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TopicAI StrategyPersonRory O’Driscoll
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
1:18:23EN
20VC with Harry Stebbings· Aug 6, 2026Podcast · 4 speakers20VC on AI Security, Software Deals and the Economics of ComputeGuest Nikesh Arora, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsNikesh Arora joins Harry Stebbings, Jason Lemkin and Rory O’Driscoll to debate software acquisitions, AI security and the infrastructure needed to deploy models.CybersecurityAI StrategyVenture Capital+2
1:27:05EN
20VC with Harry Stebbings· Jul 9, 2026Podcast · 3 speakers20VC on AI Regulation, Compute Economics and Enterprise AdoptionGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported AI policy proposals, infrastructure spending, software deployment and startup liquidity.AI StrategyVenture CapitalEnterprise AI+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
1:12:41EN
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
1:17:50EN
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
1:25:26EN
20VC with Harry Stebbings· Mar 5, 2026Podcast · 3 speakersAnthropic, Block and Cursor: A 20VC Roundtable on AI and SoftwareGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate government oversight of AI, software valuations, layoffs and coding tools. Their financial figures and predictions are estimates or reported claims, not independently verified results.AI StrategyVenture CapitalAI Regulation+2
1:24:39EN
20VC with Harry Stebbings· Feb 12, 2026Podcast · 4 speakersMike Cannon-Brookes and 20VC on AI, Software Markets and LeadershipGuest Mike Cannon-Brookes, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsThe Atlassian co-founder joins Harry Stebbings, Jason Lemkin and Rory O’Driscoll to debate AI spending, legal and support software, advertising and the demands on founders. Their financial figures and forecasts are claims or estimates, not independently verified results.AI StrategyVenture CapitalSaaS+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
1:27:29EN
20VC with Harry Stebbings· Jan 8, 2026Podcast · 3 speakersAI Chip Deals, Founder Exits and the Future of WorkGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss reported Groq and Manus deals, AI compensation, public markets and hiring.Venture CapitalAI StrategyInvesting+2
1:12:54EN
20VC with Harry Stebbings· Dec 22, 2025Podcast · 3 speakersInvestors’ 2026 Predictions: AI, Software Valuations and EmploymentGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll review 2025 and debate software stocks, possible IPOs and AI’s labor-market effects.Venture CapitalInvestingAI Strategy+2
1:21:57EN
20VC with Harry Stebbings· Dec 18, 2025Podcast · 3 speakersCursor, Figma and the Race to Build Across AI WorkflowsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss venture scale, software convergence and the risks of growth valuations.Venture CapitalAI StrategyProduct Strategy+2
1:35:32EN
20VC with Harry Stebbings· Dec 11, 2025Podcast · 3 speakersSpaceX Valuations, Harvey’s Growth and the Risks Behind AI DealsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll examine private-market prices, a proposed media deal, AI applications and fintech competition.Venture CapitalInvestingAI Strategy+2
1:11:42EN
20VC with Harry Stebbings· Dec 4, 2025Podcast · 3 speakersEventbrite, Databricks and the Search for Durable Software GrowthGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate software-market limits, AI pricing and what makes a venture investment last.Venture CapitalSaaSAI Strategy+2
1:32:23EN
20VC with Harry Stebbings· Nov 27, 2025Podcast · 3 speakersAnthropic’s Financing, NVIDIA’s Chip Risks and the Enterprise AI RaceGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss infrastructure commitments, customer-support software, AI marketing and IPO valuations.AI StrategyVenture CapitalEnterprise AI+2
1:26:40EN
20VC with Harry Stebbings· Nov 20, 2025Podcast · 4 speakersAI Coding Valuations, NVIDIA Risk and the Future of Private MarketsGuest Tomasz Tunguz, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Tomasz Tunguz, Jason Lemkin and Rory O’Driscoll debate coding tools, infrastructure risk, venture financing and secondary liquidity.Venture CapitalInvestingCoding agents+2
1:17:11EN
20VC with Harry Stebbings· Nov 13, 2025Podcast · 3 speakersAI Defensibility, Venture Risk and the Difficulty of Timing a ShortGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate fast-moving AI markets, investment risk and how founders approach fundraising.Venture CapitalInvestingAI Strategy+2
1:18:47EN
20VC with Harry Stebbings· Nov 6, 2025Podcast · 3 speakersNavan’s IPO, Harvey’s Valuation and the New Economics of VentureGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss liquidity, AI software growth, public-market competition and board oversight.Venture CapitalInvestingEnterprise AI+2
1:26:49EN
20VC with Harry Stebbings· Oct 30, 2025Podcast · 3 speakersOpenAI’s Restructuring, Mercor’s Valuation and the Math of Venture ReturnsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI financing, large venture platforms and what investors really get for a high entry price.Venture CapitalOpenAIAI startups & small teams+2
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