodInside• LinkedIn: https://www.linkedin.com/in/drbecky• Instagram: https://www.instagram.com/drbeckyatgoodinside• TikTok: https://www.tiktok.com/@drbeckyatgoodinside• Website: https://www.goodinside.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Dr. Becky Kennedy(05:14) Connecting parenting and leadership(08:40) The power of repair(11:05) Connecting before correcting(17:45) Good Inside framework at work(22:08) The most generous interpretation (MGI)(25:46) Curiosity over judgment(27:07) Understanding behavior change(31:08) What potty training can teach us about workplace behavior(34:40) Naming your intention(35:41) Sturdy leadership(40:52) How to set boundaries well(46:33) The role of leadership and consensus(50:50) The importance of being “locatable”(52:40) A powerful story of betrayal and realization(57:12) Building resilience over happiness(01:00:34) The power of the phrase “I believe you, and I believe in you.”(01:09:08) The Good Inside community and resources(01:16:22) AI corner(01:19:52) Good Inside’s mission(01:22:26) Lightning round and final thoughts—Referenced:• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng• Punch: https://en.wikipedia.org/wiki/Punch_(play)• Figma: https://www.figma.com• Andrew Hogan on LinkedIn: https://www.linkedin.com/in/ahhogan• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Lovable: https://lovable.dev• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Claude: https://claude.ai• ChatGPT: https://chatgpt.com• Secrets We Keep on Netflix: https://www.netflix.com/title/81697668• K Pop Demon Hunters on Netflix: https://www.netflix.com/title/81498621• Liberty puzzles: https://libertypuzzles.com—Recommended books:• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375• Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481• Leave Me Alone!: A Good Inside Story About Deeply Feeling Kids: https://www.amazon.com/Leave-Me-Alone-Inside-Feeling/dp/1250413117• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765/• The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

A child psychologist’s guide to working with difficult adults | Dr. Becky Kennedy

Marc Andreessen is a founder, investor, and co-founder of Netscape, as well as co-founder of the venture capital firm Andreessen Horowitz (a16z). In this conversation, we dig into why we’re living through a unique and one of the most incredible times in history, and what comes next.We discuss:1. Why AI is arriving at the perfect moment to counter demographic collapse and declining productivity2. How Marc has raised his 10-year-old kid to thrive in an AI-driven world3. What’s actually going to happen with AI and jobs (spoiler: he thinks the panic is “totally off base”)4. The “Mexican standoff” that’s happening between product managers, designers, and engineers5. Why you should still learn to code (even with AI)6. How to develop an “E-shaped” career that combines multiple skills, with AI as a force multiplier7. The career advice he keeps coming back to (“Don’t be fungible”)8. How AI can democratize one-on-one tutoring, potentially transforming education9. His media diet: X and old books, nothing in between—Brought to you by:DX—The developer intelligence platform designed by leading researchersBrex—The banking solution for startupsDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Episode transcript: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Marc Andreessen:• X: https://x.com/pmarca• Substack: https://pmarca.substack.com• Andreessen Horowitz’s website: https://a16z.com• Andreessen Horowitz’s YouTube channel: https://www.youtube.com/@a16z—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Marc Andreessen(04:27) The historic moment we’re living in(06:52) The impact of AI on society(11:14) AI’s role in education and parenting(22:15) The future of jobs in an AI-driven world(30:15) Marc's past predictions(35:35) The Mexican standoff of tech roles(39:28) Adapting to changing job tasks(42:15) The shift to scripting languages(44:50) The importance of understanding code(51:37) The value of design in the AI era(53:30) The T-shaped skill strategy(01:02:05) AI’s impact on founders and companies(01:05:58) The concept of one-person billion-dollar companies(01:08:33) Debating AI moats and market dynamics(01:14:39) The rapid evolution of AI models(01:18:05) Indeterminate optimism in venture capital(01:22:17) The concept of AGI and its implications(01:30:00) Marc's media diet(01:36:18) Favorite movies and AI voice technology(01:39:24) Marc's product diet(01:43:16) Closing thoughts and recommendations—Referenced:• Linus Torvalds on LinkedIn: https://www.linkedin.com/in/linustorvalds• The philosopher’s stone: https://en.wikipedia.org/wiki/Philosopher%27s_stone• Alexander the Great: https://en.wikipedia.org/wiki/Alexander_the_Great• Aristotle: https://en.wikipedia.org/wiki/Aristotle• Bloom’s 2 sigma problem: https://en.wikipedia.org/wiki/Bloom%27s_2_sigma_problem• Alpha School: https://alpha.school• In Tech We Trust? A Debate with Peter Thiel and Marc Andreessen: https://a16z.com/in-tech-we-trust-a-debate-with-peter-thiel-and-marc-andreessen• John Woo: https://en.wikipedia.org/wiki/John_Woo• Assembly: https://en.wikipedia.org/wiki/Assembly_language• C programming language: https://en.wikipedia.org/wiki/C_(programming_language)• Python: https://www.python.org• Netscape: https://en.wikipedia.org/wiki/Netscape• Perl: https://www.perl.org• Scott Adams: https://en.wikipedia.org/wiki/Scott_Adams• Larry Summers’s website: https://larrysummers.com• Nano Banana: https://gemini.google/overview/image-generation• Bitcoin: https://bitcoin.org• Ethereum: https://ethereum.org• Satoshi Nakamoto: https://en.wikipedia.org/wiki/Satoshi_Nakamoto• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann• Inside Google’s AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search): https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year• DeepSeek: https://www.deepseek.com• Cowork: https://support.claude.com/en/articles/13345190-getting-started-with-cowork• Definite vs. indefinite thinking: Notes from Zero to One by Peter Thiel: https://boxkitemachine.net/posts/zero-to-one-peter-thiel-definite-vs-indefinite-thinking• Henry Ford: https://www.thehenryford.org/explore/stories-of-innovation/visionaries/henry-ford• Lex Fridman Podcast: https://lexfridman.com/podcast• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz• Eddington: https://www.imdb.com/title/tt31176520• Joaquin Phoenix: https://en.wikipedia.org/wiki/Joaquin_Phoenix• Pedro Pascal: https://en.wikipedia.org/wiki/Pedro_Pascal• George Floyd: https://en.wikipedia.org/wiki/George_Floyd• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Grok Bad Rudi: https://grok.com/badrudi• Wispr Flow: https://wisprflow.ai• Star Trek: The Next Generation: https://www.imdb.com/title/tt0092455• Star Trek: Starfleet Academy: https://www.imdb.com/title/tt8622160• a16z: The Power Brokers: https://www.notboring.co/p/a16z-the-power-brokers—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Marc Andreessen: The real AI boom hasn’t even started yet

Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team.We discuss:1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market2. A small tweak that’ll double response rates on your cancellation surveys3. Why “it’s too expensive” is almost never the real reason customers cancel4. The “elephant curve” of growth5. How repositioning the same product can increase revenue 8x6. When to reconsider if growth is even the right goal for your business—Brought to you by:10Web—Vibe coding platform as an APIStrella—The AI-powered customer research platformBrex—The banking solution for startups—Episode transcript: https://www.lennysnewsletter.com/p/why-your-product-stopped-growing—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jason Cohen:• Preorder Jason’s book: https://preorder.hiddenmultipliers.com/• X: https://x.com/asmartbear• LinkedIn: https://www.linkedin.com/in/jasoncohen• Blog: https://longform.asmartbear.com• Website: https://wpengine.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jason Cohen(05:19) Jason’s writing journey(08:25) Questions to ask when your product stops growing(18:17) Getting real customer feedback(20:27) Analyzing cancellation reasons(26:54) Onboarding and activation(29:35) Quick summary(35:46) Revisiting pricing strategies(41:46) Positioning strategies(47:52) Why pricing is inseparable from your strategy(52:06) The importance of net revenue retention (NRR)(01:00:25) Asking whether or not this is good for the customer(01:04:34) Leveraging existing customers(01:06:42) Are your acquisition channels saturated? The “elephant curve”(1:09:41) Why all marketing channels eventually decline(01:12:04) Direct vs. indirect marketing channels(1:13:36) Getting creative with new channels(01:19:04) Do you actually need to grow?(01:25:57) Deciding when to quit(01:29:27) Book announcement(01:33:21) AI corner(01:34:35) Contrarian corner(01:37:43) Lightning round and final thoughts—Referenced:• Tyler Cowen’s website: https://tylercowen.com• How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn• Linear: https://linear.app• Jira: https://www.atlassian.com/software/jira• Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy• M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• Buffer: https://buffer.com• AG1: https://drinkag1.com• How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com): https://www.lennysnewsletter.com/p/how-to-find-hidden-growth-opportunities-albert-cheng• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth• The Elephant in the room: The myth of exponential hypergrowth: https://longform.asmartbear.com/exponential-growth• HubSpot: https://www.hubspot.com• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• Adjacency Matrix: How to expand after PMF: https://longform.asmartbear.com/adjacency/• Ecosystem is the next big growth channel: https://www.lennysnewsletter.com/p/ecosystem-is-the-next-big-growth• ChatGPT apps are about to be the next big distribution channel: Here’s how to build one: https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead• ER on Prime Video: https://www.amazon.com/ER-Season-1/dp/B0FWK5WJQ4• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD• Wispr Flow: https://wisprflow.ai• Anker: https://www.anker.com—Recommended books:• Will: https://www.amazon.com/Will-Smith/dp/1984877925• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867• Hidden Multipliers: Small Things That Accelerate Growth: https://preorder.hiddenmultipliers.com• On Writing Well: The Essential Guide to Mastering Nonfiction Writing and Effective Communication: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548• Crossing the Chasm, 3rd Edition: The Updated Version of the Insightful Guide on Bringing Cutting-Edge Products to the Mainstream: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

5 questions to ask when your product stops growing | Jason Cohen (2x unicorn founder)

Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor.We discuss:1. The complete AI workflow that lets non-technical people build real products in Cursor2. How to use multiple AI models for different tasks (Claude for planning, Gemini for UI)3. Using slash commands to automate prompts4. Zevi’s “peer review” technique, which uses different AI models to review each other’s code5. Why this might be the best time to be a junior in tech, despite the challenging job market6. How Zevi used AI to prepare for his Meta PM interviews—Brought to you by:10Web—Vibe coding platform as an APIDX—The developer intelligence platform designed by leading researchersFramer—Build better websites faster—Zevi's Slash Command Bank for Claude: ⁠https://zeviarnovitz.com/⁠—Episode transcript: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor—Archive of all Lenny's Podcast transcripts:https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Zevi Arnovitz• X: https://x.com/ArnovitzZevi• LinkedIn: https://www.linkedin.com/in/zev-arnovitz• Website: https://zeviarnovitz.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Zevi Arnovitz(04:48) Zevi’s background and journey into AI(07:41) Overview of Zevi’s AI workflow(14:41) Screenshare: Exploring Zevi’s workflow in detail(17:18) Building a feature live: StudyMate app(30:52) Executing the plan with Cursor(38:32) Using multiple AI models for code review(40:40) Personifying AI models(43:37) Peer review process(45:40) The importance of postmortems(51:05) Integrating AI in large companies(53:42) How AI has impacted the PM role(57:02) How to improve AI outputs(58:15) AI-assisted job interviews(01:02:57) Failure corner(01:06:20) Lightning round and final thoughts—Referenced:• Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv• Wix: https://www.wix.com• Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w• Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw• Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg• Bolt: https://bolt.new• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Lovable: https://lovable.dev• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• StudyMate: https://studymate.live• Dibur2text: https://dibur2text.app• Claude: https://claude.ai• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code• Bun: https://bun.com• Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Wispr Flow: https://wisprflow.ai• Linear: https://linear.app• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu• Cursor Composer: https://cursor.com/blog/composer• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Base44: https://base44.com• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo• v0: https://v0.app• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Cursor Browser mode: https://cursor.com/docs/agent/browser• Google Antigravity: https://antigravity.google• Grok: https://grok.com• Zapier: https://zapier.com• Airtable: https://www.airtable.com• Build Your Personal PM Productivity System & AI Copilot: https://maven.com/tal-raviv/product-manager-productivity-system• The definitive guide to mastering analytical thinking interviews: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering-f81• AI tools are overdelivering: results from our large-scale AI productivity survey: https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results-c08• Yaara Asaf on LinkedIn: https://www.linkedin.com/in/yaarasaf• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx• Loom: https://www.loom.com• Cap: https://cap.so• Supercut: https://supercut.ai...References continued at: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor—Recommended books:• The Fountainhead: https://www.amazon.com/Fountainhead-Ayn-Rand/dp/0451191153• Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910• Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The non-technical PM’s guide to building with Cursor | Zevi Arnovitz (Meta)

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and quickly build trust.We discuss:1. Why etiquette matters2. Sam’s framework for showing up confidently, with a low heart rate, in any room3. How to navigate introductions, small talk, meetings, and meals like a pro4. Simple hacks for remembering names and handling awkward social situations5. 30+ specific etiquette tips—Brought to you by:10Web—Vibe-coding platform as an APIDX—The developer intelligence platform designed by leading researchersWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs—Episode transcript: https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook—Archive of all Lenny's Podcast transcripts:https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Sam Lessin:• X: https://x.com/lessin• LinkedIn: https://www.linkedin.com/in/wlessin• Website: https://www.wlessin.com• Podcast: https://moreorlesspod.com• Lettermeme: https://lettermeme.com/lessin—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Sam’s background(04:18) The role of etiquette in business success(09:30) Introductions and entering a room(16:20) Engaging conversations and building relationships(23:55) Hygiene and dress code essentials(33:42) Dining etiquette(37:15) Tipping etiquette(41:36) The “B&D trick”(43:05) Humor in social settings(45:18) Self-deprecating humor(47:42) Winding down conversations(49:20) Scheduling etiquette(55:23) Communication and email etiquette(01:02:28) Meeting etiquette tips(01:04:03) Virtual meeting best practices(01:05:15) The importance of cleaning up after yourself(01:05:58) Exiting and follow-up etiquette(01:07:24) Final thoughts(01:09:20) AI corner(01:11:13) Contrarian corner(01:16:25) Lightning round—Referenced:• Y Combinator: https://www.ycombinator.com• Kleiner Perkins: https://www.kleinerperkins.com• “Lose Yourself” by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq• Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan• Bain & Company: https://www.bain.com• Evernote: https://evernote.com• Calendly: https://calendly.com• Morning Brew: https://www.morningbrew.com• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• DigitalOcean: https://www.digitalocean.com• Cloudflare: https://www.cloudflare.com• SpaceX: https://www.spacex.com• Marc Andreessen on X: https://x.com/pmarca• Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD• Dave Morin on X: https://x.com/davemorin—Recommended books:• Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5• Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A• The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and Rome: https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI• Area 51: An Uncensored History of America’s Top Secret Military Base: https://www.amazon.com/Area-51-Uncensored-Americas-Military-ebook/dp/B004THU68Q• The Lessons of History: https://www.amazon.com/Lessons-History-Will-Durant/dp/143914995X• The Fish That Ate the Whale: The Life and Times of America’s Banana King: https://www.amazon.com/Fish-That-Ate-Whale-Americas/dp/1250033314• The Last Kings of Shanghai: The Rival Jewish Dynasties That Helped Create Modern China: https://www.amazon.com/Last-Kings-Shanghai-Jewish-Dynasties/dp/0735224439—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin

Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering.We discuss:1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built2. Common patterns and anti-patterns in companies that build strong AI products versus those that struggle3. A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement4. Why obsessing about customer trust and reliability is an underrated driver of successful AI products5. Why evals aren’t a cure-all, and the most common misconceptions people have about them6. The skills that matter most for builders in the AI era—Brought to you by:Merge—The fastest way to ship 220+ integrations: https://merge.dev/lennyStrella—The AI-powered customer research platform: https://strella.io/lennyBrex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs—Transcript: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/183007822/referenced—Get 15% off Aishwarya and Kiriti’s Maven course, Building Agentic AI Applications with a Problem-First Approach, using this link: https://bit.ly/3V5XJFp—Where to find Aishwarya Naresh Reganti:• LinkedIn: https://www.linkedin.com/in/areganti• GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide• X: https://x.com/aish_reganti—Where to find Kiriti Badam:• LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam• X: https://x.com/kiritibadam—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Aishwarya and Kiriti(05:03) Challenges in AI product development(07:36) Key differences between AI and traditional software(13:19) Building AI products: start small and scale(15:23) The importance of human control in AI systems(22:38) Avoiding prompt injection and jailbreaking(25:18) Patterns for successful AI product development(33:20) The debate on evals and production monitoring(41:27) Codex team’s approach to evals and customer feedback(45:41) Continuous calibration, continuous development (CC/CD) framework(58:07) Emerging patterns and calibration(01:01:24) Overhyped and under-hyped AI concepts(01:05:17) The future of AI(01:08:41) Skills and best practices for building AI products(01:14:04) Lightning round and final thoughts—Referenced:• LevelUp Labs: https://levelup-labs.ai/• Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different• Booking.com: https://www.booking.com• Research paper on agents in production (by Matei Zaharia’s lab): https://arxiv.org/pdf/2512.04123• Matei Zaharia’s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en• The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis• Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah• Rackspace: https://www.rackspace.com• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper• Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html• LMArena: https://lmarena.ai• Artificial Analysis: https://artificialanalysis.ai/leaderboards/providers• Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck• Airline held liable for its chatbot giving passenger bad advice—what this means for travellers: https://www.bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know• Demis Hassabis on LinkedIn: https://www.linkedin.com/in/demishassabis• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents• Socrates’s quote: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living• Noah Smith’s newsletter: https://www.noahpinion.blog• Silicon Valley on HBO Max: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d• Clair Obscur: Expedition 33: https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33/• Wisprflow: https://wisprflow.ai• Raycast: https://www.raycast.com• Steve Jobs’s quote: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only—Recommended books:•  When Breath Becomes Air: https://www.amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032• A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth.We discuss:1. “Give away your Legos”: a framework for scaling yourself as a leader2. “J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path3. “The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”)4. Six rules for creating effective goals (and aligning everyone around them)5. Rules of thumb for leading through rapid scale and change6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor—Brought to you by:DX—The developer intelligence platform designed by leading researchersBrex—The banking solution for startupsGoFundMe Giving Funds—Make helping a habit—Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation—Where to find Molly Graham:• X: https://x.com/molly_g• LinkedIn: https://www.linkedin.com/in/mograham• Substack: https://mollyg.substack.com• Website: https://glueclub.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Molly Graham(04:28) Molly’s background at Google, Facebook, Quip, and CZI(11:29) The “Give away your Legos” framework(16:44) Managing your inner monster(19:49) When not to give away your Legos(21:28) Embracing a long career(23:25) The J-curve vs. stairs approach to career growth(32:00) The gift of knowing yourself(34:28) Learning to be a professional idiot(38:30) The waterline model: snorkel before you scuba(47:16) Six rules for creating strong alignment around goals(57:15) Rules of thumb for leading through rapid scale(01:07:49) Investing in high performers vs. low performers(01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor(1:21:15) Pivoting from ambition to purpose(1:26:32) Finding stability in instability(01:29:44) Final thoughts—Referenced:• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652• Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage• Quip: https://quip.com• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Chan Zuckerberg Initiative: https://chanzuckerberg.com• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups• The Muppets: https://muppets.disney.com• Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell• J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve• Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks• Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath• Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you• Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz• Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model• Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc• I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics• James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals• Founder mode: https://paulgraham.com/foundermode.html• Stripe: https://stripe.com• Patrick Collison on X: https://www.linkedin.com/in/patrickcollison• John Collison on X: https://x.com/collision• Seth Godin’s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow—Recommended books:• The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.We discuss:1. How AI is fundamentally changing the sales function2. Why most SDRs and BDRs will be “extinct” within a year3. What Jason is observing across his portfolio about AI adoption in GTM4. How to become “hyper-employable” in the age of AI5. The specific AI tools and tactics he’s using that have been working best6. Practical frameworks for integrating AI into your sales motion without losing what works7. Jason’s 2026 predictions on where SaaS and GTM are heading next—Brought to you by:DX—The developer intelligence platform designed by leading researchersVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation—Where to find Jason Lemkin:• X: https://x.com/jasonlk• LinkedIn: https://www.linkedin.com/in/jasonmlemkin• Website: https://www.saastr.com• Substack: https://substack.com/@cloud—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jason Lemkin(04:36) What SaaStr does(07:13) AI’s impact on sales teams(10:11) How SaaStr's AI agents work and their performance(14:18) How go-to-market is changing in the AI era(19:19) The future of SDRs, BDRs, and AEs in sales(22:03) Why leadership roles are safe(23:43) How to be in the 20% who thrive in the AI sales future(28:40) Why you shouldn't build your own AI tools(30:10) Specific AI agents and their applications(36:40) Challenges and learnings in AI deployment(42:11) Making AI-generated emails good (not just acceptable)(47:31) When humans still beat AI in sales(52:39) An overview of SaaStr's org(53:50) The role of human oversight in AI operations(58:37) Advice for salespeople and founders in the AI era(01:05:40) Forward-deployed engineers(01:08:08) What's changing and what's staying the same in sales(01:16:21) Why AI is creating more work, not less(01:19:32) Why Jason says these are magical times(01:25:25) The "incognito mode test" for finding AI opportunities(01:27:19) The impact of AI on jobs(01:30:18) Lightning round and final thoughts—Referenced:• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• SaaStr Annual: https://www.saastrannual.com• Delphi: https://www.delphi.ai/saastr/talk• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/• Vercel: https://vercel.com• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• ElevenLabs: https://elevenlabs.io• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack• Bolt: https://bolt.new• Lovable: https://lovable.dev• Harvey: https://www.harvey.ai• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence• UiPath: https://www.uipath.com• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser• Agentforce: https://www.salesforce.com/form/agentforce• SaaStr’s AI Agent Playbook: https://saastr.ai/agents• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan• Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan• Sierra: https://sierra.ai• Fin: https://fin.ai• Deccan: https://www.deccan.ai• Artisan: https://www.artisan.co• Qualified: https://www.qualified.com• Claude: https://claude.ai• HubSpot: https://www.hubspot.com• Gamma: https://gamma.app• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b• Brex: https://www.brex.com• Outreach: https://www.outreach.io• Gong: https://www.gong.io• Salesloft: https://www.salesloft.com• Mixmax: https://www.mixmax.com• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• Clay: https://www.clay.com• Owner: https://www.owner.com• Momentum: https://www.momentum.io• Attention: https://www.attention.com• Granola: https://www.granola.ai• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Palantir: https://www.palantir.com• Databricks: https://www.databricks.com• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan• Rippling: https://www.rippling.com• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza• Sora: https://openai.com/sora• Reve: https://app.reve.com• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/• The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you’ve gone too far3. Matt’s transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion’s success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling’s vision and success(01:17:48) AI’s impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman’s website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage.We discuss:1. The difference between jailbreaking and prompt injection attacks on AI systems2. Why AI guardrails don’t work3. Why we haven’t seen major AI security incidents yet (but soon will)4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages5. The practical steps organizations should take instead of buying ineffective security tools6. Why solving this requires merging classical cybersecurity expertise with AI knowledge—Brought to you by:Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyMetronome—Monetization infrastructure for modern software companies: https://metronome.com/GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation—Where to find Sander Schulhoff:• X: https://x.com/sanderschulhoff• LinkedIn: https://www.linkedin.com/in/sander-schulhoff• Website: https://sanderschulhoff.com• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Sander Schulhoff and AI security(05:14) Understanding AI vulnerabilities(11:42) Real-world examples of AI security breaches(17:55) The impact of intelligent agents(19:44) The rise of AI security solutions(21:09) Red teaming and guardrails(23:44) Adversarial robustness(27:52) Why guardrails fail(38:22) The lack of resources addressing this problem(44:44) Practical advice for addressing AI security(55:49) Why you shouldn’t spend your time on guardrails(59:06) Prompt injection and agentic systems(01:09:15) Education and awareness in AI security(01:11:47) Challenges and future directions in AI security(01:17:52) Companies that are doing this well(01:21:57) Final thoughts and recommendations—Referenced:• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff• The AI Security Industry is Bullshit: https://sanderschulhoff.substack.com/p/the-ai-security-industry-is-bullshit• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0• OpenAI: https://openai.com• Scale: https://scale.com• Hugging Face: https://huggingface.co• Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition: https://www.semanticscholar.org/paper/Ignore-This-Title-and-HackAPrompt%3A-Exposing-of-LLMs-Schulhoff-Pinto/f3de6ea08e2464190673c0ec8f78e5ec1cd08642• Simon Willison’s Weblog: https://simonwillison.net• ServiceNow: https://www.servicenow.com• ServiceNow AI Agents Can Be Tricked Into Acting Against Each Other via Second-Order Prompts: https://thehackernews.com/2025/11/servicenow-ai-agents-can-be-tricked.html• Alex Komoroske on X: https://x.com/komorama• Twitter pranksters derail GPT-3 bot with newly discovered “prompt injection” hack: https://arstechnica.com/information-technology/2022/09/twitter-pranksters-derail-gpt-3-bot-with-newly-discovered-prompt-injection-hack• MathGPT: https://math-gpt.org• 2025 Las Vegas Cybertruck explosion: https://en.wikipedia.org/wiki/2025_Las_Vegas_Cybertruck_explosion• Disrupting the first reported AI-orchestrated cyber espionage campaign: https://www.anthropic.com/news/disrupting-AI-espionage• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske• Prompt Optimization and Evaluation for LLM Automated Red Teaming: https://arxiv.org/abs/2507.22133• MATS Research: https://substack.com/@matsresearch• CBRN: https://en.wikipedia.org/wiki/CBRN_defense• CaMeL offers a promising new direction for mitigating prompt injection attacks: https://simonwillison.net/2025/Apr/11/camel• Trustible: https://trustible.ai• Repello: https://repello.ai• Do not write that jailbreak paper: https://javirando.com/blog/2024/jailbreaks—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The coming AI security crisis (and what to do about it) | Sander Schulhoff

Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they’ve shifted from activation to building new features, and why giving away their product for free has become their most powerful growth strategy.We discuss:1. Why 60% to 70% of traditional growth tactics no longer apply in AI2. Why you have to re-find product-market fit every 3 months3. The specific growth tactics driving Lovable’s unprecedented growth4. Why giving away product is a growth strategy that beats paid ads5. “Minimum lovable product” as the new standard (not minimum viable product)6. Why activation now belongs to product teams, not growth teams7. Whether you should join an AI startup (honest tradeoffs)—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webPersona—A global leader in digital identity verification—Transcript: ⁠https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna⁠—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/181207556/my-biggest-takeaways-from-this-conversation⁠—Where to find Elena Verna:• X: https://x.com/elenaverna• LinkedIn: https://www.linkedin.com/in/elenaverna• Newsletter: https://www.elenaverna.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Elena Verna(05:19) The scale and growth of Lovable(08:55) Confidence in Lovable as a business(12:17) Retention at Lovable(15:02) Lovable’s unique growth levers(28:13) The role of marketing in Lovable’s success(38:09) Launching new features(40:59) Hiring and team dynamics(43:17) The value of vibe coding(49:46) The importance of community(51:47) Giving away your product for free(56:26) Tripling their company size(01:00:23) Product-market-fit challenges(01:08:50) Advice for joining AI companies(01:12:00) Work-life balance(01:15:20) What it’s like to work at Lovable(01:19:45) Women in tech(01:25:29) Final thoughts and lightning round—Referenced:• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna• Lovable: https://lovable.dev• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Stripe: https://stripe.com• What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra• “Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO): https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn• Eric Ries on LinkedIn: https://www.linkedin.com/in/eries• Elena’s post on LinkedIn about Lovable Missions: https://www.linkedin.com/posts/elenaverna_everythingispossible-lovableway-activity-7401627519646474242-hn6e• SheBuilds: https://shebuilds.lovable.app• Shopify + Lovable: https://lovable.dev/shopify• The Product-Market Fit Treadmill: Why every AI company is sprinting just to stay in place: https://www.elenaverna.com/p/the-product-market-fit-treadmill• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba• The adjacent user: https://brianbalfour.com/quick-takes/the-adjacent-user• Granola: https://www.granola.ai• Wispr Flow: https://wisprflow.ai• I’m worried about women in tech: https://www.elenaverna.com/p/im-worried-about-women-in-tech• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth)

Alexander Embiricos leads product on Codex, OpenAI’s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a software engineering teammate—an AI agent designed to participate across the entire development lifecycle.We discuss:1. Why Codex has grown 20x since launch and what product decisions unlocked this growth2. How OpenAI built the Sora Android app in just 18 days using Codex3. Why the real bottleneck to AGI-level productivity isn’t model capability—it’s human typing speed4. The vision of AI as a proactive teammate, not just a tool you prompt5. The bottleneck shifting from building to reviewing AI-generated work6. Why coding will be a core competency for every AI agent—because writing code is how agents use computers best—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyFin—The #1 AI agent for customer service: https://fin.ai/lennyJira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc—Transcript: https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180365355/my-biggest-takeaways-from-this-conversation—Where to find Alexander Embiricos:• X: https://x.com/embirico• LinkedIn: https://www.linkedin.com/in/embirico—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Alexander Embiricos (05:13) The speed and ambition at OpenAI(11:34) Codex: OpenAI’s coding agent(15:43) Codex’s explosive growth(24:59) The future of AI and coding agents(33:11) The impact of AI on engineering(44:08) How Codex has impacted the way PMs operate(45:40) Throwaway code and ubiquitous coding(47:10) Shipping the Sora Android app(49:01) Building the Atlas browser(53:34) Codex’s impact on productivity(55:35) Measuring progress on Codex(58:09) Why they are building a web browser(01:01:58) Non-engineering use cases for Codex(01:02:53) Codex’s capabilities(01:04:49) Tips for getting started with Codex(01:05:37) Skills to lean into in the AI age(01:10:36) How far are we from a human version of AI?(01:13:31) Hiring and team growth at Codex(01:15:47) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com• Codex: https://openai.com/codex• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Dropbox: http://dropbox.com• Datadog: https://www.datadoghq.com• Andrej Karpathy on X: https://x.com/karpathy• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Atlas: https://openai.com/index/introducing-chatgpt-atlas• How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna: https://www.lennysnewsletter.com/p/how-block-is-becoming-the-most-ai-native• Goose: https://block.xyz/inside/block-open-source-introduces-codename-goose• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennysnewsletter.com/p/lessons-on-building-product-sense• Sora Android app: https://play.google.com/store/apps/details?id=com.openai.sora&hl=en_US&pli=1• The OpenAI Podcast—ChatGPT Atlas and the next era of web browsing: https://www.youtube.com/watch?v=WdbgNC80PMw&list=PLOXw6I10VTv9GAOCZjUAAkSVyW2cDXs4u&index=2• How to measure AI developer productivity in 2025 | Nicole Forsgren: https://www.lennysnewsletter.com/p/how-to-measure-ai-developer-productivity• Compiling: https://3d.xkcd.com/303• Jujutsu Kaisen on Netflix: https://www.netflix.com/title/81278456• Tesla: https://www.tesla.com• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Andreas Embirikos: https://en.wikipedia.org/wiki/Andreas_Embirikos• George Embiricos: https://en.wikipedia.org/wiki/George_Embiricos: https://en.wikipedia.org/wiki/George_Embiricos—Recommended books:• Culture series: https://www.amazon.com/dp/B07WLZZ9WV• The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411• A Fire Upon the Deep (Zones of Thought series Book 1): https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/1250237750• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead)

Edwin Chen is the founder and CEO of Surge AI, the company that teaches AI what’s good vs. what’s bad, powering frontier labs with elite data, environments, and evaluations. Surge surpassed $1 billion in revenue with under 100 employees last year, completely bootstrapped—the fastest company in history to reach this milestone. Before founding Surge, Edwin was a research scientist at Google, Facebook, and Twitter and studied mathematics, computer science, and linguistics at MIT.We discuss:1. How Surge reached over $1 billion in revenue with fewer than 100 people by obsessing over quality2. The story behind how Claude Code got so good at coding and writing3. The problems with AI benchmarks and why they’re pushing AI in the wrong direction4. How RL environments are the next frontier in AI training5. Why Edwin believes we’re still a decade away from AGI6. Why taste and human judgment shape which AI models become industry leaders7. His contrarian approach to company building that rejects Silicon Valley’s “pivot and blitzscale” playbook8. How AI models will become increasingly differentiated based on the values of the companies building them—Brought to you by:Vanta—Automate compliance. Simplify security.WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsCoda—The all-in-one collaborative workspace—Transcript: https://www.lennysnewsletter.com/p/surge-ai-edwin-chen—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180055059/my-biggest-takeaways-from-this-conversation—Where to find Edwin Chen:• X: https://x.com/echen• LinkedIn: https://www.linkedin.com/in/edwinzchen• Surge’s blog: https://surgehq.ai/blog—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Edwin Chen(04:48) AI’s role in business efficiency(07:08) Building a contrarian company(08:55) An explanation of what Surge AI does(09:36) The importance of high-quality data(13:31) How Claude Code has stayed ahead(17:37) Edwin’s skepticism toward benchmarks(21:54) AGI timelines and industry trends(28:33) The Silicon Valley machine(33:07) Reinforcement learning and future AI training(39:37) Understanding model trajectories(41:11) How models have advanced and will continue to advance(42:55) Adapting to industry needs(44:39) Surge’s research approach(48:07) Predictions for the next few years in AI(50:43) What’s underhyped and overhyped in AI(52:55) The story of founding Surge AI(01:02:18) Lightning round and final thoughts—Referenced:• Surge: https://surgehq.ai• Surge’s product page: https://surgehq.ai/products• Claude Code: https://www.claude.com/product/claude-code• Gemini 3: https://aistudio.google.com/models/gemini-3• Sora: https://openai.com/sora• Terrence Rohan on LinkedIn: https://www.linkedin.com/in/terrencerohan• Richard Sutton—Father of RL thinks LLMs are a dead end: https://www.dwarkesh.com/p/richard-sutton• The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html• Reinforcement learning: https://en.wikipedia.org/wiki/Reinforcement_learning• Grok: https://grok.com• Warren Buffett on X: https://x.com/WarrenBuffett• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong• Interstellar on Prime Video: https://www.amazon.com/Interstellar-Matthew-McConaughey/dp/B00TU9UFTS• Arrival on Prime Video: https://www.amazon.com/Arrival-Amy-Adams/dp/B01M2C4NP8• Travelers on Netflix: https://www.netflix.com/title/80105699• Waymo: https://waymo.com• Soda versus pop: https://flowingdata.com/2012/07/09/soda-versus-pop-on-twitter—Recommended books:• Stories of Your Life and Others: https://www.amazon.com/Stories-Your-Life-Others-Chiang/dp/1101972122• The Myth of Sisyphus: https://www.amazon.com/Myth-Sisyphus-Vintage-International/dp/0525564454• Le Ton Beau de Marot: In Praise of the Music of Language: https://www.amazon.com/dp/0465086454• Gödel, Escher, Bach: An Eternal Golden Braid: https://www.amazon.com/G%C3%B6del-Escher-Bach-Eternal-Golden/dp/0465026567—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The 100-person AI lab that became Anthropic and Google's secret weapon | Edwin Chen (Surge AI)

Tomer Cohen is the longtime chief product officer at LinkedIn, where he’s pioneering the Full Stack Builder program, a radical new approach to product development that fully embraces what AI makes possible. Under his leadership, LinkedIn has scrapped its traditional Associate Product Manager program and replaced it with an Associate Product Builder program that teaches coding, design, and PM skills together. He’s also introduced a formal “Full Stack Builder” title and career ladder, enabling anyone from any function to take products from idea to launch. In this conversation, Tomer explains why product development has become too complex at most companies and how LinkedIn is building an AI-powered product team that can move faster, adapt more quickly, and do more with less.We discuss:1. How 70% of the skills needed for jobs will change by 20302. The broken traditional model: organizational bloat slows features to a six-month cycle3. The Full Stack Builder model4. Three pillars of making FSB work: platform, agents, and culture (culture matters most)5. Building specialized agents that critique ideas and find vulnerabilities6. Why off-the-shelf AI tools never work on enterprise code without customization7. Top performers adopt AI tools fastest, contrary to expectations about leveling effects8. Change management tactics: celebrating wins, making tools exclusive, updating performance reviews—Brought to you by:Vanta—Automate compliance. Simplify security: https://vanta.com/lennyFigma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/Miro—The AI Innovation Workspace where teams discover, plan, and ship breakthrough products: https://miro.com/lenny—Transcript: https://www.lennysnewsletter.com/p/why-linkedin-is-replacing-pms—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180042347/my-takeaways-from-this-conversation—Where to find Tomer Cohen:• LinkedIn: https://www.linkedin.com/in/tomercohen• Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Tomer Cohen(04:42) The need for change in product development(11:52) The full-stack builder model explained(16:03) Implementing AI and automation in product development(19:17) Building and customizing AI tools(27:51) The timeline to launch(31:46) Pilot program and early results(37:04) Feedback from top talent(39:48) Change management and adoption(46:53) Encouraging people to play with AI tools(41:21) Performance reviews and full-stack builders(48:00) Challenges and specialization(50:05) Finding talent(52:46) Tips for implementing in your own company(56:43) Lightning round and final thoughts—Referenced:• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen• LinkedIn: https://www.linkedin.com• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Devin: https://devin.ai• Figma: https://www.figma.com• Microsoft Copilot: https://copilot.microsoft.com• Windsurf: https://windsurf.com• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Lovable: https://lovable.dev• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• APB program at LinkedIn: https://careers.linkedin.com/pathways-programs/entry-level/apb• Naval Ravikant on X: https://x.com/naval• One Song podcast: https://podcasts.apple.com/us/podcast/%D7%A9%D7%99%D7%A8-%D7%90%D7%97%D7%93-one-song/id1201883177• Song Exploder podcast: https://songexploder.net• Grok on Tesla: https://www.tesla.com/support/grok• Reid Hoffman on X: https://x.com/reidhoffman—Recommended books:• Why Nations Fail: The Origins of Power, Prosperity, and Poverty: https://www.amazon.com/Why-Nations-Fail-Origins-Prosperity/dp/0307719227• Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599• The Beginning of Infinity: Explanations That Transform the World: https://www.amazon.com/Beginning-Infinity-Explanations-Transform-World/dp/0143121359—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why LinkedIn is turning PMs into AI-powered "full stack builders” | Tomer Cohen (LinkedIn CPO)

Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy.We discuss:1. Why GTM is becoming more strategically important in the AI era2. The rise of the GTM engineer3. A primer on segmentation4. How to build a sales org that engineers and product teams respect5. The changing calculus of build vs. buy for go-to-market tools in the AI era6. Why most customers buy to avoid pain rather than to gain upside—Brought to you by:Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyLovable—Build apps by simply chatting with AI: https://lovable.dev/Stripe—Helping companies of all sizes grow revenue: https://stripe.com/—Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation—Where to find Jeanne DeWitt Grosser:• X: https://x.com/jdewitt29• LinkedIn: https://www.linkedin.com/in/jeannedewitt—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jeanne DeWitt Grosser(05:26) Defining go-to-market(08:43) The evolution of go-to-market roles(11:23) The rise of the go-to-market engineer(14:21) Implementing AI in sales processes(15:28) Optimizing sales with AI agents(23:47) Defining sales roles: SDRs and AEs(26:04) When to hire a GTM engineer(29:04) Hiring and scaling sales teams(30:50) The ideal go-to-market engineer(34:24) The go-to-market tool stack(40:39) Advice on building a great sales bot(44:34) Vercel’s unfair advantage(46:37) Go-to-market as a product(47:04) Innovative sales tactics at Stripe(52:38) Effective go-to-market tactics(01:00:37) Segmentation strategies(01:09:31) Building a sales org that engineers love(01:14:00) Thoughts on PLG and pricing(01:16:44) Sales compensation and hiring(01:19:24) Lightning round and final thoughts—Referenced:• Vercel: https://vercel.com• Stripe: https://stripe.com• Rosalind Franklin: https://en.wikipedia.org/wiki/Rosalind_Franklin• Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman• SDK: https://ai-sdk.dev/docs/introduction• Gong: https://www.gong.io• Lyft: https://www.lyft.com• Instacart: https://www.instacart.com• DoorDash: https://www.instacart.com• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting• Kate Jensen on LinkedIn: https://www.linkedin.com/in/kateearle• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics• Atlassian: atlassian.com—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)

Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me.We discuss:* When to coach and when to just tell people what to do [09:00]* The GROW technique for helping people figure out a solution for themselves [18:37]* Techniques for making difficult conversations less difficult [01:20:28]* Avoiding burnout and designing a more energizing career [41:55]* Building and sustaining a healthy co-founder relationship [01:06:50]* Creating a one-page plan that aligns your entire company [01:31:47]* Practical ways AI is transforming executive coaching and leadership development [01:36:50]* Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions [23:55]Also on Spotify and Apple PodcastsBrought to you by:Stripe—Helping companies of all sizes grow revenueVanta—Automate compliance. Simplify security.Persona—A global leader in digital identity verificationWhere to find Rachel Lockett:• LinkedIn: https://www.linkedin.com/in/rhlockett/• Website: https://www.lockettcoaching.comReferenced:• One-page plan template: https://www.lockettcoaching.com/#resources• Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0• Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/• First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0• Coinbase: https://www.coinbase.com• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey• Chuck Palahniuk’s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to• Patrick Collison on X: https://x.com/patrickc• Stripe: https://stripe.com• Remind: https://www.remind.com• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams• Brex: https://www.brex.com• Bridge: https://www.bridge.xyz• Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• The Enneagram Institute: https://www.enneagraminstitute.com• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence• What Is PeopleFirst?: https://alpineinvestors.com/story/what-is-peoplefirst• How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors): https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver• Granola: https://www.granola.ai• KPop Demon Hunters on Netflix: https://www.netflix.com/title/81498621• Loom: https://www.loom.com• Joseph Campbell’s quote: https://www.goodreads.com/quotes/21396-if-you-can-see-your-path-laid-out-in-front• Wes Anderson’s short films (Roald Dahl) on Netflix: https://www.netflix.com/tudum/articles/wes-anderson-netflix-short-filmsRecommended books:• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904• Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321• Roald Dahl books: https://www.amazon.com/Roald-Dahl-Collection-Books-Box/dp/0241377293Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett

Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusion” to “hyper-realistic work-like activities,” his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams.We discuss:1. Hyper-realistic work-like activities2. The owner’s delusion3. Utility curves4. “Don’t make me think”5. “We don’t sell saddles here”6. Tilting your umbrella7. When to pivot—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsMetronome—Monetization infrastructure for modern software companiesLovable—Build apps by simply chatting with AI—Transcript: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation—Where to find Stewart Butterfield:• X: https://x.com/stewart• LinkedIn: https://www.linkedin.com/in/butterfield—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Stewart Butterfield(04:58) Stewart’s current life and reflections(06:44) Understanding utility curves(10:13) The concept of divine discontent(15:11) The importance of taste in product design(19:03) Tilting your umbrella(28:32) Balancing friction and comprehension(45:07) The value of constant dissatisfaction(47:06) Embracing continuous improvement(50:03) The complexity of making things work(54:27) Parkinson’s law and organizational growth(01:03:17) Hyper-realistic work-like activities(01:13:23) Advice on when to pivot(01:18:36) The importance of generosity in leadership(01:26:34) The owner’s delusion—Referenced:• Slack: https://slack.com• Flickr: https://www.flickr.com• Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal• Blok: https://blok.so• Brandon Velestuk on LinkedIn: https://www.linkedin.com/in/brandon-velestuk-6018721b• Magic Link: https://en.wikipedia.org/wiki/Magic_Link• Ticketmaster: https://www.ticketmaster.com• John Collison on X: https://x.com/collision• Patrick Collison on X: https://x.com/patrickc• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai• Three Questions with Slack’s CEO: https://www.technologyreview.com/2014/11/21/170330/three-questions-with-slacks-ceo• Six Sigma: https://www.6sigma.us• What is kaizen and how does Toyota use it?: https://mag.toyota.co.uk/kaizen-toyota-production-system• John Collison’s post on X about passion projects: https://x.com/collision/status/1529452415346302976• Parkinson’s law: https://www.economist.com/news/1955/11/19/parkinsons-law• We Don’t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d• Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)• IRC: https://en.wikipedia.org/wiki/IRC• This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke• The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins: https://www.lennysnewsletter.com/p/the-making-of-canva• Prisoner’s dilemma: https://en.wikipedia.org/wiki/Prisoner%27s_dilemma• Stewart Little: https://en.wikipedia.org/wiki/Stuart_Little• Dharma and Greg: https://en.wikipedia.org/wiki/Dharma_%26_Greg• Stewart’s post on X referencing “the owner’s delusion”: https://x.com/stewart/status/1223286626991796224—Recommended books:• Principles: Life and Work: https://www.amazon.com/Principles-Life-Work-Ray-Dalio/dp/1501124021• Why Nothing Works: Who Killed Progress―and How to Bring It Back: https://www.amazon.com/Why-Nothing-Works-Killed-Progress_and/dp/154170021X• Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586• Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Slack founder: Mental models for building products people love ft. Stewart Butterfield

Dr. Fei-Fei Li is known as the “godmother of AI.” She’s been at the center of AI’s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we’re living right now, served as Google Cloud’s Chief AI Scientist, directed Stanford’s Artificial Intelligence Lab, and co-founded Stanford’s Institute for Human-Centered AI. In this conversation, Fei-Fei shares the rarely told history of how we got here—including the wild fact that just nine years ago, calling yourself an AI company was basically a death sentence.We discuss:1. How ImageNet helped spark the AI explosion we’re living through2. Why world models and spatial intelligence represent the next frontier in AI, beyond large language models3. Why Fei-Fei believes AI won’t replace humans but will require us to take responsibility for ourselves4. The surprising applications of Marble, from movie production to psychological research5. Why robotics faces unique challenges compared with language models and what’s needed to overcome them6. How to participate in AI regardless of your role—Brought to you by:Figma Make—A prompt-to-code tool for making ideas realJustworks—The all-in-one HR solution for managing your small business with confidenceSinch—Build messaging, email, and calling into your product—Transcript: https://www.lennysnewsletter.com/p/the-godmother-of-ai—My biggest takeaways (for paid newsletter subscribers):https://www.lennysnewsletter.com/i/178223233/my-biggest-takeaways-from-this-conversation—Where to find Dr. Fei-Fei Li• X: https://x.com/drfeifei• LinkedIn: https://www.linkedin.com/in/fei-fei-li-4541247• World Labs: https://www.worldlabs.ai—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Dr. Fei-Fei Li(05:31) The evolution of AI(09:37) The birth of ImageNet(17:25) The rise of deep learning(23:53) The future of AI and AGI(29:51) Introduction to world models(40:45) The bitter lesson in AI and robotics(48:02) Introducing Marble, a revolutionary product(51:00) Applications and use cases of Marble(01:01:01) The founder’s journey and insights(01:10:05) Human-centered AI at Stanford(01:14:24) The role of AI in various professions(01:18:16) Conclusion and final thoughts—References: https://www.lennysnewsletter.com/p/the-godmother-of-ai—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The Godmother of AI on jobs, robots, and why world models are next | Dr. Fei-Fei Li

Grant Lee is the co-founder of Gamma, the AI-powered presentation tool that’s one of the hottest and most interesting AI startups in the world right now. They’re valued at over $2 billion, and they hit $100 million ARR in just over two years, with a lean team of just around 30 people. Unlike many fast-growing AI startups, Gamma has been profitable for most of its history, has not raised significant funding, and they built a massive business in a category most investors dismissed. In fact, one investor told Grant his idea was “the dumbest idea he had ever heard.”We discuss:• How Gamma found product-market fit by rethinking their onboarding• Their process for building a “word-of-mouth machine”• How they leveraged more than 1,000 micro-influencers instead of big names• Why focusing on the “first 30 seconds” transformed their business• Their approach to pricing that led to profitability within months• How Grant thinks about building a durable “GPT wrapper” business—Brought to you by:Vanta—Automate compliance. Simplify security.Justworks—The all-in-one HR solution for managing your small business with confidenceMiro—A collaborative visual platform where your best work comes to life—Where to find Grant Lee:• X: https://x.com/thisisgrantlee• LinkedIn: https://www.linkedin.com/in/grantslee—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Grant Lee and Gamma(05:59) The founding story of Gamma(09:52) Achieving product-market fit(15:43) Self-awareness as a founder(17:17) The power of onboarding(20:41) The original insight that led to Gamma(22:42) Founder-led marketing and growth tactics(29:20) Sharing online(37:40) Getting to $100M ARR(41:19) Influencer marketing as a growth strategy(54:08) Virality is not an accident(58:30) Investing in brand before paid ads(01:02:04) Tips for getting started with performance marketing(01:04:49) Prototyping and user feedback(01:16:12) Adapting and moving quickly(01:19:21) The concept of GPT wrapper companies(01:22:16) Deep dive into workflow and model utilization(01:29:06) Pricing strategies(01:34:53) Hiring philosophy and practices(01:43:24) Betting big on high performers(01:45:03) Final thoughts and lightning round—References: https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

“Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO)

Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She’s one of the smartest people I’ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (covering the zero to $1 million ARR founder-led sales phase), we focus on the skills founders need to learn to go from $1M to $10M ARR.We discuss:1. Why the “mid-market” doesn’t exist2. Why tier-one logos like Stripe and Tesla counterintuitively make the best early customers3. The dangers of pricing your product at $10K-$20K4. Why you need to vision-cast instead of problem-solve to win enterprise deals5. Why services are the fastest way to get your foot in the door with enterprises6. How to find and work with design partners7. When to hire your first salesperson and what profile to look for—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsLovable—Build apps by simply chatting with AICoda—The all-in-one collaborative workspace—Where to find Jen Abel:• X: https://x.com/jjen_abel• LinkedIn: https://www.linkedin.com/in/earlystagesales• Website: https://www.jjellyfish.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome back, Jen!(04:38) The myth of the mid-market(08:08) Targeting tier-one logos(10:50) Vision-casting vs. problem-selling(15:35) The importance of high ACVs(20:45)  Don’t play the small business game with an enterprise company(25:09) Design partners: the double-edged sword(28:11) Finding the right company(36:55) Enterprise sales: the art of the deal(43:21) The problem with channel partnerships(44:41) Quick summary(50:24) Hiring the right enterprise salespeople(56:49) Structuring sales compensation(01:01:01) Building relationships in enterprise sales(01:02:07) The art of cold outreach(01:07:31) Outbound tooling and AI(01:14:08) Lightning round and final thoughts—Referenced:• The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel• Mario meme: https://www.linkedin.com/pulse/missing-meme-led-me-woman-johann-van-tonder-im6df• Kathy Sierra: https://en.wikipedia.org/wiki/Kathy_Sierra• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Justin Lawson on X: https://x.com/jjustin_lawson• Stripe: https://stripe.com• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Linear: https://linear.app• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu• Gemini: https://gemini.google.com• Microsoft Copilot: https://copilot.microsoft.com• How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi• McKinsey & Company: https://www.mckinsey.com• Deloitte: https://www.deloitte.com• Accenture: https://www.accenture.com• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• Peter Dedene on X: https://x.com/peterdedene• Hang Huang on X: https://x.com/HH_HangHuang• Hugo Alves on X: https://x.com/Ugo_alves• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting• Clay: https://www.clay.com• Apollo: https://www.apollo.io• Jason Lemkin on X: https://x.com/jasonlk• Gavin Baker on X: https://x.com/GavinSBaker• Jason Cohen on X: https://x.com/asmartbear• Baywatch on Prime Video: https://www.primevideo.com/detail/Baywatch/0NU9YS8WWRNQO1NZD5DOQ3I8W6• Playground: https://www.tryplayground.com• ClassDojo: https://www.classdojo.com• Jason Lemkin’s post about Replit: https://x.com/jasonlk/status/1946069562723897802—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel

Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a technical rewrite, and the company pivoted early from a yearbook publishing platform to become the design powerhouse it is today. Through it all, she maintained what she calls “column B” thinking: building toward a dream future rather than just using the bricks around you.We discuss:1. How “column B” thinking helped Melanie build Canva, by starting with an impossible vision rather than existing constraints2. The power of setting “crazy big goals”3. How Canva survived a painful two-year period without shipping any new features while rewriting their codebase4. How Melanie pushed through 100 investor rejections, and how she used each rejection to strengthen her pitch5. Canva’s “two-step plan”: build one of the world’s most valuable companies, then do the most good possible6. Melanie’s vision for 2050 and why she believes imagination is the first step toward a better world—Brought to you by:Vanta—Automate compliance. Simplify security. https://vanta.com/lennyStripe—Helping companies of all sizes grow revenue: https://stripe.com/Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.com—Transcript: ⁠https://www.lennysnewsletter.com/p/the-making-of-canva⁠⁠—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/176082995/my-biggest-takeaways-from-this-conversation—Where to find Melanie Perkins:• X: https://x.com/melaniecanva• LinkedIn: https://www.linkedin.com/in/melanieperkins/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Melanie Perkins and Canva(04:44) Building a “column B” company(06:36) Operationalizing big visions(13:13) Crazy big goals and celebrations(22:00) Challenges and setbacks in Canva’s journey(26:30) Fundraising and investor rejections(29:36) Leadership and growth lessons(34:38) Canva’s goal-driven structure(35:46) Balancing work and personal life(38:02) Community-driven product development(40:37) The two-step plan for global impact(45:04) Canva’s biggest launch yet(48:10) How Canva approaches product expansion(52:37) AI integration in Canva(53:56) AI corner(55:22) Melanie’s vision for 2050 and beyond(01:00:07) Lightning round and final thoughts—Referenced:• Canva: https://www.canva.com/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa• UserTesting: https://www.usertesting.com/• Figma: https://www.figma.com/• Adobe: https://www.adobe.com/• Calm: https://www.calm.com/• Gandhi’s quote about happiness: https://www.brainyquote.com/quotes/mahatma_gandhi_105593• Help us improve Canva: https://www.canva.com/help/get-in-touch/general-feedback/—Recommended books:• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898/• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765• Designing the Obvious: A Common Sense Approach to Web and Mobile Application Design: https://www.amazon.com/Designing-Obvious-Common-Approach-Application/dp/0321749855—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins

Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transformation (and his promotion to CTO).We discuss:1. How Block’s internal open-source agent, called Goose, is saving employees 8 to 10 hours weekly2. How the company measures AI productivity gains across technical and non-technical teams3. Which teams are benefiting most from AI (it’s not engineering)4. The boring organizational change that boosted productivity even more than AI tools5. Why code quality has almost nothing to do with product success6. How to drive AI adoption throughout an organization (hint: leadership needs to use the tools daily)7. Lessons from building Google Wave, Google+, and other failed products—Brought to you by:Sinch—Build messaging, email, and calling into your product: https://sinch.com/lennyFigma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/Persona—A global leader in digital identity verification: https://withpersona.com/lenny—Where to find Dhanji R. Prasanna:• LinkedIn: https://www.linkedin.com/in/dhanji/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Dhanji(05:26) The AI manifesto: convincing Jack Dorsey(07:33) Transforming into a more AI-native company(12:05) How engineering teams work differently today(15:24) Goose: Block’s open-source AI agent(20:18) Measuring AI productivity gains across teams(21:38) What Goose is and how it works(32:15) The future of AI in engineering and productivity(37:42) The importance of human taste(40:10) Building vs. buying software(44:08) How AI is changing hiring and team structure(53:45) The importance of using AI tools yourself before deploying them(55:13) How Goose helped solve a personal problem with receipts(58:01) What makes Goose unique(59:57) What Dhanji wishes he knew before becoming CTO(01:01:49) Counterintuitive lessons in product development(01:04:56) Why controlled chaos can be good for engineering teams(01:08:07) Core leadership lessons(01:13:36) Failure corner(01:15:50) Lightning round and final thoughts—Referenced:• Jack Dorsey on X: https://x.com/jack• Block: https://block.xyz/• Square: https://squareup.com/• Cash App: https://cash.app/• What is Conway’s Law?: https://www.microsoft.com/en-us/microsoft-365-life-hacks/organization/what-is-conways-law#• Goose: https://github.com/block/goose• Gosling: https://github.com/block/goose-mobile• Salesforce: https://www.salesforce.com/• Snowflake: https://www.snowflake.com/• Claude: https://claude.ai/• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann• OpenAI: https://openai.com/• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Llama: https://www.llama.com/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Top Gun: https://www.imdb.com/title/tt0092099/• Lenny’s vibe-coded Lovable app: https://gdoc-images-grab.lovable.app/• Afterpay: https://github.com/afterpay• Bitkey: https://bitkey.world/• Proto: https://github.com/proto-at-block• Brad Axen on LinkedIn: https://www.linkedin.com/in/bradleyaxen/• Databricks: https://www.databricks.com/• Carl Sagan’s quote: https://www.goodreads.com/quotes/32952-if-you-wish-to-make-an-apple-pie-from-scratch• Google Wave: https://en.wikipedia.org/wiki/Google_Wave• Google Video: https://en.wikipedia.org/wiki/Google_Video• Secret: https://en.wikipedia.org/wiki/Secret_(app)• Alien Earth on FX: https://www.fxnetworks.com/shows/alien-earth• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o• Fargo TV series on Prime Video: https://www.amazon.com/Fargo-Season-1/dp/B09QGRGH6M• Steam Deck OLED display: https://www.steamdeck.com/en/oled• Doc Brown: https://backtothefuture.fandom.com/wiki/Emmett_Brown—Recommended books:• The Master and Margarita: https://www.amazon.com/Master-Margarita-Mikhail-Bulgakov/dp/0802130119• Tennyson Poems: https://www.amazon.com/Tennyson-Poems-Everymans-Library-Pocket/dp/1400041872/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

Chip Huyen is a core developer on Nvidia’s Nemo platform, a former AI researcher at Netflix, and taught machine learning at Stanford. She’s a two-time founder and the author of two widely read books on AI, including AI Engineering, which has been the most-read book on the O’Reilly platform since its launch. Unlike many AI commentators, Chip has built multiple successful AI products and platforms and works directly with enterprises on their AI strategies, giving her unique visibility into what’s actually happening inside companies building AI products.We discuss:1. What people think makes AI apps better vs. what actually makes AI apps better2. What pre-training vs. post-training is, and why fine-tuning should be your last resort3. How RLHF (reinforcement learning from human feedback) actually works4. Why data quality matters more than which vector database you choose5. Why high performers are seeing the most gains from AI coding tools6. Why most AI problems are actually UX issues—Brought to you by:Dscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.comPersona—A global leader in digital identity verification: https://withpersona.com/lenny—Where to find Chip Huyen:• X: https://x.com/chipro• LinkedIn: https://www.linkedin.com/in/chiphuyen/• Website: https://huyenchip.com/• Substack: https://substack.com/@chiphuyen—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Chip Huyen(04:28) Chip’s viral LinkedIn post(07:05) Understanding AI training: pre-training vs. post-training(08:50) Language modeling explained(13:55) The importance of post-training(15:20) Reinforcement learning and human feedback(22:23) The importance of evals in AI development(31:55) Retrieval augmented generation (RAG) explained(38:50) Challenges in AI tool adoption(43:19) Challenges in measuring productivity(45:20) The three-bucket test(49:10) The future of engineering roles(55:31) ML Engineers vs. AI engineers(57:12) Looking forward: the impact of AI(01:05:48) Model capabilities vs. perceived performance(01:08:23) Lightning round and final thoughts—Referenced:• Chip’s LinkedIn post on what actually improves AI apps: https://www.linkedin.com/posts/chiphuyen_aiapplications-aiengineering-activity-7358971409227792384-y0mf/• Prediction and Entropy of Printed English: https://www.princeton.edu/~wbialek/rome/refs/shannon_51.pdf• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody•Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO): https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord• First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course): https://www.lennysnewsletter.com/p/why-ai-evals-are-the-hottest-new-skill• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Stanford webinar—How AI Is Changing Coding and Education, Andrew Ng & Mehran Sahami: https://www.youtube.com/watch?v=J91_npj0Nfw• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann• Lenny’s vibe-coded app made on Lovable: https://gdoc-images-grab.lovable.app/• Story of Yanxi Palace: https://www.imdb.com/title/tt8865016/• Steve Jobs’s quote: https://www.goodreads.com/quotes/427317-remembering-that-i-ll-be-dead-soon-is-the-most-important—Recommended books:• The Complete Sherlock Holmes: https://www.amazon.com/Complete-Sherlock-Holmes-Volumes/dp/0553328255• AI Engineering: Building Applications with Foundation Models: https://www.amazon.com/AI-Engineering-Building-Applications-Foundation/dp/1098166302• The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152• From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Al Engineering 101 with Chip Huyen (Nvidia, Stanford, Netflix)

Nicole Forsgren created the most widely used frameworks for measuring developer productivity—DORA and SPACE. She wrote the foundational book Accelerate and is about to release her newest book, Frictionless, a practical guide for helping teams move faster in the AI era. She’s currently Senior Director of Developer Intelligence at Google.We discuss:1. Why most productivity metrics are a lie2. Signs that your engineering team could be moving much faster3. Why AI accelerates coding but developers aren’t speeding up as much as you think4. AI’s impact on engineers getting into “flow”5. Her framework for building and scaling a developer experience team6. The three components of developer experience: flow state, cognitive load, and feedback loops—Brought to you by:Mercury—The art of simplified finances: https://mercury.com/WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyCoda—The all-in-one collaborative workspace: https://coda.io/lenny—Where to find Nicole Forsgren:• Twitter: https://twitter.com/nicolefv• LinkedIn: https://www.linkedin.com/in/nicolefv/• Website: https://nicolefv.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nicole Forsgren(05:09) The concept of developer experience (DevEx)(08:33) Flow state and cognitive load in the age of AI(12:02) Challenges in measuring productivity with AI(21:19) The importance of developer experience for business value(22:20) Common issues and solutions in developer experience(26:49) Signs your eng team is moving too slow(29:52) How AI is improving productivity(33:32) Real examples of productivity improvements(36:35) Introducing her new book, Frictionless(43:40) How to get started building a DevEx team(45:15) The impact of forming developer experience teams(46:15)  How to measure the impact of DevEx teams(48:53) Measuring the impact of AI tools on productivity(55:16) Survey design for developer experience(57:59) Popular AI tools for developers(59:08) Bringing a product mindset to DevEx improvements(01:00:40) AI corner(01:02:33) Lightning round and final thoughts—Referenced:• How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennysnewsletter.com/p/how-to-measure-and-improve-developer• DORA: https://dora.dev/• The SPACE framework: A comprehensive guide to developer productivity: https://getdx.com/blog/space-metrics/• Measuring developer productivity with the DX Core 4: https://getdx.com/research/measuring-developer-productivity-with-the-dx-core-4/• Gloria Mark’s website: https://gloriamark.com/• Taking Flight with Copilot: https://dl.acm.org/doi/10.1145/3589996• DevEx in Action: https://spawn-queue.acm.org/doi/10.1145/3639443• CodeX: https://openai.com/codex/• Devin: https://devin.ai/• Abi Noda on LinkedIn: https://www.linkedin.com/in/abinoda/• DX is joining Atlassian: https://getdx.com/blog/dx-is-joining-atlassian/• GitHub Copilot: https://github.com/features/copilot• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Gemini Code Assist: https://codeassist.google/• Claude Code: https://www.claude.com/product/claude-code• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper• Love Is Blind on Netflix: https://www.netflix.com/title/80996601• Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking/umc.cmc.apzybj6eqf6pzccd97kev7bs• Ninja Creami: https://www.amazon.com/Ninja-NC301-CREAMi-Containers-Bundle/dp/B0BLGR5JPV/• Jura coffee maker: https://www.amazon.com/Jura-Nordic-Automatic-Coffee-Machine/dp/B0CF65BFZ1/—Recommended books:• Frictionless: https://developerexperiencebook.com/• DevEx Workbook: https://developerexperiencebook.com/#workbook• Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599• Back Mechanic: https://www.amazon.com/Back-Mechanic-Stuart-McGill-2015-09-30/dp/B01FKSGJYC• How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/• The Undoing Project: A Friendship That Changed Our Minds: https://www.amazon.com/dp/B01KBM82M4/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How to measure AI developer productivity in 2025 | Nicole Forsgren

Dylan Field is co-founder and CEO of Figma, a beloved tool used by every modern product team. Founded in 2012, Figma has expanded from a single design tool to a comprehensive platform including FigJam, Slides, Dev Mode, and, most recently, Figma Make. After a $20 billion acquisition by Adobe fell through due to regulatory pushback, Dylan led the company to a successful IPO in 2025.What you’ll learn:• How Dylan kept internal morale up after the Adobe acquisition fell through• His approach to maintaining pace and a sense of urgency 13 years in• How to systematically develop taste• How Figma decides which product lines to add• Why Dylan obsesses over “time to value”• How AI is making design more valuable—Brought to you by:Stripe—Helping companies of all sizes grow revenue—Transcript: ⁠https://www.lennysnewsletter.com/p/why-ai-makes-design-craft-and-quality-the-new-moat⁠—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175569466/my-biggest-takeaways-from-this-conversation⁠—Where to find Dylan Field:• X: https://x.com/zoink• LinkedIn: https://www.linkedin.com/in/dylanfield/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Dylan Field(03:58) The Adobe deal fallout(05:50) Maintaining team morale post-deal(09:13) Strategies for sustaining high performance(13:37) Maintaining Figma’s unique company culture(16:22) Dylan’s leadership evolution(21:03) How to improve clarity as a leader(24:40) The controversy behind FigJam(31:06) Lessons from expanding Figma’s core product line(39:32) Time-to-value(45:14) Introduction to Figma Make(48:26) AI app prototyping and the future of Figma Make(53:38) Lessons from Figma’s AI product launch(57:47) The importance of craft(59:54) Developing good taste(01:05:35) The future of product development(01:10:32) Why AI won’t steal your job(01:14:37) AI corner(01:18:32) Lightning round and final thoughts—Referenced:• Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config• Figma: https://www.figma.com/• Adobe: https://www.adobe.com/• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor• Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz• FigJam: https://www.figma.com/figjam/• Cursor chat: https://help.figma.com/hc/en-us/articles/4403130802199-Use-cursor-chat-in-Figma-Design• Figma Slides: https://www.figma.com/slides/• Figma Sites: https://www.figma.com/sites/• Figma Buzz: https://www.figma.com/buzz/• Figma Draw: https://www.figma.com/draw/• Figma Design: https://www.figma.com/design/• Dev Mode: https://www.figma.com/dev-mode/• Figma Make: https://www.figma.com/make/• Zach Lloyd on X: https://x.com/zachlloydtweets• Warp: https://www.warp.dev/• Dylan’s post on X about Figma on an AI product leaderboard: https://x.com/zoink/status/1968588014935801884• Kurt Cobain: https://en.wikipedia.org/wiki/Kurt_Cobain• Damien Correll on LinkedIn: https://www.linkedin.com/in/damiencorrell/• Marcin Wichary on LinkedIn: https://www.linkedin.com/in/mwichary/• Loredana Crisan on LinkedIn: https://www.linkedin.com/in/loredanacrisan/• Amber Bravo on LinkedIn: https://www.linkedin.com/in/amberbravo/• Figma’s 2025 AI report: Perspectives from designers and developers: https://www.figma.com/blog/figma-2025-ai-report-perspectives/• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox#Energy_conservation_policy• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff• Pantheon: https://www.imdb.com/title/tt11680642/• Retro: https://retro.app/• Thiel Fellowship: https://thielfellowship.org/—Recommended books:• Understanding Comics: The Invisible Art: https://www.amazon.com/Understanding-Comics-Invisible-Scott-McCloud/dp/006097625X• The Spy and the Traitor: The Greatest Espionage Story of the Cold War: https://www.amazon.com/Spy-Traitor-Greatest-Espionage-Story/dp/1101904216• Codex Seraphinianus: https://www.amazon.com/Codex-Seraphinianus-Anniversary-Luigi-Serafini/dp/0847871045Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Figma’s CEO: Why AI makes design, craft, and quality the new moat for startups | Dylan Field

Robby Stein is VP of Product at Google, where he oversees the core products of Google Search—including the new AI Overviews, AI Mode, search ranking, Google Lens, and more. Previously, he led consumer products at Instagram, where he and his teams built Stories, Reels, Close Friends, and other key features now used by billions.—What you’ll learn:Why Google’s AI products are suddenly taking off after years of perceived stagnation How AI is expanding Search rather than replacing it, contrary to what many predicted The three core product principles that have helped Robby build multiple billion-user products Inside Instagram’s decision to build its own version of Snapchat Stories His mantra of “relentless improvement” How Google developed AI Mode from concept to launch in just one year Why most teams give up too early on potentially transformative products —Brought to you by:Vanta—Automate compliance. Simplify security: https://vanta.com/lennyJira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imcOrkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/—Transcript: https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175041217/my-biggest-takeaways-from-this-conversation⁠—Where to find Robby Stein:• X: https://x.com/rmstein• LinkedIn: https://www.linkedin.com/in/robbystein/—Referenced:• Google Gemini: https://gemini.google.com/app• Nano Banana: https://aistudio.google.com/models/gemini-2-5-flash-image• Chat GPT: https://chatgpt.com/• Perplexity: https://www.perplexity.ai/• Google Lens: https://lens.google/• AI Google search: https://www.google.com/ai• Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge): https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour• Alex Rampell on X: https://x.com/arampell• A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype): https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products• Look broader, look closer, think younger: Tony Fadell speaks at TED2015: https://blog.ted.com/look-broader-look-closer-think-younger-tony-fadell-speaks-at-ted2015/• Jobs to Be Done: https://www.christenseninstitute.org/theory/jobs-to-be-done/• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta• Rinstagram or Finstagram? The curious duality of the modern Instagram user: https://www.theguardian.com/technology/2016/sep/26/rinstagram-finstagram-instagram-accounts• V03: https://v03ai.com/• Pirate GPT: https://www.kickstarter.com/projects/silentmeditation/pirate-gpt/• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f• Dune on HBO Max: https://www.hbomax.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7• Top Gun: Maverick: https://www.imdb.com/title/tt1745960/• Purple pillows: https://purple.com/pillows• Avocado pillow: https://www.avocadogreenmattress.com/products/green-pillow• Justin Bieber’s website: https://www.justinbiebermusic.com/• Scooter Braun’s website: https://scooterbraun.com/—Recommended books:• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654• Aurora: https://www.amazon.com/Aurora-High-Stakes-Survival-Navigate-Darkness/dp/0062916475• Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135202—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Inside Google's AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search)

Jason Droege is the CEO of Scale AI, a company that provides foundational training data to every major AI lab. He previously co-founded Scour with Travis Kalanick and built Uber Eats from idea to $20 billion in revenue. In this conversation, Jason shares lessons from getting sued for $250 billion, discovering restaurant economics by weighing sandwich ingredients, and over 25 years of launching transformative technology businesses.What you’ll learn:What actually happened with Meta’s $14 billion investment in Scale AIWhy AI models still need human experts to improve, and how that relationship is evolvingHow AI models learn from experts building websites and debugging codeThe business lessons from building Uber Eats from zero to $20 billionWhy most enterprise data is useless for AI models todayWhy urgent daily problems beat super-valuable occasional problems when building productsHow to think independently when building new products and businesses—Brought to you by:Merge—The fastest way to ship 220+ integrations: http://merge.dev/lennyFigma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/Mercury—The art of simplified finances: https://mercury.com/—Transcript: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174979621/my-biggest-takeaways-from-this-conversation—Where to find Jason Droege:• X: https://x.com/jdroege• LinkedIn: https://www.linkedin.com/in/jasondroege/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jason Droege(06:01) Jason’s early career and lessons learned(10:27) The current state of Scale AI(12:37) The shift to expert data labeling(17:02) Challenges and strategies in finding experts(18:48) Reinforcement learning and AI environments(28:18) The future of AI and human involvement(31:21) The role of evals(35:25) What AI models will look like in the next few years(41:43) Building Uber Eats and understanding customer needs(48:19) The importance of independent thinking(50:45) Setting high standards for new businesses(53:03) Exploring and selecting business ideas(57:07) The McDonald’s story(01:00:13) The role of gross margins in business feasibility(01:04:49) Why Jason says, “Not losing is a precursor to winning”(01:09:12) Hiring and building teams(01:12:11) AI corner(01:14:47) Lightning round and final thoughts—Referenced:• Travis Kalanick on X: https://x.com/travisk• Scour: https://en.wikipedia.org/wiki/Scour_Inc.• Scale: https://scale.com/• Alexandr Wang on X: https://x.com/alexandr_wang• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody• Brendan Foody’s post on X about knowledge work changing: https://x.com/BrendanFoody/status/1970163503702188048• MIT Finds 95% of GenAI Pilots Fail Because Companies Avoid Friction: https://www.forbes.com/sites/jasonsnyder/2025/08/26/mit-finds-95-of-genai-pilots-fail-because-companies-avoid-friction/• Uber Eats: https://www.ubereats.com/• Stephen Chau on X: https://x.com/thestephenchau• a16z Podcast: https://a16z.com/podcasts/a16z-podcast/• F1: The Movie: https://www.imdb.com/title/tt16311594/• V03: https://v03ai.com/• Careers at Scale: https://scale.com/careers—Recommended books:• The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152• The Road Less Traveled: A New Psychology of Love, Traditional Values, and Spiritual Growth: https://www.amazon.com/Road-Less-Traveled-Timeless-Traditional/dp/0743243153/• Good to Great: Why Some Companies Make the Leap . . . And Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege

Albert Cheng has led growth at three of the world’s most successful consumer subscription companies: Duolingo, Grammarly, and Chess.com. A former Google product manager (and serious pianist!), Albert developed a unique approach to finding and scaling growth opportunities through rapid experimentation and deep user psychology. His teams run 1,000 experiments a year, discovering counterintuitive insights that have driven tens of millions in revenue.What you’ll learn:1. How to use the explore-exploit framework to find new growth opportunities2. How showing premium features to free users doubled Grammarly’s upgrades to paid plans3. What good retention looks like for a consumer subscription app4. Why resurrected users drive 80% of mature product growth5. Why “reverse trials” work better than time-based trials6. The three pillars of successful gamification: core loop, metagame, and profile —Brought to you by:Vanta—Automate compliance. Simplify security.Jira Product Discovery—Confidence to build the right thingMiro—A collaborative visual platform where your best work comes to life—Where to find Albert Cheng:• X: https://x.com/albertc248• LinkedIn: https://www.linkedin.com/in/albertcheng1/• Chess.com: https://www.chess.com/member/Goniners—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Referenced:• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Explore vs. Exploit: https://brianbalfour.com/quick-takes/explore-vs-exploit• Grammarly: https://www.grammarly.com/• Reforge: https://www.reforge.com/• Chess.com: https://www.chess.com/• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Figma: https://www.figma.com/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Claude Code: https://www.anthropic.com/claude-code• GitHub Copilot: https://github.com/features/copilot• Noam Lovinsky on LinkedIn: https://www.linkedin.com/in/noaml/• The happiness and pain of product management | Noam Lovinsky (Grammarly, Facebook, YouTube, Thumbtack): https://www.lennysnewsletter.com/p/the-happiness-and-pain-of-product• Kyla Siedband on LinkedIn: https://www.linkedin.com/in/kylasiedband/• The Duolingo handbook: https://blog.duolingo.com/handbook/• Lenny’s post on X about the Duolingo handbook: https://x.com/lennysan/status/1889008405584683091• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir• Duolingo on TikTok: https://www.tiktok.com/@duolingo• Kasparov vs. Deep Blue | The Match That Changed History: https://www.chess.com/article/view/deep-blue-kasparov-chess• Magnus Carlsen: https://en.wikipedia.org/wiki/Magnus_Carlsen• Elo rating system: https://www.chess.com/terms/elo-rating-chess• Stockfish: https://en.wikipedia.org/wiki/Stockfish_(chess)• AlphaGo on Prime Video: https://www.primevideo.com/detail/AlphaGo/0KNQHKKDAOE8OCYKQS9WSSDYN0• Statsig: https://www.statsig.com/• The State of Product in 2026: Navigating Change, Challenge, and Opportunity: https://www.atlassian.com/blog/announcements/state-of-product-2026• Erik Allebest on LinkedIn: https://www.linkedin.com/in/erikallebest/• Daniel Rensch on X: https://x.com/danielrensch• Chariot: https://en.wikipedia.org/wiki/Chariot_(company)• San Francisco 49ers: https://www.49ers.com/• Breville Barista Express: https://www.breville.com/en-us/product/bes870—Recommended books:• Snuggle Puppy!: A Little Love Song: https://www.amazon.com/Snuggle-Puppy-Little-Boynton-Board/dp/1665924985• Ogilvy on Advertising: https://www.amazon.com/Ogilvy-Advertising-David/dp/039472903X• Dark Squares: How Chess Saved My Life: https://www.amazon.com/Dark-Squares-Chess-Saved-Life/dp/1541703286—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)

