Hector Serrano runs one of the most innovative and successful paid growth programs in Silicon Valley. As Head of Content at Wispr Flow, a leading AI voice-to-text tool, he built a roster of 50 creators who drive 500 to 600 paid user-generated content (UGC) ads every month. The creators are paid a cut of ad spend, and the best of them earn over $13,000 a month. It’s a playbook the best DTC brands have used for years, now adapted for SaaS. Hector joined Wispr Flow at 19, before the product had PMF, and over the past year, Wispr Flow has grown revenue 30x and raised at a $2 billion valuation. We discuss: 1. Why paid UGC is one of the biggest untapped growth levers right now 2. The step-by-step playbook for building a successful paid-UGC program 3. Why the best marketers are “allergic to AI” 4. What makes a great modern marketing hire 5. Why YouTube is the most underrated growth lever in SaaS — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Where to find Hector Serrano: • X: https://x.com/hectorserrranoo • LinkedIn: linkedin.com/in/hector-serrano-martin • YouTube: https://www.youtube.com/@hectorchats — 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) Teaser (01:17) What Hector does at Wispr Flow (03:10) The number-one growth lever: product-market fit (04:25) When to start investing in paid ads (08:27) The paid-UGC strategy and how it developed (13:44) How creator compensation works: percent of ad spend vs. GMV (20:07) The profile of a great modern marketing hire (25:03) The importance of young talent (28:22) Hector’s journey from D1 soccer to Wispr Flow (31:03) Step-by-step: How to build a paid-UGC group from zero (43:03) Reaching out to creators (45:37) Building culture inside your creator group (48:31) The role of the media buyer alongside the creative lead (50:05) Team size and structure (53:44) Why UGC works even in technical and enterprise SaaS (56:15) Advice for people embarking on the creator path (59:50) Common mistakes to avoid (01:02:21) The sports approach to hiring (01:03:52) Why the best marketers are allergic to AI output (01:08:07) Founder-led content (01:16:01) Why YouTube packaging matters more than production quality (01:20:06) Lightning round and final thoughts — Referenced: • Wispr Flow: https://wisprflow.ai • Tanay Kothari on X: https://x.com/tankots • Matt Swulinski on LinkedIn: https://www.linkedin.com/in/mattswulinski • Viktor: https://viktor.com • Tobin Tang on LinkedIn: https://www.linkedin.com/in/tobinwtang • Polymarket: https://polymarket.us • Trybe: https://jointrybe.com • Lukas Pakter on LinkedIn: https://www.linkedin.com/in/lukas-pakter-402117204 • SquidHaus: https://gohaus.com • Daniel McCallum on LinkedIn: https://www.linkedin.com/in/danielmccallum • “Everyone wants a great head of content but you won’t find one” on X: https://x.com/hectorserrranoo/status/2109703739754037530 • Eric Zaworski on LinkedIn: https://www.linkedin.com/in/eric-zaworski • Jimmy Farley on LinkedIn: https://www.linkedin.com/in/jimmy-farley-349215296 • Physician’s Choice: https://physicianschoice.com • Hector’s paid-UGC playbook on X: https://x.com/hectorserrranoo/status/2108260769603486100 • “The most successful founders, investors, or creators I’ve met...” on X: https://x.com/hectorserrranoo/status/2113109670491783661 • “Startups should recruit more like sports teams” on X: https://x.com/hectorserrranoo/status/2113676414973259782 • Real Madrid La Liga: https://www.laliga.com/en-GB/clubs/real-madrid • “The best marketers are allergic to AI” on X: https://x.com/hectorserrranoo/status/2110432634451169699 • 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 • Naval Ravikant on X: https://x.com/naval • You Can See Everything: https://www.imdb.com/title/tt45368240 • Miso: https://miso.com • Steve Jobs quote: https://www.brainyquote.com/quotes/steve_jobs_416875 — Recommended books: • The Almanack of Naval Ravikant: A Guide to Wealth and Happiness: https://www.amazon.com/dp/1544514212 • Ego Is the Enemy: The Fight to Master Our Greatest Opponent: https://www.amazon.com/dp/1781257019 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Rob Snyder is the author of The Power of Pull and writes the newsletter The Physics of Startups. He has advised more than 50 startups on growing from zero to $1 million in ARR, drawing on his own experience as a founder who spent two years pushing a product the market didn’t want before accidentally stumbling onto what actually works. In this episode, we walk step by step through his framework for finding product-market fit, from coming up with an idea to closing