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1:14:03ENThere Is No Marketing Playbook: Krithika Shankarraman's DATE FrameworkGuest Krithika Shankarraman · Host Lenny RachitskyThe first marketing hire at OpenAI and Stripe explains why diagnosing your own problem beats copying other companies' tactics.
1:39:22ENRust-Proofing a Company: Eric Ries on Why Success Corrupts and Governance ProtectsHost Lenny RachitskyThe author of The Lean Startup explains why good companies go bad, and the charters, trusts and habits that keep a mission intact.
1:07:20ENRiding the Lightning: What Hypergrowth Companies Share, According to Atlassian's Former Marketing ChiefGuest Carilu Dietrich · Host Lenny RachitskyCarilu Dietrich draws on her years at Atlassian and her advisory work with fast-growing B2B companies to explain how to build a career, a brand and a growth engine.
1:22:50ENRadical Self-Inquiry: Jerry Colonna on Growing Up Without Feeling Like CrapGuest Jerry Colonna · Host Lenny RachitskyExecutive coach Jerry Colonna explains why leadership and resilience come from honest inner work, not just practical skills, and how unexamined childhood patterns quietly shape our teams and companies.
1:36:17ENUnderstaff on Purpose, Never Be Chill: Matt MacInnis on Leading Rippling Through EntropyHost 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 OneHost 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.
1:21:17ENScaling People: Claire Hughes Johnson on Building the Company Behind the ProductGuest Claire Hughes Johnson · Host Lenny RachitskyStripe's former COO explains why operating structure, self-awareness and plain-spoken management matter as much as product-market fit.
1:19:24ENLoops, Local Maxima and Ambition: Anish Acharya on How AI Rewires Companies and Consumer ProductsHost 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 PressGuest Jason Feifer · Host 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 SpreadGuest Lulu Cheng Meservey · Host 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.
1:31:50ENZero to $80M in Six Months: How a Solo Founder Bootstrapped Base44 to a Wix ExitHost 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 SkipHost 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.
1:38:00ENRun Toward the Pain: Ben Horowitz on Hesitation, Confidence and Leading a Company Through the AbyssGuest Ben Horowitz · Host 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 AwayGuest Dhanji R. Prasanna · Host Lenny RachitskyBlock CTO Dhanji Prasanna explains how a reorg, an open-source agent and a learning-first culture made the company unusually AI-forward.
1:12:18ENThe Lego Inside Notion: Ivan Zhao on Lost Years, Small Teams, and Horizontal BetsHost 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 VernaGuest Elena Verna · Host 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.
1:09:38ENRyan Hoover on Experiments, Launches and the Mask Every Founder WearsGuest Ryan Hoover · Host 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.
1:02:51ENThe Unreasonable Playbook Behind Gojek: Super Apps, Cash Vaults, and Brand as a MoatHost Lenny RachitskyKevin Aluwi explains how Gojek scaled across Southeast Asia by building brand, running brutal operations, and rejecting copycat strategy.
1:06:53ENLenny Rachitsky Answers Questions From His Wife: How a Newsletter Nobody Planned Became a BusinessHost 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.
1:50:55ENTwo Hierarchies for Consumer and Marketplace Startups: Focus First, Tip Second, Dominate LastGuest Sarah Tavel · Host 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 AIGuest Howie Liu · Host 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.
1:21:08ENThe Magic Loop: How a Former Amazon VP Says You Can Earn Promotions by Helping Your BossGuest Ethan Evans · Host Lenny RachitskyEthan Evans explains his five-step career loop, how to break through at senior manager, how to invent on purpose, and what he learned from failing Jeff Bezos on a very public launch.
1:39:10ENAfter the Keyboard: Why Physical AI Is the Next Frontier, According to a Veteran Hardware LeaderHost 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.
1:13:37ENTen Hot Takes From a Bootstrapped SaaS Founder: Pricing, Retention, Tempo and the Middle of the FunnelGuest Patrick Campbell · Host Lenny RachitskyPatrick Campbell, who sold ProfitWell for more than $200 million without outside funding, runs through ten operating topics, from team culture and bootstrapping to pricing, churn and freemium.
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