Nesrine Changuel helped build Spotify, Google Chrome, and Google Meet. Her work has helped her discover the importance of emotional connection in building successful products. At Google, she served as a dedicated “delight PM,” a role specifically focused on making products more delightful. She recently published Product Delight, a book that provides a practical framework for creating products that serve both functional and emotional needs. Based in Paris, she now coaches founders and CPOs on implementing delight strategies in their organizations.What you’ll learn:1. Why delight is a business strategy, not just “sprinkling confetti” on top of functionality2. How to identify emotional motivators that drive product retention3. The 50-40-10 rule for balancing delight in your roadmap4. The 4-step delight model5. The origin story of Spotify’s Discover Weekly6. Why B2B products need delight just as much as B2C products7. How to get buy-in from skeptical leaders who think delight is a luxury—Brought to you by:DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lennyJira Product Discovery—Confidence to build the right thing: https://atlassian.com/lennyLucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny—Transcript: https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174199489/my-biggest-takeaways-from-this-conversation—Where to find Nesrine Changuel:• LinkedIn: https://www.linkedin.com/in/nesrinechanguel/• Newsletter: https://nesrinechanguel.substack.com/• Website: https://nesrine-changuel.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nesrine and product delight(04:56) Why delight matters(09:17) What makes a feature “delightful”(12:29) The three pillars of delight(13:03) Pillar 1: Removing friction (Uber refund example)(15:07) Pillar 2: Anticipating needs (Revolut eSIM example)(17:21) Pillar 3: Exceeding expectations (Edge coupon example)(18:35) The “confetti effect” and when it actually works(22:02) B2B vs. B2C: Why all products need emotional connection(29:52) The Delight Model: A 4-step framework(30:57) Step 1: Identifying user motivators (functional and emotional)(33:55) Step 2: Converting motivators into product opportunities(34:46) Step 3: Identifying solutions with the delight grid(36:46) Step 4: Validating ideas with the delight checklist(40:22) The Delight Model summarized(42:18) The importance of familiarity (Spotify Discover Weekly story)(45:21) Real examples: Chrome’s tab management solution(51:32) Google Meet’s solution for “Zoom fatigue”(55:02) Getting buy-in from skeptical leaders(59:39) Prioritizing delight: The 50-40-10 rule(1:02:41) Creating a culture of delight in your organization(1:06:45) The habituation effect(1:08:15) When delight goes wrong: Apple reactions example(1:10:21) How delight motivates product teams(1:12:24) Lightning round and final thoughts—Referenced:• Spotify: https://open.spotify.com/• Linear: https://linear.app/• How Linear builds product: https://www.lennysnewsletter.com/p/how-linear-builds-product• Jira: https://www.atlassian.com/software/jira• Asana: https://asana.com/• Monday: https://monday.com/• The Product Delight Model: https://nesrinechanguel.substack.com/p/the-product-delight-model• Revolut: https://www.revolut.com/• How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers• Microsoft Cashback: https://www.microsoft.com/en-us/edge/features/shopping-cashback• Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra• Brian Chesky’s secret mentor who died 9 times, started the Burning Man board, and built the world’s first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley• Workday: https://www.workday.com/• SAP: https://www.sap.com/• ServiceNow: https://www.servicenow.com/• Salesforce: https://www.salesforce.com/• GitHub: https://github.com/• Atlassian: https://www.atlassian.com/• Snowflake: https://www.snowflake.com/• Data Superheroes: https://www.snowflake.com/en/data-superheroes/• Google Meet: https://meet.google.com/• Andy Nesling on LinkedIn: https://www.linkedin.com/in/andynesling/• Matic: https://maticrobots.com/• Diego Sanchez’s (Senior Product Manager at Buffer) post on LinkedIn: https://www.linkedin.com/feed/update/urn:li:activity:7365014292091346945/• Miro: https://miro.com/• Arc browser: https://arc.net/• Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look• Migros Supermarket: https://www.migros.ch/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu• Suno: https://suno.com• Snapchat: https://www.snapchat.com/• Use Reactions, Presenter Overlay, and other effects when videoconferencing on Mac: https://support.apple.com/en-us/105117• Dr. Lipp: https://drlipp.com/• How to be the best coach to product people | Petra Wille (Strong Product People): https://www.lennysnewsletter.com/p/how-to-be-the-best-coach-to-product• The Great American Baking Show: https://www.imdb.com/title/tt21822674/• Le Meilleur Pâtissier: https://en.wikipedia.org/wiki/Le_Meilleur_P%C3%A2tissier• The Upside on Amazon Prime: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.3cb8500f-31af-9f4f-5dec-701e086d58e8• The Intouchables: https://www.imdb.com/title/tt1675434/• Yoyo stroller: https://www.stokke.com/USA/en-us/category/strollers/yoyo-strollers• UppaBaby strollers: https://uppababy.com/strollers/—Recommended books:• Product Delight: How to Make Your Product Stand Out with Emotional Connection: https://www.amazon.com/Product-Delight-Stand-Emotional-Connection-ebook/dp/B0FGZ93D9Y/• Factfulness: Ten Reasons We’re Wrong About the World—and Why Things Are Better Than You Think: https://www.amazon.com/Factfulness-Reasons-World-Things-Better/dp/1250107814• STRONG Product Communities: The Essential Guide to Product Communities of Practice: https://www.amazon.com/STRONG-Product-Communities-Essential-Practice/dp/3982235189/r—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype)

Hamel Husain and Shreya Shankar teach the world’s most popular course on AI evals and have trained over 2,000 PMs and engineers (including many teams at OpenAI and Anthropic). In this conversation, they demystify the process of developing effective evals, walk through real examples, and share practical techniques that’ll help you improve your AI product.What you’ll learn:1. WTF evals are2. Why they’ve become the most important new skill for AI product builders3. A step-by-step walkthrough of how to create an effective eval4. A deep dive into error analysis, open coding, and axial coding5. Code-based evals vs. LLM-as-judge6. The most common pitfalls and how to avoid them7. Practical tips for implementing evals with minimal time investment (30 minutes per week after initial setup)8. Insight into the debate between “vibes” and systematic evals—Brought to you by:Fin—The #1 AI agent for customer serviceDscout—The UX platform to capture insights at every stage: from ideation to productionMercury—The art of simplified finances—Where to find Shreya Shankar• X: https://x.com/sh_reya• LinkedIn: https://www.linkedin.com/in/shrshnk/• Website: https://www.sh-reya.com/• Maven course: https://bit.ly/4myp27m—Where to find Hamel Husain• X: https://x.com/HamelHusain• LinkedIn: https://www.linkedin.com/in/hamelhusain/• Website: https://hamel.dev/• Maven course: https://bit.ly/4myp27m—In this episode, we cover:(00:00) Introduction to Hamel and Shreya(04:57) What are evals?(09:56) Demo: Examining real traces from a property management AI assistant(16:51) Writing notes on errors(23:54) Why LLMs can’t replace humans in the initial error analysis(25:16) The concept of a “benevolent dictator” in the eval process(28:07) Theoretical saturation: when to stop(31:39) Using axial codes to help categorize and synthesize error notes(44:39) The results(46:06) Building an LLM-as-judge to evaluate specific failure modes(48:31) The difference between code-based evals and LLM-as-judge(52:10) Example: LLM-as-judge(54:45) Testing your LLM judge against human judgment(01:00:51) Why evals are the new PRDs for AI products(01:05:09) How many evals you actually need(01:07:41) What comes after evals(01:09:57) The great evals debate(1:15:15) Why dogfooding isn’t enough for most AI products(01:18:23) OpenAI’s Statsig acquisition(1:23:02) The Claude Code controversy and the importance of context(01:24:13) Common misconceptions around evals(1:22:28) Tips and tricks for implementing evals effectively(1:30:37) The time investment(1:33:38) Overview of their comprehensive evals course(1:37:57) Lightning round and final thoughts—LLM Log Open Codes Analysis Prompt:Please analyze the following CSV file. There is a metadata field which has an nested field called z_note that contains open codes for analysis of LLM logs that we are conducting. Please extract all of the different open codes. From the _note field, propose 5-6 categories that we can create axial codes from.—Referenced:• Building eval systems that improve your AI product: https://www.lennysnewsletter.com/p/building-eval-systems-that-improve• Mercor: https://mercor.com/• Brendan Foody on LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b• Nurture Boss: https://nurtureboss.io/• Braintrust: https://www.braintrust.dev/• Andrew Ng on X: https://x.com/andrewyng• Carrying Out Error Analysis: https://www.youtube.com/watch?v=JoAxZsdw_3w• Julius AI: https://julius.ai/• Brendan Foody on X—“evals are the new PRDs”: https://x.com/BrendanFoody/status/1939764763485171948• Who Validates the Validators? Aligning LLM-Assisted Evaluation of LLM Outputs with Human Preferences: https://dl.acm.org/doi/abs/10.1145/3654777.3676450• Lenny’s post on X about evals: https://x.com/lennysan/status/1909636749103599729• Statsig: https://statsig.com/• Claude Code: https://www.anthropic.com/claude-code• Cursor: https://cursor.com/• Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor• Frozen: https://www.imdb.com/title/tt2294629/• The Wire on HBO: https://en.wikipedia.org/wiki/The_Wire—Recommended books:• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563935• Apple in China: The Capture of the World’s Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373/• Machine Learning: https://www.amazon.com/Machine-Learning-Tom-M-Mitchell/dp/1259096955• Artificial Intelligence: A Modern Approach: https://www.amazon.com/Artificial-Intelligence-Modern-Approach-Global/dp/1292401133/Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course)

Julie Zhuo is the former VP and Head of Design at Facebook (now Meta), author of the bestselling book The Making of a Manager, and co-founder of Sundial, an AI-powered data analysis company. Also, my first-ever podcast guest over 3 years ago!In our conversation, we discuss:1. The three core manager skills that translate directly to managing AI agents2. How her team uses AI to learn new skills 10x faster3. The “diagnose with data, treat with design” framework for balancing gut and data4. Why hypergrowth AI companies have terrible data infrastructure (and why it doesn’t matter)5. How to give feedback that actually lands—including Julie’s exact script for difficult conversations6. What Julie’s teaching her kids about an AI future (hint: it’s not coding or STEM)—Brought to you by:Mercury — The art of simplified financesDX — The developer intelligence platform designed by leading researchersPostHog—How developers build successful products—Transcript: https://www.lennysnewsletter.com/p/from-managing-people-to-managing-ai-julie-zhuo—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/172723725/my-biggest-takeaways-from-this-conversation—Where to find Julie Zhuo:• X: https://x.com/joulee• LinkedIn: https://www.linkedin.com/in/julie-zhuo/• Website: https://www.juliezhuo.com/• Newsletter: https://lg.substack.com/• Sundial: https://sundial.so/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome back, Julie!(05:18) The success of The Making of a Manager(08:41) Why AI will make everyone a manager(11:38) The future of management roles(14:00) Empowering teams with AI(21:30) Specific roles being accelerated by AI(26:53) Data analysis in AI companies(32:02) The role of data in design(37:21) The evolving role of managers in the AI era(40:22) Embracing change and uncertainty(42:14) Timeless lessons for managers(49:03) Balancing strengths and weaknesses(57:49) Building a feedback culture(01:05:33) Creating win-win situations(01:09:27) Being aware of your own energy and conviction(01:12:12) Navigating disagreements with higher-ups(01:15:57) AI corner(01:20:08) Contrarian corner(01:23:14) Lightning round and final thoughts—Referenced:• Julie Zhuo on accelerating your career, impostor syndrome, writing, building product sense, using intuition vs. data, hiring designers, and moving into management: https://www.lennysnewsletter.com/p/episode-2-julie-zhuo• Waymo: https://waymo.com/• How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO): https://www.lennysnewsletter.com/p/how-we-restructured-airtables-entire-org-for-ai• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• The Magic Loop: https://www.lennysnewsletter.com/p/the-magic-loop• Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/• Methaphone: https://methaphone.com/• Replit: https://replit.com/• “Baby” by Justin Bieber on Spotify: https://open.spotify.com/track/6epn3r7S14KUqlReYr77hA• Kingdom Rush: https://www.kingdomrush.com/• Dr. Becky on TikTok: https://www.tiktok.com/@drbeckyatgoodinside• Emily Oster on TikTok: https://www.tiktok.com/@profemilyoster• La La Land on Netflix: https://www.netflix.com/title/80095365• Granola: https://www.granola.ai/• Matic robots: https://maticrobots.com/• Limitless pendant: https://www.limitless.ai/• How I AI: https://www.youtube.com/@howiaipodcast—Recommended books:• The Making of a Manager: What to Do when Everyone Looks to You: https://www.amazon.com/Making-Manager-What-Everyone-Looks/dp/0525540423• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0061673730• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

From managing people to managing AI: The leadership skills everyone needs now | Julie Zhuo (Facebook VP, Sundial CEO, The Making of a Manager author)

Brendan Foody is the CEO and co-founder of Mercor, the fastest-growing company in history to go from $1M to $500M in revenue (in just 17 months!). At 22, he is also the youngest American unicorn founder ever. Mercor works with 6 of the Magnificent 7 and all top 5 AI labs to help them hire experts to create evaluations and training data that improve their models. In this conversation, Brendan explains why evals have become the critical bottleneck for AI progress, how he discovered this massive opportunity, and what the future of work might look like in an AI-driven economy.What you’ll learn:1. Why evals are becoming the primary bottleneck for AI progress and what this means for AI startups2. How Mercor grew to $500M revenue in 17 months (fastest in history)3. Brendan’s meeting with xAI that changed his company’s trajectory4. Which skills and jobs will remain most valuable as AI continues to advance (hint: jobs with “elastic” demand)5. Why Brendan believes AGI and superintelligence are not happening anytime soon6. The three unique core values that drove Mercor’s success7. How Harvard Lampoon writers are making Claude funnier—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsJira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teamsEnterpret—Transform customer feedback into product growth—Transcript: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/173303790/my-biggest-takeaways-from-this-conversation—Where to find Brendan Foody:• X: https://x.com/BrendanFoody• LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Brendan Foody and Mercor(05:38) The “era of evals”(09:26) Understanding the AI training landscape(17:10) The future of work and AI(25:54) The evolution of labor markets(29:55) Understanding how AI models are trained(38:58) Building Mercor(53:27) Lessons from past ventures(56:55) The future of AI and model improvement(01:00:41) His personal use of AI and final thoughts—References: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor)

Ethan Smith is the CEO of Graphite—the leading SEO growth agency—and my go-to expert on SEO. After 18 years of mastering traditional SEO, Ethan has been at the forefront of what is called AEO: answer engine optimization, or, more simply, getting your product to show up in ChatGPT/Claude/Gemini/Perplexity answers. He’s discovered that ChatGPT traffic converts six times better than Google search—and most companies are completely missing this opportunity.In our conversation, we discuss:1. His 7-step playbook to rank #1 in ChatGPT2. Why ChatGPT traffic converts 6x better than Google3. How early-stage startups can win at AEO immediately (unlike with SEO, which takes years)4. The three tactics that actually work: landing pages, YouTube videos, and Reddit comments5. Why help-center content can suddenly be your highest-ROI investment6. The specific Reddit strategy that works (spoiler: be authentic)7. Why AI-generated content doesn’t work—Brought to you by:Orkes—The enterprise platform for reliable applications and agentic workflowsVanta—Automate compliance. Simplify security.Great Question—Empower everyone to run great research—Where to find Ethan Smith:• Twitter: https://twitter.com/ethan_l_s• LinkedIn: https://bit.ly/ethans-linkedin• Graphite: https://graphite.io/• Graphite Research Papers: https://bit.ly/graphite-five-percent—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome back, Ethan(04:34) The changing landscape of SEO(06:19) AEO (answer engine optimization) vs. GEO (generative engine optimization)(08:13) The impact of AEO(11:51) How early-stage startups can win at AEO(14:34) The quality of AEO leads(15:35) On-site vs. off-site traffic(16:32) Reddit’s role in AEO and avoiding spam(20:11) How AI models use citations (RAG)(21:41) Key principles for winning at AEO(25:00) Avoiding hyper-SEOed content, and the importance of originality(28:55) Actionable AEO playbook: steps and experiments(33:35) Tracking, measuring, and share of voice(38:34) Adapting AEO for B2B, commerce, and early-stage companies(41:11) Is letting AI index your content good?(43:06) Experimentation, control groups, and measuring results(46:15) The future of AEO, SEO, and search channels(51:35) AI-generated content: what works and what doesn’t(55:25) The dangers of infinite AI derivatives(58:44) The future: convergence of LLMs and search(01:00:40) Help-center optimization and the long tail(01:03:18) Lightning round and final thoughts—Resources and episode mentions: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-aeo-ethan-smith—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite)

Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Airbnb to OpenAI to Databricks (now worth more than $100 billion). His management philosophy—forged through near-death experiences and refined through coaching hundreds of CEOs—contradicts most conventional startup wisdom.In our conversation, Ben shares:1. Why “founder mode” is half right and half dangerously wrong2. The story behind “Good Product Manager/Bad Product Manager” and why it went viral despite being written in anger3. Where the biggest AI startup opportunities remain4. Why you need to run toward fear, never away5. The one trait that predicts that a founder will fail as CEO6. Inside Paid in Full, Ben’s nonprofit awarding pensions to pioneering hip-hop artists—Brought to you by:DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lennyBasecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lennyMiro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny—Transcript: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/172439345/my-biggest-takeaways-from-this-conversation—Where to find Ben Horowitz:• X: https://x.com/bhorowitz• LinkedIn: https://www.linkedin.com/in/behorowitz/• Website: https://benhorowitz.com/• Andreessen Horowitz’s website: https://a16z.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Ben Horowitz(04:09) Important leadership lessons from Shaka Senghor(10:15) Running toward fear and why hesitation kills companies(19:35) Who shouldn’t start a company(22:36) The Databricks story: thinking bigger(24:54) Managerial leverage and CEO psychology(28:06) When founders should be replaced as CEOs(31:20) Normalizing failure for CEOs(37:57) Counterintuitive lessons about building companies(42:31) “Good Product Manager/Bad Product Manager”(48:21) Product managers as leaders(51:16) Why a16z invested in Adam Neumann after WeWork(56:23) Is AI in a bubble?(01:02:43) The biggest opportunities in AI(01:12:51) Why U.S. leadership in AI matters(01:18:53) The Paid in Full Foundation for hip-hop pioneers(01:23:18) Lightning round: book recommendations, products, and life mottos—References: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder)

Ezinne and Oji Udezue have over 50 years of combined product leadership experience at Microsoft, Twitter, Atlassian, WP Engine, Typeform, and Calendly. They’ve witnessed every major shift in product management, and, despite their seniority, they’re taking beginner AI courses and learning from engineers half their age, and Oji is coding more now than in the past decade—from Waterfall to Agile to AI. They are also the authors of Building Rocketships, a guide to building great products. In this conversation, the couple shares hard-won lessons they’ve learned from companies successfully adapting to AI, including their “shipyard” framework and their “sharp problem” methodology.What you’ll learn:1. The “shipyard” framework: why the best AI teams embrace controlled chaos2. Why Oji writes more code now than in the past 10 years—despite being a PM for more than 25 years3. The three skills that matter most for PMs in 2025: curiosity, humility, and agency4. How to identify “sharp problems”5. AI at the core vs. AI at the edge: why companies that are building entirely new AI-centric codebases will beat those just “sprinkling AI” on existing products6. The counterintuitive truth: engineers are moving so fast with AI that PMs are now the bottleneck7. Their biggest product lesson from 50 combined years—Brought to you by:Mercury—The art of simplified financesVanta—Automate compliance. Simplify security.Coda—The all-in-one collaborative workspace—Where to find Oji and Ezinne:• ProductMind on Substack: https://substack.com/@ojiudezue• ProductMind on LinkedIn: https://www.linkedin.com/company/productmindco• ProductMind on YouTube: https://www.youtube.com/@ProductMindX/videos• ProductMind on Spotify: https://open.spotify.com/show/07OVh5pdSv0szHPwWktzQQ• ProductMind website: https://www.productmind.co/• Oji on LinkedIn: https://www.linkedin.com/in/ojiudezue/• Ezinne on LinkedIn: https://www.linkedin.com/in/ezinne/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Oji and Ezinne(04:14) The evolving role of product managers(08:01) Challenges and opportunities in product management(10:34) Sharp problems(12:37) The shipyard model for product development(17:02) Hiring PMs in the AI era(24:55) The importance of staying humble(27:16) Hands-on learning and personal projects(39:10) Companies succeeding with AI adoption(46:25) Lessons from 50 years in product(49:22) Simplicity in design(51:24) The role of communication in strategy(55:17) Career intentions and personal growth(01:00:00) Ethics and responsibility in product management(01:03:09) Introducing Building Rocketships(01:06:42) Lightning round and final thoughts—Referenced:• How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft): https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma• Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform, Twitter, Calendly, Atlassian): https://www.lennysnewsletter.com/p/picking-sharp-problems-increasing• Atlassian: https://www.atlassian.com/• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/• Brownian motion: https://en.wikipedia.org/wiki/Brownian_motion• Calendly: https://calendly.com/• Women in Product: https://womenpm.org/• Brian Chesky’s secret mentor who died 9 times, started the Burning Man board, and built the world’s first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley• Home Assistant: https://www.home-assistant.io/• What people are vibe coding (and actually using): https://www.lennysnewsletter.com/p/what-people-are-vibe-coding-and-actually• How many layers should I wear today?: https://layers.today/• Typeform: https://www.typeform.com/• David Okuniev on X: https://x.com/okuiux• Clay: https://www.clay.com/• Martin Eriksson on LinkedIn: https://www.linkedin.com/in/martineriksson/• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead• Dave Mendlen on LinkedIn: https://www.linkedin.com/in/davemendlen/• Deepfake: https://en.wikipedia.org/wiki/Deepfake• How to kickstart and scale a marketplace business: https://www.lennysnewsletter.com/p/how-to-kickstart-and-scale-a-marketplace• Forever on Netflix: https://www.netflix.com/title/81418639• Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f• Sinners: https://www.imdb.com/title/tt31193180/• Claude: https://claude.ai/• Nespresso Vertuo: https://www.nespresso.com/us/en/vertuo-coffee-machines• Gamma: https://gamma.app/• Framer: https://www.framer.com/• Lovable: https://lovable.dev/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Llama: https://www.llama.com/—Recommended books:• Building Rocketships: Product Management for High-Growth Companies: https://www.amazon.com/Building-Rocketships-Management-High-Growth-Companies/dp/1962339068• Coda version of Building Rocketships: https://www.productmind.co/brpro• Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067• The Let Them Theory: A Life-Changing Tool That Millions of People Can’t Stop Talking About: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369/Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

How AI is reshaping the product role | Oji and Ezinne Udezue

Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow.What you’ll learn:1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman)2. Why Howie uses AI hourly (not daily) and is Airtable’s #1 inference-cost user globally3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible)4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era6. Why evals can kill innovation (and when to use “vibes” instead)—Brought to you by:LucidLink—Real-time cloud storage for teamsDX—The developer intelligence platform designed by leading researchersClaude.ai—The AI for problem solvers and enterprise—Where to find Howie Liu• X: https://x.com/howietl• LinkedIn: https://www.linkedin.com/in/howieliu/• Email: howie@airtable.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Howie Liu and Airtable(04:05) The “Airtable is dead” viral tweet controversy(08:07) The rise of IC CEOs(10:57) AI’s paradigm shift in product development(16:27) Specific changes Airtable has made(21:38) Fast- and slow-thinking teams(32:57) The emergence of new form factors in AI models(34:48) Airtable’s vision and philosophy(40:20) Empowering teams with AI tools(46:50) Encouraging experimentation and play(50:55) Cross-functional skills in product teams(01:03:35) The importance of evals and open-ended testing(01:08:06) Key strategies for AI-driven success(01:12:43) Counterintuitive startup wisdom(01:22:21) Don't step away from the details that you love(01:25:50) Advice for aspiring engineers and designers(01:30:00) Lightning round and final thoughts—Referenced:• Airtable: https://www.airtable.com/• All In podcast: https://allin.com/• Nikita Bier on X: https://x.com/nikitabier• Figma: https://www.figma.com/• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper• Every: https://every.to/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Windsurf: https://windsurf.com/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Rippling: https://www.rippling.com/• Omni: https://www.airtable.com/lp/ai-psu-plp• How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Palantir: https://www.palantir.com/• Harvey: https://www.harvey.ai/• v0: https://v0.dev/• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Replit: https://replit.com/• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Lovable: https://lovable.dev/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Runway Game Worlds: https://play.runwayml.com/login• Sesame: https://www.sesame.com• NotebookLM: https://notebooklm.google• Salesforce: https://www.salesforce.com• Andrew Ofstad on LinkedIn: https://www.linkedin.com/in/aofstad/• Stripe: https://stripe.com/• Eames chair: https://en.wikipedia.org/wiki/Eames_Lounge_Chair• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• IDEO design thinking: https://designthinking.ideo.com/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• The Studio on AppleTV+: https://tv.apple.com/us/show/the-studio/umc.cmc.7518algxc4lsoobtsx30dqb52• Silicon Valley on HBOMax: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d• Self Edge: https://www.selfedge.com/• Studio D’Artisan: https://www.selfedge.com/studio-dartisan• Whitesville T-shirt: https://store.toyo-enterprise.co.jp/shopbrand/ct48/• Guest Series | Dr. Paul Conti: How to Understand & Assess Your Mental Health: https://www.hubermanlab.com/episode/guest-series-dr-paul-conti-how-to-understand-and-assess-your-mental-health—Recommended books:• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032• Trauma: The Invisible Epidemic: How Trauma Works and How We Can Heal From It: https://us.amazon.com/Trauma-Invisible-Epidemic-Works-Heal/dp/1683647351/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO)

Asha Sharma leads AI product strategy at Microsoft, where she works with thousands of companies building AI products and has unique visibility into what’s working (and what’s not) across more than 15,000 startups and enterprises. Before Microsoft, Asha was COO at Instacart, and VP of Product & Engineering at Meta, notably leading product for Messenger.What you’ll learn:1. Why we’re moving from “product as artifact” to “product as organism” and what this means for builders2. Microsoft’s “seasons” planning framework that allows them to adapt quickly in the AI era3. The death of the org chart: how agents are turning hierarchies into task networks and why “the loop, not the lane” is the new organizing principle4. Why post-training will soon see more investment than pre-training—and how to build your own AI moat with fine-tuning5. Her prediction for the “agentic society”—where org charts become work charts and agents outnumber humans in your company6. The three-phase pattern every successful AI company follows (and why most fail at phase one)7. The rise of code-native interfaces and why GUIs might be going the way of the desktop8. What Asha learned from Satya Nadella about optimism—Brought to you by:Enterpret—Transform customer feedback into product growth: https://enterpret.com/lennyDX—The developer intelligence platform designed by leading researchers: http://getdx.com/lennyFin—The #1 AI agent for customer service: https://fin.ai/lenny—Transcript: ⁠https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/171413445/my-biggest-takeaways-from-this-conversation⁠—Where to find Asha Sharma:• LinkedIn: https://www.linkedin.com/in/aboutasha/• Blog: https://azure.microsoft.com/en-us/blog/author/asha-sharma/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Asha Sharma(04:18) From “product as artifact” to “product as organism”(06:20) The rise of post-training and the future of AI product development(09:10) Successful AI companies: patterns and pitfalls(12:01) The evolution of full-stack builders(14:15) “The loop, not the lane”—the new organizing principle(16:24) The future of user interfaces: from GUI to code-native(19:34) The rise of the agentic society(22:58) The “work chart” vs. the “org chart”(26:24) How Microsoft is using agents(28:23) Planning and strategy in the AI landscape(35:38) The importance of platform fundamentals(39:31) Lessons from industry giants(42:10) What’s driving Asha(44:30) Reinforcement learning (RL) and optimization loops(49:19) Lightning round and final thoughts—Referenced:• Copilot: https://copilot.microsoft.com/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• GitHub: https://github.com• Dragon Medical One: https://www.microsoft.com/en-us/health-solutions/clinical-workflow/dragon-medical-one• Windsurf: https://windsurf.com/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Lovable: https://lovable.dev/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Bolt: http://bolt.com• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Replit: https://replit.com/•Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Sierra: https://sierra.ai/• Spark: https://github.com/features/spark• Peter Yang on X: https://x.com/petergyang• How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management• Instacart: http://instacart.com/• Terminator: https://en.wikipedia.org/wiki/Terminator_(franchise)• Porch Group: https://porchgroup.com/• WhatsApp: https://www.whatsapp.com/• Maslow’s Hierarchy of Needs: https://www.simplypsychology.org/maslow.html• Satya Nadella on X: https://x.com/satyanadella• Perfect Match 360°: Artificial intelligence to find the perfect donor match: https://ivi-fertility.com/blog/perfect-match-360-artificial-intelligence-to-find-the-perfect-donor-match/• OpenAI’s GPT-5 shows potential in healthcare with early cancer detection capabilities: https://economictimes.indiatimes.com/news/international/us/openais-gpt-5-shows-potential-in-healthcare-with-early-cancer-detection-capabilities/articleshow/123173952.cms• F1: The Movie: https://www.imdb.com/title/tt16311594/• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7• The Home Depot: https://www.homedepot.com/• Dewalt Powerstack: https://www.dewalt.com/powerstack• Regret Minimization Framework: https://s3.amazonaws.com/kajabi-storefronts-production/sites/2147500522/themes/2148012322/downloads/rLuObc2QuOwjLrinx5Yu_regret-minimization-framework.pdf—Recommended books:• The Thinking Machine: Jensen Huang, Nvidia, and the World’s Most Coveted Microchip: https://www.amazon.com/Thinking-Machine-Jensen-Coveted-Microchip/dp/0593832698• Tomorrow, and Tomorrow, and Tomorrow: https://www.amazon.com/dp/0593466497Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft)

