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1:24:58ENFewer PMs, More Reps: Whatnot's CPO on Why Senior Product People Should Go Back to Doing the WorkHost Lenny RachitskyTom Verrilli explains why Whatnot built its product team on the premise that it regrets product management exists, and what that means for hiring, AI tooling and the shape of the role.
1:54:54ENSlow Down, Ask Questions, Sell the Vacation: An Executive Negotiator's PlaybookHost Lenny RachitskyJacob Warwick explains how senior operators win bigger offers by treating a job search like an enterprise sale and negotiating collaboratively rather than confrontationally.
1:21:08ENSpeed Is a Symptom of Competence: How Linear Builds Beloved B2B SoftwareHost Lenny RachitskyNan Yu explains Linear’s operating principles for fast iteration, resisting bloat, discovering emotional customer pain, and making product management a go-to-market discipline.
1:23:46ENSurviving the Next Crisis: Waze Co-Founder Uri Levine on Cash Shocks, Lost Product-Market Fit and Never Giving UpGuest Uri Levine · Host Lenny RachitskyUri Levine explains how founders should diagnose a startup crisis, act within days, keep their teams on board and decide whether to pivot or shut down.
1:23:08ENMost Ideas Fail: Ronny Kohavi on Running A/B Tests You Can TrustGuest Ronny Kohavi · Host Lenny RachitskyThe author of Trustworthy Online Controlled Experiments explains failure rates, overall evaluation criteria, sample ratio mismatch, Twyman's law and how to build an experimentation culture.
59:50ENThe Nature of Product: Why Feature Factories Lose to Empowered TeamsHost 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.
1:07:32ENMinimal Lovable Products, the Airbnb Plus Post-Mortem, and the Trust Bank: Product Lessons from Jiaona ZhangHost 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.
1:35:39ENMake Time: Pick a Daily Highlight and Build Barriers Against DistractionGuest Jake Knapp, John Zeratsky · Host Lenny RachitskyJake Knapp and John Zeratsky walk through their four-step Make Time framework (highlight, laser, energize, reflect) and close with a short look at the design sprint.
56:39ENDeals Don’t Die From Competition—They Die From IndecisionHost Lenny RachitskyMatt Dixon distills 2.5 million sales conversations into the JOLT method for frozen buyers and the Challenger lesson on teaching insight.
1:11:08ENFear Gives Bad Advice: An Executive Coach's Playbook for Firing, Layoffs and FocusGuest Matt Mochary · Host Lenny RachitskyExecutive coach Matt Mochary tells Lenny Rachitsky how he helps CEOs act through fear, let people go humanely, run layoffs, innovate inside big companies and audit their energy.
45:34ENThe Four Questions Shreyas Doshi Wishes He Had Asked Himself SoonerHost Lenny RachitskyA live conversation about scope, strategy, taste, and listening as the hidden drivers of product leadership.
1:37:19ENImpact, Inquiry and Letting Fires Burn: Vlad Loktev's Playbook from a Decade Inside AirbnbHost Lenny RachitskyFormer Airbnb homes GM and new Index Ventures partner Vlad Loktev tells Lenny Rachitsky how he prioritizes, disagrees, scales teams and keeps his balance in hypergrowth.
1:12:52ENFrom Google+ to the Tabbed Inbox: How to Build Products on Evidence, Not OpinionGuest Itamar Gilad · Host Lenny RachitskyFormer Google product manager Itamar Gilad contrasts a failed social network with a hit Gmail feature and walks through the GIST framework from his book Evidence-Guided.
1:24:42ENDistraction Is an Emotion Problem, Not a Technology Problem: Nir Eyal's Playbook for Becoming IndistractableGuest Nir Eyal · Host Lenny RachitskyThe author of Hooked and Indistractable explains why most distraction starts within us, and walks through a dozen tactics for focus, scheduling, pacts and workplace culture.
1:47:22ENStrategy Is Not a Gift: A Five-Phase Playbook You Can Run in 8–12 WeeksGuest Chandra Janakiraman · Host Lenny RachitskyChandra Janakiraman, CPO of VRChat, walks through an operator's recipe for building product strategy, from leadership interviews to a three-pillar rollout, plus a longer "big S" process for aspirational futures.
1:18:05ENAllow the Fear: J.M. Nickels on Conscious Leadership, Strategy, and Choosing Your Life's Objective FunctionHost Lenny RachitskyA product leader who built Uber Pool and led commercialization at Waymo explains how inner work, first-principles futures, and an explicit life objective function make better leaders and better products.
26:40ENGet to the Punchline: How Figma's Slides Team Won Trust Instead of Just a Green LightHost Lenny RachitskyFigma's Mika and Yuki explain why the standard PM playbook for product reviews backfires — and the tactics they used instead to get Figma Slides built, funded and launched.
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.
1:12:13ENOne Wish From a Genie: A Stanford Professor's Method for Getting Off AutopilotGuest Graham Weaver · Host Lenny RachitskyGraham Weaver, a Stanford GSB lecturer and founder of Alpine Investors, shares practical exercises for working out what you actually want to do with your life and staying with it long enough to succeed.
12:53ENPrinciples, Not Black Boxes: Ray Dalio on When to Trust AIGuest Ray Dalio · Host Lex FridmanRay Dalio explains how Bridgewater turns human thinking into algorithms, why machine learning is risky when the future differs from the past, and why writing down principles is the route to better decisions.
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.
1:18:28ENCuriosity Loops: Ada Chen Rekhi's Method for Better Decisions and a Career You Won't RegretGuest Ada Chen Rekhi · Host Lenny RachitskyAn executive coach and Notejoy co-founder on structured advice-gathering, values exercises, explore-and-exploit careers, coaching and co-founding with a spouse.
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.
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