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59:41EN20VC: Venture Fund Size, AI Valuations and the Changing Software MarketGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O'Driscoll debate venture concentration, infrastructure risk, code review and the assumptions behind fast-growing AI companies.
1:17:09EN20VC on Pro Rata Rights, AI Pricing and the Changing Software MarketGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate investor rights, model economics and the choices facing software companies and their employees.
1:15:51ENThe AI Race, Founder Loyalty and the New Rules of Enterprise SoftwareGast: Dev Ittycheria, Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Dev Ittycheria, Jason Lemkin and Rory O’Driscoll debate model competition, startup exits and what happens when AI agents choose vendors.
1:20:28ENAI Valuations, Talent Wars and the Venture Capital Tradeoffs Behind ThemGast: Jack Altman, Jason Lemkin, Rory O’Driscoll · Moderation: 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.
1:20:43ENAI Agents, Venture Pricing and the Tradeoffs Behind the Funding BoomGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI products, high-priced venture rounds, enterprise software and infrastructure risk.
1:19:28ENAI Safety, Personal Agents and the Venture Market’s Uneven ExitsGast: Jason Lemkin, Rory O’Driscoll · Moderation: 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.
1:22:31ENAI Assistants, Enterprise Adoption and the Venture Market’s New RisksGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate personal agents, legal AI, autonomous vehicles and the economics of financing AI companies.
1:20:29ENAI Compute, Agent Security and the Race to Build More SoftwareGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss chip demand, personal agents, software competition and how AI may change enterprise buying.
1:26:43EN20VC: AI Funding, Model Competition and the Economics of AgentsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate capital intensity, AI company economics and where agents may create value.
1:17:47EN20VC: AI Acquisitions, Model Costs and Software ValuationsGast: Jason Lemkin, Rory O’Driscoll · Moderation: 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.
1:29:42EN20VC on AI Competition, Founder Control and Software ValuationsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate how AI is reshaping software markets, talent, infrastructure and investor incentives.
1:18:23EN20VC on AI Security, Software Deals and the Economics of ComputeGast: Nikesh Arora, Jason Lemkin, Rory O’Driscoll · Moderation: 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.
1:20:22EN20VC Roundtable on Open Weights, AI Spending and Software InvestingGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI safety, chip investment, enterprise budgets and the future of software.
1:27:39EN20VC Roundtable on Open Models, AI Economics and Payments DealsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss model security, inference investment and a reported PayPal proposal.
1:26:12EN20VC Roundtable on AI Competition, Enterprise Spending and Venture CapitalGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss a reported Apple lawsuit, AI pricing, memory markets and venture financing.
1:27:05EN20VC on AI Regulation, Compute Economics and Enterprise AdoptionGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported AI policy proposals, infrastructure spending, software deployment and startup liquidity.
1:18:07EN20VC Roundtable: AI Spending, Model Competition and Software AcquisitionsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate enterprise AI returns, prediction markets, SaaS roll-ups and the cost of raising capital.
1:28:02EN20VC Roundtable: Open Models, AI Spending and the Cost of CompetitionGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI talent, model economics, consulting and whether labs should build their own chips.
1:28:10EN20VC Roundtable: AI Policy, Software Valuations and RoboticsGast: Rory O’Driscoll, Everett Randle · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll and Everett Randle debate reported AI restrictions, enterprise software competition and the practical challenges of robotics.
1:15:56EN20VC on IPO Expectations, Lean AI Startups and Investor RiskGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported listings, AI company economics and the changing cost of building a startup.
1:39:00EN20VC on AI Financing, Token Budgets and the Cost of Startup IntensityGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported listings, software valuations, AI spending and demanding work cultures.
1:27:44ENAI Spending, Layoffs and IPO Speculation: Jason Lemkin and Rory O’Driscoll on the Economics of AgentsGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsA 20VC roundtable examines how businesses weigh AI tokens against human work, and how investors assess infrastructure startups amid uncertain valuations and reported IPO plans.
1:27:17ENAI Funding, IPO Expectations and the Politics of Layoffs: Jason Lemkin and Rory O’DriscollGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsA 20VC roundtable examines reported Anthropic financing, AI spending, software valuations, chip infrastructure and speculative IPOs, then considers the politics of job losses.
1:19:05ENAI Compute Deals, Cerebras’s IPO and the Cost of Building: A 20VC RoundtableGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsJason Lemkin and Rory O’Driscoll debate AI infrastructure, software competition and IPO valuations, then discuss the personal demands of founding a company.
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