your first handful of deals. We discuss: 1. The PULL framework: Project, Unavoidable, List of options, Limitations 2. Where the best startup ideas come from 3. Tactics for cold outreach and running your first sales call 4. Why Rob advises against design partners 5. Goblin mode: what to do when nothing is working 6. How to apply the PULL framework inside larger companies — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Where to find Rob Snyder: • LinkedIn: https://www.linkedin.com/in/rsnyder1 • Newsletter: https://thephysicsofstartups.substack.com • Podcast: https://open.spotify.com/show/4Cic56E1UEbU25P3v14Vkq • Website: https://robsnyder.org — 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 Rob Snyder (01:13) The PULL framework: what makes customers buy (07:30) The “PULL” acronym (09:44) How Jump found pull with financial advisors (13:53) Why pull is discovered, not created (16:10) Selling to a person, not a company (17:13) Finding startup ideas through firsthand experience (22:34) Testing your pull hypothesis with two slides (26:41) Recognizing real buying intent (27:24) When solving your own problem works (29:02) The Hail Mary question that can unlock a pivot (31:01) Common traps to avoid (32:50) Quick recap (34:46) Landing your first customer conversations (39:18) Outreach benchmarks and diagnosing what isn’t working (41:27) How to run your first sales call (46:56) Successful pitch tactics (49:59) Does your product need to be 10 times better? (54:08) Closing the deal (01:00:41) Using the PULL framework to set pricing (01:02:22) Revising your hypothesis and going into goblin mode (01:06:56) Designing onboarding to make customers stay (01:09:28) What churn can teach you about your ideal customer (01:11:37) Building a repeatable case study factory (01:16:15) Applying the framework inside established companies (01:20:03) Lightning round and final thoughts — Referenced: • The PULL framework: https://thephysicsofstartups.substack.com/p/the-pull-framework • The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta • How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of “Job Moves”): https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta • Jump: https://jump.ai • Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu • Josh Woodward on LinkedIn: https://www.linkedin.com/in/joshwoodward/ • Clearly AI: https://clearly-ai.com • Emily Choi-Greene on LinkedIn: https://www.linkedin.com/in/emilycg • Spanx: https://spanx.com • Floodgate: https://www.floodgate.com • Snoop Dogg on X: https://x.com/SnoopDogg • Jira: https://www.atlassian.com/software/jira • Linear: https://linear.app • “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 • How to close $100K+ enterprise deals, step by step | Jen Abel: https://www.lennysnewsletter.com/p/how-to-close-100k-1m-deals-step-by • Teero: https://www.teero.com • A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit • Retention is the hard part: https://thephysicsofstartups.substack.com/p/retention-is-the-hard-part • Mark Roberge on LinkedIn: https://www.linkedin.com/in/markroberge/ • Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/ • Pride and Prejudice: https://www.imdb.com/title/tt0414387 • Penguins of Madagascar: https://www.imdb.com/title/tt1911658 • Muse: https://muse.ai • Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups • Lemlist: https://www.lemlist.com — Recommended books: • The Power of Pull: What You Need to Know About Customer Demand to Build a Successful Startup (and Why Most Founders Get It Wrong): https://www.amazon.com/Power-Pull-Customer-Successful-Founders/dp/1541705955 • The Nature of Order, Book One: The Phenomenon of Life: An Essay on the Art of Building and the Nature of the Universe: https://www.amazon.com/dp/B0BHLGZHHD • The Nature of Order, Book Two: The Process of Creating Life: An Essay on the Art of Building and the Nature of the Universe: https://www.amazon.com/Nature-Order-Book-Two-Creating-ebook/dp/B0F2SMKQT8 • The Nature of Order, Book Three: A Vision of a Living World: An Essay on the Art of Building and the Nature of the Universe: https://www.amazon.com/dp/B0F2SS62LG • The Nature of Order, Book Four: The Luminous Ground: https://www.amazon.com/Luminous-Ground-Building-Alexander-Christopher/dp/B00CB5JTI6 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Emmanuel Ameisen is an interpretability researcher at Anthropic, where he looks inside LLMs like Claude to understand how they think. Before joining Anthropic, he spent years in applied ML at Stripe and Insight, and is the author of Building Machine Learning