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20VC with Harry Stebbings· Oct 10, 2026Podcast · 2 speakersMax Freeman on Building Ramp’s Sales MachineGuest Max Freeman · Host Harry StebbingsRamp’s sales leader explains how he hires, trains and equips sellers, from early outbound experiments to enterprise forecasting and AI-assisted research.
1:05:01EN20VC with Harry Stebbings· Oct 3, 2026Podcast · 2 speakersChase Lochmiller on AI Data Centers, Energy and GPU EconomicsGuest Chase Lochmiller · Host Harry StebbingsCrusoe’s CEO discusses the constraints on AI infrastructure, the economics of GPU capacity and his company’s approach to energy and managed inference.
1:08:54EN20VC with Harry Stebbings· Sep 26, 2026Podcast · 2 speakersParag Agrawal on Web Search and Business Models for AI AgentsGuest Parag Agrawal · Host Harry StebbingsParallel’s co-founder explains why agent search needs different economics, how content owners might be paid and why agent safety requires more than model capability.
1:21:52EN20VC with Harry Stebbings· Sep 12, 2026Podcast · 2 speakersMatteo Franceschetti on Eight Sleep, AI Teams and the Cost of AmbitionGuest Matteo Franceschetti · Host Harry StebbingsEight Sleep's CEO discusses customer acquisition, hardware economics, AI-assisted operations and the personal trade-offs behind building a company.
1:04:35EN20VC with Harry Stebbings· Sep 5, 2026Podcast · 2 speakersCliff Weitzman on Owning GPUs, Voice AI and Building SpeechifyGuest Cliff Weitzman · Host Harry StebbingsSpeechify's CEO makes the case for owning part of a compute fleet, reflects on a missed business-software opportunity and discusses AI-assisted teams.
1:05:56EN20VC with Harry Stebbings· Aug 31, 2026Podcast · 2 speakersAaron Katz on ClickHouse, AI Revenue Durability and Enterprise DataGuest Aaron Katz · Host Harry StebbingsClickHouse’s CEO discusses agent workloads, open models, fundraising and the metrics he uses to judge durable growth.
1:28:28EN20VC with Harry Stebbings· Aug 24, 2026Podcast · 2 speakersJulien Bek on Sequoia’s Investment Process, Founder Judgment and AI MarketsGuest Julien Bek · Host Harry StebbingsThe Sequoia partner explains how he develops conviction, evaluates founders and thinks about a market where AI agents may become customers.
1:05:02EN20VC with Harry Stebbings· Aug 1, 2026Podcast · 2 speakersJoon Sung Park on Simulating Human Behavior and Building SimileGuest Joon Sung Park · Host Harry StebbingsThe Simile co-founder explains his research on generative agents, the challenges of validating simulations, and his ambitions for a business built around modeling people.
1:04:36EN20VC with Harry Stebbings· Jul 13, 2026Podcast · 2 speakersWix CEO Avishai Abrahami on Base44, AI and Building for Small BusinessesGuest Avishai Abrahami · Host Harry StebbingsThe Wix co-founder discusses AI-assisted application building, software economics, customer support and leadership through market uncertainty.
1:11:53EN20VC with Harry Stebbings· Jul 4, 2026Podcast · 2 speakersSierra Co-founder Clay Bavor on Open Models, Enterprise AI and Building TeamsGuest Clay Bavor · Host Harry StebbingsBavor discusses model selection and compute costs, deploying AI agents for enterprises, and how Sierra approaches hiring and company culture.
1:06:10EN20VC with Harry Stebbings· Jun 29, 2026Podcast · 2 speakersK. R. Sridhar on Distributed Power, AI Demand and Energy AccessGuest K. R. Sridhar · Host Harry StebbingsBloom Energy’s CEO discusses data-center power, manufacturing, natural gas and his vision for broader electricity access.
54:29EN20VC with Harry Stebbings· Jun 27, 2026Podcast · 2 speakersfomo CEO Paul Erlanger on Social Trading, Fundraising and Product GrowthGuest Paul Erlanger · Host Harry StebbingsErlanger discusses building a trading app, raising from angels and venture firms, and combining social features with financial products.