Garrett Lord is co-founder and CEO of Handshake, which started as a career network for college students and new grads but recently discovered something extraordinary: they were sitting on the world’s largest network of academic experts—exactly what frontier AI labs desperately needed. With 500,000 PhDs and 3 million advanced degree holders creating training data, in just eight months they’ve built a new business that hit $50 million in revenue in its first four months and is on track to blow past $100M in the first 12 months.What you’ll learn:1. How Handshake found an opportunity to leverage their proprietary network of experts to launch a data-labeling business that’s on track to blow past $100 million ARR in 12 months2. Why AI models need human experts (e.g. physics PhDs) to improve, and what this “data labeling” actually involves3. Inside the actual work: what a biology PhD does for 8 hours that makes GPT-5 smarter4. The playbook for building a startup inside a startup: separate teams, separate offices, separate everything5. Why the shift from “generalist” to “expert” data labeling created a once-in-a-lifetime business opportunity6. Why AI won’t eliminate entry-level jobs—it’s creating “Iron Man suits” that make junior employees 10x more productive—Brought to you by:CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lennyOrkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/—Transcript: https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/171410958/my-biggest-takeaways-from-this-conversation—Where to find Garrett Lord:• X: https://x.com/garrettlord• LinkedIn: https://www.linkedin.com/in/garrettlord/• Email: Garrett@joinhandshake.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Garrett Lord(05:00) Understanding data labeling and its importance(13:08) The role of experts in AI model training(15:35) The future of AI and human collaboration(24:17) Why AI won’t eliminate entry-level jobs(27:58) The continuous improvement of AI models(33:05) The emergence of Handshake’s new business model(37:07) Incubating new ideas in established companies(40:42) Handshake's competitive advantage(45:43) Scaling up and meeting market demand(48:38) Overcoming challenges and adapting(53:08) The importance of separate teams and ownership(57:26) The future of job matching with AI(01:00:30) The biggest bottlenecks to advancing models further(01:02:37) Lightning round and final thoughts—Referenced:• GPQA: https://github.com/idavidrein/gpqa• Handshake: https://joinhandshake.com/• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Goldman Sachs: https://www.goldmansachs.com/• General Motors: https://www.gm.com/• Google: https://about.google/• Sahil Bhaiwala on LinkedIn: https://www.linkedin.com/in/sahil-bhaiwala-459b0354/• Francisco “Paco” Guzman on LinkedIn: https://www.linkedin.com/in/guzmanhe/• Avery Yip on LinkedIn: https://www.linkedin.com/in/averyyip/• Game of Thrones on HBO: https://www.hbomax.com/shows/game-of-thrones/4f6b4985-2dc9-4ab6-ac79-d60f0860b0ac• SNOO: https://www.happiestbaby.com/products/snoo-smart-bassinet• Careers at Handshake: https://joinhandshake.com/careers/—Recommended books:• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO)

Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company’s growth had stalled. Just one month after his return, ChatGPT launched, and within six weeks, Intercom had a working prototype of what would become Fin. In this conversation, Eoghan shares the brutal reality of transforming a late-stage SaaS business valued at multiple billions into an AI-first company that’s now growing faster than most public software companies.We discuss:1. Why Eoghan believes most late-stage companies won’t survive the AI transition2. The “founder mode” transformation that required firing 40% of staff and resulted in 98% employee satisfaction3. Why having “nothing to lose” is the ultimate advantage in AI transformation (and why comfortable companies will fail)4. How Intercom transformed from a plateauing SaaS business to an AI-first company growing at 300%+5. How Intercom’s pricing evolved from “the most hated in SaaS” to a model that charges just $0.99 per resolved ticket6. The cultural transformation required to compete with AI-native startups7. How 12 years of therapy and a period of “ego death” shaped Eoghan’s leadership approach—Brought to you by:Great Question—Empower everyone to run great research: https://www.greatquestion.com/lennyWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyDX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny—Transcript: ⁠https://www.lennysnewsletter.com/p/how-intercom-rose-from-the-ashes-eoghan-mccabe—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170710700/my-biggest-takeaways-from-this-conversation—Where to find Eoghan McCabe:• X: https://x.com/eoghan• LinkedIn: https://www.linkedin.com/in/eoghanmccabe/• Website: https://eoghanmccabe.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Eoghan(05:00) The state of Intercom(09:53) The decision to pivot to AI(12:33) Why Eoghan is "anti-bot" in customer service(16:19) Pricing strategy evolution(19:26) Implementing the AI transformation(26:11) Cultural and organizational changes(31:18) Surviving a coup attempt(40:05) The future of AI and business(45:11) AI's impact on jobs(48:44) AI and human creativity(50:26) The importance of young AI talent(55:00) The cultural shift in AI adoption(58:00) Personal growth and leadership(01:04:34) Intercom’s success in producing product leaders(01:11:05) Intercom’s unique company culture(01:14:11) Lightning round and final thoughts—Referenced:• Intercom: https://www.intercom.com/• Fin: https://fin.ai/• Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann• Fergal Reid on LinkedIn: https://www.linkedin.com/in/fergalreid/• How Perplexity builds product: https://www.lennysnewsletter.com/p/how-perplexity-builds-product• Yosi Amram’s website: https://yamram.com/• (Nathaniel Russell) Ego Death Now: https://heythereprojects.shop/products/copy-of-nathaniel-russell-space-is-a-place• Daniel Kahneman: https://en.wikipedia.org/wiki/Daniel_Kahneman• Palantir: https://www.palantir.com/• Stripe: https://stripe.com/• Revolut: https://www.revolut.com/en-US/• Paul Adams on LinkedIn: https://www.linkedin.com/in/pauladams• What AI means for your product strategy | Paul Adams (CPO of Intercom): https://www.lennysnewsletter.com/p/what-ai-means-for-your-product-strategy• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm• N26: https://n26.com/en-eu• Notion: https://www.notion.so/• Coinbase: https://www.coinbase.com/• True Detective on Max: https://www.hbomax.com/shows/true-detective/9a4a3645-74e0-4e4d-9f35-31464b402357• 28 Years Later: https://www.imdb.com/title/tt10548174/• Trainspotting: https://www.imdb.com/title/tt0117951/• 28 Days Later: https://www.imdb.com/title/tt0289043/• Fellow: https://fellowproducts.com/• Porsche 911: https://www.porsche.com/usa/models/911/• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto—Recommended book:• Nuclear War: A Scenario: https://www.amazon.com/Nuclear-War-Scenario-Annie-Jacobsen/dp/0593476093Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Brian Balfour is the founder of Reforge, the former VP of Growth at HubSpot, and a student (and teacher) of product growth. Brian has studied every major platform shift—from Facebook to Apple to Google—and he’s spotted a pattern that’s about to repeat with ChatGPT.In this conversation, you’ll learn:1. The 4-step cycle every platform follows (and why ChatGPT just entered step 2)2. Why ChatGPT’s platform launch could be bigger than Facebook’s early platform3. The exact signals that ChatGPT will launch a third-party platform within six months4. Why you have six months (not years) to make your platform bet5. Why companies that don’t integrate with ChatGPT will lose to competitors that do6. How Zynga grew to $1B by betting on Facebook’s platform early (before it was obvious)7. Why so few companies are actually doing what they need to be doing right now—Brought to you by:DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lennyBasecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lennyMiro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny—Transcript: https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170294620/my-biggest-takeaways-from-this-conversation—Where to find Brian Balfour:• X: https://twitter.com/bbalfour• LinkedIn: https://www.linkedin.com/in/bbalfour/• Website: https://brianbalfour.com/• Substack: https://blog.brianbalfour.com/• Podcast: https://www.reforge.com/podcast/unsolicited-feedback—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome back, Brian!(04:13) The changing landscape of product growth(05:09) The importance of distribution(08:14) The role of new distribution platforms(09:45) The four-step cycle of distribution platforms(17:38) Examples of platform cycles(30:01) The rise of ChatGPT(44:47) The future of AI agents(46:01) Preferred partners and platform credibility(47:18) Monetization mechanisms and free tiers(48:14) Betting strategies for startups(01:04:34) Adopting AI tools: challenges and strategies(01:08:41) The importance of hard constraints(01:14:23) Effective AI adoption in companies(01:19:05) Lightning round and final thoughts—Referenced:• The Next Great Distribution Shift: https://blog.brianbalfour.com/p/the-next-great-distribution-shift• Brian Balfour: 10 lessons on career, growth, and life: https://www.lennysnewsletter.com/p/brian-balfour-10-lessons-on-career• This Week #9: Breaking into growth, leading with influence, and (not) stepping on toes: https://www.lennysnewsletter.com/p/this-week-9-breaking-into-growth• Distribution vs. Innovation: https://a16z.com/distribution-vs-innovation/• On Platform Shifts and AI: https://caseyaccidental.com/on-platform-shifts-and-ai/• How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within• Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey• ChatGPT: https://chatgpt.com/• Claude: https://claude.ai/• Gemini: https://gemini.google.com/• Vine: https://en.wikipedia.org/wiki/Vine_(service)• Periscope: https://en.wikipedia.org/wiki/Periscope_(service)• Myspace: https://en.wikipedia.org/wiki/Myspace• Friendster: https://en.wikipedia.org/wiki/Friendster• AltaVista: https://en.wikipedia.org/wiki/AltaVista• Lycos: https://www.lycos.com/• HubSpot: https://www.hubspot.com/• Zynga: https://www.zynga.com/• TBPN: https://www.tbpn.com/• Deedy Das on LinkedIn: https://www.linkedin.com/in/debarghyadas/• ChatGPT’s product retention curves are a product manager's wet dream: https://www.linkedin.com/posts/debarghyadas_chatgpts-product-retention-curves-are-a-activity-7338384752393035776-ice1/• Windsurf: https://windsurf.com/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Udemy: https://www.udemy.com/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Notion: https://www.notion.com/• Airtable: https://www.airtable.com/• Monday: monday.com• Sierra: http://sierra.ai• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Introducing ChatGPT agent: bridging research and action: https://openai.com/index/introducing-chatgpt-agent/• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• Marc Andreessen on Why Optimism Is the Safest Bet: https://nymag.com/marc-andressen-2014-10-20/• Reforge: https://www.reforge.com• Reforge Insights: https://www.reforge.com/insights• Shopify: https://www.shopify.com/• 25 proven tactics to accelerate AI adoption at your company: https://www.lennysnewsletter.com/p/25-proven-tactics-to-accelerate-ai• Clouded Judgement: https://cloudedjudgement.substack.com/• NFX: https://www.nfx.com/news• James Currier: https://www.nfx.com/team/james-currier• Hallway Chat: https://www.hallwaychat.co/• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/• Silicon Valley on HBO: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d• Stick: https://tv.apple.com/us/show/stick/umc.cmc.52w04zy67tiv11p8xvbc57wmc• Ergonofis standing desks: https://ergonofis.com/en-us/collections/standing-desks• Coping with the loss of a child and protecting your time | Brian Balfour (father of 2, CEO and founder Reforge, venture partner): https://www.startupdadpod.com/coping-with-the-loss-of-a-child-and-protecting-your-time-brian-balfour-father-of-2-ceo-and-found/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge)

Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things.In this conversation, you’ll learn:1. The one question that predicts if your team will survive the next layoffs (and why most teams can’t answer it)2. Why following product “best practices” perfectly can actually accelerate your path to unemployment3. The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant4. How to push back on executives without saying “no” (the options, plus a recommendation framework)5. The counterintuitive reason why the happiest PMs are also the most commercially minded6. The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management—Brought to you by:Enterpret—Transform customer feedback into product growth: https://enterpret.com/lennyPragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications: https://pragmaticinstitute.com/lennyClaude.ai—The AI for problem solvers and enterprise: http://claude.ai/—Transcript: https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109376/my-biggest-takeaways-from-this-conversation—Where to find Matt LeMay:• Instagram: https://www.instagram.com/mttlmy• LinkedIn: https://www.linkedin.com/in/mattlemay/• Website: https://mattlemay.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt LeMay(04:23) Matt’s background and transition to product management(06:47) The goal of Matt's new book(12:00) How to stress test your thinking as a PM(15:32) Thinking like the CEO(17:33) The role of a product manager(23:36) The low-impact PM death spiral(27:47) Case study: Mailchimp’s transition to a platform company(32:53) Radical acceptance(41:24) Embracing constraints in product management(44:23) Steps to become an impact-first product team(49:38) Setting effective goals(01:02:15) Prioritization and impact estimation(01:07:58) Navigating stakeholder management(01:12:35) Summarizing the 3 steps(01:16:36) Lightning round and final thoughts—Referenced:• Pitchfork: https://pitchfork.com/• Daniel Ek’s memo: https://newsroom.spotify.com/2023-12-04/an-update-on-december-2023-organizational-changes/• How to create a winning product strategy | Melissa Perri: https://www.lennysnewsletter.com/p/how-to-create-a-winning-product-strategy• Everything you’ve ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute): https://www.lennysnewsletter.com/p/product-owners-melissa-perri• Mailchimp: https://mailchimp.com/• Intuit: https://www.intuit.com/• Natalia Williams on LinkedIn: https://www.linkedin.com/in/nataliatwilliams/• The ultimate guide to OKRs | Christina Wodtke (Stanford): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-okrs-christina• Miro: https://miro.com/• Prioritizing: https://www.lennysnewsletter.com/p/prioritizing• Temptation Island on Netflix: https://www.netflix.com/title/81744518• Mark L. Walberg’s website: https://markwalbergtv.com/about• Antiques Roadshow on PBS: https://www.pbs.org/wgbh/roadshow/• Milkman amp: https://milkmansound.com/collections/amplifiers/products/the-amp• Matt’s review of Liz Phair’s self-titled album: https://pitchfork.com/reviews/albums/6255-liz-phair/• Pitchfork Critic Apologizes for Bashing Liz Phair Album; Singer Graciously Accepts: https://variety.com/2019/music/news/pitchfork-critic-apologizes-liz-phair-album-review-zero-score-1203326897/• RedMonk: https://redmonk.com/—Recommended books:• Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After: https://www.amazon.com/Product-Management-Practice-Practical-Tactical/dp/1098119738/r• Impact-First Product Teams: Define Success. Do Work That Matters. Be Indispensable.: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJ• Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/B08B46C8R1/• Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results: https://www.amazon.com/Radical-Focus-Achieving-Important-Objectives/dp/0996006028• The Wisdom of Insecurity: A Message for an Age of Anxiety: https://www.amazon.com/Wisdom-Insecurity-Message-Age-Anxiety/dp/0307741206/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The one question that saves product careers | Matt LeMay

Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched.We discuss:1. The 10-day sprint from deciding to ship ChatGPT to Sam Altman’s tweet (and why it was originally called “Chat with GPT-3.5”)2. How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied3. The “Is it maximally accelerated?” philosophy that drives OpenAI’s insane shipping velocity4. Why ChatGPT’s retention curve “smiles”—users leave, then come back months later using it more5. The accidental decisions that changed history, including not having a waitlist6. The impact ChatGPT will have on SEO and product growth7. The counterintuitive reason why shipping unpolished AI features beats waiting for perfection8. Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown9. How TikTok comments became a primary user research channel early on—Brought to you by:Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/Vanta—Automate compliance. Simplify security: https://vanta.com/lennyPostHog—How developers build successful products: https://posthog.com/lenny—Transcript: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170411252/my-biggest-takeaways-from-this-conversation—Where to find Nick Turley• X: https://x.com/nickaturley• LinkedIn: https://www.linkedin.com/in/nicholasturley/• Website: https://nickturley.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nick Turley(04:52) GPT-5 launch(09:13) The vision for ChatGPT and AI assistants(13:52) The early days of ChatGPT(17:14) The success and impact of ChatGPT(20:44) Product development and iteration(23:11) Maximally accelerated: the OpenAI approach(26:17) Retention and user engagement(33:42) The future of chat interfaces(36:31) The evolution of ChatGPT(38:52) Subscription model and pricing strategies(42:10) Enterprise adoption and challenges(44:10) Balancing multiple product lines(52:13) Emergent use cases and user feedback(01:02:15) OpenAI’s unique product development approach(01:05:07) The importance of team composition(01:08:50) Balancing speed and quality in AI development(01:14:23) The role of evals in product development(01:16:13) The future of AI-driven content and GPTs(01:21:51) Philosophy and product leadership(01:23:47) Career journey and advice(01:27:49) Lightning round and final thoughts—References: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI)

Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb’s “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley’s tech mindset himself. Today, Chip leads the Modern Elder Academy, the world’s first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact.In this conversation, we discuss:1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence)5. His framework for navigating midlife transitions and finding meaning after 406. Specific tactics for older professionals to thrive in tech companies7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond8. Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes)—Brought to you by:Great Question—Empower everyone to run great research: https://www.greatquestion.com/lennyVanta—Automate compliance. Simplify security: https://vanta.com/lennyCoda—The all-in-one collaborative workspace: https://coda.io/lenny—Transcript: https://www.lennysnewsletter.com/p/chip-conley —My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation—Where to find Chip Conley:• LinkedIn: https://www.linkedin.com/in/chipconleysf/• Website: https://chipconley.com/• Modern Elder Academy: https://www.meawisdom.com/• Podcast: https://www.meawisdom.com/podcast/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Chip Conley(04:09) Chip’s journey with Airbnb(10:35) Insights on working with Brian Chesky(19:56) The value of intergenerational collaboration(25:57) Addressing ageism in tech(41:33) Chip’s early career and founding Joie de Vivre(43:54) A life-changing near-death experience(46:39) The importance of company culture(55:57) The Modern Elder Academy(59:21) The upside of aging(01:06:53) AI in daily life(01:09:14) Lightning round and final thoughts—Referenced:• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/• Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/• How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making• George Tenet: https://en.wikipedia.org/wiki/George_Tenet• Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US• Fest300: https://en.wikipedia.org/wiki/Fest300• John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/•Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html• Burning Man: https://burningman.org/• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/• Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter)• Maslow’s hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs• Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile• Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/• Becca Levy’s website: https://becca-levy.com/• Kabuki Springs & Spa: https://kabukisprings.com/• How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca• The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/• The Midlife Unraveling: https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling/• Four Seasons: https://www.fourseasons.com/• Blue Zones: https://www.bluezones.com/• The Esalen Institute: https://www.esalen.org/• Wisdom Well blog: https://www.meawisdom.com/wisdom-well/• Elizabeth Gilbert TED Talk: Your elusive creative genius: https://www.ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy• I’ll Push You: https://www.illpushyou.com/• Vuori shorts: https://vuoriclothing.com/collections/shorts• Fly Ranch: https://flyranch.burningman.org/—Recommended books:• Wisdom at Work: The Making of a Modern Elder: https://www.amazon.com/Wisdom-Work-Making-Modern-Elder/dp/0525572902• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484• Peak: How Great Companies Get Their Mojo from Maslow: https://www.amazon.com/Peak-Great-Companies-Their-Maslow/dp/0787988618• Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age: https://www.amazon.com/Learning-Love-Midlife-Reasons-Better/dp/0316567027• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807060100/• Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life: https://www.amazon.com/Emotional-Equations-Creating-Happiness-Business/dp/1451607261/• Big Magic: Creative Living Beyond Fear: https://www.amazon.com/Big-Magic-Creative-Living-Beyond/dp/1594634726—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)

Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member.In this conversation, you’ll learn:1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role3. The three AI market segments that matter4. Why AI agents will replace SaaS products5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama6. The counterintuitive go-to-market strategy most AI startups get wrong7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it)8. What he’s teaching his kids about AI that every parent should know—Brought to you by:CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lennyBasecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lennyVanta—Automate compliance. Simplify security: https://vanta.com/lenny—Transcript: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation—Where to find Bret Taylor:• X: https://x.com/btaylor• LinkedIn: https://www.linkedin.com/in/brettaylor/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Bret Taylor(04:10) Bret’s early career and first major mistake(08:24) The birth of Google Maps(11:57) Lessons from FriendFeed and the importance of honest feedback(31:30) The future of coding and AI’s role(45:26) Preparing the next generation for an AI-driven world(48:46) AI in education(52:05) Business strategies in the AI market(01:04:38) Outcome-based pricing in AI(01:09:15) Productivity gains and AI(01:17:35) Go-to-market strategies for AI products(01:21:49) Lightning round and final thoughts—Referenced:• Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/• “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98• Quip: https://quip.com/• Sierra: https://sierra.ai/• FriendFeed: https://en.wikipedia.org/wiki/FriendFeed• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/• Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/• Paul Buchheit on X: https://x.com/paultoo• Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/• Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama• Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey• Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia• Sam Altman on X: https://x.com/sama• Warren Buffett on X: https://x.com/warrenbuffett• Unix: https://en.wikipedia.org/wiki/Unix• Fortran: https://en.wikipedia.org/wiki/Fortran• C: https://en.wikipedia.org/wiki/C_(programming_language)• Python: https://www.python.org/• Perl: https://www.perl.org/• Rust: https://www.rust-lang.org/• Eleven Labs: https://elevenlabs.io/• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack• Confluent: https://www.confluent.io/• Databricks: https://www.databricks.com/• Snowflake: https://www.snowflake.com• Harvey: https://www.harvey.ai/• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Larry Summers’s website: https://larrysummers.com/• AutoCAD: https://www.autodesk.com/products/autocad/overview• Revit: https://www.autodesk.com/products/revit/• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://lenny.substack.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam• Cursor: https://cursor.com/• CodeX: https://openai.com/codex/• Claude Code: https://www.anthropic.com/claude-code• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• DirecTV: https://www.directv.com/• SiriusXM: https://www.siriusxm.com/• Wayfair: https://www.wayfair.com/• Akai: https://www.akaipro.com/• Chubbies Shorts: https://www.chubbiesshorts.com/• Weight Watchers: https://www.weightwatchers.com/• CLEAR: https://www.clearme.com/• Stripe: https://stripe.com/• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• Twilio: https://www.twilio.com/• ServiceNow: https://www.servicenow.com/• Adobe: https://www.adobe.com/• Jobs to be done: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta• Inception: https://www.imdb.com/title/tt1375666/• Alan Kay’s quote: https://www.brainyquote.com/quotes/alan_kay_100831• Jobs at Sierra: https://sierra.ai/careers—Recommended books:• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612• Endurance: Shackleton’s Incredible Voyage: https://www.amazon.com/Endurance-Shackletons-Incredible-Alfred-Lansing/dp/0465062881—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more

Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies.In this conversation, we discuss:1. The 2x2 framework that identifies your optimal pricing model2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products3. Why popular AI coding tools may have already doomed themselves with underpricing4. The “give-and-get” framework top negotiators use to extract maximum value from every deal5. The negotiation strategy that helped one founder 4x their deal size overnight6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything)7. Why AI companies must get monetization right from day one—not “figure it out later”8. How companies like Intercom’s Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution)9. The single question that reveals if your pricing is too complex—Brought to you by:Enterpret—Transform customer feedback into product growth: https://enterpret.com/lennyDX—A platform for measuring and improving developer productivity: https://getdx.com/lennyPersona—A global leader in digital identity verification: https://withpersona.com/lenny—Transcript: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation—Where to find Madhavan Ramanujam:• X: https://x.com/madhavansf• LinkedIn: https://www.linkedin.com/in/madhavansf/• Promo email for Scaling Innovation: promo@49palmsvc.com — If you’re purchasing more than five copies, send a screenshot of your receipt to enter Madhavan’s exclusive bundle raffle.—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Madhavan and his work(04:30) The core thesis of Scaling Innovation(09:20) Common traps founders fall into(12:06) Beautifully simple pricing(15:00) Mastering negotiations(26:51) Other strategies for effective pricing and monetization(27:35) How AI pricing is different(31:33) Handling POCs(36:25) The importance of mastering monetization(38:58) Choosing the right AI pricing model(43:13) Current trends in AI pricing(44:48) Strategizing for outcome-based models(50:23) Packaging strategies for scaling(51:37) Adapting pricing strategies over time(53:40) Key axioms for pricing success(58:00) Takeaways for founders(01:01:33) Lightning round and final thoughts—Referenced:• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan• Cursor: https://www.cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Sierra Finn: http://www.sierrafinn.com/• Chargeflow: https://www.chargeflow.io/• GitHub: https://github.com/• Intercom: https://www.intercom.com/• Warren Buffett’s quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing• Sierra: https://sierra.ai/• Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/• Mission: Impossible—The Final Reckoning: https://www.imdb.com/title/tt9603208/• Delphi: https://www.delphi.ai/• Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/• Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/• Lennybot: https://www.lennybot.com/• Granola: https://www.granola.ai/• Simon-Kucher: https://www.simon-kucher.com/• Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/—Recommended books:• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867• Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060• Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers: https://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417• Thinking Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/• Contagious: Why Things Catch On: https://www.amazon.com/Contagious-Things-Catch-Jonah-Berger/dp/1451686587/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to steer it responsibly.In this conversation, we discuss:1. The inside story of leaving OpenAI with the entire safety team to start Anthropic2. How Meta’s $100M offers reveal the true market price of top AI talent3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential4. Ben’s “economic Turing test” for knowing when we’ve achieved AGI—and why it’s likely coming by 2027-20285. Why he believes 20% unemployment is inevitable6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them7. How focusing on AI safety created Claude’s beloved personality8. What three skills he’s teaching his kids instead of traditional academics—Brought to you by:Sauce—Turn customer pain into product revenue: https://sauce.app/lennyLucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lennyFin—The #1 AI agent for customer service: https://fin.ai/lenny—Transcript: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168107911/my-biggest-takeaways-from-this-conversation—Where to find Ben Mann:• X: https://x.com/8enmann• LinkedIn: https://www.linkedin.com/in/benjamin-mann/• Website: https://benjmann.net/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Benjamin(04:43) The AI talent war(06:28) AI progress and scaling laws(10:50) Defining AGI and the economic Turing test(12:26) The impact of AI on jobs(17:45) Preparing for an AI future(24:05) Founding Anthropic(27:06) Balancing AI safety and progress(29:10) Constitutional AI and model alignment(34:21) The importance of AI safety(43:40) The risks of autonomous agents(45:40) Forecasting superintelligence(48:36) How hard is it to align AI?(53:19) Reinforcement learning from AI feedback (RLAIF)(57:03) AI's biggest bottlenecks(01:00:11) Personal reflections on responsibilities(01:02:36) Anthropic’s growth and innovations(01:07:48) Lightning round and final thoughts—Referenced:• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/• Anthropic CEO: AI Could Wipe Out 50% of Entry-Level White Collar Jobs: https://www.marketingaiinstitute.com/blog/dario-amodei-ai-entry-level-jobs• Alexa+: https://www.amazon.com/dp/B0DCCNHWV5• Azure: https://azure.microsoft.com/• Sam Altman on X: https://x.com/sama• Opus 3: https://www.anthropic.com/news/claude-3-family• Claude’s Constitution: https://www.anthropic.com/news/claudes-constitution• Greg Brockman on X: https://x.com/gdb• Anthropic’s Responsible Scaling Policy: https://www.anthropic.com/news/anthropics-responsible-scaling-policy• Agentic Misalignment: How LLMs could be insider threats: https://www.anthropic.com/research/agentic-misalignment• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff• Unitree: https://www.unitree.com/• Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke• How Reinforcement Learning from AI Feedback Works: https://www.assemblyai.com/blog/how-reinforcement-learning-from-ai-feedback-works• RLHF: https://en.wikipedia.org/wiki/Reinforcement_learning_from_human_feedback• Jared Kaplan on LinkedIn: https://www.linkedin.com/in/jared-kaplan-645843213/• Moore’s law: https://en.wikipedia.org/wiki/Moore%27s_law• Machine Intelligence Research Institute: https://intelligence.org/• Raph Lee on LinkedIn: https://www.linkedin.com/in/raphaeltlee/• “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question• Beth Barnes on LinkedIn: https://www.linkedin.com/in/elizabethmbarnes/• “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard• Pantheon on Netflix: https://www.netflix.com/title/81937398• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy• Kurzgesagt—In a Nutshell: https://www.youtube.com/channel/UCsXVk37bltHxD1rDPwtNM8Q• 5 tips to poop like a champion: https://8enmann.medium.com/5-tips-to-poop-like-a-champion-3292481a9651—Recommended books:• Superintelligence: Paths, Dangers, Strategies: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/0198739834• The Hacker and the State: Cyber Attacks and the New Normal of Geopolitics: https://www.amazon.com/Hacker-State-Attacks-Normal-Geopolitics/dp/0674987551• Replacing Guilt: Minding Our Way: https://www.amazon.com/Replacing-Guilt-Minding-Our-Way/dp/B086FTSB3Q• Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239• The Alignment Problem: Machine Learning and Human Values: https://www.amazon.com/Alignment-Problem-Machine-Learning-Values/dp/0393635821—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann

Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work.Learn:1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S.2. The most underrated AI tool for non-programmers3. An inside look at Every’s AI-first workflow4. Why every company needs an “AI operations lead”5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools—Brought to you by:CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lennyDX—A platform for measuring and improving developer productivity: https://getdx.com/lennyPostHog—How developers build successful products: https://posthog.com/lenny—Transcript: https://www.lennysnewsletter.com/p/inside-every-dan-shipper—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167681269/my-biggest-takeaways-from-this-conversation—Where to find Dan Shipper:• X: https://x.com/danshipper• LinkedIn: https://www.linkedin.com/in/danshipper/• Podcast: https://every.to/podcast—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome and introduction(04:04) Hot takes on AI and job reshoring(07:06) The power of Claude Code for non-coders(14:35) The future of AI in business operations(18:45) AI’s role in enhancing human skills(22:26) The evolution of AI tools and their applications(25:40) Building an AI-first company(29:50) Innovative AI operations and team dynamics(35:35) Dan's AI stack(41:26) Compounding engineering(48:29) The impact of AI on learning and development(50:10) Accelerating career growth with AI(51:36) Revolutionizing code review and workflow(53:07) The importance of coding knowledge(57:26) Building AI-driven products(01:02:01) Innovative fundraising strategies(01:08:45) Consulting and AI adoption in companies(01:17:01) The allocation economy and future skills(01:20:12) The value of generalists in the AI age(01:24:07) Lightning round and final thoughts—Referenced:• Claude Code: https://www.anthropic.com/claude-code• Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/• Microsoft Copilot: https://copilot.microsoft.com/• Cursor: https://www.cursor.com/• Base44: https://base44.com/• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng• Granola: https://www.granola.ai/• Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Every: https://every.to/• Cora: https://www.cora.computer/• Sparkle: https://makeitsparkle.co/• Spiral: https://spiral.computer/• Lex: https://lex.page/• Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/• Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/• Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/• Animalz: https://www.animalz.co/• Rachel Woods on X: https://x.com/rachel_l_woods• Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga• Claude Opus 4: https://www.anthropic.com/claude/opus• Codex: https://openai.com/index/introducing-codex/• Superwhisper: https://superwhisper.com/• Wispr Flow: https://wisprflow.ai/• Notion: https://www.notion.com/• Kieran Klaassen on LinkedIn: https://www.linkedin.com/in/kieran-klaassen/• Friday: https://www.friday.run/• Charlie: https://www.gocharlie.ai/product/ai-agents/• Avengers: https://en.wikipedia.org/wiki/Avengers_(Marvel_Cinematic_Universe)• Alex Duffy on LinkedIn: https://www.linkedin.com/in/alex-d/• Danny Aziz on LinkedIn: https://www.linkedin.com/in/dannyaziz/• Dia: https://www.diabrowser.com/• Reid Hoffman’s website: https://www.reidhoffman.org/• Starting Line VC: https://www.startingline.vc/• Walleye Capital: https://walleyecapital.com/• At This $10 Billion Hedge Fund, Using AI Just Became Mandatory: https://every.to/podcast/at-this-10-billion-hedge-fund-using-ai-just-became-mandatory• Reflexive AI usage is now a baseline expectation at Shopify: https://x.com/tobi/status/1909251946235437514• Klarna CEO Sebastian Siemiatkowski on Getting AI to Do the Work of 700 Customer Service Reps: https://www.sequoiacap.com/podcast/training-data-sebastian-siemiatkowski/• The Pin Factory: https://www.adamsmithworks.org/pin_factory.html• Deadwood on HBO: https://www.hbo.com/deadwood• Joel Spolsky on X: https://x.com/spolsky• Jason Fried’s website: https://world.hey.com/jason• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking• Sam Harris’s website: https://www.samharris.org/• Bill Simmons on X: https://x.com/billsimmons—Recommended books:• War and Peace: https://www.amazon.com/War-Peace-Vintage-Classics-Tolstoy/dp/1400079985• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002• Playing and Reality: https://www.amazon.com/Playing-Reality-Routledge-Classics-86/dp/0415345464• The Death of Ivan Ilyich: https://www.amazon.com/Death-Ivan-Ilyich-Leo-Tolstoy/dp/1468014315• A Swim in a Pond in the Rain: https://www.amazon.com/Swim-Pond-Rain-Russians-Writing/dp/1984856022• The Master and His Emissary: The Divided Brain and the Making of the Western World: https://www.amazon.com/Master-His-Emissary-Divided-Western/dp/0300245920/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every)

Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can’t build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days.What you’ll learn:1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days—including templates you can use immediately2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team)3. The three fundamental questions every founder should answer before writing a line of code4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues5. The seven “magic lenses” for choosing between multiple product ideas6. The biggest mistake engineers make when building with AI tools7. The paradox of speed: why “building nothing first” can get you to product-market fit faster—Brought to you by:Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fsParagon—Ship every SaaS integration your customers want: https://www.useparagon.com/lennyCoda—The all-in-one collaborative workspace: https://coda.io/lenny—Transcript: https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky—My biggest takeaways (for paid newsletter subscribers):https://www.lennysnewsletter.com/i/167485876/my-biggest-takeaways-from-this-conversation—Where to find Jake Knapp:• X: https://twitter.com/jakek• LinkedIn: https://www.linkedin.com/in/jake-knapp/• Website: https://jakeknapp.com/—Where to find John Zeratsky:• X: https://twitter.com/jazer• LinkedIn: https://www.linkedin.com/in/johnzeratsky/• Website: https://johnzeratsky.com/—In this episode, we cover:(00:00) Introduction to Jake Knapp and John Zeratsky(04:41) Origins of the Design Sprint(11:06) The Foundation Sprint process(14:40) Phase one: The basics(16:57) Case study: Latchet(28:50) Phase two: Differentiation(36:24) The importance of differentiation(40:15) Thoughts on price differentiation(43:37) Case study: Mellow(46:04) Custom differentiators(49:30) The mini manifesto(52:02) Phase three: Approach to the project(54:50) Magic lenses activity(01:02:39) Prototyping and testing(01:10:00) Real-world examples and success stories(01:15:15) Motivation behind The Foundation Sprint(01:17:15) The outcome of the sprint: The founding hypothesis(01:19:28) The Design Sprint(01:28:19) The role of AI in prototyping(01:36:50) Final thoughts and resources—Referenced:• Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint• Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake• Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/• Character Capital: https://www.character.vc/• Character Labs: https://www.character.vc/labs• Etsy: https://www.etsy.com/• Shopify: https://www.shopify.com/• Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek• Sonos: https://www.sonos.com/• Vercel: https://vercel.com/• Windsurf: https://windsurf.com/• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning• Positioning: https://www.lennysnewsletter.com/p/positioning• 10 things we know to be true: https://about.google/company-info/philosophy/• Gandalf: https://en.wikipedia.org/wiki/Gandalf• Frodo: https://en.wikipedia.org/wiki/Frodo_Baggins• Mordor: https://en.wikipedia.org/wiki/Mordor• 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley: https://www.lennysnewsletter.com/p/35-years-of-product-design-wisdom-bob-baxley• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas• Base44: https://base44.com/• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo• Google Meet: https://meet.google.com/• Blue Bottle Coffee: https://bluebottlecoffee.com• Reclaim: https://reclaim.ai/• The official Foundation Sprint + Design Sprint template: https://www.character.vc/miro-template• Rippling: https://www.rippling.com/• Latchet: https://latchet.com/• Mellow: http://getmellow.com/• AxionOrbital: https://axionorbital.space/—Recommended books:• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422• Click: How to Make What People Want: https://www.amazon.com/Click-Make-What-People-Want/dp/1668072114Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Rapidly test and validate any startup idea with the 2-day Foundation Sprint (from the creators of the Design Sprint) | Jake Knapp & John Zeratsky (Character Capital)

Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 users, all while navigating two wars in Israel and never raising a dollar of outside funding.What you’ll learn:1. The growth playbook that took Base44 from three friends to 400,000 users without spending any money on marketing2. How he hasn’t written a single line of front-end code in three months—and how to structure your code repository to make it easier for AI to write your code3. His AI productivity stack that allowed him to compete against heavily funded competitors4. Why being a solo founder in AI might be the ultimate advantage (and the wedding story that almost killed the business)5. The story of signing the $80M acquisition deal while war broke out with Iran6. How to identify when to sell vs. stay independent (and why Maor chose acquisition despite being highly profitable)7. The counterintuitive product decision that tripled activation by removing a “helpful” feature8. How building in public on LinkedIn drove more growth than any paid channel—Brought to you by:Sauce—Turn customer pain into product revenue: https://sauce.app/lennyDscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/Contentsquare—Create better digital experiences: https://contentsquare.com/lenny/—Transcript: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167384119/my-biggest-takeaways-from-this-conversation—Where to find Maor Shlomo:• X: https://x.com/ms_base44• LinkedIn: https://www.linkedin.com/in/maor-shlomo-1088b4144/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Maor and Base44(08:16) The origin story: how Base44 came to be(14:55) Bootstrapping and solo founding: challenges and insights(22:52) Productivity hacks and tech stack for solo founders(27:23) How to get started using Base44(28:47) Thoughts on raising money(34:05) Distribution in the age of AI(36:09) Ambition and goals(40:05) Growth strategies: from first users to thousands(51:32) Building in public(57:42) The solo founder journey(01:00:23) Community support(01:03:23) Hackathons and partnerships(01:06:42) The importance of velocity in product development(01:08:20) Technical stack and infrastructure insights(01:15:24) Activation lessons(01:18:19) The acquisition journey with Wix(01:25:14) Final thoughts and advice for founders—Referenced:• Base44: https://base44.com/• Retool: https://retool.com/• Tzofim: https://www.israelscouts.org/• Y Combinator: https://www.ycombinator.com/• RescueTime: https://www.rescuetime.com/• Cursor: https://www.cursor.com/• Wix: https://www.wix.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Snowflake: https://www.snowflake.com• Yoav Orlev on LinkedIn: https://www.linkedin.com/in/yoav-orlev-4a044b72• WhatsApp: https://www.whatsapp.com/• Amazon: https://www.amazon.com/• Google: https://about.google/• MongoDB: https://www.mongodb.com/• Deloitte: https://www.deloitte.com/• Render: Render.com• Claude 4: https://www.anthropic.com/news/claude-4• Gemini: https://gemini.google.com/app• Cloudflare: https://www.cloudflare.com/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo

Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital.In this conversation, you’ll learn:1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant)3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership”4. Telltale signs you should shut down (or never start) that startup idea5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication6. His prediction that most knowledge work will be automated—and the skills to teach your kids now—Brought to you by:Sauce—Turn customer pain into product revenueEnterpret—Transform customer feedback into product growthMiro—A collaborative visual platform where your best work comes to life—Where to find Andrew Wilkinson:• X: https://x.com/awilkinson• LinkedIn: https://www.linkedin.com/in/awilkinson/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Andrew Wilkinson(04:07) Finding the right business idea(07:18) Avoiding common business pitfalls(11:58) Finding your unfair advantage(17:08) Fish where the fish are(20:08) Why boring is good(25:30) Bootstrapping vs. venture capital(31:20) Lessons from acquiring and managing businesses(36:47) Avoiding people problems(42:39) Leveraging AI in business and life(49:30) The Limitless device(53:13) Job displacement and AI’s future impact(58:20) Advice for new grads(01:02:50) Parenting in the age of AI(01:05:26) The pursuit of happiness beyond wealth(01:10:10) Mental health and medication(01:16:45) Lightning round and final thoughts—Referenced:• Andrew’s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182• Metalab: https://www.metalab.com/• Letterboxd: https://letterboxd.com/• AeroPress: https://aeropress.com/• Brian Armstrong on X: https://x.com/brian_armstrong• Warren Buffett’s quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman• Flow: https://www.getflow.com/• Instacart: https://www.instacart.com/• Things: https://culturedcode.com/things/• Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/• Salesforce: https://www.salesforce.com/• Serato: https://serato.com/• Chris Sparling on X: https://x.com/_sparling_• Lindy: https://www.lindy.ai/• Replit: https://replit.com/• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman)• Malcolm Gladwell’s website: https://www.gladwellbooks.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Limitless: https://www.limitless.ai/• Perplexity: https://www.perplexity.ai/• Claude: https://claude.ai/• ChatGPT: https://chatgpt.com/• Gemini: https://gemini.google.com/app• William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly• Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo• Sam Altman on X: https://x.com/sama• Dario Amodei on X: https://x.com/darioamodei• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Challengers on AppleTV+: https://tv.apple.com/us/movie/challengers/umc.cmc.53cuz33n4e74ixj8whccj87oc• Matic vacuum: https://maticrobots.com/• Jerzy Gregorek’s quote: https://www.goodreads.com/quotes/8652595-hard-choices-easy-life-easy-choices-hard-life• Tiny: https://www.tiny.com/• Dribbble: https://dribbble.com/—Recommended books:• The Laws of Human Nature: https://www.amazon.com/Laws-Human-Nature-Robert-Greene/dp/0525428143• How to Get Rich: One of the World’s Greatest Entrepreneurs Shares His Secrets: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)

David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft’s Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel’s Pentium, Apple’s PowerBook, and Swiffer. Over 40 years, David’s team has named nearly 4,000 brands and companies, employing over 250 linguists and pioneering naming innovation.What you’ll learn:1. The three-step process that generated names like Windsurf and Vercel2. How a name can give you the edge that no marketing budget can buy3. Why you won’t “know it when you see it”4. Why Microsoft called Azure “a dumb name” before it became their billion-dollar cloud platform5. Why polarizing opinions are the strongest signal that you’ve found the right name6. How every letter of the alphabet creates a specific psychological vibration7. The diamond framework: a 4-step process any founder can use to find their perfect name8. Why domain names don’t matter anymore in the age of AI—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsStripe—Helping companies of all sizes grow revenueOneSchema—Import CSV data 10x faster—Where to find David Placek:• LinkedIn: https://www.linkedin.com/in/david-placek-05a82/• Website: https://www.lexiconbranding.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to David and Lexicon Branding(04:44) The story of Sonos(09:27) The psychology of naming(11:33) The initial resistance to Microsoft's Azure(14:35) The importance of a great brand name(18:11) The three steps of naming: create, invent, implement(28:23) Qualities of great brand name creators(31:24) How long the naming process takes(32:12) The Windsurf case study(36:10) Naming in the AI era(39:37) When to change your name(43:10) The role of linguists(45:54) The power of letters in branding(48:15) The Vercel case study(50:12) The implementation phase(52:52) Client management and market success(55:16) The diamond exercise(01:04:23) Suspending judgment(01:07:31) Polarization and boldness(01:11:01) Domain names(01:12:48) Final thoughts and lightning round—Referenced:• PowerBook: https://en.wikipedia.org/wiki/PowerBook• Pentium: https://en.wikipedia.org/wiki/Pentium• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry• Swiffer: https://www.swiffer.com/• Impossible Burger: https://impossiblefoods.com/• Vercel: https://vercel.com/• Windsurf: https://windsurf.com/• CapCut: https://www.capcut.com/• Azure: https://azure.microsoft.com/• Sonos: https://www.sonos.com/• John MacFarlane on LinkedIn: https://www.linkedin.com/in/john-macfarlane-08a8aa20/• Harry Potter: https://en.wikipedia.org/wiki/Harry_Potter_(film_series)• The Call of the Wild: https://en.wikipedia.org/wiki/The_Call_of_the_Wild• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Sound symbolism: https://en.wikipedia.org/wiki/Sound_symbolism• Anduril: https://www.anduril.com/• Anthropic: https://www.anthropic.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Y Combinator: https://www.ycombinator.com/• Chevrolet Corvette: https://en.wikipedia.org/wiki/Chevrolet_Corvette• Viagra: https://www.viagra.com/• In vino veritas: https://en.wikipedia.org/wiki/In_vino_veritas• Infoseek: https://en.wikipedia.org/wiki/Infoseek• Andy Grove: https://en.wikipedia.org/wiki/Andrew_Grove• Churchill at War on Netflix: https://www.netflix.com/title/81609374• Yellowstone on Prime Video: https://www.amazon.com/Yellowstone-Season-1/dp/B07D7FBB8Z• 1883 on Prime Video: https://www.amazon.com/1883-Season-1/dp/B0B8JTS8QW• 1923 on Paramount+: https://www.paramountplus.com/shows/1923/• Taylor Sheridan on X: https://x.com/taylorSheridan• Hardy fly rods: https://www.hardyfishing.com/collections/fly-rods• T.E. Lawrence quote: https://www.goodreads.com/quotes/11340-all-men-dream-but-not-equally-those-who-dream-by• Lawrence of Arabia: https://www.imdb.com/title/tt0056172/• DreamWorks: https://www.dreamworks.com/—Recommended books:• Thucydides’ Melian Dialogue: Commentary, Text, and Vocabulary: https://www.amazon.com/Thucydides-Melian-Dialogue-Commentary-Vocabulary/dp/0692772367• Resilience: Hard-Won Wisdom for Living a Better Life: https://www.amazon.com/Resilience-Hard-Won-Wisdom-Living-Better/dp/054432398X/• Churchill: Walking with Destiny: https://www.amazon.com/Churchill-Walking-Destiny-Andrew-Roberts/dp/1101980990—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding)

Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions—including Facebook’s News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he’s investing in early-stage founders at Felicis. In this episode, Peter dives into his most valuable lessons from building and scaling some of tech’s most iconic products and companies.What you’ll learn:1. Peter’s one‑sentence test for hiring superstars2. Why your product (probably) doesn’t matter3. Why you don’t need a tech breakthrough to build a huge business4. The five PM archetypes, and how to build a team of Avengers5. Counterintuitive lessons on growing products from 0 to 1, and 1 to 1006. The importance of data flywheels and workflows—Brought to you by:Paragon—Ship every SaaS integration your customers wantPragmatic Institute—Industry‑recognized product, marketing, and AI training and certificationsContentsquare—Create better digital experiences—Where to find Peter Deng:• X: https://x.com/pxd• LinkedIn: https://www.linkedin.com/in/peterxdeng/—In this episode, we cover:(00:00) Introduction to Peter Deng(05:41) AI and AGI insights(11:35) The future of education with AI(16:53) The power of language in leadership(21:01) Building iconic products(36:44) Scaling from zero to 100(41:56) Balancing short- and long-term goals(47:12) Creating a healthy tension in teams(50:02) The five archetypes of product managers(55:39) Primary and secondary archetypes(58:47) Hiring for growth mindset and autonomy(01:15:52) Effective management and communication strategies(01:19:23) Presentation advice and self-advocacy(01:25:50) Balancing craft and practicality in product management(01:30:40) The importance of empathy in design thinking(01:35:45) Career decisions and learning opportunities(01:42:05) Lessons from product failures(01:45:42) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com/• Artificial general intelligence (AGI): https://en.wikipedia.org/wiki/Artificial_general_intelligence• Head of ChatGPT answers philosophical questions about AI at SXSW 2024 with SignalFire’s Josh Constine: https://www.youtube.com/watch?v=mgbgI0R6XCw• Professors Are Using A.I., Too. Now What?: https://www.npr.org/2025/05/21/1252663599/kashmir-hill-ai#:~:text=Now%20What• Herbert H. Clark: https://web.stanford.edu/~clark/• Russian speakers get the blues: https://www.newscientist.com/article/dn11759-russian-speakers-get-the-blues/• Ilya Sutskever (OpenAI Chief Scientist)—Building AGI, Alignment, Future Models, Spies, Microsoft, Taiwan, & Enlightenment: https://www.dwarkesh.com/p/ilya-sutskever• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Granola: https://www.granola.ai/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/• Airtable: https://www.airtable.com/• George Lee on LinkedIn: https://www.linkedin.com/in/geolee/• Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/• Lauryn Motamedi on LinkedIn: https://www.linkedin.com/in/laurynmotamedi/• Twilio: https://www.twilio.com/• Nick Turley on LinkedIn: https://www.linkedin.com/in/nicholasturley/• Ian Silber on LinkedIn: https://www.linkedin.com/in/iansilber/• Thomas Dimson on LinkedIn: https://www.linkedin.com/in/thomasdimson/• Joey Flynn on LinkedIn: https://www.linkedin.com/in/joey-flynn-8291586b/• Ryan O’Rourke’s website: https://www.rourkery.com/• Joanne Jang on LinkedIn: https://www.linkedin.com/in/jangjoanne/• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Jill Hazelbaker on LinkedIn: https://www.linkedin.com/in/jill-hazelbaker-3aa32422/• Guy Kawasaki’s website: https://guykawasaki.com/• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/• Sachin Kansal on LinkedIn: https://www.linkedin.com/in/sachinkansal/• IDEO design thinking: https://designthinking.ideo.com/• The 7 Steps of the Design Thinking Process: https://www.ideou.com/blogs/inspiration/design-thinking-process• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu• Jeff Bezos’s quote: https://news.ycombinator.com/item?id=27778175• Friendster: https://en.wikipedia.org/wiki/Friendster• Myspace: https://en.wikipedia.org/wiki/Myspace• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen• “Smile” by Jay-Z: https://www.youtube.com/watch?v=SSumXG5_rs8&list=RDSSumXG5_rs8&start_radio=1• The Wire on HBO: https://www.hbo.com/the-wire• Felicis: https://www.felicis.com/—Recommended books:• Sapiens: A Brief History of Humankind: https://www.amazon.com/Sapiens-Humankind-Yuval-Noah-Harari/dp/0062316095• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654• The Silk Roads: A New History of the World: https://www.amazon.com/Silk-Roads-New-History-World/dp/1101912375—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng

Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT’s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn’t). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques.In this episode, you’ll learn:1. The 5 most effective prompt engineering techniques2. Why “role prompting” and threatening the AI no longer works—and what to do instead3. The two types of prompt engineering: conversational and product/system prompts4. A primer on prompt injection and AI red teaming—including real jailbreak tactics that are still fooling top models5. Why AI agents and robots will be the next major security threat6. How to get started in AI red teaming and prompt engineering7. Practical defense to put in place for your AI products—Brought to you by:Eppo—Run reliable, impactful experimentsStripe—Helping companies of all sizes grow revenueVanta—Automate compliance. Simplify security—Where to find Sander Schulhoff:• X: https://x.com/sanderschulhoff• LinkedIn: https://www.linkedin.com/in/sander-schulhoff/• Website: https://sanderschulhoff.com/• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC• Free Lightning Lesson “How to Secure Your AI System” on 6/24: https://bit.ly/4ld9vZL—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Sander Schulhoff(04:29) The importance of prompt engineering(06:30) Real-world applications and examples(10:54) Basic prompt engineering techniques(23:46) Advanced prompt engineering techniques(29:00) The role of context and additional information(39:24) Ensembling techniques and thought generation(49:48) Conversational techniques for better results(50:46) Introduction to prompt injection(52:27) AI red teaming and competitions(54:23) The growing importance of AI security(01:02:45) Techniques to bypass AI safeguards(01:05:21) Challenges in AI security and future outlook(01:18:33) Misalignment and AI's potential risks(01:25:03) Final thoughts and lightning round—Referenced:• Reid Hoffman’s tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822• AI Engineer World’s Fair: https://www.ai.engineer/• What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi• Devin: https://devin.ai/• Cursor: https://www.cursor.com/• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Granola: https://www.granola.ai/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Technique #3: Examples in Prompts: From Zero-Shot to Few-Shot: https://learnprompting.org/docs/basics/few_shot?srsltid=AfmBOor2owyGXtzJZ8n0fJVCctM7UPZgZmH-mBuxRW4t9-kkaMd3LJVv• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0• State-of-the-Art Prompting for AI Agents | Y Combinator: https://www.youtube.com/watch?v=DL82mGde6wo• Use XML tags to structure your prompts: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags• Role Prompting: https://learnprompting.org/docs/basics/roles?srsltid=AfmBOor2jcxJQvWBZyFa030Qt0fIIov3hSiWvI9VFyjO-Qp478EPJIU7• Is Role Prompting Effective?: https://learnprompting.org/blog/role_prompting?srsltid=AfmBOooiiyLD-0CsCYZ4m3SDhYOmtTyaTzeDo0FvK_i1x1gLM8MJS-Sn• Introduction to Decomposition Prompting Techniques: https://learnprompting.org/docs/advanced/decomposition/introduction?srsltid=AfmBOoojJmTQgBlmSlGYQ8kl-JPpVUlLKkL4YcFGS5u54JyeumUwlcBI• LLM Self-Evaluation: https://learnprompting.org/docs/reliability/lm_self_eval• Philip Resnik on X: https://x.com/psresnik• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Introduction to Ensembling Prompting: https://learnprompting.org/docs/advanced/ensembling/introduction?srsltid=AfmBOooGSyqsrjnEbXSYoKpG0ZlpT278NHQA6Fd8gMvNTJlWu7-qEYzh• Random forest: https://en.wikipedia.org/wiki/Random_forest• Chain-of-Thought Prompting: https://learnprompting.org/docs/intermediate/chain_of_thought?srsltid=AfmBOoqwE7SXlluy2sx_QY_VOKduyBplWtIWKEJaD6FkJW3TqeKPSJfx• Prompt Injecting: https://learnprompting.org/docs/prompt_hacking/injection?srsltid=AfmBOoqGgqbfXStrD6vlw5jy8HhEaESgGo2e57jyWL8lkZKktt_P6Zvn• Announcing HackAPrompt 2.0: The World’s Largest AI Red-Teaming Hackathon: https://learnprompting.org/blog/announce-hackaprompt-2?srsltid=AfmBOopXKsHxy4aUtsvPCUtEu7x74NCAEnlTIdNzo7nfMDVwZ9ilTlkp• Infant with rare, incurable disease is first to successfully receive personalized gene therapy treatment: https://www.nih.gov/news-events/news-releases/infant-rare-incurable-disease-first-successfully-receive-personalized-gene-therapy-treatment• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Copilot: https://copilot.microsoft.com/chats/rcxhzvKgZvz8ajUrKdBtX• GitHub Copilot: https://github.com/features/copilot• Defensive Measures: https://learnprompting.org/docs/prompt_hacking/defensive_measures/introduction• Sam Altman on X: https://x.com/sama• Three Laws of Robotics: https://en.wikipedia.org/wiki/Three_Laws_of_Robotics• Anthropic’s new AI model turns to blackmail when engineers try to take it offline: https://techcrunch.com/2025/05/22/anthropics-new-ai-model-turns-to-blackmail-when-engineers-try-to-take-it-offline/• Palisade Research: https://palisaderesearch.org/• When AI Thinks It Will Lose, It Sometimes Cheats, Study Finds: https://time.com/7259395/ai-chess-cheating-palisade-research/• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html• 1883 on Paramount+: https://www.paramountplus.com/shows/1883/• Black Mirror on Netflix: https://www.netflix.com/title/70264888• Daylight Computer: https://daylightcomputer.com/• Theodore Roosevelt’s quote: https://www.goodreads.com/quotes/622252-i-wish-to-preach-not-the-doctrine-of-ignoble-ease• HackAPrompt 2.0: https://www.hackaprompt.com/—Recommended books:• Ender’s Game: https://www.amazon.com/Enders-Ender-Quintet-Orson-Scott/dp/0812550706• The River of Doubt: Theodore Roosevelt’s Darkest Journey: https://www.amazon.com/River-Doubt-Theodore-Roosevelts-Darkest/dp/0767913736—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)

Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox.In this episode, you’ll learn:• How to teach your team to be able to “take a punch”• Specific tactics to counter negative perceptions and reframe setbacks productively• Powerful behavioral strategies to form positive habits• Practical approaches for creating space in your workday to encourage creativity and deep thinking• The underestimated potential of AI in accelerating your personal and professional growth• Why you’re not the protagonist at your company (and why that’s liberating)• How WHOOP uses reward loops to drive real behavior change—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsPersona—A global leader in digital identity verificationAttio—The powerful, flexible CRM for fast-growing startups—Where to find Hilary Gridley:• X: https://x.com/yourgirlhils• LinkedIn: https://www.linkedin.com/in/hilarygridley/• Newsletter: https://hils.substack.com/• Maven course: https://maven.com/hilary-gridley/ai-powered-people-management—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Hilary’s background(04:31) Teaching teams to handle criticism and setbacks(17:57) Behavioral activation and mental health in the workplace(22:59) The importance of putting yourself out there(27:51) Transparency and communication in leadership(38:10) How to respectfully disagree with your manager(41:49) How to use “magic questions” to decode how people think(49:54) Why you’re not the protagonist at your company(52:48) Aligning with the CEO's vision(01:01:02) Building effective habits(01:11:14) Promoting team well-being(01:14:28) Creating space for creativity(01:20:45) AI’s role in accelerating learning(01:30:35) Pivotal career moments(01:37:21) Lessons from failure(01:39:49) Exciting new features of WHOOP 5.0(01:44:19) Lightning round and final thoughts—Referenced:• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/how-custom-gpts-can-make-you-a-better-manager• WHOOP: https://www.whoop.com/• Big Health: https://www.bighealth.com/• What is behavioral activation?: https://www.medicalnewstoday.com/articles/behavioral-activation• Will Ahmed on LinkedIn: https://www.linkedin.com/in/willahmed/• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams/• Coinbase: https://www.coinbase.com/• Bridge: https://www.bridge.xyz/• Stripe: https://stripe.com/• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer• Paths to Power course: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf• VO₂ max: https://en.wikipedia.org/wiki/VO2_max• Peter Attia on X: https://x.com/PeterAttiaMD• Hilary Gridley’s 30 days of GPT: https://docs.google.com/spreadsheets/d/1zJ4rbi9YcQuGqGxc6-AQD0-44oT9l4Eyono0AdpgJbA/edit?gid=0#gid=0• The Handle Bar in Boston: https://www.thehandlebarstudios.com/ourstudios/charlestown• From chalkboards to chatbots: Transforming learning in Nigeria, one prompt at a time: https://blogs.worldbank.org/en/education/From-chalkboards-to-chatbots-Transforming-learning-in-Nigeria• Product Management Logic Coach GPT: https://chatgpt.com/g/g-673290301700819084afa36bdbcdfa3b-product-management-logic-coach• Dropbox: https://www.dropbox.com/• WHOOP Advanced Labs: https://www.whoop.com/us/en/waitlist/?srsltid=AfmBOor2pP5qC3n7I23Z0ZIrYE99CjAKT9xSHQxbuyxmz_wFUBGH3e-n• Negative capability: https://en.wikipedia.org/wiki/Negative_capability• John Keats: https://en.wikipedia.org/wiki/John_Keats• The Rehearsal: https://www.hbo.com/the-rehearsal• Zwift: https://www.zwift.com/• Beavis and Butthead Do ‘Creep’: https://www.youtube.com/watch?v=zv_gSmH0Ieg• “Sea Grapes” by Derek Walcott: https://www.poetryfoundation.org/poems/57111/sea-grapes• Free month of WHOOP: https://join.whoop.com/us/en/hilary/—Recommended books:• 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/• Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599• East of Eden: https://www.amazon.com/East-Eden-John-Steinbeck-Centennial/dp/0142004235• The Sun Also Rises: https://www.amazon.com/Sun-Also-Rises-Hemingway-Library/dp/1501121960/• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions.What you’ll learn:• Why design should report to engineering, not product• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60• How to create design tenets vs. principles (with real examples)• The counterintuitive reason to delay drawing or prototyping as long as possible• Why software is fundamentally a medium, like film or music (not just a tool)• Why Bob “bounced off the culture” at Pinterest, and lessons from failure• The lunar landing story that teaches us about championing radical ideas• How to evaluate if a company truly values design before joining• The moral obligation of software makers to build great products—This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.—Where to find Bob Baxley:• Instagram: https://www.instagram.com/baxley/• LinkedIn: https://www.linkedin.com/in/bbaxley/• Website: http://www.bobbaxley.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Bob Baxley(03:52) Apple's lasting culture(06:15) Navigating unique company cultures(13:19) Finding a company that truly values your role(15:46) What is design?(17:17) How to help founders understand the value of design(23:08) How to align product managers and designers(26:31) Design reporting to engineering(30:54) Integrating engineers early in the design process(33:43) The maker mindset(35:14) Challenging the assumption that design is time-intensive(38:04) Design tenets vs. design principles(45:25) The moral obligation of great design(51:48) Understanding software as a medium(01:01:20) Reducing ambiguity for product teams(01:07:04) Giving designers space for creativity(01:08:48) The "primal mark" concept(01:12:05) AI prototyping tools: benefits and risks(01:17:00) AI as a life coach(01:21:22) Life lessons from the Apollo program(01:28:24) Lightning round and final thoughts—Referenced:• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney• Pinterest: https://www.pinterest.com/• X: https://x.com/• Uber: https://www.uber.com/• Airbnb: https://www.airbnb.com/• Slack: https://slack.com/• Ed Catmull on X: https://x.com/edcatmull• John Lasseter on X: https://x.com/johnlasseter5• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on• Humane: https://en.wikipedia.org/wiki/Humane_Inc.• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/• Tim Cook on X: https://x.com/tim_cook• ThoughtSpot: https://www.thoughtspot.com/• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/• Honeywell: https://www.honeywell.com• IDEO: https://www.ideo.com/• Nutanix: https://www.nutanix.com/• Lego: https://www.lego.com/• Leica: https://leica-camera.com/• Porsche: https://www.porsche.com/• Patagonia: https://www.patagonia.com• Brian Eno’s website: https://www.brian-eno.net/• Scenius: why creatives are stronger together: https://thecreativelife.net/scenius/• The Beatles website: https://www.thebeatles.com/• Disneyland: https://disneyland.disney.go.com/destinations/disneyland/• Tomorrowland: https://disneyland.disney.go.com/destinations/disneyland/tomorrowland/• Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product): https://www.lennysnewsletter.com/p/unorthodox-product-lessons-from-n26-and-more• Larry Page: https://en.wikipedia.org/wiki/Larry_Page• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin• Design Principles: https://principles.design/• Tableau: https://www.tableau.com/• Figma: https://www.figma.com/• Target self-checkout: https://corporate.target.com/press/fact-sheet/2024/03/checkout-improvements• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• eBay: https://www.ebay.com/• Williams Sonoma: https://www.williams-sonoma.com/• Amazon: https://www.amazon.com/• Monument to a Dead Child | Raw Data: https://podcasts.apple.com/ca/podcast/monument-to-a-dead-child/id1042137974• Toast: https://pos.toasttab.com/• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas• The Plant: https://pixar.fandom.com/wiki/The_Plant• Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/• John C. Houbolt: https://www.nasa.gov/centers-and-facilities/langley/john-c-houbolt/• The Apollo program: https://www.nasa.gov/the-apollo-program/• Archive clip: JFK at Rice University, Sept. 12, 1962—“We choose to go to the moon”: https://www.youtube.com/watch?v=QXqlziZV63k• Alan Shepard: https://www.nasa.gov/former-astronaut-alan-shepard/\• Blue Origin: https://www.blueorigin.com/• Yuri Gagarin: https://en.wikipedia.org/wiki/Yuri_Gagarin• Wernher von Braun: https://en.wikipedia.org/wiki/Wernher_von_Braun• Yuri Kondratyuk: https://en.wikipedia.org/wiki/Yuri_Kondratyuk• John Houbolt’s memo: https://space.stackexchange.com/questions/2823/text-of-john-houbolts-letter-proposing-lunar-orbit-rendezvous-for-apollo• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx• Lawrence of Arabia on Prime Video: https://www.amazon.com/Lawrence-Arabia-Peter-OToole/dp/B0088OINTU• Leica M6: https://leica-camera.com/en-US/photography/cameras/m/m6• Habitica: https://habitica.com/static/home• Andor on Disney+: https://www.disneyplus.com/browse/entity-faba988a-a9f5-45f2-a074-0775a7d6f67a• Edward Tufte quote: https://quotefancy.com/quote/1449650/Edward-Tufte-Good-design-is-clear-thinking-made-visible-bad-design-is-stupidity-made• Ansel Adams quote: https://www.brainyquote.com/quotes/ansel_adams_106035• It Takes a Village to Determine the Origins of an African Proverb: https://www.npr.org/sections/goatsandsoda/2016/07/30/487925796/it-takes-a-village-to-determine-the-origins-of-an-african-proverb• Henry Modisett on LinkedIn: https://www.linkedin.com/in/henrymodisett/• Perplexity: https://www.perplexity.ai/• Golden State Warriors: https://www.nba.com/warriors/• Steph Curry: https://www.espn.com/nba/player/_/id/3975/stephen-curry—Recommended books:• From Counterculture to Cyberculture: Stewart Brand, the Whole Earth Network, and the Rise of Digital Utopianism: https://www.amazon.com/Counterculture-Cyberculture-Stewart-Network-Utopianism/dp/0226817423• Hare Brain, Tortoise Mind: How Intelligence Increases When You Think Less: https://www.amazon.com/Hare-Brain-Tortoise-Mind-Intelligence/dp/0060955414• The Elements of Typographic Style: https://www.amazon.com/Elements-Typographic-Style-Robert-Bringhurst/dp/0881791326• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0060589469• Time and the Art of Living: https://www.amazon.com/Time-Art-Living-Robert-Grudin/dp/0062503553/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley

Sebastian Barrios was the longtime head of product and engineering at Mercado Libre, the largest company in Latin America—valued at over $100 billion and home to more than 100,000 employees. There, he led a team of more than 18,000 engineers across 18 countries and oversaw an astonishing 30,000 code deployments a day. Before Mercado Libre, he founded multiple startups, including a ridesharing company that competed directly with Uber in Latin America. And at just 17, he got a personal phone call from Steve Jobs asking him to take his app off the App Store. Today, Sebastian is the SVP of Engineering at Roblox.What you’ll learn:• Why Mercado Libre operates with 95% fewer PMs than typical tech companies (and how it actually works)• How to maintain product quality with 30,000 daily deployments and distributed ownership• The weekly email system Sebastian uses to maintain alignment with leadership• How to build a culture of radical candor and direct feedback in a traditionally hierarchical region• The counterintuitive approach to product reviews that keeps 18,000 engineers aligned• How to evaluate hype cycles (crypto, AI) pragmatically while staying innovative—Brought to you by:Merge—A single API to add hundreds of integrations into your appVanta—Automate compliance. Simplify securityLinkedIn Ads—Reach professionals and drive results for your business—Where to find Sebastian Barrios:• LinkedIn: https://www.linkedin.com/in/zebas/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Sebastian Barrios and Mercado Libre(05:03) Mercado Libre’s scale and unique ways of operating(14:48) AI’s impact on operations(19:19) Empowering teams and reducing fear of failure(34:20) The importance of radical candor(38:26) Weekly updates(41:03) Avoiding hype cycles(44:24) When Steve Jobs personally called 17-year-old Sebastian(49:00) Building successful app businesses(55:33) Unique personal habits(01:04:00) Raising independent children(01:07:15) Lightning round and final thoughts—Referenced:• Mercado Libre: https://www.mercadolibre.com/• Claude: https://claude.ai/• Salesforce: https://www.salesforce.com/• Nvidia: https://www.nvidia.com/• TikTok: https://www.tiktok.com/• Adobe: https://www.adobe.com/• Uber: https://www.uber.com/• OpenAI: https://openai.com/• Marcos Galperin on LinkedIn: https://www.linkedin.com/in/marcosgalperin/• Cursor: https://www.cursor.com/• Windsurf: https://windsurf.com/• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm• How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers• Intercom: https://www.intercom.com/• Atlassian: https://www.atlassian.com/• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Managing up: https://www.lennysnewsletter.com/p/managing-up• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Everything Everywhere All at Once: https://www.imdb.com/title/tt6710474/• Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7• Bluey on Disney+: https://www.disneyplus.com/browse/entity-fa6973b9-e7cf-49fb-81a2-d4908e4bf694• Mentava: https://www.mentava.com/• Matt Bateman’s website: https://mattbateman.xyz/• Beast Academy: https://beastacademy.com/• David protein bars: https://davidprotein.com/• Marc Andreessen on X: https://x.com/pmarca• Tatami mats: https://en.wikipedia.org/wiki/Tatami—Recommended books:• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/• The Odyssey: https://www.amazon.com/Odyssey-Homer/dp/0140268863• The Dream Machine: https://www.amazon.com/Dream-Machine-M-Mitchell-Waldrop/dp/1732265119/• Dune: https://www.amazon.com/Dune-Chronicles-Book-1/dp/0441013597/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

How Mercado Libre built Latin America's most valuable company: 18k engineers, 30k deploys a day, and their own fleet of planes | Sebastian Barrios

Mike Krieger is the chief product officer of Anthropic and the co-founder of Instagram. After leaving Meta, he co-founded Artifact, an AI-powered news app that I absolutely loved, and joined Anthropic to lead product in 2024.In this episode, you'll learn:• How Anthropic uses AI to write 90-95% of code for some products and the surprising new bottlenecks this creates• Why embedding product managers with AI researchers yields 10x the impact of traditional product development• The three areas where product teams can still add massive value as AI gets smarter• How Anthropic plans to compete with OpenAI long-term• How to use Claude as your product strategy partner (with specific prompting techniques)• Why Mike shut down Artifact despite loving the product, and what founders can learn from it• Where AI startups should build to avoid getting killed by OpenAI, Anthropic, and Google• Why MCP (Model Context Protocol) might reshape how all software works• The counterintuitive product metrics that matter for AI• How to evaluate whether your company is maximizing AI’s potential or just scratching the surface—Brought to you by:Productboard—Make products that matterStripe—Helping companies of all sizes grow revenueOneSchema—Import CSV data 10x faster—Where to find Mike Krieger:• X: https://x.com/mikeyk• LinkedIn: https://www.linkedin.com/in/mikekrieger/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Mike Krieger(04:20) What Mike has changed his mind about regarding AI capabilities(07:38) How to avoid scary AI scenarios(08:55) Skills kids will need in an AI world(11:53) How product development changes when 90% of code is written by AI(17:07) Claude helping with product strategy(21:16) A new way of working(23:55) The future value of product teams in an AI world(27:18) Prompting tricks to get more out of Claude(29:52) The Rick Rubin collaboration on “vibe coding”(32:42) How Mike was recruited to Anthropic(35:55) Why Mike shut down Artifact(42:41) Anthropic vs. OpenAI(47:11) Where AI founders should play to avoid getting squashed(51:58) How companies can best leverage Anthropic’s models and APIs(54:29) The role of MCPs (Model Context Protocols)(58:25) Claude’s questions for Mike(01:03:15) Claude’s heartfelt message to Mike—Referenced:• Anthropic: https://www.anthropic.com/• Claude Opus 4: https://www.anthropic.com/claude/opus• Dario Amodei on X: https://x.com/darioamodei• AI 2027: https://ai-2027.com/• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Claude Shannon: https://en.wikipedia.org/wiki/Claude_Shannon• Information theory: https://en.wikipedia.org/wiki/Information_theory• TypeScript: https://www.typescriptlang.org/• Python: https://www.python.org/• Rust: https://www.rust-lang.org/• Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor• Announcing a brand-new podcast: “How I AI” with Claire Vo: https://www.lennysnewsletter.com/p/announcing-a-brand-new-podcast-how• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k• Jack Clark on LinkedIn: https://www.linkedin.com/in/jack-clark-5a320317/• Artifact: https://en.wikipedia.org/wiki/Artifact_(app)• Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein/• Daniela Amodei on LinkedIn: https://www.linkedin.com/in/daniela-amodei-790bb22a/• Boris Cherny on LinkedIn: https://www.linkedin.com/in/bcherny/• Gunnar Gray on LinkedIn: https://www.linkedin.com/in/gunnargray/• The Model Context Protocol: https://www.anthropic.com/news/model-context-protocol• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Jimmy Kimmel Live: https://www.youtube.com/user/JimmyKimmelLive• ChatGPT: https://chatgpt.com/• Gemini: https://gemini.google.com/app• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Windsurf: https://windsurf.com/• Menlo Ventures: https://menlovc.com/• Harvey: https://www.harvey.ai/• Manus: https://manus.im/• Bench: https://www.bench-ai.com/• Strategy Letter V: https://www.joelonsoftware.com/2002/06/12/strategy-letter-v/• Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/—Recommended books:• The Goal: A Process of Ongoing Improvement: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951• The Way of the Code: The Timeless Art of Vibe Coding: https://www.thewayofcode.com/• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram)

Sachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He’s been in product for over 25 years (at Google, Palm, Flywheel, and now Uber). He is known for his “extreme dogfooding” ethos—personally completing almost a thousand Uber driving and delivery trips to sharpen his product insight and user empathy—and his “ship, ship, ship” mantra, which drives rapid iteration across Uber’s global teams.What you will learn:1. Dogfooding at scale2. “Ship, ship, ship” as a cultural mantra3. Obsession with inputs over outputs4. Uber’s hybrid marketplace vision for autonomy5. How Uber changed its culture to focus on profitability6. What to do when data says “no” but your gut says “yes”7. Career advice: maximize cycles8. AI as a research assistant, not an oracle9. Uber rider etiquette tips—Brought to you by:• Paragon—Ship every SaaS integration your customers want• Stripe—Financial infrastructure to grow your revenue• Coda—The all-in-one collaborative workspace—Where to find Sachin Kansal:• LinkedIn: https://www.linkedin.com/in/sachinkansal/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Sachin’s background(05:00) Dogfooding in practice(11:24) Empathy and understanding drivers(20:18) Balancing metrics and user experience(22:04) Operationalizing dogfooding(24:26) Challenges and solutions in dogfooding(29:49) The motto: “ship, ship, ship”(36:37) Product announcements and live demos(40:49) Career advice for product managers(43:51) The evolution of product management with AI(46:55) Collaboration between engineers and product managers(49:36) Uber’s vision for self-driving cars(55:59) Uber’s path to profitability(01:01:58) Balancing data and gut decisions(01:07:21) AI tools in product management(01:10:14) Failure corner(01:13:48) Lightning round and final thoughts—Referenced:• Uber: https://www.uber.com/• Oracle: https://www.oracle.com/• Snowflake: https://www.snowflake.com/en/• Fivetran: https://go.fivetran.com/• Uber for Business: https://www.uber.com/us/en/business• McDonald’s: https://www.mcdonalds.com/• Domino’s: https://www.dominos.com• PalmPilot: https://en.wikipedia.org/wiki/PalmPilot• Praveen Neppalli Naga on LinkedIn: https://www.linkedin.com/in/pneppalli/• May Mobility: https://maymobility.com/• Uber strikes deal with May Mobility to deploy ‘thousands’ of robotaxis: https://www.theverge.com/news/659563/uber-may-mobility-autonomous-ridehail-partnership• Waymo: https://waymo.com/• WeRide: https://www.weride.ai/• Uber and Avride Announce Autonomous Delivery and Mobility Partnership: https://investor.uber.com/news-events/news/press-release-details/2024/Uber-and-Avride-Announce-Autonomous-Delivery-and-Mobility-Partnership/default.aspx• Dara Khosrowshahi on X: https://x.com/dkhos• Uber Elevate: https://www.uber.com/us/en/elevate/vision/• Uber AV: https://www.uber.com/us/en/autonomous/• Uber Reserve: https://www.uber.com/us/en/ride/how-it-works/reserve/• Uber for teens: https://www.uber.com/us/en/ride/teens/• Flywheel: https://www.flywheel.com/• ChatGPT: https://chatgpt.com/• Gemini: https://gemini.google.com/app• NotebookLM: https://notebooklm.google/• Behind the product: NotebookLM | Raiza Martin (Senior Product Manager, AI @ Google Labs): https://www.lennysnewsletter.com/p/googles-notebooklm-raiza-martin• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry• Peaky Blinders on Netflix: https://www.netflix.com/title/80002479• Deep research: https://openai.com/index/introducing-deep-research/—Recommended books:• Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies: https://www.amazon.com/Blitzscaling-Lightning-Fast-Building-Massively-Companies/dp/1524761419• Nobody Wants to Read Your Sh*t: Why That Is And What You Can Do About It: https://www.amazon.com/Nobody-Wants-Read-Your-Sh-ebook/dp/B01GZ1TJBI• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648537• Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Why Uber’s CPO delivers food on weekends | Sachin Kansal

Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing.What you will learn:1. Why do most marketing playbooks often fail, and what’s a better way?2. Which marketing lever should I pull first?3. Why is trying to be better than competitors usually a losing strategy?4. How do I craft positioning that actually converts?5. What makes messaging stick with developers, enterprises, and consumers?6. What pricing experiments actually move revenue?7. What is working at OpenAI really like?8. Why does consistency and quality matter more than speed?—Brought to you by:Eppo — Run reliable, impactful experimentsAirtable ProductCentral—Launch to new heights with a unified system for product developmentLinkedIn Ads—Reach professionals and drive results for your business—Where to find Krithika Shankarraman:• X: https://x.com/krithix• LinkedIn: https://www.linkedin.com/in/krithix/• Website: https://krithix.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Krithika(04:22) Early marketing lessons from OpenAI(11:17) Diagnosing marketing needs(15:06) The DATE framework and why being cheaper is a race to the bottom(17:11) Marketing strategies at Retool(22:29) Insights from marketing at Stripe(32:33) The importance of consistent marketing communication(39:55) Criteria for hiring a marketing expert(41:43) “Capital M” vs. “lowercase m” marketing(43:05) ChatGPT vs. Claude: market dominance(45:31) The future of AI and its societal impact(47:09) Work-life balance(48:41) Transitioning to Thrive(52:35) Career advice for marketers(55:00) The importance of taste and creativity in the AI era(01:00:04) AI product pricing(01:03:21) AI tools in marketing(01:05:17) Failure corner(01:08:46) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com/• Stripe: https://stripe.com/• Retool: https://retool.com/• Dropbox: https://www.dropbox.com/• Sam Altman talks about his business model: https://www.youtube.com/watch?v=pLnyjxgFxew• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy• Netflix: https://www.netflix.com/• Stripe Connect: https://stripe.com/connect• John Collison on X: https://x.com/collision• Patrick Collison on X: https://x.com/patrickc• Cristina Cordova on LinkedIn: https://www.linkedin.com/in/cristinajcordova/• Hackpad: https://en.wikipedia.org/wiki/Hackpad• Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg• Wiz: https://www.wiz.io/• Thrive Capital: https://thrivecap.com/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Claude: https://claude.ai/new• ChatGPT: https://chatgpt.com/• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics• Databricks: https://www.databricks.com/• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting• Severance on AppleTV+: https://tv.apple.com/us/show/severance/• Granola: https://www.granola.ai/• Some people think AI writing has a tell—the em dash. Writers disagree: https://www.washingtonpost.com/technology/2025/04/09/ai-em-dash-writing-punctuation-chatgpt/—Recommended books:• Obviously Awesome: How to Nail Product Positioning So Customers Get It, Buy It, Love It: https://www.amazon.com/Obviously-Awesome-Product-Positioning-Customers/dp/1999023005• Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman

