Lenny's Podcast: Product | Career | Growth

Roman 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

Tara 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

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 [email protected].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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 [email protected].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com