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1:20:28EN
20VC 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.Venture CapitalAI startups & small teamsInference+2
1:19:28EN
20VC 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.AI SafetyAI agentsVenture Capital+2
1:26:43EN
20VC 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.Venture CapitalAI StrategyInvesting+2
1:17:47EN
20VC 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.Venture CapitalAI StrategyInvesting+2
1:23:12EN
20VC with Harry Stebbings· Jan 22, 2026Podcast · 3 speakersVenture Returns, OpenAI Litigation and the Economics of AI GrowthGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate public software prices, research talent, AI advertising and late-stage venture valuations.Venture CapitalSaaSAI Strategy+2
1:32:50EN
20VC with Harry Stebbings· Sep 18, 2025Podcast · 4 speakersKaz Nejatian on Opendoor, AI Financing and the Cost of GrowthGuest Kaz Nejatian, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsOpendoor’s new CEO explains his housing strategy; Harry Stebbings and investors examine AI infrastructure commitments, software margins and the return of IPOs.Company BuildingVenture CapitalAI Strategy+2
1:14:45EN
20VC with Harry Stebbings· Sep 4, 2025Podcast · 4 speakersAnthropic, Statsig and the Economics of AI Growth: Cliff Obrecht and 20VCGuest Cliff Obrecht, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsCanva’s Cliff Obrecht joins Harry Stebbings and investors to discuss AI financing, employee liquidity and the real cost of putting models into software.Venture CapitalAnthropicAI cost & performance+2
1:34:20EN
20VC with Harry Stebbings· Aug 14, 2025Podcast · 3 speakersGPT-5, Palantir and the Economics of AI GrowthGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI competition, the price of growth and what leaner companies could mean for workers.Venture CapitalOpenAIAI Strategy+2
1:28:36EN
20VC with Harry Stebbings· Aug 7, 2025Podcast · 4 speakersFigma’s IPO, Executive Pay and the Price of AI GrowthGuest Brian Halligan, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHubSpot co-founder Brian Halligan joins Harry Stebbings, Jason Lemkin and Rory O’Driscoll to unpack IPO pricing, public ownership and venture strategy.Venture CapitalInvestingCompany Building+2
1:28:12EN
20VC with Harry Stebbings· Jul 31, 2025Podcast · 3 speakersApple, Google and the Race to Fund AI GrowthGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate venture-fund scale, AI infrastructure and how large technology companies can respond to new competition.Venture CapitalAI StrategyInvesting+2
1:09:30EN
20VC with Harry Stebbings· Jun 19, 2025Podcast · 4 speakersChime’s IPO, Scale AI’s Deal and the Return of Public-Market LiquidityGuest Rory O’Driscoll, Jason Lemkin, Garrett · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll, Jason Lemkin and Garrett from Handshake discuss AI suppliers, venture exits and the IPO market in June 2025.Venture CapitalInvestingAI Strategy+2
1:19:24EN
20VC with Harry Stebbings· May 29, 2025Podcast · 3 speakersOpenAI’s Jony Ive Deal, YC’s Scale and the Math Behind Venture ReturnsGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate hardware, IPO terms, dilution and the changing economics of venture investing.Venture CapitalInvestingAI Strategy+2
1:19:32EN
20VC with Harry Stebbings· May 8, 2025Podcast · 3 speakersBenchmark, a16z and the Math of Venture Capital in the AI EraGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate stage focus, large funds and how AI could reshape software and employment.Venture CapitalInvestingAI Strategy+2
1:35:02EN
20VC with Harry Stebbings· Apr 17, 2025Podcast · 3 speakersa16z, Founders Fund and the Risks Behind Venture’s Biggest FundsGuest Rory O’Driscoll, Jason Lemkin · Host Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate fund size, late-stage returns, AI uncertainty and delayed liquidity.Venture CapitalInvestingAI Strategy+2
50:15EN
20VC with Harry Stebbings· Jul 24, 2024Podcast · 2 speakersJason Lemkin on Wiz, CrowdStrike and the SaaS Liquidity CrunchGuest Jason Lemkin · Host Harry StebbingsThe SaaStr founder discusses a reported acquisition approach, a major outage and the economics of legal-tech and venture exits.Venture CapitalCybersecurityInvesting+2
57:16EN
20VC with Harry Stebbings· Nov 3, 2023Podcast · 4 speakersJack Altman, Auren Hoffman and Jason Lemkin Debate Founder-Led Venture FundsGuest Jack Altman, Auren Hoffman, Jason Lemkin · Host Harry StebbingsThe operators and investors discuss founder advice, limited-partner obligations, time trade-offs and whether their model can scale.Venture CapitalFoundersInvesting+2
1:12:29EN
20VC with Harry Stebbings· Aug 23, 2023Podcast · 3 speakersJason Lemkin and Rick Zullo Debate Venture Fund Size, Paper Marks and Founder RelationshipsGuest Jason Lemkin, Rick Zullo · Host Harry StebbingsThe investors disagree over pitching and portfolio construction while examining how fund economics shape founders, boards and returns.Venture CapitalInvestingFounders+2
1:03:10EN
20VC with Harry Stebbings· Aug 11, 2023Podcast · 4 speakersJason Lemkin, Sam Lessin and Frank Rotman Debate the Future of Seed InvestingGuest Jason Lemkin, Sam Lessin, Frank Rotman · Host Harry StebbingsThe investors disagree over startup financing, fund size and founder support while examining how seed prices and capital efficiency affect returns.Venture CapitalInvestingFounders+2
2:01:57EN
Lenny's PodcastPodcast · 2 speakersBuild the Sales Team Like a Founder: Jason Lemkin on Hiring, Comp and Keeping Product CloseGuest Jason Lemkin · Host Lenny RachitskySaaStr founder Jason Lemkin walks through when to hire your first reps, who to hire, how to pay them, how product and sales should work together, and why customer-hostile tactics don't compound.Enterprise & strategyGo-to-MarketCompany Building+3