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1:17:46ENShopify’s Anti-Playbook: Optimize for Churn, Hold Experiments for Years, and Ban KPIsHost Lenny RachitskyArchie Abrams explains how Shopify grows by lowering barriers, measuring cohort GMV, running multi-year holdouts, and letting a 100-year vision guide core product.
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.
2:04:21EN"AI Doctors Are Here": A Father's Account of Fighting His Son's Burkitt Leukemia With GPT-5 Pro and Gemini 3Host Nathan LabenzNathan Labenz recounts the first three weeks of his 6-year-old son's cancer diagnosis and how frontier models served as second opinions, bedside co-pilots and relapse planners.
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.
14:38ENPlay Badly, Have Fun: Lex Fridman and RZA Trade Trash Talk Over a Casual Chess GameHost Lex FridmanAn impromptu post-podcast chess match between Lex Fridman and RZA, framed by Lex's case for playing chess for the joy of it.
53:42ENThe Missing Middle: Why Product Teams Work Hard Without a StrategyHost Lenny RachitskyMelissa Perri explains how product organizations scale strategy, hire their first CPO, write a usable vision, and use product operations to make it last.
1:17:55ENThe Quiet Advantage: How Introverts Can Thrive Without Pretending to Be ExtrovertsHost Lenny RachitskySusan Cain explains what introversion really is and offers practical ways to build visibility, run meetings, parent quiet kids, and design a career around your temperament.
1:33:38ENSell Before You Tell: Wes Kao's Tactics for Communication That Actually LandsHost Lenny RachitskyExecutive-communication teacher Wes Kao breaks down the frameworks — sales before logistics, signposting, MOO, CEDAF — that turn clear thinking into buy-in.
1:29:39ENFive Customers, Three Prototypes, One Day: How to Find Your Bullseye CustomerHost Lenny RachitskyMichael Margolis of GV explains how to narrow to the customer most likely to adopt first — and how to prove it with a one-day research sprint.
1:31:56ENPerfect Is Creepy: What a Child Psychologist Knows About Leading Difficult AdultsHost Lenny RachitskyDr. Becky Kennedy explains how the principles she uses to raise resilient kids apply to managers, teams and colleagues.
10:39ENStatistics as Decision-Making: Michael I. Jordan on Bayesians, Frequentists and the Ideas Between ThemHost Lex FridmanBerkeley's Michael I. Jordan explains where statistics came from, why it is really about decisions, and how empirical Bayes and false discovery rate bridge two rival philosophies.
1:01:12ENThe Failure Dividend: What Leaders from Airbnb, Google, Pets.com, Quibi, Duolingo, and Toast Learned from Their Worst MomentsHost Lenny RachitskyA compilation of product leaders' most searing failures—and the operating lessons they extracted from them.
1:14:37ENLead Like You Own the Next Play: Brian Halligan's Playbook for Founder CEOs in the AI EraHost Lenny RachitskySequoia's in-house CEO coach and HubSpot co-founder on hiring spiky talent, the LOCKS framework, the future of go-to-market, and the "Halliganisms" he learned the hard way.
30:20ENDraw the Circle: Julie Zhuo’s Five-Step Playbook for Influencing Hard Product DecisionsHost Lenny RachitskyA practical process for turning prioritization fights into shared learning, evidence gathering, and clear decision ownership.
24:50ENThe Rituals Behind Great Decisions: Eigenquestions, Dory/Pulse, and the Forum That Replaces Standing MeetingsHost Lenny RachitskyHow Coda and other companies design decision rituals—from eigenquestions and two-way write-ups to multi-threaded forums and proactive stakeholder tags.









