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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
1:17:09EN
20VC with Harry Stebbings· Oct 15, 2026Podcast · 3 speakers20VC on Pro Rata Rights, AI Pricing and the Changing Software MarketGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate investor rights, model economics and the choices facing software companies and their employees.Venture CapitalAI cost & performanceRobotics+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
1:29:42EN
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
1:18:07EN
20VC with Harry Stebbings· Jul 2, 2026Podcast · 3 speakers20VC Roundtable: AI Spending, Model Competition and Software AcquisitionsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate enterprise AI returns, prediction markets, SaaS roll-ups and the cost of raising capital.AI cost & performanceVenture CapitalEnterprise 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
1:19:18EN
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
1:37:01EN
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
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
1:34:12EN
20VC with Harry Stebbings· Oct 23, 2025Podcast · 3 speakersThe Venture Capital Cycle: AI Markets, Compute and the Cost of Moving Too FastGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll join Harry Stebbings to debate AI market size, infrastructure spending and how venture investors can survive a boom.Venture CapitalInvestingAI Strategy+2
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