Powered Applications. His research has produced some of the most striking findings in the field: that models form general representations of concepts, plan many tokens ahead without stating those plans explicitly, and may exhibit something structurally similar to the distinction between conscious and unconscious processing in humans. We discuss: 1. Why the “next-token predictor” framing undersells how models actually plan and think 2. Why anthropomorphizing AI can actually be the right approach 3. Why models are “grown,” not built 4. What the “J space” reveals about model self-awareness 5. The smooth scaling curve behind what look like sudden capability jumps 6. How interpretability connects to AI alignment and safety — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Episode transcript: https://www.lennysnewsletter.com/p/a-mind-expanding-conversation-on — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Highlights: https://lennyspodcast.com/mostreplayedmoments — Where to find Emmanuel Ameisen: • X: https://x.com/mlpowered • LinkedIn: https://www.linkedin.com/in/ameisen • Website: https://www.mlpowered.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 Emmanuel Ameisen (01:30) Why AI models are grown, not built (05:57) Why next-token prediction is harder than it sounds (11:49) How models represent concepts and understand the world (17:06) How LLMs plan ahead (23:10) Could AI be conscious? (24:44) Scaling laws and the power of text (28:29) Why smooth progress creates sudden breakthroughs (32:59) Why watching AI isn’t enough to solve alignment (38:21) The Golden Gate Claude experiment (39:01) Why Anthropic takes AI safety seriously (42:06) When anthropomorphizing AI is useful (48:06) What AI can teach us about intelligence (51:44) Reasons for optimism about AI alignment (55:43) Are we living in a simulation? (59:00) Jev, decision models, and AI’s gut instincts (01:01:37) Two more surprising findings about how models think (01:03:33) How to get into interpretability research (01:04:55) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/a-mind-expanding-conversation-on — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Josh Woodward is the head of Google Labs, the Gemini app, and AI Studio. He has spent over 17 years at Google and oversees its longest-running and largest labs team, whose products include NotebookLM (now Gemini Notebook), Project Genie, and Flow. His job is to find, experiment with, and scale new AI products, and he has built one of the most distinctive product cultures in the industry for generating ideas, running experiments, and, even more importantly, knowing when to quit. In our in-depth conversation, we discuss: 1. Why every company now needs to think and operate like a labs team 2. Where the best ideas really come from 3. The “almost possible” framework 4. How to recognize genuine product-market fit early 5. When to kill an idea 6. What skills are rising in value in the AI era 7. Why roles are not actually blurring into one universal builder role 8. How to set up your internal labs team — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Episode transcript: https://www.lennysnewsletter.com/p/why-every-company-now-needs-to-think — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Highlights: https://lennyspodcast.com/mostreplayedmoments — Where to find Josh Woodward: • X: https://x.com/joshwoodward • LinkedIn: https://www.linkedin.com/in/joshwoodward — 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 (02:53) Why every company now needs to think like a labs team (05:43) Where great ideas come from (07:43) The “almost possible” framework (11:52) Finding product-market fit (16:09) Falling in love with the problem, not the solution (17:57) When to kill an idea (19:35) Overseeing Google Labs and the Gemini app (22:21) Next consumer AI breakthroughs (24:32) Google’s vision for a personal assistant (27:18) What is overhyped and underhyped in AI right now (31:36) Skills rising in value: unlearning rate, explosive endurance, trust (35:45) Why roles are not blurring into one universal builder role (38:59) Explosive endurance rhythms (41:31) How planning has changed: rolling windows and 100-day milestones (43:37) Labs lifecycle stages (47:37) Tips for setting up an internal lab (54:00) The future of products in an AI world (56:26) Google Labs culture, rituals, and closing thoughts — References: https://www.lennysnewsletter.com/p/why-every-company-now-needs-to-think — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Tibo Sottiaux leads ChatGPT and Codex at OpenAI. Under his