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TopicCompany BuildingPersonRory O’Driscoll
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