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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.
1:34:27ENMatt Mullenweg on Open Source Ideals, the WP Engine Fight and Why Llama Isn't Really OpenGuest Matt Mullenweg · Host Lenny RachitskyThe WordPress co-creator and Automattic CEO gives his side of the WP Engine dispute, explains his open source philosophy, and talks AI, community building and acquisitions with Lenny Rachitsky.
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.
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.
1:30:00ENInside Stripe's Product Engineering Culture: Friction Logs, Engineer Occasions and 45-Minute DeploysGuest David Singleton · Host Lenny RachitskyStripe CTO David Singleton explains how the company hires, builds with early users, sweats the details and ships constantly without breaking a business-critical system.
1:11:13ENAfter Code: Cursor's CEO on Logic Design, Custom Models and Why One Winner Will Take the MarketHost Lenny RachitskyMichael Truell explains how Cursor went from a mechanical-engineering pivot to a $300M ARR product, and where he thinks programming is heading.
1:18:58ENDelta 4, Dharma and Second-Order Thinking: Kunal Shah's Philosophy of Building in IndiaGuest Kunal Shah · Host Lenny RachitskyCRED founder Kunal Shah explains his product framework, why India's market behaves differently, and the habits of curiosity he credits for his success.
1:17:34ENThe Three Flavors of AI Product Management — and What Separates the Top 5%Host Lenny RachitskyAman Khan, director of product at Arize AI, explains how PMs can break into AI, prototype their way to influence, and thrive as a long-term individual contributor.
52:09ENDifferent, Better, and Instant: What Cash App Taught Ayo Omojola About Building ProductsGuest Ayo Omojola · Host Lenny RachitskyCarbon Health's chief product officer on differentiation at Cash App, building inside a big company, hiring founders, and going deep on the details.
1:08:37ENBeing Strategic Is a Simple Why Plus a Big Change: Anneka Gupta on Product LeadershipGuest Anneka Gupta · Host Lenny RachitskyRubrik's chief product officer shares how she defines strategy, makes decisions, works with founders, gives feedback and keeps a positive mindset.
18:32ENBuild a Lab Inside Your Product Team: Dan Shipper on Keeping Up With a Moving AI FrontierHost Lenny RachitskyEvery CEO Dan Shipper explains how a tiny, disposable-experiment lab can coexist with a focused product team, and how to move winners from one into the other.
1:14:41ENCaring Deeply, Measuring Clearly: Melissa Tan on Building High-Performing Growth TeamsHost Lenny RachitskyA growth leader's guide to hiring, developing, and organizing teams—from Dropbox's early lessons to Webflow's operating rhythms.
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.
1:14:34ENInside the Frontier Lab: How Karina Nguyen Builds Products by Training the ModelGuest Karina Nguyen · Host Lenny RachitskyOpenAI researcher Karina Nguyen explains synthetic data, evals, how Canvas and Tasks were made, and which human skills matter as models get smarter.
1:09:48ENLovable's Anton Osika on Building "the Last Piece of Software" With 18 PeopleGuest Anton Osika · Host Lenny RachitskyThe Lovable CEO demos an AI software engineer live and explains how a tiny, obsessive team reached explosive growth.
1:18:47ENBefriend the Voice in Your Head: Executive Coach Joe Hudson on Emotions, Enjoyment and ExperimentsGuest Joe Hudson · Host Lenny RachitskyJoe Hudson, a coach to leaders at OpenAI, SpaceX and Apple, explains how to work with your inner critic, welcome your emotions and replace "should" with "want".
1:06:22ENWhen AI Writes 90% of the Code: Anthropic's CPO on New Bottlenecks, Builders and MCPHost Lenny RachitskyMike Krieger on how product work changes inside Anthropic, why he shut down Artifact, and where AI founders can build without being squashed.
1:46:35ENHire Your Agents Like Employees: Claire Vo's Field Guide to Running Nine OpenClawsHost Lenny RachitskyClaire Vo explains how she went from losing her family calendar to OpenClaw to running a team of specialized agents across her business, podcast, course and household.
1:19:56ENAnalytics With a Seat at the Table: How DoorDash Builds a Centralized Data TeamGuest Jessica Lachs · Host Lenny RachitskyDoorDash analytics chief Jessica Lachs explains why she keeps data scientists in one central org, how she hires for curiosity, and how she picks metrics that actually move a business.
22:15ENFrom Purpose to Product: Ebi Atawodi’s Playbook for a Vision That ShipsHost Lenny RachitskyHow YouTube Studio’s vision was built, socialized, and turned into live products—plus a practical playbook for product managers at any level.
1:19:34ENFei-Fei Li on ImageNet, World Models and Why Everyone Has a Role in AIHost Lenny RachitskyThe scientist often called the godmother of AI traces how big data sparked deep learning, explains why spatial intelligence is the next frontier, and shows what World Labs' first product, Marble, can do.
1:14:51ENLeaving Uber to Write Full Time: Gergely Orosz on Building The Pragmatic EngineerGuest Gergely Orosz · Host Lenny RachitskyThe author of the top engineering newsletter on Substack explains why he walked away from a big-tech career, what a week of full-time writing really looks like, and what it takes to make it work.
1:08:32ENSmall Teams, Hard Problems First: How Rippling's Jeremy Henrickson Keeps Velocity at ScaleGuest Jeremy Henrickson · Host Lenny RachitskyThe Rippling product chief and former Coinbase CPO on small teams, designing for the hardest case, fast decisions, and going all the way to the ground.
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