stewardship, OpenAI has shipped some of its most consequential consumer launches: Codex, ChatGPT Work, and most recently, the new Dots personal agent platform. He joined me at DevDay, hours after his team launched more than 20 new products, to talk about where things are heading. We discuss: 1. Dots, OpenAI’s new personal AI assistant 2. Why most actions on the internet will soon be taken by agents 3. Why loops, graphs, and fine-tuning agent workflows are a passing phase 4. Which skills are trending up and down in the AI era 5. How Tibo’s Dot warned him about a production outage five minutes before the launch 6. OpenAI’s approach to AI safety — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Episode transcript: https://www.lennysnewsletter.com/p/openais-head-of-chatgpt-were-entering — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Tibo Sottiaux: • X: https://x.com/thsottiaux • LinkedIn: https://www.linkedin.com/in/thibault-sottiaux-27195366 — 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 Tibo Sottiaux (01:12) How Tibo uses AI in his daily work (03:10) The vision for always-on AI agents (06:15) How AI will continue to change work (07:32) Bringing Codex, ChatGPT, and Dots together (08:20) The sci-fi inspiration behind the technology (09:02) Building AI with the community (10:13) Understanding the Dots structure (11:34) OpenAI’s open ecosystem and plugin revenue sharing (13:39) How plugins get discovered and recommended (14:39) The research behind Dots (16:20) Where humans will remain valuable (17:25) Agent fatigue, loneliness, and context switching (18:55) The pressure to do more with AI (20:09) An agent that spotted a production outage before a live demo (21:42) Agent guardrails and connecting multiple devices (23:25) The skills becoming more valuable in the AI era (25:56) Advice for people early in their careers (27:18) How teams build and ship inside OpenAI (28:59) Autonomy, trust, and learning from mistakes (30:45) Building for a future where agents dominate internet activity (32:41) What Tibo has changed his mind about (33:55) OpenAI’s approach to AI safety and alignment (36:15) Moving beyond model pickers toward simpler AI — Referenced: • OpenAI Dots: https://chatgpt.com/features/dots • Her on Netflix: https://www.netflix.com/title/70278933 • Star Trek: https://www.imdb.com/title/tt0060028 • Pi: https://pi.ai • OpenCode: https://opencode.ai • Notion: https://www.notion.com • Figma: https://www.figma.com • OpenClaw: https://openclaw.ai • Peter Steinberger on X: https://x.com/steipete • Grok Bot: https://x.ai/bot • Muse: https://muse.ai • Instinct: https://instinct.com • Ahmed Ibrahim on LinkedIn: linkedin.com/in/ahmedibrhm • The Hugging Face incident and the road ahead: https://openai.com/index/hugging-face-incident-and-the-road-ahead — Recommended book: • Neuromancer: https://www.amazon.com/Neuromancer-William-Gibson/dp/0441007465 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Molly Graham is back for round two, and this one is even more powerful. Molly has spent more than 20 years helping organizations and the humans inside them navigate growth and change. She’s held leadership roles at Google, Facebook, Quip, and the Chan Zuckerberg Initiative and is the host of TED’s WorkLife podcast (which she took over from Adam Grant). She also runs Glue Club, a leadership community for senior operators, and writes a popular newsletter called Lessons. In our in-depth conversation, we discuss: 1. Why Molly’s famous “give away your Legos” career advice no longer holds true in an AI world 2. The grief, loneliness, and burnout sweeping through the tech industry right now 3. Why delegating to AI is fundamentally different from delegating to a human 4. The fear narrative around AI job displacement, and why it’s overblown 5. Which Legos you should never give to AI 6. What the best managers are doing right now — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Episode transcript: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 Highlights: https://lennyspodcast.com/mostreplayedmoments — Where to find Molly Graham • X: https://x.com/molly_g • LinkedIn: https://www.linkedin.com/in/mograham • Substack: https://mollyg.substack.com • Website: https://glueclub.