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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.
1:20:43ENAI 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.
1:18:23EN20VC 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.
1:27:44ENAI 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.
1:21:53ENCitrini’s Hypothetical 2028 Scenario, AI Agents and Figma: A 20VC RoundtableGast: Jason Lemkin, Rory O’Driscoll · Moderation: 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.
1:37:01ENAnthropic, OpenClaw and Software Valuations: A 20VC Investor RoundtableGast: Jason Lemkin, Rory O’Driscoll · Moderation: 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.
1:37:14ENSoftware Stocks, AI Financing and Autonomous Agents: A 20VC RoundtableGast: Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss software valuations, infrastructure financing, autonomous driving and the risks of networked agents.








