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1:21:44ENFrom Rowing to Steering: Inside OpenAI's Push Toward Persistent AI CoworkersModeration: Lenny RachitskyTara Seshan, who leads product for Codex and ChatGPT Work at OpenAI, explains how PM work changes when agents do the rowing and people do the steering.
1:01:00ENControl Over Attention: How Substack Builds Product for Writers and ReadersGast: Sachin Monga · Moderation: Lenny RachitskySubstack's head of product, Sachin Monga, explains the principle behind the company's roadmap, the story of the Recommendations feature, and what he thinks the next era of writing on the internet looks like.
1:26:22ENStart Small, Earn Autonomy: What 50+ AI Product Deployments Taught Two BuildersModeration: Lenny RachitskyAishwarya Naresh Reganti and Kiriti Badam explain why AI products need a different build process, and how to grow agent autonomy step by step without losing customer trust.
1:25:13ENCodex Is Not Just a Coding Tool: OpenAI's Plan for an Agent That Behaves Like a TeammateModeration: Lenny RachitskyCodex product lead Alexander Embiricos explains the 20x growth, why every useful agent may need to write code, and why human review speed is the real bottleneck.
1:15:29ENThe Zero-Day Marketing Exploits Behind Breakout StartupsModeration: Lenny RachitskyAlistair Croll explains how founders can find unfair distribution advantages by subverting platforms, norms, and regulations—without actually being evil.
1:27:13ENFour Levels of Product-Market Fit: First Round's Playbook for B2B FoundersGast: Todd Jackson · Moderation: Lenny RachitskyTodd Jackson of First Round Capital walks through a staged framework for finding product-market fit, the benchmarks for each stage, and the four Ps you can change when you're stuck.
1:21:35ENLook Outside the Building: Shaun Clowes on Why Most PMs Fall Short and How AI Changes the JobGast: Shaun Clowes · Moderation: Lenny RachitskyConfluent's chief product officer explains how to become a far better product manager, why data matters more than models, and what AI will and won't do to SaaS.
1:35:11ENDon't Chase the Fake Rabbit: A Meta Product Leader's Guide to a 60-Year PM CareerGast: Nikhyl Singhal · Moderation: Lenny RachitskyNikhyl Singhal walks through early, mid and late career for product managers, from avoiding ex-growth companies to finding a North Star for "act three".
1:08:29ENTaste, Authenticity and Small Pods: Instagram's Adam Mosseri on Building Products in an AI WorldModeration: Lenny RachitskyThe head of Instagram explains how Meta's product teams are shrinking, why human judgment and creator identity matter more as AI content grows, and what he learned from his biggest failures.
48:08ENDylan Field on Taste, Simplicity, and Designing Through the AI HypeModeration: Lenny RachitskyFigma's CEO explains how intuition, feedback, and relentless simplification shape products—and why craft matters more as AI generates more software.
1:00:51ENInflict Pain, But Do It With a Smile: Julia Schottenstein on dbt's Rise and the Art of Getting AcquiredGast: Julia Schottenstein · Moderation: Lenny RachitskyA former NEA investor turned dbt Cloud product leader explains why dbt won, how to approach M&A and pricing, and how venture habits make her a better PM.
1:22:03ENWin Where Rivals Say "Life's Too Short": Roger Martin on the Five Questions of StrategyGast: Roger Martin · Moderation: Lenny RachitskyThe Playing to Win author walks through his strategy choice cascade, explains why differentiation or low cost is non-negotiable, and shows how to start fixing strategy one gap at a time.
1:10:40ENInside the New York Times' Plan to Build the Essential SubscriptionGast: Alex Hardiman · Moderation: Lenny RachitskyChief Product Officer Alex Hardiman on bundling news, games, cooking and sports, working alongside journalists, and measuring impact against a mission.
2:14:15ENEric Ries on the Lean Startup After 12 Years: What MVPs Really Mean, When to Pivot, and Building Companies for Human FlourishingGast: Eric Ries · Moderation: Lenny RachitskyThe author of The Lean Startup revisits misconceptions about MVPs and pivots, offers advice for stuck founders, and argues that governance, not just product, decides whether companies do good.
53:17ENCharge Sooner, Price Higher, Never Set It and Forget It: Naomi Ionita on MonetizationGast: Naomi Ionita · Moderation: Lenny RachitskyMenlo Ventures partner and former Evernote growth leader Naomi Ionita explains when to start charging, how to set and evolve prices, and what a "modern growth stack" looks like.
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.
1:09:54ENThe Context Makes the Irrational Rational: Bob Moesta's Guide to Jobs to Be DoneModeration: Lenny RachitskyBob Moesta explains how struggling moments create demand, how to interview customers like an investigator, and how to design products and sales processes around the progress people are trying to make.
1:28:40ENBuild First, Then Product Manage: Kevin Yien's Unorthodox PM PlaybookModeration: Lenny RachitskyKevin Yien shares contrarian PM lessons on starting as a builder, writing for clarity, decision logs, unsell emails, research automation and career resilience.
1:03:09ENCanva's Co-Founder on Joyful Products, Giving Away Your Lego, and Growing to $2.3 BillionGast: Cameron Adams · Moderation: Lenny RachitskyCameron Adams, Canva's co-founder and chief product officer, explains how product obsession, coaching culture, onboarding, SEO, localization, freemium and AI shaped one of the fastest-growing profitable software companies.
1:24:19ENThe Product Owner Trap: Why SAFe Creates Order-Takers and How to Build Real Product Management at ScaleModeration: Lenny RachitskyMelissa Perri explains the history of Scrum and SAFe, why product owners often become backlog clerks, and how large organizations can reconnect product work to customer value.
1:05:20ENPolite Interest Is Not Demand: How Wiz Found Product-Market Fit, and Then Made Some NoiseGast: Raaz Herzberg · Moderation: Lenny RachitskyRaaz Herzberg, Wiz's CMO and VP of product strategy, tells how the company's early pivot worked, why she moved from product into marketing, and what she learned along the way.
1:40:40ENThe Keeper of the Flame: Figma's Mihika Kapoor on Vision, Conviction, and Building Zero to One Inside a CompanyModeration: Lenny RachitskyA Figma PM's field guide to crafting a vision people can see, engineering hype honestly, and keeping a new idea alive inside a large company.
56:15ENPredictably Irrational: How Behavioral Science Reshapes Product DesignGast: Kristen Berman · Moderation: Lenny RachitskyKristen Berman of Irrational Labs explains her three-B framework and the experiments behind TikTok, One Medical and a failed budgeting feature.
1:32:09ENImpact First: How Product Teams Escape the Low-Impact Death SpiralGast: Matt LeMay · Moderation: Lenny RachitskyMatt LeMay explains why product teams must tie their work directly to business-critical outcomes, and the three steps for doing it whatever their company looks like.
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