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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.
1:20:28EN20VC with Harry Stebbings· Oct 1, 2026Podcast · 4 speakersAI Valuations, Talent Wars and the Venture Capital Tradeoffs Behind ThemGuest Jack Altman, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jack Altman, Jason Lemkin and Rory O’Driscoll debate large early-stage bets, open-weight models and the changing market for exits.
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.
1:19:28EN20VC with Harry Stebbings· Sep 17, 2026Podcast · 3 speakersAI Safety, Personal Agents and the Venture Market’s Uneven ExitsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate oversight of advanced AI, the economics of personal assistants and what a weaker software exit market means for investors.
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.
1:26:43EN20VC with Harry Stebbings· Aug 27, 2026Podcast · 3 speakers20VC: AI Funding, Model Competition and the Economics of AgentsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate capital intensity, AI company economics and where agents may create value.
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.
1:17:47EN20VC with Harry Stebbings· Aug 20, 2026Podcast · 3 speakers20VC: AI Acquisitions, Model Costs and Software ValuationsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss reported deals, frontier-model economics and the challenges of valuing software in a fast-changing market.
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.
1:23:34EN20VC with Harry Stebbings· May 23, 2026Podcast · 3 speakers20VC on Enterprise Sales Hiring, Compensation and AIGuest Chad Peets, Chris Degnan · Host Harry StebbingsChad Peets and Chris Degnan discuss building sales teams, forecasting revenue and competing for talent while AI changes enterprise markets.
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.Load moreShowing 24 of 126