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1:25:49ENShip Weekly, Cut Scope, and Keep a Secret Roadmap: How Captions Builds in the AI EraPresenta: Lenny RachitskyGaurav Misra explains how a modern AI startup turns constant model progress into weekly shipped products, technical debt as leverage, and talking-video tools for non-professionals.
1:09:56ENWhen Anyone Can Build Anything, Taste Becomes the Product JobPresenta: Lenny RachitskyCodex desktop lead Andrew Ambrosino on how AI has inverted product development, why roles are blurring but shouldn't vanish, and where Codex and ChatGPT are headed.
1:36:17ENUnderstaff on Purpose, Never Be Chill: Matt MacInnis on Leading Rippling Through EntropyPresenta: 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.
1:51:30ENNever Search Alone: Why a Job Search Council Beats Going It SoloInvitado: Phyl Terry · Presenta: Lenny RachitskyPhyl Terry explains how job seekers can borrow product-management methods and a small peer group to find work they actually want, even in a down market.
1:08:36ENStorytelling, Customer Proximity and Community: How Figma's CPO Thinks About Building Great ProductInvitado: Yuhki Yamashita · Presenta: Lenny RachitskyYuhki Yamashita on product storytelling, owning the why, staying close to customers, rethinking OKRs, hiring, and community-led growth at Figma.
1:11:43ENTwo Engines, One Price: Madhavan Ramanujam on Monetizing AI Products from Day OnePresenta: 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.
1:03:21ENBring the Insight: How a Young Product Leader Earns Trust at AsanaInvitado: Paige Costello · Presenta: Lenny RachitskyAsana's Paige Costello on planning, the Double Diamond process, coaching PMs, and what holds new product managers back.
1:18:28ENCuriosity Loops: Ada Chen Rekhi's Method for Better Decisions and a Career You Won't RegretInvitado: Ada Chen Rekhi · Presenta: 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 ProductInvitado: Claire Hughes Johnson · Presenta: Lenny RachitskyStripe's former COO explains why operating structure, self-awareness and plain-spoken management matter as much as product-market fit.
1:21:57ENBehind the Wheel: How Uber's Product Chief Dogfoods His Way to Better ProductsPresenta: Lenny RachitskySachin Kansal on extreme dogfooding, shipping fast, Uber's hybrid autonomy strategy and making gut calls against the data.
1:11:26ENManage Your Career Like a Product: Deb Liu on Resilience, Introversion and Big SwingsInvitado: Deb Liu · Presenta: Lenny RachitskyThe former Facebook VP and current Ancestry CEO explains how to keep learning, bounce back from failure, build new businesses inside large companies, and plan a career with intention.
1:21:08ENThe Opposite of Play Is Fear: How Jira's Head of Product Builds Safe, Fast-Moving TeamsInvitado: Megan Cook · Presenta: Lenny RachitskyMegan Cook of Atlassian on psychological safety, remote work habits, winning buy-in, and how a 12,000-person company keeps launching new products.
37:23ENFrom Chat to Always-On Agents: OpenAI's Tibo Sottiaux on Dots, Open Ecosystems and What Comes NextPresenta: Lenny RachitskyThe head of ChatGPT and Codex, speaking hours after a DevDay launch of more than 20 products, explains the vision for a personal agent that works around the clock.
1:35:27ENSacred Cows Are Your Roadmap: Kayvon Beykpour on Reviving Twitter's Product CultureInvitado: Kayvon Beykpour · Presenta: Lenny RachitskyThe former head of product at Twitter on meeting Elon Musk, being fired during paternity leave, shipping through a risk-averse culture, and the lessons of Periscope.
1:11:58ENDare to Be Dull: A Stanford Communication Teacher's Playbook for Calmer, Sharper SpeakingInvitado: Matt Abrahams · Presenta: Lenny RachitskyMatt Abrahams shares practical ways to calm speaking anxiety and structure on-the-spot talk, from small talk and feedback to toasts, Q&A and apologies.
1:19:24ENLoops, Local Maxima and Ambition: Anish Acharya on How AI Rewires Companies and Consumer ProductsPresenta: Lenny Rachitskya16z's Anish Acharya argues that companies will become stacks of AI loops guided by human intuition, and that the biggest consumer prize is a loop that makes people happier.
1:42:28ENJournalists Don't Care About You: A Magazine Editor's Field Guide to Getting PressInvitado: Jason Feifer · Presenta: Lenny RachitskyEntrepreneur editor-in-chief Jason Feifer explains how to prepare, pick the right writer, and pitch a story that an editor will actually say yes to.
1:03:27ENFind the Cultural Erogenous Zone: A Comms Playbook for Making Ideas SpreadInvitado: Lulu Cheng Meservey · Presenta: Lenny RachitskyLulu Cheng Meservey, the former Substack comms head, explains how underdog startups can build their own audiences, take smarter risks and shape messages people want to repeat.
1:32:06ENHow monday.com Turned a Competitor's Surprise Launch into a New Operating SystemPresenta: Lenny RachitskyChief Product and Technology Officer Daniel Lereya explains how impossible goals, radical transparency and timeboxed deadlines took monday.com past $1 billion in ARR.
1:31:50ENZero to $80M in Six Months: How a Solo Founder Bootstrapped Base44 to a Wix ExitPresenta: Lenny RachitskyMaor Shlomo explains how he built and grew the AI app builder Base44 without outside funding, the stack and habits that let one person compete with well-funded rivals, and how the Wix acquisition came together.
1:14:35ENThe User Research Reckoning: Why Most Research Is the Wrong KindInvitado: Judd Antin · Presenta: Lenny RachitskyFormer Airbnb head of research Judd Antin explains why the UX research field is shrinking, what kind of research actually moves the business, and how PMs and researchers can fix the system together.
1:28:51ENSeven Years in the Making: How StackBlitz Turned Bolt into a $40M ARR Overnight SuccessInvitado: Eric Simons · Presenta: Lenny RachitskyStackBlitz CEO Eric Simons explains how a browser-based operating system, a bootstrapped team and a better Claude model turned a nearly bankrupt company into one of the fastest-growing products ever.
1:26:35ENThe Low-Heart-Rate Playbook: Sam Lessin on Etiquette Rules Silicon Valley Founders SkipPresenta: Lenny RachitskySlow Ventures partner Sam Lessin walks through introductions, conversation, dress, dining, scheduling, email and meetings, then closes with a contrarian take on seed investing in AI.
1:13:36ENAsk for What You Want: Kenneth Berger on Integrity, Hearing No, and Getting Fired from Slack Three TimesInvitado: Kenneth Berger · Presenta: Lenny RachitskyThe first PM at Slack turned executive coach lays out a three-step practice for naming your desires, asking for them, and accepting whatever answer comes back.
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