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Molly Graham returns (03:34) What is “Give away your Legos”? (05:44) The origin story: Google, Facebook, and rapid scale (11:27) What still holds true in an AI world (18:13) Engineering’s identity shift: from rowing to steering (22:09) Loneliness and the collapse of team structure (24:06) The centaur and the reverse centaur (25:36) The fear narrative: AI-branded layoffs and overblown doom (29:20) Survey data: burnout is up to 55%, but half of people are thriving (35:07) Cleaning up AI slop (40:01) What’s actually different: delegating to AI vs. giving Legos to a human (42:02) Why every worker is now a manager, whether they want to be or not (49:07) Why giving things away creates space for new opportunities (55:27) Advice for people in the age of AI (59:38) What Legos you should never give away (01:03:12) The human sandwich: vision at the top, AI in the middle, humans at the end (01:05:00) Holding on to the things you love: grief, funerals, and what comes next (01:09:39) Slow takeoff: why you’re not too late (01:13:32) The most important skill to build right now (01:18:58) A message for managers and leaders (01:24:17) Key takeaways (01:31:42) Final thoughts — References: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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 Bot 2. The key decision to build it from scratch instead of adding it to Cursor 3. Why the team personally onboarded nearly 300 of its first users 4. The two early product decisions that made Grok Bot so successful 5. Their “colleague-pilled” product philosophy 6. 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 more Mercury—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 podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Anish 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 loops 3. What’s happening in consumer right now 4. Why the biggest opportunity in consumer is “/loop, make me happier” 5. Why moats are discovered, not designed 6. The rising importance of distribution as a moat 7. Being a model sommelier — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—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 podcast@lennyrachitsky.com. — 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 execution 2. How OpenAI thinks about building for model capabilities two to three months out 3. 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 job 5. Writing as thinking vs. writing as reporting — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—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 podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jen 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 like 2. The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously 3. 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 demo 5. The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away 6. 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 more Mercury—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 podcast@lennyrachitsky.com. — 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 designer 2. Why engineers 10x’d with AI but design teams haven’t 3. What OpenAI looks for when hiring designers 4. “Just do less”: Ian’s counterintuitive advice to his designers 5. The future of ChatGPT as a super app 6. 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 more Mercury—Radically different banking, now with Command — Where to find Ian Silber: • X: https://x.com/iansilber • LinkedIn: https://www.linkedin.com/in/iansilber • Website: https://iansilber.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Ian Silber (02:14) Why designers in general feel anxious about AI (09:01) What makes specific designers thrive in the AI era (13:41) Why Ian says it’s the best time in history to be a designer (17:13) How product roles are converging (22:24) Can AI design great products? (23:54) Where human judgment still matters (27:34) What Ian looks for when hiring designers (30:20) Why systems thinking matters (32:53) Balancing speed and craft (38:05) Designing for vastly different audiences (41:57) Solving the blank-box problem (43:31) How ChatGPT is evolving beyond chat (46:07) The vision for Codex (49:07) What Ian wishes he knew on day one (51:40) Why humility matters in AI (53:41) Advice for designers who are feeling overwhelmed (55:16) AI corner (57:43) Failure corner (01:00:45) Lightning round and final thoughts (01:05:52) Lessons from Groupon — Referenced: • OpenAI: https://openai.com • How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026 • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • 3 Spiderman Pointing meme template: https://www.kapwing.com/explore/3-spiderman-pointing-meme-template • OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape • Notion: https://www.notion.com • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • ChatGPT Work: https://openai.com/chatgpt-work • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Please Stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater • The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna • Maybe Happy Ending: https://www.maybehappyending.com • The Invite: https://www.imdb.com/title/tt14173636 • Rivian: https://rivian.com • Waymo: https://waymo.com • Groupon: https://www.groupon.com • How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital): https://www.lennysnewsletter.com/p/how-a-vc-and-a-tech-founder-used • Andrew Mason on X: https://x.com/andrewmason • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom • Sam Altman on X: https://x.com/sama — Recommended book: • The Design of Everyday Things: https://www.amazon.com/dp/0465050654 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Adam Ward is the Head of Talent at Cursor, one of the fastest-growing developer tools in history. Before joining Cursor, he founded Growth by Design, an independent recruiting and talent strategy firm that helped build teams at the most ambitious AI and technology companies in the world. Adam has spent more than 20 years building elite, high-talent-density teams across the industry and is widely regarded as one of the most effective and creative recruiters in tech. In our in-depth conversation, we discuss: 1. Inside today’s “tale of two cities” talent market 2. Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires 3. Adam’s three-step playbook: scoping, mapping, and relentless pursuit 4. The worst question to ask when sourcing great talent 5. The rise of the forward deployed engineer—and how to become one 6. 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 more Mercury—Radically different banking, now with Command — Where to find Adam Ward • X: https://x.com/wardadamp • LinkedIn: https://www.linkedin.com/in/adampward — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction (03:01) The state of the hiring market (06:41) What roles are trending up and what roles are trending down (11:25) The three-step hiring framework that changes everything (21:58) Getting the right people to actually respond (25:42) Keeping talent a top priority (29:16) Inside Cursor’s recruiting operation (32:19) How to relentlessly pursue top talent (35:42) “Caring is free” (38:33) The conversation most companies underestimate (39:19) Rethinking the atomic unit of a search (40:12) Other recruiting tactics (45:04) What the on-site is really for (49:35) The importance of work trials (53:10) The offer stage (57:53) Negotiations and comp (01:01:50) The details that actually close the deal (01:07:23) What it’s like working with an exec team who values recruiting (01:09:42) Talent density (01:11:18) The first recruiting hire most founders get wrong (01:15:00) Building incredible teams (01:18:12) The time between offer and acceptance (01:19:48) What’s next for the recruiting function (01:21:00) Lightning round — Referenced: • Cursor: https://cursor.com • Trilogy: https://trilogy.com • Brie Wolfson on LinkedIn: https://www.linkedin.com/in/brie-wolfson-17758724 • Inside Cursor: https://colossus.com/article/inside-cursor • SpaceX: https://www.spacex.com • Joe Gebbia’s website: https://joegebbia.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • The Pitt on HBO Max: https://www.hbomax.com/shows/pitt-2024/e6e7bad9-d48d-4434-b334-7c651ffc4bdf • The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f • Granola: https://www.granola.ai • Wispr Flow: https://wisprflow.ai • 11 products I love, free for a year—the biggest Product Pass expansion in 2 years: https://www.lennysnewsletter.com/p/productpass-summer2026launch • How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working • The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham — Recommended books: • Emotional Intelligence: Why It Can Matter More Than IQ: https://www.amazon.com/dp/055338371X • High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100 • Scaling People: Tactics for Management and Company Building: https://press.stripe.com/scaling-people — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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 role 3. What Tom looks for when hiring PMs 4. The shift toward senior ICs doing the work 5. How AI has transformed data science at Whatnot 6. Tom’s “play the accordion” mental model 7. Why “hire great people and get out of their way” fails 8. His biggest lessons from his time at Twitter — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Episode transcript: https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Tom