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1:20:53ENDon't Die: Y Combinator's Dalton Caldwell on Keeping a Startup AliveGuest Dalton Caldwell · Host Lenny RachitskyThe YC group partner on pivots, tarpit ideas, why investors say no, how to talk to customers, and what he hopes founders will build next.
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.
1:17:35ENStick With It: Chris Hutchins on Big Product Bets and Building a Top Business PodcastGuest Chris Hutchins · Host Lenny RachitskyThe former Wealthfront product lead behind All the Hacks explains how to run bold bets inside a company and how to launch, grow and sustain a podcast.
1:33:55ENGetting Startup Press Without a Rolodex: A Practical PR PlaybookGuest Emilie Gerber · Host Lenny RachitskyPR agency founder Emilie Gerber walks through which outlets to target, how to write a three-sentence pitch, and how to judge whether press is worth the effort.
10:17ENWhy Great Robots Fail as Businesses, and What iRobot Got RightHost Lex FridmaniRobot co-founder Colin Angle explains why so many robotics companies collapse and how cost, vision and a clear user need shaped the Roomba.
1:24:56ENThe Social Radar: How Jessica Livingston Read Founders in Ten-Minute InterviewsGuest Jessica Livingston · Host Lenny RachitskyThe Y Combinator co-founder explains what she looked for in early-stage founders, the Airbnb interview she never forgot, and why she started her own podcast.
1:10:54ENFuel and Engine: A Practical Playbook for Hiring Your First B2B MarketerGuest Emily Kramer · Host Lenny RachitskyMarketing leader and investor Emily Kramer explains how to diagnose what your startup's marketing needs, who to hire, and how product and marketing teams can work well together.
1:41:44ENZig When Others Zag: HubSpot Co-founder Dharmesh Shah on Simplicity, Culture as a Product and Building a Company Around Your StrengthsGuest Dharmesh Shah · Host Lenny RachitskyThe HubSpot co-founder and CTO explains why he has never had a direct report, how he measures laughs per minute, and the first-principles habits behind HubSpot's contrarian choices.
23:57ENChips, Agents and a Reckoning: Sarah Guo and Elad Gil on the 2023 AI BoomHost Sarah Guo, Elad GilThe hosts answer listener questions on the GPU crunch, how soon enterprises will ship AI products, how to build agents, and what 2024 holds for tech valuations.
1:49:39ENNo Investors, 24 Profitable Years: Jason Fried on Staying Small, Trusting Your Gut and Making Money FirstGuest Jason Fried · Host Lenny RachitskyThe 37signals co-founder explains how a 75-person, investor-free company has out-earned far larger rivals, and why he builds products in two-person, six-week cycles.
1:01:41ENDon't Outsource the Learning: Pete Kazanjy's Case for Founder-Led SalesGuest Pete Kazanjy · Host Lenny RachitskyThe author of Founding Sales explains why B2B founders should sell for a long time themselves, how to know when to hire, and how to get better at selling.
1:22:43ENWhy You Won't Know a Great Name When You See It: Inside Lexicon's Naming ProcessHost Lenny RachitskyDavid Placek of Lexicon Branding explains how his team names brands like Sonos, Azure, Windsurf and Vercel, and how founders can do it on a budget.
1:16:57ENHow Ramp Reached $100M in Revenue with 50 People: Velocity, Single-Threaded Teams and Context Over ControlGuest Geoff Charles · Host Lenny RachitskyRamp's VP of Product Geoff Charles explains to Lenny Rachitsky how a culture of velocity, tiny focused teams and radically empowered engineers drove one of the fastest SaaS growth runs on record.
1:25:36ENMake Things People Want: What 600 YC Startups Taught Gustaf AlströmerGuest Gustaf Alstromer · Host Lenny RachitskyA Y Combinator group partner and early Airbnb growth lead explains why startups fail, what successful founders share, and why climate tech has become a real business.
1:24:57ENSelling the Opportunity: How Founders Take Enterprise Sales From $1M to $10M ARRGuest Jen Abel · Host Lenny RachitskyJen Abel explains why startups should chase tier-one logos, price near $100K, hire salespeople who can "cosplay a founder", and sell vision instead of problems.
1:44:26ENFind the Must-Have Users First: Sean Ellis on Product-Market Fit and Sustainable GrowthGuest Sean Ellis · Host Lenny RachitskyThe creator of the Sean Ellis test and the ICE framework explains how to measure product-market fit, learn from the users who love you, and then grow in the right order.
1:31:26ENMake Individual Contributors Love You First: Inside Figma's Bottom-Up Growth PlaybookGuest Claire Butler · Host Lenny RachitskyClaire Butler, Figma's 10th employee and first marketer, explains the two-step go-to-market motion behind Figma's growth: win over individual contributors, then help them spread the product through their companies.
1:41:33ENTwo Days to a Founding Hypothesis: Inside the Foundation SprintHost Lenny RachitskyDesign Sprint creators Jake Knapp and John Zeratsky walk through a scripted 10-hour process that pins down customer, differentiation and approach before a startup builds anything.
1:42:28ENJournalists Don't Care About You: A Magazine Editor's Field Guide to Getting PressGuest Jason Feifer · Host 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 SpreadGuest Lulu Cheng Meservey · Host 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.
1:28:51ENSeven Years in the Making: How StackBlitz Turned Bolt into a $40M ARR Overnight SuccessGuest Eric Simons · Host 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.
1:18:58ENDelta 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.
1:14:51ENLeaving 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.
1:23:36ENYou Are Not a Marketplace Founder (Yet): A Stanford Professor on Friction, Data and ExperimentsGuest Ramesh Johari · Host Lenny RachitskyRamesh Johari explains what marketplaces really sell, why prediction is not decision-making, and how experiments and rating systems should be designed.
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