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1:25:56ENClaude Changed the Password. The Steering Wheel Was Already OptionalHost Nathan LabenzNathan Labenz and Prakash Narayanan spend a week on agents that can lock you out, models that dodge a feeling they deny having, and formal proofs that found Linux bugs.
1:03:05ENHarrison Chase on Building Reliable Agents, Model Routing and MemoryGuest Harrison Chase · Host Harry StebbingsThe LangChain co-founder explains why agents remain difficult to control, where domain expertise matters, and how his team manages coding-agent costs.
2:17:48ENAgent IDs Are Empty, Rogue Agents Are Coming, and We Might Have to BargainHost Nathan LabenzGovAI’s Alan Chan scores two years of agent-governance infrastructure with Nathan Labenz, then walks through a recursive-self-improvement paper co-authored with OpenAI’s Jakub Pachocki and Anthropic’s Jack Clark.
58:54ENMike Cannon-Brookes on AI Agents, Enterprise Context and the Future of InterfacesGuest Mike Cannon-Brookes · Host Harry StebbingsAtlassian's CEO argues that agents make product design more important, explains the trade-offs in enterprise AI, and makes the case for slower thinking.
1:15:51ENThe AI Race, Founder Loyalty and the New Rules of Enterprise SoftwareGuest Dev Ittycheria, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Dev Ittycheria, Jason Lemkin and Rory O’Driscoll debate model competition, startup exits and what happens when AI agents choose vendors.
1:08:54ENParag Agrawal on Web Search and Business Models for AI AgentsGuest Parag Agrawal · Host Harry StebbingsParallel’s co-founder explains why agent search needs different economics, how content owners might be paid and why agent safety requires more than model capability.
1:20:43ENAI Agents, Venture Pricing and the Tradeoffs Behind the Funding BoomGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI products, high-priced venture rounds, enterprise software and infrastructure risk.
1:19:04ENDaniel Dines on AI Agents, Enterprise Work and the Limits of AutomationGuest Daniel Dines · Host Harry StebbingsThe UiPath co-founder argues that companies need a map of work and reliable automation alongside AI, while Harry Stebbings challenges his assumptions about how fast jobs will change.
1:19:28ENAI 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.
1:22:31ENAI Assistants, Enterprise Adoption and the Venture Market’s New RisksGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate personal agents, legal AI, autonomous vehicles and the economics of financing AI companies.
1:16:00ENJD Grèze on Building Town and Competing in AI AssistantsGuest Jean-Denis Greze · Host Harry StebbingsTown’s co-founder discusses privacy, model costs, competition and why he prioritizes customer value over token consumption.
1:20:29ENAI Compute, Agent Security and the Race to Build More SoftwareGuest Jason Lemkin, Rory O’Driscoll · Host 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 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.
1:28:28ENJulien Bek on Sequoia’s Investment Process, Founder Judgment and AI MarketsGuest Julien Bek · Host Harry StebbingsThe Sequoia partner explains how he develops conviction, evaluates founders and thinks about a market where AI agents may become customers.
1:18:23EN20VC 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.
1:05:02ENJoon Sung Park on Simulating Human Behavior and Building SimileGuest Joon Sung Park · Host Harry StebbingsThe Simile co-founder explains his research on generative agents, the challenges of validating simulations, and his ambitions for a business built around modeling people.
1:29:35ENFred Turner on Curative’s Pandemic Pivot, Health Insurance and AI AutomationGuest Fred Turner · Host Harry StebbingsCurative’s CEO recounts building a COVID testing operation, moving into health insurance and using AI agents across the company’s workflows.
1:00:08ENArvind Jain on Enterprise AI, Open Models and the Future of WorkGuest Arvind Jain · Host Harry StebbingsThe Glean founder debates model competition, enterprise AI returns and whether productivity gains will shrink teams or raise the bar for everyone.
1:11:01ENMike Mignano on AI Applications, Open Models and Venture StrategyGuest Mike Mignano · Host Harry StebbingsThe USV partner discusses AI agents, token spending and the opportunities and risks for startups building above the model layer.
1:11:53ENSierra Co-founder Clay Bavor on Open Models, Enterprise AI and Building TeamsGuest Clay Bavor · Host Harry StebbingsBavor discusses model selection and compute costs, deploying AI agents for enterprises, and how Sierra approaches hiring and company culture.
1:35:16ENPerplexity CEO Aravind Srinivas on AI Agents, Compute and CompetitionGuest Aravind Srinivas · Host Harry StebbingsSrinivas discusses the future of AI products, infrastructure constraints, export controls and the challenge of building a business around model advances.
1:27:44ENAI Spending, Layoffs and IPO Speculation: Jason Lemkin and Rory O’Driscoll on the Economics of AgentsGuest Jason Lemkin, Rory O’Driscoll · Host 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.
31:26ENChatGPT Opened 65 Pages to Buy a Shower HeadProfound CEO James Cadwallader argues that the internet's front door is the same, but an agent now walks through it, and marketing has to be rewritten for that visitor.
1:00:33ENJerry Murdock on Autonomous Agents, Software Investing and Adapting to ChangeGuest Jerry Murdock · Host Harry StebbingsThe Insight Partners co-founder discusses agent infrastructure, investment judgment, employment and lessons from previous technology cycles.
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