Verrilli: • X: https://x.com/tdrobbo • LinkedIn: https://www.linkedin.com/in/tom-robertson-042 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction (02:40) “We regret that product management exists”: what it means and why (08:30) When specialization makes sense, and when it doesn’t (15:20) How Whatnot structures its PM org (17:28) What 31,832 PM applications revealed about the function (19:40) How to develop systems thinking (22:10) The shift to senior ICs doing IC work (32:26) Advice for PMs struggling in today’s market (35:22) How AI has transformed work at Whatnot (41:14) The data scientist problem (42:48) Which roles are trending up and down (44:48) What the product team of the future looks like (46:29) Why core PM skills are the most durable in an AI world (49:23) How to get the most out of the people you hire (53:32) Navigating the CPO-founder relationship (57:34) Advice for aspiring CPO’s (59:16) How to know when to stand firm and when to step back (01:01:38) Play the accordion: balancing strategic vision with fast iteration (01:06:35) Agentic commerce vs. live commerce (01:09:46) Lessons from Twitter (01:13:07) Failure corner (01:15:45) Lightning round and final thoughts — Referenced: • Whatnot: https://www.whatnot.com • Building, and Whatnot: https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc • Twitch: https://www.twitch.tv • Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future • Peter Bailis on LinkedIn: https://www.linkedin.com/in/pbailis • Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Ben Kus on LinkedIn: https://www.linkedin.com/in/benkus • Henry Shi on LinkedIn: https://www.linkedin.com/in/henrythe9th • Hex Threads: https://hex.tech/product/threads • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty • Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine • Logan Head on LinkedIn: https://www.linkedin.com/in/logan-head • Emmett Shear on LinkedIn: https://www.linkedin.com/in/emmettshear • Kara Swisher on X: https://x.com/karaswisher • Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY • Star City on AppleTV+: https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1 • For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7 • Service NSW Mobile App: https://www.service.nsw.gov.au/services/service-nsw-mobile-app • Rudyard Kipling: https://en.wikipedia.org/wiki/Rudyard_Kipling • E-fish.com: https://www.e-fish.com — Recommended books: • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/dp/0062273205 • The Purpose Driven Church: Every Church Is Big in God’s Eyes: https://www.amazon.com/dp/0310201063 • Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase. In our in-depth conversation, we discuss: 1. What Anthropic’s early days were like 2. The inflection points that turned Anthropic from an underdog into the fastest-growing company in history 3. How exactly Claude got so good at coding 4. The eval-driven development loop her team is pioneering 5. How to find joy in AI when everything is moving this fast 6. Why Claude’s willingness to push back is key to its success 7. Where human judgment remains irreplaceable — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Episode transcript: https://www.lennysnewsletter.com/p/anthropics-first-technical-pm-on — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Dianne Penn: • LinkedIn: linkedin.com/in/dianne-na-penn — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction (02:31) Early Anthropic days (08:55) Big milestones (13:50) Inside the exponential (20:02) Token maxing (23:30) Anthropic Labs and the incubation model (27:30) How the research role works (31:35) How to become a top researcher (35:18) Frontier model safeguards (39:38) Hiring in the AI era (44:16) Building an eval set (47:48) Evals vs PRDs (49:55) The importance of hands-on leadership (52:46) Finding joy in AI (58:10) How Dianne uses Claude (01:01:05) Avoiding overreliance on AI (01:03:50) The constitution that makes Claude better (01:07:11) AI writing and verification (01:11:40) Where human brains will continue to be valuable (01:14:10) Navigating AI with kids (01:16:26) Alignment, the future of the PM role, and burnout (01:21:54) Lightning round and final thoughts — Referenced: • Anthropic: https://www.anthropic.com • Golden Gate Claude: https://www.anthropic.com/news/golden-gate-claude • Dario Amodei’s website: https://darioamodei.com • Scaling Laws and Interpretability of Learning from Repeated Data: https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data • Tokenmaxxing: How Top Builders Use AI To Do The Work Of 400 Engineers: https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers • Garry Tan on X: https://x.com/garrytan • Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Introducing Labs: https://www.anthropic.com/news/introducing-anthropic-labs • Louis CK | about airplane Wi Fi: https://www.youtube.com/watch?v=me4BZBsHwZs • What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering • The Anthropic Hive Mind: https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b • How to build a company that withstands any era | Eric Ries, Lean Startup author: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands • Fallout on Prime Video: https://www.amazon.com/dp/B0CN4GGGQ2 • Fallout (video game): https://fallout.bethesda.net • Claude Tag: https://www.anthropic.com/news/introducing-claude-tag — Recommended books: • Crucial Conversations: Tools for Talking When Stakes Are High: https://www.amazon.com/dp/0071771328 • How to Raise an Adult: Break Free of the Overparenting Trap and Prepare Your Kid for Success: https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779 • Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great: https://www.amazon.com/dp/B0FWZZBPZB — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Elizabeth Stone is the Chief Product and Technology Officer (CPTO) at Netflix, where she oversees Engineering, Product, and Design. Since her first appearance on the podcast two years ago—which remained my second-most-popular episode for more than a year—she has expanded her role to lead product, in addition to engineering. Before Netflix, Elizabeth was VP of Science at Lyft, Chief Operating Officer at Nuna, an economist at Analysis Group, and a trader at Merrill Lynch. In our in-depth conversation, we discuss: 1. Why “systems thinking” is now the most important skill she looks for 2. How to manage the flood of AI-generated output without losing quality or signal 3. How Netflix thinks about AI fluency as a universal expectation rather than a level-specific skill 4. 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/lenny Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign — Episode transcript: https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Elizabeth Stone: • LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction (02:25) AI and role confusion: the storming phase before the forming phase (07:36) How roles have changed in the past two and a half years (11:55) Will functions survive? The case for craft specialism (13:26) What Netflix is hiring more of—and less of (17:22) Why systems thinking is the rising skill across every function (20:20) Is the design process dead? (22:08) Skills trending down (28:33) AI fluency and Netflix’s career ladder overlay (31:00) AI use cases beyond coding (35:12) Netflix’s AI history (38:36) Excellence as an operating system (41:11) The pillars of the excellence OS (46:41) The keeper’s test—and why it’s mostly a positive conversation (50:21) Attracting top talent in the age of frontier AI labs (52:54) Junior talent, craft mastery, and the mentorship question (56:25) Where engineering goes in 5 to 10 years (59:45) The future of entertainment: beyond film and TV (1:02:18) AI in Hollywood: Netflix’s creator-enablement position (1:06:15) Lightning round and final thoughts — Referenced: • How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • Claude Code: https://www.anthropic.com/product/claude-code • Claude Cowork: https://www.anthropic.com/product/claude-cowork • Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it • Innovation for Filmmaking, By Filmmakers: Why InterPositive Is Joining Netflix: https://about.netflix.com/en/news/why-interpositive-is-joining-netflix • InterPositive: https://weareinterpositive.com • Netflix Prize: https://en.wikipedia.org/wiki/Netflix_Prize • Quarterback on Netflix: https://www.netflix.com/title/81482895 • The Bill Simmons Podcast on Netflix: https://www.netflix.com/title/82186214 • Spencer Pratt on Instagram: https://www.instagram.com/spencerpratt • Salman Rushdie’s Substack: https://salmanrushdie.substack.com • Remarkably Bright Creatures on Netflix: https://www.netflix.com/title/81911351 • Eight Sleep: https://www.eightsleep.com • Tour de France: https://www.letour.fr/en — Recommended books: • Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557 • Into Thin Air: A Personal Account of the Mt. Everest Disaster: https://www.amazon.com/Into-Thin-Air-Personal-Disaster/dp/0385494785 • Liar’s Poker: https://www.amazon.com/Liars-Poker-Norton-Paperback-Michael/dp/039333869X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com