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PersonJason Lemkin
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
1:30:31EN
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
1:25:26EN
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
1:21:53EN
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
1:24:39EN
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
1:37:14EN
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
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
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