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1:24:56ENThe Social Radar: How Jessica Livingston Read Founders in Ten-Minute InterviewsGast: Jessica Livingston · Moderation: Lenny RachitskyThe Y Combinator co-founder explains what she looked for in early-stage founders, the Airbnb interview she never forgot, and why she started her own podcast.
59:50ENThe Nature of Product: Why Feature Factories Lose to Empowered TeamsModeration: Lenny RachitskyMarty Cagan explains why feature teams and real product teams are different animals, how companies lose product mojo as they scale, and what product managers must protect to do the job well.
1:10:54ENFuel and Engine: A Practical Playbook for Hiring Your First B2B MarketerGast: Emily Kramer · Moderation: Lenny RachitskyMarketing leader and investor Emily Kramer explains how to diagnose what your startup's marketing needs, who to hire, and how product and marketing teams can work well together.
1:34:01ENQuality Is Growth: Stripe's Katie Dill on Beauty, Walking the Store and Building Design TeamsGast: Katie Dill · Moderation: Lenny RachitskyStripe's head of design explains why beauty and function work together, how Stripe operationalises quality across 15 critical user journeys, and what she has learned leading design at Airbnb, Lyft and Stripe.
58:12ENProduct Management in a Newsroom: Equanimity, Dress Rehearsals and Journalists as CustomersGast: Upasna Gautam · Moderation: Lenny RachitskyCNN product manager Upasna Gautam explains how her team builds a content management system for journalists amid constant breaking news, and how mindfulness shapes the way she leads.
1:07:32ENMinimal Lovable Products, the Airbnb Plus Post-Mortem, and the Trust Bank: Product Lessons from Jiaona ZhangModeration: Lenny RachitskyWebflow's SVP of Product on the mistakes new PMs make, why Airbnb Plus never had a path, roadmap-as-story, OKRs that stretch instead of sandbag, surviving WeWork, and how to spend your first 90 days.
1:32:32ENDevin's Scott Wu on Building an AI Software Engineer and Turning Coders into ArchitectsGast: Scott Wu · Moderation: Lenny RachitskyThe Cognition co-founder explains how his 15-person team uses fleets of Devins to build Devin, what the product can and can't do, and why he expects more engineers, not fewer.
55:48ENWhen to Invent a Category, and How Miro Rebranded Itself into OneGast: Barbra Gago · Moderation: Lenny RachitskyFormer Miro CMO Barbra Gago explains how category creation, a rushed rebrand and opinionated software work in practice.
1:25:11ENInside Miro's Product Machine: Empathy, Competition and a Biweekly Demo Party That Saved Three MonthsGast: Varun Parmar · Moderation: Lenny RachitskyMiro chief product officer Varun Parmar walks Lenny Rachitsky through the company's product values, org design, competitive philosophy, planning cadence and growth model.
1:31:29ENLovable's Growth Playbook: Give It Away, Ship Daily and Recapture Product-Market Fit Every Three MonthsGast: Elena Verna · Moderation: Lenny RachitskyElena Verna, head of growth at Lovable, explains why most of her 15-20 years of growth experience no longer applies to a company that passed $200 million ARR in under a year.
22:31ENTen Regrets: Marty Cagan on What He Got Wrong About ProductModeration: Lenny RachitskyAt Lenny and Friends Summit, Marty Cagan revisits his decades of product advice and names the ten things he would change.
1:01:05ENThe Most Popular Product Lessons of the Year, From Positioning to Hard ConversationsModeration: Lenny RachitskyA countdown of Lenny's ten most downloaded episodes, distilled into practical lessons on positioning, analytics, growth, career leverage, product leadership, and management.
50:03ENCopilot Is a Copilot, Not a Pilot: Inbal Shani on the Future of AI in Software DevelopmentModeration: Lenny RachitskyGitHub's chief product officer explains what AI changes for developers, what it does not replace, and how teams should adopt it.
1:22:31ENPower Is a Tool: Stanford's Jeffrey Pfeffer on the Seven Rules of Getting AheadGast: Jeffrey Pfeffer · Moderation: Lenny RachitskyStanford organizational behavior professor Jeffrey Pfeffer walks Lenny Rachitsky through the seven rules of power, the homework that makes them stick, and the price power exacts.
1:17:25ENDon't Trust the Process: How Design Work Is Being Rebuilt Around Engineers and AgentsModeration: Lenny RachitskyClaude Cowork design lead Jenny Wen explains why the classic discovery-to-mock workflow is fading, what designers do instead, and who she wants to hire.
1:47:31ENFrom Fever Dream to Wilderness: Drew Houston on Dropbox's Three ErasGast: Drew Houston · Moderation: Lenny RachitskyDropbox's co-founder and CEO gives a candid account of explosive growth, the Google Photos shock, a painful pivot to productivity, and the personal and organizational reset that followed.
2:01:57ENBuild the Sales Team Like a Founder: Jason Lemkin on Hiring, Comp and Keeping Product CloseGast: Jason Lemkin · Moderation: Lenny RachitskySaaStr founder Jason Lemkin walks through when to hire your first reps, who to hire, how to pay them, how product and sales should work together, and why customer-hostile tactics don't compound.
1:37:47ENYou Can Patch a Bug, but You Can't Patch a Brain: Why AI Guardrails FailGast: Sander Schulhoff · Moderation: Lenny RachitskyAdversarial-robustness researcher Sander Schulhoff explains why prompt injection and jailbreaks remain unsolved, why guardrail products don't deliver, and what teams can do instead.
1:18:22ENShipyards, Sharp Problems and Humility: Two Veteran Product Leaders on the PM Role in the AI EraModeration: Lenny RachitskyOji and Ezinne Udezue explain how product management is changing, which skills matter now, and what the companies winning with AI do differently.
1:41:44ENZig When Others Zag: HubSpot Co-founder Dharmesh Shah on Simplicity, Culture as a Product and Building a Company Around Your StrengthsGast: Dharmesh Shah · Moderation: Lenny RachitskyThe HubSpot co-founder and CTO explains why he has never had a direct report, how he measures laughs per minute, and the first-principles habits behind HubSpot's contrarian choices.
1:02:49ENStop Being the Arrogant Doctor: Andy Raskin on Pitching a Movement, Not a ProductGast: Andy Raskin · Moderation: Lenny RachitskyStrategic narrative consultant Andy Raskin explains the five-part story structure behind pitches at Salesforce, Zuora and Gong, and how to make it your company's north star.
1:10:32ENA Billion Dollars, No VC, Under 100 People: Surge AI's Edwin Chen on Data Quality and Where AI Is HeadingGast: Edwin Chen · Moderation: Lenny RachitskySurge AI's founder explains how a bootstrapped team built the leading human-data company, why he distrusts benchmarks, and how reinforcement learning environments are the next frontier.
1:16:17ENFaster, But for What? Nicole Forsgren on Measuring Developer Productivity in the AI EraGast: Nicole Forsgren · Moderation: Lenny RachitskyThe creator of DORA and SPACE explains why most productivity metrics mislead, how AI changes flow and trust, and how to build a developer experience program that proves its value.
1:04:21ENOnboarding Is Growth's Biggest Lever: Lessons from Airtable's Former Head of GrowthGast: Lauryn Isford · Moderation: Lenny RachitskyLauryn Isford on rethinking experimentation, choosing a hard-to-reach activation metric, reverse trials, and the PLG funnel.
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