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1:21:08ENThe Opposite of Play Is Fear: How Jira's Head of Product Builds Safe, Fast-Moving TeamsGast: Megan Cook · Moderation: Lenny RachitskyMegan Cook of Atlassian on psychological safety, remote work habits, winning buy-in, and how a 12,000-person company keeps launching new products.
37:23ENFrom Chat to Always-On Agents: OpenAI's Tibo Sottiaux on Dots, Open Ecosystems and What Comes NextModeration: Lenny RachitskyThe head of ChatGPT and Codex, speaking hours after a DevDay launch of more than 20 products, explains the vision for a personal agent that works around the clock.
1:35:27ENSacred Cows Are Your Roadmap: Kayvon Beykpour on Reviving Twitter's Product CultureGast: Kayvon Beykpour · Moderation: Lenny RachitskyThe former head of product at Twitter on meeting Elon Musk, being fired during paternity leave, shipping through a risk-averse culture, and the lessons of Periscope.
1:11:58ENDare to Be Dull: A Stanford Communication Teacher's Playbook for Calmer, Sharper SpeakingGast: Matt Abrahams · Moderation: Lenny RachitskyMatt Abrahams shares practical ways to calm speaking anxiety and structure on-the-spot talk, from small talk and feedback to toasts, Q&A and apologies.
1:19:24ENLoops, Local Maxima and Ambition: Anish Acharya on How AI Rewires Companies and Consumer ProductsModeration: 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.
1:42:28ENJournalists Don't Care About You: A Magazine Editor's Field Guide to Getting PressGast: Jason Feifer · Moderation: Lenny RachitskyEntrepreneur editor-in-chief Jason Feifer explains how to prepare, pick the right writer, and pitch a story that an editor will actually say yes to.
1:03:27ENFind the Cultural Erogenous Zone: A Comms Playbook for Making Ideas SpreadGast: Lulu Cheng Meservey · Moderation: Lenny RachitskyLulu Cheng Meservey, the former Substack comms head, explains how underdog startups can build their own audiences, take smarter risks and shape messages people want to repeat.
1:32:06ENHow monday.com Turned a Competitor's Surprise Launch into a New Operating SystemModeration: 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 ExitModeration: 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.
1:14:35ENThe User Research Reckoning: Why Most Research Is the Wrong KindGast: Judd Antin · Moderation: Lenny RachitskyFormer Airbnb head of research Judd Antin explains why the UX research field is shrinking, what kind of research actually moves the business, and how PMs and researchers can fix the system together.
1:28:51ENSeven Years in the Making: How StackBlitz Turned Bolt into a $40M ARR Overnight SuccessGast: Eric Simons · Moderation: Lenny RachitskyStackBlitz CEO Eric Simons explains how a browser-based operating system, a bootstrapped team and a better Claude model turned a nearly bankrupt company into one of the fastest-growing products ever.
1:26:35ENThe Low-Heart-Rate Playbook: Sam Lessin on Etiquette Rules Silicon Valley Founders SkipModeration: 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.
1:13:36ENAsk for What You Want: Kenneth Berger on Integrity, Hearing No, and Getting Fired from Slack Three TimesGast: Kenneth Berger · Moderation: Lenny RachitskyThe first PM at Slack turned executive coach lays out a three-step practice for naming your desires, asking for them, and accepting whatever answer comes back.
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.
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