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1:30:46ENSkip the Funnel of Doom: Cursor's Playbook for Hiring the Top 50Moderation: Lenny RachitskyAdam Ward, Cursor's head of talent, explains how to scope, map and relentlessly pursue the best people instead of hiring whoever survives a recruiting funnel.
1:27:23ENGoing All In on AI at Cisco: Jeetu Patel on Platforms, Packet Loss and Telling People the TruthModeration: Lenny RachitskyCisco's president and chief product officer explains how a 90,000-person company went AI-first, what Cisco does in the AI infrastructure stack, and the leadership and career lessons behind it.
1:37:29ENInside Palantir's Founder Factory: Forward-Deployed Engineers, Ontologies and Deliberately Off-Putting HiringModeration: Lenny RachitskyFormer Palantir engineer Nabeel Qureshi explains how a services-heavy company became a data-platform giant, and why it keeps producing founders and product leaders.
1:22:39ENBarrels, Undiscovered Talent and Ugly Babies: Keith Rabois on Building Companies in the AI EraModeration: Lenny RachitskyKhosla Ventures' Keith Rabois explains how he spots talent, why he avoids customer feedback for consumer products, and how AI is reshaping product, design and engineering roles.
1:31:56ENGive Away Your Legos: Molly Graham's Handbook for Leading Through HypergrowthModeration: Lenny RachitskyMolly Graham walks through the frameworks she built at Google, Facebook, Quip and CZI, from giving away your Legos and the J-curve to the waterline model and six rules for goals.
1:41:43ENPumping Heat Into the Infinite Game: Tobi Lütke on First Principles and Human PotentialModeration: Lenny RachitskyShopify's founder explains how dissatisfaction with the status quo, long time horizons, and unquantifiable taste drive better products and companies.
1:12:07ENSystems Thinkers Over Specialists: Netflix CPTO Elizabeth Stone on Talent, AI and Excellence as an Operating SystemModeration: Lenny RachitskyNetflix's chief product and technology officer explains why blurred roles are still a storming phase, what skills she is hiring for, and how the company keeps a high bar as AI changes how work gets done.
1:19:25ENInside Mercado Libre: How 18,000 Engineers Ship 30,000 Changes a Day Without an Army of PMsModeration: Lenny RachitskySebastian Barrios, formerly head of product and engineering at Mercado Libre and now SVP of Engineering at Roblox, explains how a Latin American giant runs engineering and product as one team.
1:54:54ENSlow Down, Ask Questions, Sell the Vacation: An Executive Negotiator's PlaybookModeration: 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.
1:52:49ENInside Anthropic's Growth Team: Big Bets, Automated Experiments and Firefighting SuccessModeration: Lenny RachitskyAmol Avasare, Anthropic's Head of Growth, explains how a roughly 40-person team handles hypergrowth, automates experimentation with Claude, and rethinks the PM and engineer ratio.
1:49:13ENThe Unfair Fight: How Breakthrough Startups Escape the PresentModeration: Lenny RachitskyMike Maples Jr. explains how breakthrough startups combine inflections, non-consensus insights, and founder-future fit, then act through movements, storytelling, and disagreeableness.
56:39ENDeals Don’t Die From Competition—They Die From IndecisionModeration: Lenny RachitskyMatt Dixon distills 2.5 million sales conversations into the JOLT method for frozen buyers and the Challenger lesson on teaching insight.
1:21:34ENGitLab’s Public-by-Default Playbook: Short Toes, Clear Outcomes, and a Platform Built to ShipModeration: Lenny RachitskyDavid DeSanto explains how GitLab turns radical transparency, remote-first operations, and breadth-then-depth product strategy into a faster DevSecOps platform.
1:16:09ENFrom Free Users to Enterprise Contracts: The Product-Led Sales PlaybookModeration: Lenny RachitskyElena Verna explains how product-led sales turns self-serve usage into enterprise pipeline, and what product, sales, marketing, data, and tooling must change to make it work.
1:37:19ENImpact, Inquiry and Letting Fires Burn: Vlad Loktev's Playbook from a Decade Inside AirbnbModeration: 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.
1:24:24ENIntelligence for Heavy Machines: Qasar Younis on Why Physical AI Will Change Farms, Mines and Roads FirstModeration: Lenny RachitskyThe Applied Intuition co-founder explains why the biggest near-term AI impact is in vehicles and industrial machines, and shares the values, reading habits and management philosophy behind a quiet $15 billion company.
1:36:29ENSmiling Exhaustion: Inside the Tech Worker Sentiment Survey as AI's Honeymoon FadesModeration: Lenny RachitskyNoam Segal and Lenny Rachitsky walk through the second annual Tech Worker Sentiment Survey, which captured about 6,000 people in tech and found a workforce split down the middle by AI.
1:42:00ENThe Operating Lessons Brian Balfour Keeps Returning ToModeration: Lenny RachitskyReforge’s founder and CEO shares hard-won lessons on hiring, planning, growth systems, and defining who you are not for.
1:17:46ENShopify’s Anti-Playbook: Optimize for Churn, Hold Experiments for Years, and Ban KPIsModeration: 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.
1:25:50ENThe Skip, the Sidecar, and the Rabbit You Should Never Catch: Nikhyl Singhal on Building a 60-Year Product CareerModeration: Lenny RachitskyMeta and former Credit Karma product leader Nikhyl Singhal explains how to plan a career backwards from the job after next, spot ex-growth companies, diagnose a stalled promotion, and survive the success you've been chasing.
1:19:36ENWise and Curious: Chip Conley on Mentoring Brian Chesky, Dying Nine Times and Learning to Love MidlifeModeration: Lenny RachitskyThe hotelier who became Airbnb's "modern elder" at 52 on working for a founder in founder mode, why age diversity is a team asset, and what a near-death experience taught him.
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.
1:36:17ENUnderstaff 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.
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