Mayur Kamat is the chief product officer at N26—a $9 billion neobank serving over 7 million customers in 25 countries—where he leads product, design, data, and research. Prior to N26, Mayur was Head of Product at Binance, growing the crypto exchange to a peak $400 billion valuation. Earlier in his career, he built and scaled products at Google (Gmail Mobile, Hangouts), Microsoft, and travel unicorn Agoda.Learn:1. How to find and focus on the highest-leverage problems2. Why you shouldn’t optimize for compensation early in your career3. Why you should optimize for strengths, not weaknesses4. Why you need to decide if you truly want the C-suite path5. Why working at a fintech company creates exceptional PMs6. Strategy = hypothesis × experimentation velocity7. Small, fast wins compound faster than big, slow bets—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Paragon—Ship every SaaS integration your customers want• Vanta—Automate compliance. Simplify security.—Where to find Mayur Kamat:• X: https://x.com/5degreez• LinkedIn: https://www.linkedin.com/in/mayur/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction and Mayur’s background(04:49) Working at Binance: An inside look(18:18) Career advice for product managers(27:00) PM career paths(33:58) Understanding fintech customers(36:00) Understanding your strengths(44:46) Creating a culture of experimentation(51:14) Hiring and developing top talent(54:50) Building a diverse product portfolio(57:08) Working in high talent density areas(59:43) Personal and professional balance(01:06:32) High-leverage opportunities and decision making(01:14:28) AI tools in the workplace(01:19:14) Failure corner(01:25:11) Lightning round and final thoughts—Referenced:• Binance: https://www.binance.us/• Google: https://about.google/• Microsoft: https://www.microsoft.com/• Agoda: https://www.agoda.com• N26: https://n26.com/• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best• Bezos Says Work-Life Balance is a “Debilitating” Phrase: https://www.investopedia.com/news/bezos-says-worklife-balance-debilitating-phrase/• Maslow’s Hierarchy of Needs: https://www.simplypsychology.org/maslow.html• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia• Changpeng Zhao on LinkedIn: https://www.linkedin.com/in/cpzhao/• Ray Dalio on LinkedIn: https://www.linkedin.com/in/raydalio/• Porter’s five forces: https://en.wikipedia.org/wiki/Porter%27s_five_forces_analysis• Jonathan Rosenberg on X: https://x.com/jjrosenberg• Aura: https://buy.aura.com/• Intercom: https://www.intercom.com/• Palantir: https://www.palantir.com/• Revolut: https://www.revolut.com/• Chime: https://www.chime.com/• Stripe: https://stripe.com/• Dropbox: https://www.dropbox.com/• Alex Algard on LinkedIn: https://www.linkedin.com/in/alexalgard• Hiya: https://www.hiya.com/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Gemini: https://gemini.google.com/app• Writer: https://writer.com/• Google Hangouts: https://en.wikipedia.org/wiki/Google_Hangouts• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/• Google Meet: https://meet.google.com/landing• House on Hulu: https://www.hulu.com/series/ef39603f-eb90-4248-8237-f6168d7c1be1• Big Bang Theory on Hulu: https://www.hulu.com/series/9bde5aeb-5297-4290-b173-19a4d59cc11d• Adolescence on Netflix: https://www.netflix.com/title/81756069• The White Lotus on HBO: https://www.hbo.com/the-white-lotus• Robinhood: https://robinhood.com/us/en/• Nikita Bier’s post on X about Bible Chat: https://x.com/nikitabier/status/1915252215507210349• Bible Chat: https://apps.apple.com/us/app/bible-chat-daily-devotional/id6448849666?mt=8• Suno: https://suno.com/home• Disfrutar: https://www.disfrutarbarcelona.com/—Recommended books:• StrengthsFinder 2.0: https://www.amazon.com/StrengthsFinder-2-0-Tom-Rath/dp/159562015X• The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product)

Aparna Chennapragada is the chief product officer of experiences and devices at Microsoft, where she oversees AI product strategy for their productivity tools and work on agents. Previously, she was the CPO at Robinhood, spent 12 years at Google, and is also on the board of eBay and Capital One.What you’ll learn:1. How “prompt sets are the new PRDs” and why prototyping with AI is now essential for effective product development2. The three key characteristics of AI agents: autonomy (delegation of tasks), complexity (handling multi-step challenges), and natural interaction (conversing beyond simple chat)3. Why NLX (natural language experience) is the new UX, requiring deliberate design principles for conversational interfaces4. Why the PM role isn’t dying in the AI era—it’s evolving to emphasize tastemaking and editing5. How living “one year in the future” can be operationalized with programs like Microsoft’s Frontier6. How even traditional enterprises can balance cutting-edge AI adoption with appropriate governance through dual-track approaches7. Insights on leadership differences between Microsoft’s Satya Nadella (known for multi-level thinking and early trendspotting) and Google’s Sundar Pichai (mastery of complex ecosystems)8. The vision for human and AI collaboration in the workplace, where people and agents achieve outcomes greater than either could alone9. A practical framework for evaluating zero-to-one product opportunities—Brought to you by:Eppo—Run reliable, impactful experimentsPragmatic Institute—Industry‑recognized product, marketing, and AI training and certificationsCoda—The all-in-one collaborative workspace—Where to find Aparna Chennapragada:• X: https://x.com/aparnacd• LinkedIn: https://www.linkedin.com/in/aparnacd/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Aparna Chennapragada(04:28) Aparna’s stand-up comedy journey(07:29) Transition to Microsoft and enterprise insights(10:00) The Frontier program and AI integration(13:28) Understanding AI agents(17:59) NLX is the new UX(22:28) The future of product development(31:16) Building a custom Chrome extension(35:45) Leadership styles of Satya and Sundar(37:47) Counterintuitive lessons in product building(41:20) Inflection points for successful products(45:16) GitHub Copilot and code generation(48:34) Excel’s enduring success(50:27) Pivotal career moments(54:55) The future of human-agent collaboration(56:25) Lightning round and final thoughts—Referenced:• Google Lens: https://lens.google/• Saturday Night Live: https://www.nbc.com/saturday-night-live• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/• Robinhood: https://robinhood.com/• eBay: https://www.ebay.com/• Capital One: https://www.capitalone.com/• Microsoft: https://www.microsoft.com/• Aparna’s LinkedIn post about enterprise vs. consumer: https://www.linkedin.com/posts/aparnacd_every-enterprise-user-feature-has-a-shadow-activity-7321176091610542080-8X-E/• The Epic Split: https://en.wikipedia.org/wiki/The_Epic_Split• AI Frontiers: https://www.microsoft.com/en-us/research/lab/ai-frontiers/• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Deepseek: https://www.deepseek.com/• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Tobi Lütke’s post on X about reflexive AI: https://x.com/tobi/status/1909251946235437514• GitHub Copilot: https://github.com/features/copilot• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/• South Park “Underwear Gnomes” episode: https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17• Google Home: https://home.google.com/welcome/• Cursor: https://www.cursor.com/• v0: https://v0.dev/• Bolt: https://bolt.new/• Lovable: https://lovable.dev/• Replit: https://replit.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Microsoft Excel World Championship: https://fmworldcup.com/microsoft-excel-world-championship/• Google Now: https://en.wikipedia.org/wiki/Google_Now• Hacks on Max: https://www.max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7• Granola: https://www.granola.ai/• Alan Kay quote: https://www.brainyquote.com/quotes/alan_kay_100831• Sindhu Vee’s website: https://sindhuvee.com/• Nate Bargatze’s website: https://natebargatze.com/—Recommended book:• A Brief History of Intelligence: Evolution, AI, and the Five Breakthroughs That Made Our Brains: https://www.amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada

Dmitry Zlokazov is the head of product at Revolut, the $45 billion fintech giant operating in over 50 countries, serving more than 50 million customers, and producing some of the world’s top product leaders. Dmitry shares his hard-won lessons, contrarian org design principles, and day-to-day practices that power Revolut’s relentless shipping velocity, culture of ownership, and unparalleled “wow” product experience.What you’ll learn:1. Revolut’s unique organizational approach, where “product owners” manage cross-functional pods as “local CEOs,” with genuine end-to-end ownership and hiring/firing power2. How a radical, ultra-flat structure enables more than 150 product owners to maintain founder-level quality and velocity across dozens of parallel launches3. How Revolut maintains quality while shipping hundreds of features across over 50 countries4. Why Revolut favors “raw intellect and hunger” over experience, and how internal transfers (including ex-engineers and ops managers) become the company’s most successful product leaders5. How Revolut’s founders review every single UI shipped, and why this founder detail obsession scales rather than limits innovation6. Their framework for launching new products—from ideation, validation, and first user cohort to rapid “algorithmization” and scaling across countries7. The importance of treating products that are 99% done as closer to 0% done, vs. 100% done—This entire episode is brought to you by Stripe—Helping companies of all sizes grow revenue.—Where to find Dmitry Zlokazov:• X: https://x.com/Dzlokazov• LinkedIn: https://www.linkedin.com/in/zlokazov/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Dmitry and Revolut(03:41) Revolut’s unique approach to product management(06:58) The role and responsibilities of product owners(09:28) Types of product owners at Revolut(15:50) Building “wow” products(25:00) Hiring practices(31:33) Managing teams and projects(41:07) Revolut’s diverse product offerings(44:40) Scaling new products successfully(52:10) Attracting top talent(58:43) Failure corner(01:02:49) Lightning round and final thoughts—Referenced:• Revolut: https://www.revolut.com/• Intercom: https://www.intercom.com/• Palantir: https://www.palantir.com/• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm• Deliver WOW to our customers: https://www.revolut.com/blog/post/deliver-wow/• Nik Storonsky on LinkedIn: https://www.linkedin.com/in/nstoronsky• Vlad Yatsenko on LinkedIn: https://www.linkedin.com/in/yatsenko/• How Palantir built the ultimate founder factory | Nabeel S. Qureshi (entrepreneur and writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi• Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product• Gokul Rajaram on X: https://x.com/gokulr• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Schlep blindness: https://www.paulgraham.com/schlep.html• Revolut Launches RevPoints Loyalty Programme, Turning Daily Expenses into Exclusive Rewards: https://www.revolut.com/news/revolut_launches_revpoints_loyalty_programme_turning_daily_expenses_into_exclusive_rewards/• Gemini: https://gemini.google.com/• ChatGPT: https://chatgpt.com/• Figma: https://www.figma.com/• Oppenheimer: https://www.imdb.com/title/tt15398776/• Manus: https://manus.im/• Eisenhower quote: https://quoteinvestigator.com/2017/11/18/planning/• Wealth protection: https://help.revolut.com/help/security-logging-in/wealth-protection/what-is-wealth-protection/—Recommended books:• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205• Build: An Unorthodox Guide to Making Things Worth Making―Personal Journey from Product Designer to Mentor: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product)

Nabeel Qureshi is an entrepreneur, writer, researcher, and visiting scholar of AI policy at the Mercatus Center (alongside Tyler Cowen). Previously, he spent nearly eight years at Palantir, working as a forward-deployed engineer. His work at Palantir ranged from accelerating the Covid-19 response to applying AI to drug discovery to optimizing aircraft manufacturing at Airbus. Nabeel was also a founding employee and VP of business development at GoCardless, a leading European fintech unicorn.What you’ll learn:• Why almost a third of all Palantir’s PMs go on to start companies• How the “forward-deployed engineer” model works and why it creates exceptional product leaders• How Palantir transformed from a “sparkling Accenture” into a $200 billion data/software platform company with more than 80% margins• The unconventional hiring approach that screens for independent-minded, intellectually curious, and highly competitive people• Why the company intentionally avoids traditional titles and career ladders—and what they do instead• Why they built an ontology-first data platform that LLMs love• How Palantir’s controversial “bat signal” recruiting strategy filtered for specific talent types• The moral case for working at a company like Palantir—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Attio—The powerful, flexible CRM for fast-growing startups• OneSchema—Import CSV data 10x faster—Where to find Nabeel S. Qureshi:• X: https://x.com/nabeelqu• LinkedIn: https://www.linkedin.com/in/nabeelqu/• Website: https://nabeelqu.co/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nabeel S. Qureshi(05:10) Palantir’s unique culture and hiring(13:29) What Palantir looks for in people(16:14) Why they don't have titles(19:11) Forward-deployed engineers at Palantir(25:23) Key principles of Palantir's success(30:00) Gotham and Foundry(36:58) The ontology concept(38:02) Life as a forward-deployed engineer(41:36) Balancing custom solutions and product vision(46:36) Advice on how to implement forward-deployed engineers(50:41) The current state of forward-deployed engineers at Palantir(53:15) The power of ingesting, cleaning and analyzing data(59:25) Hiring for mission-driven startups(01:05:30) What makes Palantir PMs different(01:10:00) The moral question of Palantir(01:16:03) Advice for new startups(01:21:12) AI corner(01:24:00) Contrarian corner(01:25:42) Lightning round and final thoughts—Referenced:• Reflections on Palantir: https://nabeelqu.co/reflections-on-palantir• Palantir: https://www.palantir.com/• Intercom: https://www.intercom.com/• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best• Gotham: https://www.palantir.com/platforms/gotham/• Foundry: https://www.palantir.com/platforms/foundry/• Peter Thiel on X: https://x.com/peterthiel• Alex Karp: https://en.wikipedia.org/wiki/Alex_Karp• Stephen Cohen: https://en.wikipedia.org/wiki/Stephen_Cohen_(entrepreneur)• Joe Lonsdale on LinkedIn: https://www.linkedin.com/in/jtlonsdale/• Tyler Cowen’s website: https://tylercowen.com/• This Scandinavian City Just Won the Internet With Its Hilarious New Tourism Ad: https://www.afar.com/magazine/oslos-new-tourism-ad-becomes-viral-hit• Safe Superintelligence: https://ssi.inc/• Mira Murati on X: https://x.com/miramurati• Stripe: https://stripe.com/• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• Airbus: https://www.airbus.com/en• NIH: https://www.nih.gov/• Jupyter Notebooks: https://jupyter.org/• Shyam Sankar on LinkedIn: https://www.linkedin.com/in/shyamsankar/• Palantir Gotham for Defense Decision Making: https://www.youtube.com/watch?v=rxKghrZU5w8• Foundry 2022 Operating System Demo: https://www.youtube.com/watch?v=uF-GSj-Exms• SQL: https://en.wikipedia.org/wiki/SQL• Airbus A350: https://en.wikipedia.org/wiki/Airbus_A350• SAP: https://www.sap.com/index.html• Barry McCardel on LinkedIn: https://www.linkedin.com/in/barrymccardel/• Understanding ‘Forward Deployed Engineering’ and Why Your Company Probably Shouldn’t Do It: https://www.barry.ooo/posts/fde-culture• David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/• Retool’s Path to Product-Market Fit—Lessons for Getting to 100 Happy Customers, Faster: https://review.firstround.com/retools-path-to-product-market-fit-lessons-for-getting-to-100-happy-customers-faster/• How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe): https://www.lennysnewsletter.com/p/how-to-foster-innovation-and-big• Looker: https://cloud.google.com/looker• Sorry, that isn’t an FDE: https://tedmabrey.substack.com/p/sorry-that-isnt-an-fde• Glean: https://www.glean.com/• Limited Engagement: Is Tech Becoming More Diverse?: https://www.bkmag.com/2017/01/31/limited-engagement-creating-diversity-in-the-tech-industry/• Operation Warp Speed: https://en.wikipedia.org/wiki/Operation_Warp_Speed• Mark Zuckerberg testifies: https://www.businessinsider.com/facebook-ceo-mark-zuckerberg-testifies-congress-libra-cryptocurrency-2019-10• Anduril: https://www.anduril.com/• SpaceX: https://www.spacex.com/• Principles: https://nabeelqu.co/principles• Wispr Flow: https://wisprflow.ai/• Claude code: https://docs.anthropic.com/en/docs/agents-and-tools/claude-code/overview• Gemini Pro 2.5: https://deepmind.google/technologies/gemini/pro/• DeepMind: https://deepmind.google/• Latent Space newsletter: https://www.latent.space/• Swyx on x: https://x.com/swyx• Neural networks in chess programs: https://www.chessprogramming.org/Neural_Networks• AlphaZero: https://en.wikipedia.org/wiki/AlphaZero• The top chess players in the world: https://www.chess.com/players• Decision to Leave: https://www.imdb.com/title/tt12477480/• Oldboy: https://www.imdb.com/title/tt0364569/• Christopher Alexander: https://en.wikipedia.org/wiki/Christopher_Alexander—Recommended books:• The Technological Republic: Hard Power, Soft Belief, and the Future of the West: https://www.amazon.com/Technological-Republic-Power-Belief-Future/dp/0593798694• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296• Impro: Improvisation and the Theatre: https://www.amazon.com/Impro-Improvisation-Theatre-Keith-Johnstone/dp/0878301178/• William Shakespeare: Histories: https://www.amazon.com/Histories-Everymans-Library-William-Shakespeare/dp/0679433120/• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.In our conversation, we cover:1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?”2. Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience3. Why teams most often fail (hint: it’s not lack of talent or strategy)4. How busyness often masks deeper issues of self-worth5. Why a “growth mindset” can be problematic6. The importance of legacy and what it means to live a meaningful life7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity—Brought to you by:Eppo—Run reliable, impactful experimentsContentsquare—Create better digital experiencesOneSchema—Import CSV data 10x faster—Where to find Jerry Colonna:• X: https://x.com/jerrycolonna• LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/• Website: https://reunion.reboot.io/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jerry Colonna(04:12) Jerry’s key question(06:55) The equation for great leadership(09:37) The big lie of success and happiness(12:12) The consciousness hack(15:56) Getting over the fear of consequences(20:23) The problem with bypassing our childhood baggage(23:22) Radical self-inquiry: asking the tough questions(27:05) Shared experiences: the power of community(30:25) The trap of busyness and attachment(40:45) Understanding our own intentions(46:58) Legacy and purpose(55:43) Writing for self-discovery(57:12) The impact of AI on humanity(01:05:00) Turning a growth mindset into a fixed mindset(01:11:30) The role of radical self-inquiry in leadership(01:19:24) Final thoughts and reflections—Referenced:• Naropa University: https://www.naropa.edu/• Fitler Club: https://fitlerclub.com• Chris Fralic on LinkedIn: https://www.linkedin.com/in/chrisfralic/• Will Smith on the price of fame: ‘I have been deeply humbled and deeply inspired’: https://www.today.com/popculture/news/will-smith-fame-rcna127830• Seth Godin’s best tactics for building remarkable products, strategies, brands, and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products• The life of Buddha: https://www.britannica.com/summary/Buddha-founder-of-Buddhism• 10% Happier with Dan Harris podcast: https://podcasts.apple.com/us/podcast/10-happier-with-dan-harris/id1087147821• Simon Sinek’s website: https://simonsinek.com/• Mike Tyson Gives Morbid Response to Young Interviewer’s Question About His “Legacy”: https://www.vibe.com/news/entertainment/mike-tyson-morbid-response-young-interviewer-legacy-1234944054/• Dan Shipper’s post on X about asking ChatGPT for blind spots: https://x.com/danshipper/status/1910387987487318318• Evernote: https://evernote.com/• Claude: https://claude.ai• Peter Senge on X: https://x.com/petersenge• Carl Jung’s quote: https://www.goodreads.com/quotes/44379-until-you-make-the-unconscious-conscious-it-will-direct-your• Parker Palmer on LinkedIn: https://www.linkedin.com/in/parker-j-palmer-5a92b110/• The unexamined life is not worth living: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living—Recommended books:• Reboot: Leadership and the Art of Growing Up: https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536• Reunion: Leadership and the Longing to Belong: https://www.amazon.com/Reunion-Leadership-Longing-Jerry-Colonna/dp/0063142139• Born to Run: https://www.amazon.com/Born-Run-Bruce-Springsteen/dp/1501141511• 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works—A True Story: https://www.amazon.com/10-Happier-Self-Help-Actually-Works/dp/0062265431• Soldiers and Kings: Survival and Hope in the World of Human Smuggling: https://www.amazon.com/Soldiers-Kings-Survival-World-Smuggling/dp/0593298586• The Giving Tree: https://www.amazon.com/Giving-Tree-Shel-Silverstein/dp/0060256656/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin—the world’s first autonomous AI software engineer. Unlike other AI coding tools, Devin works like an autonomous engineer that you can interact with through Slack, Linear, and GitHub, just like with a remote engineer. With Scott’s background in competitive programming and a previous AI-powered startup, Lunchclub, teaching AI to code has become his ultimate passion.What you’ll learn:1. How a team of “Devins” are already producing 25% of Cognition’s pull requests, and they are on track to hit 50% by year’s end2. How each engineer on Cognition’s 15-person engineering team works with about five Devins each3. How Devin has evolved from a “high school CS student” to a “junior engineer” over the past year4. Why engineering will shift from “bricklayers” to “architects”5. Why AI tools will lead to more engineering jobs rather than fewer6. How Devin creates its own wiki to understand and document complex codebases7. The eight pivots Cognition went through before landing on their current approach8. The cultural shifts required to successfully adopt AI engineers—Brought to you by:Enterpret—Transform customer feedback into product growthParagon—Ship every SaaS integration your customers wantAttio—The powerful, flexible CRM for fast-growing startups—Where to find Scott Wu:• X: https://x.com/scottwu46• LinkedIn: https://www.linkedin.com/in/scott-wu-8b94ab96/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Scott Wu and Devin(09:13) Scaling and future prospects(10:23) Devin's origin story(17:26) The idea of Devin as a person(22:19) How a team of “Devins” are already producing 25% of Cognition’s pull requests(25:17) Important skills in the AI era(30:21) How Cognition’s engineering team works with Devin's(34:37) Live demo(42:20) Devin’s codebase integration(44:50) Automation with Linear(46:53) What Devin does best(52:56) The future of AI in software engineering(57:13) Moats and stickiness in AI(01:01:57) The tech that enables Devin(01:04:14) AI will be the biggest technology shift of our lives(01:07:25) Adopting Devin in your company(01:15:13) Startup wisdom and hiring practices(01:22:32) Lightning round and final thoughts—Referenced:• Devin: https://devin.ai/• GitHub: https://github.com/• Linear: https://linear.app/• Waymo: https://waymo.com/• GitHub Copilot: https://github.com/features/copilot• Cursor: https://www.cursor.com/• Anysphere: https://anysphere.inc/• Bolt: https://bolt.new/• StackBlitz: https://stackblitz.com/• Cognition: https://cognition.ai/• v0: https://v0.dev/• Vercel: https://vercel.com/• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Assembly: https://en.wikipedia.org/wiki/Assembly_language• Pascal: https://en.wikipedia.org/wiki/Pascal_(programming_language)• Python: https://www.python.org/• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox• Datadog: https://www.datadoghq.com/• Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Windsurf: https://windsurf.com/• COBOL: https://en.wikipedia.org/wiki/COBOL• Fortran: https://en.wikipedia.org/wiki/Fortran• Magic the Gathering: https://magic.wizards.com/en• Aura frames: https://auraframes.com/• AirPods: https://www.apple.com/airpods/• Steven Hao on LinkedIn: https://www.linkedin.com/in/steven-hao-160b9638/• Walden Yan on LinkedIn: https://www.linkedin.com/in/waldenyan/—Recommended books:• How to Win Friends & Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034• The Power Law: Venture Capital and the Making of the New Future: https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/052555999X• The Great Gatsby: https://www.amazon.com/Great-Gatsby-F-Scott-Fitzgerald/dp/0743273567—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Inside Devin: The world’s first autonomous AI engineer that's set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition)

Michael Truell is the co-founder and CEO of Anysphere, the company behind Cursor—the fastest-growing AI code editor in the world, reaching $300 million in annual recurring revenue just two years after its launch. In this conversation, Michael shares his vision for the future, lessons learned, and advice for preparing for the fast-approaching AI future.What you’ll learn:• Cursor's early pivot from automating CAD to automating code• Michael’s vision for “what comes after code” and how programming will evolve• Why Cursor built their own custom AI models despite not starting there• Key lessons from Cursor’s rapid growth• Why “taste” and logic design will become more valuable engineering skills than technical coding ability• Why the market for AI coding tools is much larger than people realize—and why there will likely be one dominant winner• Michael’s advice for engineers and product teams preparing for the AI future—Brought to you by:Eppo—Run reliable, impactful experimentsVanta—Automate compliance. Simplify securityOneSchema—Import CSV data 10x faster—Where to find Michael Truell:• X: https://x.com/mntruell• LinkedIn: https://www.linkedin.com/in/michael-t-5b1bbb122/• Website: https://mntruell.com/—In this episode, we cover:(00:00) Introduction to Michael Truell and Cursor(04:20) What comes after code(08:32) The importance of taste(12:39) Cursor’s origin story(18:31) Why they chose to build an IDE(22:39) Will everyone become engineering managers?(24:31) How they decided it was time to ship(26:45) Reflecting on Cursor's success(32:03) Counterintuitive lessons on building AI products(34:02) Inside Cursor's stack(38:42) Defensibility and market dynamics in AI(46:13) Tips for using Cursor(51:25) Hiring and building a strong team(59:10) Staying focused amid rapid AI advancements(01:02:31) Final thoughts and advice for aspiring AI innovators—Referenced:• Cursor: https://www.cursor.com/• Microsoft Copilot: https://copilot.microsoft.com/• Scaling laws for neural language models: https://openai.com/index/scaling-laws-for-neural-language-models/• MIT: https://www.mit.edu/• Telegram: https://telegram.org/• Signal: https://signal.org/• WhatsApp: https://www.whatsapp.com/• Devin: https://devin.ai/• Visual Studio Code: https://code.visualstudio.com/• Chromium: https://chromium.googlesource.com/chromium/src/base/• Exploring ChatGPT (GPT) Wrappers—What They Are and How They Work: https://learnprompting.org/blog/gpt_wrappers• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• DALL-E 3: https://openai.com/index/dall-e-3/• Stable Diffusion 3: https://stability.ai/news/stable-diffusion-3—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe