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1:38:00ENRun Toward the Pain: Ben Horowitz on Hesitation, Confidence and Leading a Company Through the AbyssGast: Ben Horowitz · Moderation: Lenny RachitskyThe Andreessen Horowitz co-founder talks about the psychology of being a CEO, what product managers get wrong about leadership, whether AI is a bubble, and why the US must stay in the AI race.
1:26:42ENInside Block's AI-Native Bet: Goose, Functional Orgs and Throwing Code AwayGast: Dhanji R. Prasanna · Moderation: Lenny RachitskyBlock CTO Dhanji Prasanna explains how a reorg, an open-source agent and a learning-first culture made the company unusually AI-forward.
1:12:12ENModels Are Grown, Not Built: What Anthropic's Interpretability Research Sees Inside ClaudeModeration: Lenny RachitskyAnthropic researcher Emmanuel Ameisen explains how studying a language model's intermediate computations reveals concepts, plans and surprising quirks, and why that matters for alignment.
57:11ENFrom Artifact to Organism: Microsoft's Asha Sharma on Products That Learn and an Agentic SocietyGast: Asha Sharma · Moderation: Lenny RachitskyMicrosoft's AI platform product chief explains why products are becoming living systems tuned by post-training, why interfaces are shifting toward code and composability, and how agents may reshape the org chart.
1:32:41ENYou Can Patch a Bug but You Can't Patch a Brain: Why AI Guardrails FailModeration: Lenny RachitskyHackAPrompt's Sander Schulhoff explains why prompt injection and jailbreaking remain unsolved, why the guardrail industry is selling false comfort, and what organizations can do instead.
1:42:57ENFive Seconds, Real Stakes: Matthew Dicks on How to Tell Stories People RememberGast: Matthew Dicks · Moderation: Lenny RachitskyThe 59-time Moth Story Slam winner and author of Storyworthy explains the single-moment structure of good stories, how to use them at work, and how to calm stage nerves.
40:58ENBuilding AI Products When the Ground Keeps MovingModeration: Lenny RachitskyOpenAI's Kevin Weil and Anthropic's Mike Krieger discuss how AI product management differs from traditional software, from evals and enterprise buyers to computer use, reasoning models, and proactive agents.
1:12:19ENThe Three W's: A Practical Framework for Growing as a Product ManagerGast: Vikrama Dhiman · Moderation: Lenny RachitskyGojek's head of product Vikrama Dhiman explains what separates fast-rising PMs from stalled ones, and how to move into product from another discipline.
1:27:51ENOptimism, Laziness and "What If": Lessons from the Man Behind Google DocsGast: Sam Schillace · Moderation: Lenny RachitskySam Schillace, who created Writely (later Google Docs) and now helps lead AI work at Microsoft, on disruptive ideas, user laziness, failing on purpose, and where software is headed.
1:12:18ENThe Lego Inside Notion: Ivan Zhao on Lost Years, Small Teams, and Horizontal BetsModeration: 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.
1:35:10ENTen Growth Tactics That Never Work, According to Elena VernaGast: Elena Verna · Moderation: Lenny RachitskyGrowth leader Elena Verna runs through the growth plays she sees companies waste money on, the three frameworks she trusts instead, and her case for career optionality.
1:42:11ENTwenty Agents, 1.2 Humans: Inside SaaStr's AI-Run Sales TeamModeration: Lenny RachitskyJason Lemkin explains how SaaStr replaced a ten-person go-to-market team with AI agents, what it took to train them, and who survives the shift.
1:09:38ENRyan Hoover on Experiments, Launches and the Mask Every Founder WearsGast: Ryan Hoover · Moderation: Lenny RachitskyThe Product Hunt founder and Weekend Fund investor talks about starting small, raising money for a reason, launching well, his own regrets and how he now invests.
1:22:51ENCold DMs, Dinner-Party Communities, and the Case Against Jobs-to-Be-DoneModeration: Lenny RachitskyAarthi Ramamurthy and Sriram Krishnan on techno-optimism, relationship-driven careers, content creation, imposter syndrome, executive reviews, and why real products are trade-offs.
1:01:13ENNLX Is the New UX: Microsoft's Aparna Chennapragada on Designing for AgentsGast: Aparna Chennapragada · Moderation: Lenny RachitskyMicrosoft's chief product officer explains how she is building AI products a year ahead of the market, why conversation is a designable interface, and what stays the same for product builders.
1:02:51ENThe Unreasonable Playbook Behind Gojek: Super Apps, Cash Vaults, and Brand as a MoatModeration: 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 DecisionsModeration: 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 BusinessModeration: 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.
1:02:33ENEmpathy, Half-Built Products and Staying Power: Scott Belsky on Product Sense in the Age of AIGast: Scott Belsky · Moderation: Lenny RachitskyAdobe's chief strategy officer explains how he builds product intuition, why he kills features, how AI could change creative work, and when a founder should quit.
1:50:55ENTwo Hierarchies for Consumer and Marketplace Startups: Focus First, Tip Second, Dominate LastGast: Sarah Tavel · Moderation: Lenny RachitskyBenchmark partner Sarah Tavel walks through her hierarchy of engagement and hierarchy of marketplaces, and why both start with ruthless focus.
1:40:42ENThe IC CEO: How Airtable's Howie Liu Is Re-Founding a 13-Year-Old Product for AIGast: Howie Liu · Moderation: Lenny RachitskyAirtable's co-founder explains why he returned to hands-on product work, split his org into fast- and slow-thinking groups, and what skills every product team now needs.
21:48ENDon't Build Zombie UI: Katie Dill on Scaling Intent and Craft in the AI Building BoomModeration: Lenny RachitskyStripe's head of design argues that as AI lets everyone build, a clear point of view, encoded standards, ruthless editing and real creative ambition are what keep products from turning generic.
1:45:10ENShape Up in Real Life: Fixed Time, Variable Scope, and the Shaping Session That Makes It WorkGast: Ryan Singer · Moderation: Lenny RachitskyRyan Singer, author of Shape Up, explains appetites, six-week time boxes and live shaping sessions, and why copying Basecamp's method without its conditions fails.
2:14:39ENBrains at Work: A Neuroscience Playbook for Meetings, Influence and Team CultureGast: Evan LaPointe · Moderation: Lenny RachitskyCORE Sciences founder Evan LaPointe turns the brain's safety, reward and purpose systems into practical advice for meetings, relationships, culture and focus.
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