Lenny's Podcast: Product | Career | Growth
Lenny Rachitsky
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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.
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How we built Grok Bot in a month | Roman Ugarte (SpaceXAI) 08.09.2026 1t 22minRoman Ugarte helped incubate and build Grok Bot, the popular new knowledge-work agent from SpaceXAI. A small, isolated team took it from first line of code to a working internal product in four weeks, and to a hugely successful public launch just three weeks later. Before Grok Bot, Roman led Growth at Cursor, where he helped scale the company from 15 people to over 1,000 before its acquisition by SpaceX.In our in-depth conversation, we discuss:1. The origin story of Grok Bot2. The key decision to build it from scratch instead of adding it to Cursor3. Why the team personally onboarded nearly 300 of its first users4. The two early product decisions that made Grok Bot so successful5. Their “colleague-pilled” product philosophy6. Roman’s advice on moats, and what has allowed Cursor to keep winning in the most competitive market in the world—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/how-we-built-grok-bot-in-a-month—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Roman Ugarte:• X: https://x.com/romanugarte_• LinkedIn: https://www.linkedin.com/in/romanugarte• Website: https://x.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(02:09) The origin story: building from scratch in one month(08:40) Why Grok Bot was built as a separate product(11:20) Manually onboarding a couple hundred people(14:29) Hiding internal mechanics from users(18:41) Timeline from beta to public launch(19:14) Unshipping features and simplifying(23:50) Early use cases and feedback(26:50) Product philosophy: “Grok Bot can now”(30:02) Cloud-first architecture(33:12) The fresh-start advantage(35:54) The vision: a true team of AI colleagues(39:20) The “colleague-pilled” framework(42:36) Work versus personal: one product or two?(47:14) Long-lived agents, persistent memory, and the computer abstraction(51:04) Grok Bot as an always-on infovore and chief of staff(53:35) How fast the team moves and what preserves the startup feeling(58:20) SpaceXAI pillars(1:00:44) The first 90% vs. the last 10%(1:03:30) Moving fast at scale(1:06:40) How Cursor kept winning in the most competitive market in the world(1:10:04) Company values: “deleting the product” and “just do the thing”(1:11:45) Moats: discovered, not planned(1:15:11) Tips for new users and power users(1:18:00) Lightning round and final thoughts—References: https://www.lennysnewsletter.com/p/how-we-built-grok-bot-in-a-month—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com -
Why companies are becoming a series of loops | Anish Acharya (a16z) 06.09.2026 1t 19minAnish Acharya is a General Partner at Andreessen Horowitz (a16z), where he has focused on consumer investing. Anish is one of the most insightful, thought-provoking, and in-the-weeds product investors I’ve met, and this conversation will get your mind buzzing. Before joining a16z, Anish was a serial founder and operator: he founded SocialDeck, which he sold to Google, then led multiple efforts inside Google before founding Snowball, which he sold to Credit Karma. At Credit Karma he rose to VP of Product and then GM of the consumer product and the broader credit card business.In our in-depth conversation, we discuss:1. Why you don’t have to worry about becoming part of the “permanent underclass”2. Why company building will now involve creating a series of loops3. What’s happening in consumer right now4. Why the biggest opportunity in consumer is “/loop, make me happier”5. Why moats are discovered, not designed6. The rising importance of distribution as a moat7. Being a model sommelier—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/why-companies-are-becoming-a-series—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Anish Acharya:• Andreessen Horowitz: https://a16z.com/author/anish-acharya/• LinkedIn: https://www.linkedin.com/in/anishacharya/• X: https://x.com/illscience• SoundCloud: https://soundcloud.com/illscience—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) The fear of AI creating a permanent underclass(05:25) Why AI takeoff may be slower than expected(08:02) How companies are actually adopting AI(11:25) Building AI products with loops(15:25) Why human intuition still matters(20:19) What the winners in AI are doing differently(21:41) Generalists vs. specialists(26:22) How to become a model sommelier(32:03) /loop make me happier(36:15) Why Anish is optimistic about the future of AI(42:47) What happens when models become too dangerous(46:29) How AI will change jobs and ambition(51:34) The state of consumer AI(54:30) How to build a durable moat in AI(59:25) The power of distribution and word of mouth(01:04:30) Making bigger bets and rethinking pricing(01:09:17) Advice for product builders in the AI era(01:11:48) Lightning round and final thoughts—References: https://www.lennysnewsletter.com/p/why-companies-are-becoming-a-series—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com -
AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work) 30.08.2026 1t 21minTara Seshan leads product for Codex and ChatGPT Work at OpenAI (alongside previous podcast guest Andrew Ambrosino, who’s her engineering manager). Before OpenAI, Tara spent over six years at Stripe, where she joined as one of the first five product managers. She went on to lead product for Watershed, which Time magazine named one of the best inventions of 2022, and she is also a founder and Thiel Fellow. Most personally meaningful to me: Tara is one of the three inaugural Lenny’s Newsletter Fellows, a program I ran a couple of years ago to spotlight the most exciting up-and-coming product leaders.In our in-depth conversation, we discuss:1. The shift from “rowing” to “steering,” and why human judgment and ambition will become differentiators as AI takes on execution2. How OpenAI thinks about building for model capabilities two to three months out3. OpenAI’s best internal memes, such as “Is this maximally accelerated?” and “Are you mainlining it yet?”4. Why ambition is the new bottleneck for companies, and why elevating others’ ambitions is now the key part of the PM job5. Writing as thinking vs. writing as reporting—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 Tara Seshan:• X: https://x.com/tarstarr• LinkedIn: https://www.linkedin.com/in/tarstarr• Newsletter: https://substack.com/@taraseshan—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(02:18) What makes OpenAI’s culture so different(06:42) Why AI product strategy is all about fast experimentation(09:02) How the PM role is changing(10:50) The shift from rowing to steering(15:35) What changes when agents become coworkers(20:05) Why ambition matters more than ever(26:39) Building products for models that do not exist yet(29:21) How ChatGPT’s Chat and Work modes differ(34:01) How OpenAI ships so quickly at scale(39:14) The vibe shift happening inside Codex(42:20) Why traditional roles are beginning to blur(45:59) Where humans will continue to provide unique value(48:20) How Tara uses AI in her own work(51:38) The magic of the /visualize command(52:39) Writing to think versus writing to report(57:10) How to use AI without losing your ability to think(01:00:15) Tara’s biggest lesson from Sutter Hill(01:04:16) ChatGPT’s site output(01:05:01) Why knowledge work is becoming more like coding(01:07:55) Lightning round and final thoughts—Referenced:• Codex: https://chatgpt.com/codex• ChatGPT Work: https://openai.com/chatgpt-work• Stripe: https://stripe.com• Watershed: https://watershed.com• Thiel Fellowship: https://thielfellowship.org• Meet your Lenny’s Newsletter Fellows: https://www.lennysnewsletter.com/p/meet-your-lennys-newsletter-fellows• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir• The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty• Patrick Collison’s examples of fast projects: https://patrickcollison.com/fast• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Andrew Ambrosino on X: https://x.com/ajambrosino• Tyler Cowen’s website: https://tylercowen.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• “Chop wood, carry water” quote: https://buddhism.stackexchange.com/questions/15921/what-is-the-meaning-of-the-zen-quote-before-enlightenment-chop-wood-carry-wat• 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live• Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay• Brie Wolfson on X: https://x.com/zebriez• The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor: https://www.lennysnewsletter.com/p/the-playbook-for-building-high-talent• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• Sutter Hill Ventures: https://shv.com• Snowflake: https://www.snowflake.com• Mike Speiser on LinkedIn: https://www.linkedin.com/in/mikespeiser• Footnotes and Tangents: https://footnotesandtangents.substack.com• The Power Broker Book Club: https://www.robertcaro.org/copy-of-six-books-six-ny-times-book• The Odyssey: https://www.imdb.com/title/tt33764258• Rashomon: https://www.imdb.com/title/tt0042876• Akira Kurosawa: https://en.wikipedia.org/wiki/Akira_Kurosawa• Kevin Kwok on LinkedIn: https://www.linkedin.com/in/kevinakwok• The Work You Do, the Person You Are: https://www.newyorker.com/magazine/2017/06/05/toni-morrison-the-work-you-do-the-person-you-are• Ari Weinstein on X: https://x.com/AriX• Sky: https://sky.app• Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config—Recommended books:• Barbarian Days: A Surfing Life: https://www.amazon.com/dp/0143109391• Anna Karenina: https://www.amazon.com/Anna-Karenina-LEO-TOLSTOY/dp/8175993421• The Power Broker: https://www.amazon.com/dp/0394720245• War and Peace: https://www.amazon.com/War-Peace-Leo-Tolstoy/dp/8175992832• Wolf Hall: https://www.amazon.com/dp/0312429983—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com -
