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1:14:03ENThere Is No Marketing Playbook: Krithika Shankarraman's DATE FrameworkGast: Krithika Shankarraman · Moderation: 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 ProtectsModeration: 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 ChiefGast: Carilu Dietrich · Moderation: 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 CrapGast: Jerry Colonna · Moderation: 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 EntropyModeration: 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 OneModeration: 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 ProductGast: Claire Hughes Johnson · Moderation: 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 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.
1:31:50ENZero 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.
1:26:35ENThe 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.
1:38:00ENRun 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.
1:12:18ENThe 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.
1:09:38ENRyan 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.
1:02:51ENThe 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.
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.
1:50:55ENTwo 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.
1:21:08ENThe Magic Loop: How a Former Amazon VP Says You Can Earn Promotions by Helping Your BossGast: Ethan Evans · Moderation: 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 LeaderModeration: 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 FunnelGast: Patrick Campbell · Moderation: 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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