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1:25:49ENShip Weekly, Cut Scope, and Keep a Secret Roadmap: How Captions Builds in the AI EraPresenta: Lenny RachitskyGaurav Misra explains how a modern AI startup turns constant model progress into weekly shipped products, technical debt as leverage, and talking-video tools for non-professionals.
1:36:17ENUnderstaff on Purpose, Never Be Chill: Matt MacInnis on Leading Rippling Through EntropyPresenta: Lenny RachitskyRippling's chief product officer and longtime COO explains why extraordinary outcomes demand extraordinary effort, and the frameworks he uses to hire, set process and keep intensity high.
1:11:43ENTwo Engines, One Price: Madhavan Ramanujam on Monetizing AI Products from Day OnePresenta: Lenny RachitskyPricing expert Madhavan Ramanujam walks through the ideas in his book Scaling Innovation, from negotiation tactics and proof-of-concept design to a 2x2 for choosing an AI pricing model.
1:19:24ENLoops, Local Maxima and Ambition: Anish Acharya on How AI Rewires Companies and Consumer ProductsPresenta: Lenny Rachitskya16z's Anish Acharya argues that companies will become stacks of AI loops guided by human intuition, and that the biggest consumer prize is a loop that makes people happier.
1:32:06ENHow monday.com Turned a Competitor's Surprise Launch into a New Operating SystemPresenta: Lenny RachitskyChief Product and Technology Officer Daniel Lereya explains how impossible goals, radical transparency and timeboxed deadlines took monday.com past $1 billion in ARR.
1:31:50ENZero to $80M in Six Months: How a Solo Founder Bootstrapped Base44 to a Wix ExitPresenta: Lenny RachitskyMaor Shlomo explains how he built and grew the AI app builder Base44 without outside funding, the stack and habits that let one person compete with well-funded rivals, and how the Wix acquisition came together.
1:26:35ENThe Low-Heart-Rate Playbook: Sam Lessin on Etiquette Rules Silicon Valley Founders SkipPresenta: Lenny RachitskySlow Ventures partner Sam Lessin walks through introductions, conversation, dress, dining, scheduling, email and meetings, then closes with a contrarian take on seed investing in AI.
1:12:18ENThe Lego Inside Notion: Ivan Zhao on Lost Years, Small Teams, and Horizontal BetsPresenta: Lenny RachitskyIvan Zhao explains how Notion survived its lost years, stayed lean, corrected a non-Lego product detour, and built a horizontal platform now being reshaped by AI.
1:02:51ENThe Unreasonable Playbook Behind Gojek: Super Apps, Cash Vaults, and Brand as a MoatPresenta: Lenny RachitskyKevin Aluwi explains how Gojek scaled across Southeast Asia by building brand, running brutal operations, and rejecting copycat strategy.
56:42ENInside Gong's Product Machine: Pods, Design Partners, and Fast 51/49 DecisionsPresenta: Lenny RachitskyEilon Reshef explains how Gong pairs autonomous product pods with design partners, makes quick decisions, and builds AI products with measurement and expertise.
1:06:53ENLenny Rachitsky Answers Questions From His Wife: How a Newsletter Nobody Planned Became a BusinessPresenta: Lenny RachitskyIn a role-reversal episode, author Michelle Rial interviews Lenny about the moments that led to his newsletter, the stress behind the scenes, and what he has learned about quality and iteration.
44:53ENLegora's CEO on Building Legal AI That Survives the Next Model ReleasePresenta: Jacob EffronMax explains how Legora turns fast-moving model capabilities into end-to-end legal work, enterprise adoption, and a durable product strategy.
1:39:10ENAfter the Keyboard: Why Physical AI Is the Next Frontier, According to a Veteran Hardware LeaderPresenta: Lenny RachitskyCaitlin Kalinowski, who has built products at Apple, Meta and OpenAI, explains why robotics is heating up, what actually gates it, and how to build hardware that ships.
1:30:18ENNight Markets and Chip Foundries: A Week in Taiwan with Jensen HuangPresenta: Lex FridmanLex Fridman follows NVIDIA's CEO through Computex, street food and long chats about Taiwan's tech history, export controls and how to choose business partners.
53:42ENThe Missing Middle: Why Product Teams Work Hard Without a StrategyPresenta: Lenny RachitskyMelissa Perri explains how product organizations scale strategy, hire their first CPO, write a usable vision, and use product operations to make it last.
1:11:13ENAfter Code: Cursor's CEO on Logic Design, Custom Models and Why One Winner Will Take the MarketPresenta: Lenny RachitskyMichael Truell explains how Cursor went from a mechanical-engineering pivot to a $300M ARR product, and where he thinks programming is heading.
18:32ENBuild a Lab Inside Your Product Team: Dan Shipper on Keeping Up With a Moving AI FrontierPresenta: Lenny RachitskyEvery CEO Dan Shipper explains how a tiny, disposable-experiment lab can coexist with a focused product team, and how to move winners from one into the other.
1:14:41ENCaring Deeply, Measuring Clearly: Melissa Tan on Building High-Performing Growth TeamsPresenta: Lenny RachitskyA growth leader's guide to hiring, developing, and organizing teams—from Dropbox's early lessons to Webflow's operating rhythms.
1:22:31ENFall in Love With the Problem: Uri Levine on Product-Market Fit, Fundraising, and Firing FastPresenta: Lenny RachitskyA tactical founder playbook covering problem validation, product-market fit, fundraising narratives, hard hiring decisions, and user understanding.
1:11:51ENBuild the Skeleton Before the Makeup: Deel’s Playbook for $0 to $295M ARRPresenta: Lenny RachitskyMeltem Kuran Berkowitz explains how Deel used question-answering communities, disciplined SEO, long-tail paid bets and revenue-accountable hiring to scale.
1:01:12ENThe Failure Dividend: What Leaders from Airbnb, Google, Pets.com, Quibi, Duolingo, and Toast Learned from Their Worst MomentsPresenta: Lenny RachitskyA compilation of product leaders' most searing failures—and the operating lessons they extracted from them.
1:19:32ENProduct Ops Is the Operating System Your Product Team Is MissingPresenta: Lenny RachitskyMelissa Perri and Denise Tilles explain how product operations frees product managers from busywork, improves decision speed, and scales product organizations without adding unnecessary overhead.
1:36:53ENIdeology, Restraint and the Core: Peter Sellis on Building Product Teams That WinPresenta: Lenny RachitskySnapchat's first PM and former Discord head of product speaks candidly about team design, why the median PM is weak, and where consumer growth really comes from.
1:16:05ENThe Founder Is the Product: A Tactical Guide to Founder-Led SalesPresenta: Lenny RachitskyJen Abel walks through outbound messaging, first calls, co-authored scoping, procurement, and closing for early-stage founders.
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