How to close $100K+ enterprise deals, step by step | Jen Abel 23.08.2026 1t 24minJen Abel is the co-founder of JJellyfish and GM of enterprise sales at State Affairs. She is widely regarded as one of the sharpest practitioners in enterprise sales, and for that reason, this is her third visit to the podcast. In our first conversation we went deep on founder-led sales; in our second we mapped the $1M–$10M playbook. This time we do something I’ve never seen on another podcast: walk step by step through the full enterprise sales cycle. Most people think it’s five steps. Jen shows it’s closer to 15.In our in-depth conversation, we discuss:1. Why the standard five-stage CRM pipeline is a forecasting tool, not a sales process, and what the real 15-step cycle looks like2. The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously3. How to craft a two-to-three-sentence message around giving them “alpha”4. How to run an intro call that extracts maximum intelligence before you ever show a demo5. The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away6. Navigating pricing, procurement, redline negotiations, and the final signature without losing momentum—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 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) Introduction(02:49) Why Jen is giving away her enterprise sales playbook(05:54) Example: selling AI legal tech to SpaceX(09:11) Step 1: Landing the meeting(18:44) Step 2: Running the intro call(30:00) Step 3: Running a follow-up call(36:30) Step 4: Prepping the pitch/frame for demo(38:36) Step 5: Running the demo(46:45) Step 6: Post-demo debrief(48:59) Step 7 through 9: Preparing for and running the pilot(01:03:44) Why the standard five-stage CRM pipeline doesn’t work(01:04:49) Step 10: Post-pilot session(01:07:48) What a healthy enterprise win rate looks like(01:11:45) Steps 11 through 14: Navigating procurement and getting the signature(01:18:01) How to think about expansion(01:19:18) How buyers can say no without wasting everyone’s time(01:21:53) Why enterprise sales is a lot like product management(01:22:27) Closing thoughts—Referenced:• State Affairs: https://stateaffairs.com• The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel• “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• SpaceX: https://www.spacex.com• Lemlist: https://www.lemlist.com• Palantir: https://www.palantir.com• Jason Lemkin on X: https://x.com/jasonlk• 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• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• Careers at State Affairs: https://stateaffairs.com/careers—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—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 16.08.2026 1t 12minIan 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 [email protected].—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 09.08.2026 1t 30minAdam 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 [email protected].—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) 02.08.2026 1t 24minTom 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 [email protected].—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 26.07.2026 1t 33minDianne 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 [email protected].—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) 19.07.2026 1t 12minElizabeth 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 [email protected].—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) 12.07.2026 1t 36minNoam 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 [email protected].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com -
Adam Mosseri: AI is a tailwind for authenticity 09.07.2026 1t 8minAdam 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 [email protected].—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 28.06.2026 1t 9minAndrew 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 [email protected].—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) 21.06.2026 1t 38minFiona 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 [email protected].—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) 14.06.2026 1t 39minMark 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 [email protected].—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 07.06.2026 1t 35minTony 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 [email protected].—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 31.05.2026 1t 19minBenedict 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 [email protected].—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 24.05.2026 1t 34minDan 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 [email protected].—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) 17.05.2026 1t 39minCaitlin 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 [email protected].—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 10.05.2026 1t 39minEric 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 [email protected] 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) 03.05.2026 1t 27minMax 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 [email protected].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com
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