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59:41EN
20VC with Harry Stebbings· Oct 22, 2026Podcast · 3 speakers20VC: Venture Fund Size, AI Valuations and the Changing Software MarketGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O'Driscoll debate venture concentration, infrastructure risk, code review and the assumptions behind fast-growing AI companies.Venture CapitalInvestingAI cost & performance+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
1:29:42EN
20VC with Harry Stebbings· Aug 13, 2026Podcast · 3 speakers20VC on AI Competition, Founder Control and Software ValuationsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate how AI is reshaping software markets, talent, infrastructure and investor incentives.SaaSAI StrategyVenture Capital+2
1:15:56EN
20VC with Harry Stebbings· Jun 11, 2026Podcast · 3 speakers20VC on IPO Expectations, Lean AI Startups and Investor RiskGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported listings, AI company economics and the changing cost of building a startup.Venture CapitalInvestingAI startups & small teams+2
1:39:00EN
20VC with Harry Stebbings· Jun 4, 2026Podcast · 3 speakers20VC on AI Financing, Token Budgets and the Cost of Startup IntensityGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported listings, software valuations, AI spending and demanding work cultures.Venture CapitalAI cost & performanceFuture of Work+2
1:27:17EN
20VC with Harry Stebbings· May 21, 2026Podcast · 3 speakersAI Funding, IPO Expectations and the Politics of Layoffs: Jason Lemkin and Rory O’DriscollGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsA 20VC roundtable examines reported Anthropic financing, AI spending, software valuations, chip infrastructure and speculative IPOs, then considers the politics of job losses.Venture CapitalAI cost & performanceEnterprise AI+2
1:19:05EN
20VC with Harry Stebbings· May 14, 2026Podcast · 3 speakersAI Compute Deals, Cerebras’s IPO and the Cost of Building: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll debate AI infrastructure, software competition and IPO valuations, then discuss the personal demands of founding a company.Venture CapitalAI cost & performanceEnterprise AI+2
1:36:35EN
20VC with Harry Stebbings· May 7, 2026Podcast · 3 speakersAI Spending, Software Stocks and IPO Speculation: A 20VC Earnings RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll assess technology earnings, software growth and reported AI funding, then debate how leaders and workers adapt to AI.Venture CapitalAI cost & performanceEnterprise AI+2
1:28:19EN
20VC with Harry Stebbings· Apr 30, 2026Podcast · 3 speakersAI Compute, Private Equity and the Narrowing Exit: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll debate reported AI financing, software’s future and what private-equity losses could mean for venture investors.Venture CapitalAI cost & performanceEnterprise AI+2
1:50:05EN
20VC with Harry Stebbings· Apr 23, 2026Podcast · 3 speakersCursor Deal Claims, AI Valuations and the Enterprise Agent Race: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll weigh a purported Cursor transaction, design software and enterprise agent infrastructure, while debating IPO and valuation risk.Venture CapitalEnterprise AIInvesting+2
1:03:25EN
20VC with Harry Stebbings· Apr 18, 2026Podcast · 3 speakersJake Paul and Geoffrey Woo on Attention, Investing and BoxingGuest Jake Paul, Geoffrey Woo · Host Harry StebbingsThe Anti Fund partners discuss their venture strategy, creator culture, public life and ambitions in sport and business.Venture CapitalCreator EconomyInvesting+2
1:30:31EN
20VC with Harry Stebbings· Apr 16, 2026Podcast · 3 speakersAI Security, Software Valuations and SpaceX IPO Speculation: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll debate AI security claims, enterprise software and the assumptions behind reported private-company valuations.Venture CapitalAI securityEnterprise AI+2
1:32:21EN
20VC with Harry Stebbings· Apr 9, 2026Podcast · 3 speakersAI Financing, Model Routing and Security Risks: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll debate reported OpenAI and Anthropic finances, model routing, database infrastructure and security, with attention to uncertainty and conflicts.Venture CapitalModel routing & gatewaysEnterprise AI+2
1:12:41EN
20VC with Harry Stebbings· Apr 2, 2026Podcast · 3 speakersAI Security, Revenue Claims and Wearable Economics: A 20VC Investor RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI product strategy, security spending, startup valuations and the durability of consumer subscriptions. Their discussion includes reported developments and unverified estimates, as well as O’Driscoll’s disclosure of an indirect Oura investment.AI StrategyVenture CapitalCybersecurity+2
1:19:18EN
20VC with Harry Stebbings· Mar 26, 2026Podcast · 3 speakersSeries A Fund Math, SpaceX Ambitions and the AI Valuation DebateGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll examine AI competition, speculative space infrastructure and the rising cost of venture investing.Venture CapitalInvestingEnterprise AI+2
1:17:50EN
20VC with Harry Stebbings· Mar 19, 2026Podcast · 3 speakersNvidia’s AI Spending Outlook, Anduril’s Army Contract and the Venture Math Behind Big BetsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate infrastructure spending, AI-driven organizational change and the challenge of investing in huge markets.Venture CapitalAI StrategyFuture of Work+2
1:21:20EN
20VC with Harry Stebbings· Mar 12, 2026Podcast · 3 speakersAnthropic’s Pentagon Dispute, AI Infrastructure and the Venture Investors’ Market DebateGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate an unresolved government dispute, the economics of compute, junior hiring and software valuations.Venture CapitalAI StrategyFuture of Work+2
1:21:53EN
20VC with Harry Stebbings· Feb 26, 2026Podcast · 3 speakersCitrini’s Hypothetical 2028 Scenario, AI Agents and Figma: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI adoption, employment, security and software valuations, separating a hypothetical crisis scenario from their investment views.Future of WorkEnterprise AIInvesting+2
1:37:01EN
20VC with Harry Stebbings· Feb 19, 2026Podcast · 3 speakersAnthropic, OpenClaw and Software Valuations: A 20VC Investor RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate the concentration of AI capital, the pressure on software companies and the risks of autonomous agents.Venture CapitalSaaSAI agents+2
1:37:14EN
20VC with Harry Stebbings· Feb 5, 2026Podcast · 3 speakersSoftware Stocks, AI Financing and Autonomous Agents: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss software valuations, infrastructure financing, autonomous driving and the risks of networked agents.SaaSInvestingVenture Capital+2
1:18:04EN
20VC with Harry Stebbings· Jan 29, 2026Podcast · 3 speakersBrex, AI Inference Costs and the IPO Market: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported deals, AI economics and public-market exits. Their valuations, financial figures and predictions are estimates or reported claims, not independently verified results.Venture CapitalAI cost & performanceInvesting+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
1:30:52EN
20VC with Harry Stebbings· Jan 15, 2026Podcast · 3 speakersAI Financing, Venture Scale and the Risks Behind Growth ValuationsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate model-provider competition, large venture funds and a proposed wealth tax.Venture CapitalInvestingAnthropic+2
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