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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.
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.
1:18:49ENIf AGI Is Cheap Intelligent Labor, Cyber Defense Should Become Continuous ForensicsHost Nathan LabenzAsymmetric Security founder Alexis Carlier argues that assuming AGI means redesigning defense around proactive digital forensics instead of alert triage.
1:40:51ENReasoning Models Just Made the Other 80–90% of Enterprise Data UsableHost Nathan LabenzSnowflake VP of AI Baris Gultekin on text-to-SQL, RAG, agent design, and why inference has to run next to governed data.
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