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TopicAI agentsPersonHarry Stebbings
1:03:05EN
20VC with Harry Stebbings· Oct 17, 2026Podcast · 2 speakersHarrison 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.AI agentsAgent orchestrationEvals+2
58:54EN
20VC with Harry Stebbings· Oct 12, 2026Podcast · 2 speakersMike 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.AI interface designEnterprise AIAI agents+2
1:15:51EN
20VC with Harry Stebbings· Oct 8, 2026Podcast · 4 speakersThe 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.Enterprise AIFoundation ModelsStartups+2
1:08:54EN
20VC with Harry Stebbings· Sep 26, 2026Podcast · 2 speakersParag 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.Search & retrievalAI agentsAI security+2
1:20:43EN
20VC with Harry Stebbings· Sep 24, 2026Podcast · 3 speakersAI 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.Venture CapitalAI agentsEnterprise AI+2
1:19:04EN
20VC with Harry Stebbings· Sep 21, 2026Podcast · 2 speakersDaniel 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.Enterprise AIWorkflow automationAI agents+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
1:22:31EN
20VC with Harry Stebbings· Sep 10, 2026Podcast · 3 speakersAI 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.AI agentsEnterprise AIAI Safety+2
1:16:00EN
20VC with Harry Stebbings· Sep 7, 2026Podcast · 2 speakersJD 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.AI agentsAI cost & performanceProduct Strategy+2
1:20:29EN
20VC with Harry Stebbings· Sep 3, 2026Podcast · 3 speakersAI 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.AI agentsInferenceAI security+2
1:26:43EN
20VC with Harry Stebbings· Aug 27, 2026Podcast · 3 speakers20VC: 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.Venture CapitalAI StrategyInvesting+2
1:28:28EN
20VC with Harry Stebbings· Aug 24, 2026Podcast · 2 speakersJulien 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.Venture CapitalCompany BuildingAI agents+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
1:05:02EN
20VC with Harry Stebbings· Aug 1, 2026Podcast · 2 speakersJoon 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.Multi-agent systemsAI agentsData quality & curation+2
1:29:35EN
20VC with Harry Stebbings· Jul 18, 2026Podcast · 2 speakersFred 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.AI in healthcareEntrepreneurshipWorkflow automation+2
1:00:08EN
20VC with Harry Stebbings· Jul 11, 2026Podcast · 2 speakersArvind 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.Enterprise AIAI agentsOpen-weight models+2
1:11:01EN
20VC with Harry Stebbings· Jul 6, 2026Podcast · 2 speakersMike 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.Venture CapitalAI StrategyAI agents+2
1:11:53EN
20VC with Harry Stebbings· Jul 4, 2026Podcast · 2 speakersSierra 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.Enterprise AIOpen-weight modelsAI agents+2
1:35:16EN
20VC with Harry Stebbings· Jun 15, 2026Podcast · 2 speakersPerplexity 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.AI agentsAI StrategyInfrastructure & deployment+2
1:27:44EN
20VC with Harry Stebbings· May 28, 2026Podcast · 3 speakersAI 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.AI cost & performanceVenture CapitalEnterprise AI+2
1:00:33EN
20VC with Harry Stebbings· Feb 28, 2026Podcast · 2 speakersJerry 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.Venture CapitalAI agentsEnterprise AI+2
1:21:53EN
20VC with Harry Stebbings· Feb 26, 2026Podcast · 3 speakersCitrini’s Hypothetical 2028 Scenario, AI Agents and Figma: A 20VC RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host 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.Future of WorkEnterprise AIInvesting+2
1:03:18EN
20VC with Harry Stebbings· Feb 21, 2026Podcast · 2 speakersAlexander Embiricos on Codex, Coding Agents and the Future of BuildingGuest Alexander Embiricos · Host Harry StebbingsOpenAI’s Codex product lead discusses delegation, review, enterprise adoption and his vision for general-purpose agents. His product claims and forecasts reflect his role at OpenAI and are not independently tested in the interview.Coding agentsProduct StrategyAI agents+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
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