1:20:59EN20VC with Harry Stebbings· Jun 20, 2026Podcast · 2 speakersFlexport CEO Ryan Petersen on Logistics, AI and FundraisingGuest Ryan Petersen · Host Harry StebbingsPetersen discusses the economics of global freight, automating operational work, venture financing and the lessons he has taken from building Flexport.
56:55EN20VC with Harry Stebbings· May 30, 2026Podcast · 2 speakersNico Laqua on Corgi’s Work Culture, Fundraising and AIGuest Nico Laqua · Host Harry StebbingsCorgi’s co-founder describes a seven-day work culture, the company’s cafe and equity practices, and his approach to investors and AI.
1:35:14EN20VC with Harry Stebbings· May 18, 2026Podcast · 2 speakersJosh Browder on Early Investing, DoNotPay and Founder DecisionsGuest Josh Browder · Host Harry StebbingsThe DoNotPay founder discusses backing young founders, fundraising, company operations and his personal investment views.
1:08:23EN20VC with Harry Stebbings· May 16, 2026Podcast · 2 speakersShiv Rao on Building Abridge, Clinical Workflows and AIGuest Shiv Rao · Host Harry StebbingsThe Abridge co-founder discusses years of market development, model choices, data trust and the limits of automating clinical work.
1:13:48EN20VC with Harry Stebbings· May 11, 2026Podcast · 2 speakersPatrick Forquer on Selling Legal AI and Scaling Legora’s Revenue TeamGuest Patrick Forquer · Host Harry StebbingsLegora’s chief revenue officer explains how his team runs pilots, trains salespeople and forecasts rapid growth, and shares company-reported performance figures.
1:57:54EN20VC with Harry Stebbings· May 9, 2026Podcast · 2 speakersCliff Weitzman on Speechify, AI Tools and Learning Through IterationGuest Cliff Weitzman · Host Harry StebbingsThe Speechify founder discusses growth experiments, engineering culture, personal health experiences and the promise and risks he sees in AI.
1:20:30EN20VC with Harry Stebbings· May 4, 2026Podcast · 2 speakersTobi Lütke on Building Shopify, AI and the Future of WorkGuest Tobi Lütke · Host Harry StebbingsShopify’s CEO discusses long-term leadership, AI-assisted engineering and his views on employment and public policy.
1:20:29EN20VC with Harry Stebbings· Apr 27, 2026Podcast · 2 speakersAdam Foroughi on AppLovin, AI and Building a Lean CompanyGuest Adam Foroughi · Host Harry StebbingsAppLovin’s CEO discusses staff cuts, AI-assisted engineering, compensation and public-market decisions, offering his account of a volatile company turnaround.
48:49EN20VC with Harry Stebbings· Apr 25, 2026Podcast · 2 speakersAmjad Masad on Replit, Coding Agents and the Future of SoftwareGuest Amjad Masad · Host Harry StebbingsReplit’s CEO discusses model routing, software economics, maintenance and the changing roles of builders and engineers.
54:54EN20VC with Harry Stebbings· Apr 20, 2026Podcast · 2 speakersAaron Levie on Enterprise AI, Software Value and the Future of WorkGuest Aaron Levie · Host Harry StebbingsThe Box CEO discusses how agents could reshape enterprise workflows, token budgets and software markets while humans remain involved.
1:15:19EN20VC with Harry Stebbings· Apr 14, 2026Podcast · 2 speakersAnj Midha on Anthropic, Compute Bottlenecks and Building Frontier AIGuest Anjney Midha · Host Harry StebbingsThe AMP founder recounts Anthropic’s early fundraising and explains his investment thesis around scientific feedback, compute coordination and AI infrastructure.
57:04EN20VC with Harry Stebbings· Mar 23, 2026Podcast · 2 speakersMatthew Steckman on Anduril’s Defense Business, Procurement and Product BetsGuest Matthew Steckman · Host Harry StebbingsAnduril’s president explains a $20 billion procurement ceiling, the company’s approach to building military products and his view of the responsibilities of defense suppliers. His forecasts and company claims reflect his position as an interested executive.Load moreShowing 24 of 238