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1:35:02ENa16z, Founders Fund and the Risks Behind Venture’s Biggest FundsGast: Rory O’Driscoll, Jason Lemkin · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate fund size, late-stage returns, AI uncertainty and delayed liquidity.
51:08ENThe Transformer Co-Author Who Says Scaling Hit a WallModeration: Jacob EffronCohere CEO Aidan Gomez tells Redpoint that a $100 million model is still an amnesiac genius, and that enterprise AI money is concentrating in support, research, and the back office.
41:52ENMercor Hit $100 Million ARR Teaching Models to Hire. Humans Now Write the Exams.Moderation: Sarah Guo, Elad GilBrendan Foody tells Sarah Guo and Elad Gil how Mercor automated recruiting for frontier labs — and why building evals may become the world's most common knowledge job.
43:51ENThe $177 Billion GPU Bet Only Works If AI Becomes a $1.5 Trillion MarketModeration: Jacob EffronFour Redpoint partners walk their limited partners through where AI value will accrue—and why revenue is now the easiest metric to misread.
1:10:19ENCarvana CEO Ernie Garcia on Conviction, Debt and Building Through Difficult MarketsGast: Ernest Garcia · Moderation: Harry StebbingsThe co-founder reflects on fundraising, operations, public markets and the personal trade-offs of leading a company.
27:45ENNasdaq Down 8% and Ghibli Everywhere: AI Is Already in Inning ThreeModeration: Sarah Guo, Elad GilSarah Guo and Elad Gil on the latest image-gen wow cycle, why public-market panic is mostly noise for software startups, and where specialized models still have room.
1:11:05ENThe Man Who Took HubSpot CRM to $40 Million Says the Data Model Has to Be Thrown OutDay.ai founder Christopher O’Donnell tells Sequoia’s Pat Grady why classic CRM is compressed pixel art, why full self-driving scared his users, and why every line of code has to make every other line more valuable.
1:01:53ENOpen-source models are 5% of enterprise use — and GPT wrappers wonModeration: Jacob EffronLatent Space's Swyx and Alessio join Redpoint to map what actually has product-market fit in AI, and why the application layer is the fight that matters.
38:43ENTwo in Five Doctors Want Out. An On-Call Cardiologist Built the Note That Lets Them StayModeration: Sarah Guo, Elad GilAbridge CEO Shiv Rao on treating the doctor-patient conversation as healthcare's source of truth, and why the company ran straight at the hardest health systems.
1:24:12ENMitchell Green on Finding Software Companies and Returning Capital to InvestorsGast: Mitchell Green · Moderation: Harry StebbingsLead Edge Capital’s founder explains his sourcing framework, exit discipline and skepticism about paying high prices for AI.
1:12:05ENPeter Singlehurst on Growth Investing, Mistakes and Private-Market LiquidityGast: Peter Singlehurst · Moderation: Harry StebbingsBaillie Gifford’s head of private companies explains how he assesses durable business models, reinvestment decisions and investment risk.
1:12:13ENNiklas Östberg on Delivery Hero’s Growth, Acquisitions and the Cost of Moving Too FastGast: Niklas Östberg · Moderation: Harry StebbingsThe Delivery Hero founder reflects on pandemic-era financing, a costly Gorillas investment and how to distinguish sustainable delivery growth from subsidized volume.
1:30:57ENAnt's $320 Billion IPO Was Stopped at the Eleventh Hour: Angela Zhang on China's Tech TightropeModeration: Nathan LabenzA USC law professor walks through the dynamic pyramid that governs Chinese tech, from Didi's listing to DeepSeek's price war, and why she thinks the United States is starting to look more like China.
54:10ENHarvey Built Legal AI for the Work the Next Model Still Cannot DoCEO Winston Weinberg on citations, process data, and the unscalable tactics that won over century-old law firms.
1:33:55ENJake Saper on Zoom, AI and the Hard Decision of When to SellGast: Jake Saper · Moderation: Harry StebbingsThe Emergence Capital partner explains collective diligence, fund distributions and the trade-off between liquidity and holding winners.
1:04:52ENThe Consumer Playbook That Put Medical AI in 100,000 Exam RoomsOpenEvidence CEO Daniel Nadler explains how a free App Store product, trained only on peer-reviewed literature, reached as much as a quarter of U.S. physicians in a year.
40:33ENModerna was only company 18. The real product is the company factoryModeration: Sarah Guo, Elad GilNoubar Afeyan tells No Priors how Flagship Pioneering turned starting companies into a profession, underwrites scientific uncertainty, and wants AI to run discovery the way Waymo drives.
1:09:19ENOscar Pierre on Glovo’s Fight for Funding, Expansion and Sale to Delivery HeroGast: Oscar Pierre · Moderation: Harry StebbingsThe Glovo founder recounts a pivotal McDonald’s deal, repeated financing crises, a costly Brazil expansion and the decision to join Delivery Hero.
54:55ENNew Jersey Cut Phone Waits from 40 Minutes to 90 SecondsModeration: Nathan LabenzGovernor Phil Murphy on the state AI assistant, a Princeton hub, and why he wants the best catcher's mitt in the country when superhuman systems arrive.
38:14ENKyle Vogt Pitched 120 Investors for Cruise. He Will Not Sell the Home-Robot CompanyModeration: Sarah Guo, Elad GilThe Twitch and Cruise co-founder tells Sarah Guo and Elad Gil why Tesla won on business model, why chores should be automated, and why a tiny AI-era team is enough.
49:36EN86 Out of 100: Harvey's Playbook for Selling AI Into LawModeration: Sarah Guo, Elad GilWinston Weinberg on a Reddit blind test, expanding-and-collapsing product design, and why Harvey started with century-old firms instead of the mid-market.
5:06:18ENDeepSeek's $5 million training claim and the five-year bet on computeModeration: Lex FridmanDylan Patel and Nathan Lambert walk Lex Fridman through DeepSeek-V3 and R1, export controls, TSMC, megaclusters, and who actually makes money in the AI race.
57:31ENTS Anil on Monzo’s Turnaround, Product Strategy and Global AmbitionsGast: TS Anil · Moderation: Harry StebbingsThe Monzo CEO explains how the bank addressed interlocking funding and control problems, built a diversified revenue model and is thinking about expansion.
56:07ENBox Holds 100 Billion Files. Its CEO Says Enterprises Only Move for a 10xModeration: Nathan LabenzAaron Levie tells Nathan Labenz why AI excitement in the enterprise already outruns the early cloud — and why 98% reliability, seat-based SaaS, and incremental savings still will not ship.
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