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42:06ENDario and Daniela Amodei on Building Anthropic, AI Safety, and Human MeaningGuest Dario Amodei, Daniela Amodei · Host Walter IsaacsonThe Anthropic co-founders discuss the roots of their partnership, the challenge of keeping AI systems honest, and the choices facing a world of more capable models.
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.
1:00:08ENArvind 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.
1:25:00ENMatan Grinberg on AI Coding, Token Costs and Building FactoryGuest Matan Grinberg · Host Harry StebbingsFactory’s CEO discusses enterprise AI budgets, model choice, engineering culture and the uncertain effects of automation on work.
1:15:56EN20VC on IPO Expectations, Lean AI Startups and Investor RiskGuest Jason Lemkin, Rory O’Driscoll · Host 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 IntensityGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate reported listings, software valuations, AI spending and demanding work cultures.
1:14:12ENBrendan Foody on Mercor, AI Data and the Future of WorkGuest Brendan Foody · Host Harry StebbingsThe Mercor CEO discusses a security incident, data-provider economics, enterprise agents and the uncertain effects of AI on employment.
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.
1:27:17ENAI Funding, IPO Expectations and the Politics of Layoffs: Jason Lemkin and Rory O’DriscollGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsA 20VC roundtable examines reported Anthropic financing, AI spending, software valuations, chip infrastructure and speculative IPOs, then considers the politics of job losses.
1:20:30ENTobi Lütke on Building Shopify, AI and the Future of WorkGuest Tobi Lütke · Host Harry StebbingsShopify’s CEO discusses long-term leadership, AI-assisted engineering and his views on employment and public policy.
1:20:29ENAdam Foroughi on AppLovin, AI and Building a Lean CompanyGuest Adam Foroughi · Host Harry StebbingsAppLovin’s CEO discusses staff cuts, AI-assisted engineering, compensation and public-market decisions, offering his account of a volatile company turnaround.
48:49ENAmjad Masad on Replit, Coding Agents and the Future of SoftwareGuest Amjad Masad · Host Harry StebbingsReplit’s CEO discusses model routing, software economics, maintenance and the changing roles of builders and engineers.
54:54ENAaron Levie on Enterprise AI, Software Value and the Future of WorkGuest Aaron Levie · Host Harry StebbingsThe Box CEO discusses how agents could reshape enterprise workflows, token budgets and software markets while humans remain involved.
30:17ENMarc Benioff on Slack Agents, AI Jobs and Enterprise SafetyMatthew Berman, Marc Benioff · Forward FutureSalesforce’s CEO speaks with Matthew Berman about human oversight, company structure, his account of an attempted OpenAI investment and enterprise agent plans.
37:23ENMarc Benioff on AI Agents, Human Work and Salesforce’s StrategyMatthew Berman, Marc Benioff · Forward FutureSalesforce CEO Marc Benioff discusses Slack as an AI interface, the limits of agent autonomy, workforce changes and safety with Matthew Berman.
49:34ENBrad Lightcap on OpenAI’s Early Years, Agents and the Future of SoftwareGuest Brad Lightcap · Host Jack AltmanThe OpenAI COO traces the shift from research to widely used products and discusses coding, startups, enterprise software and human oversight.
1:16:32ENMarc Andreessen on Venture Investing, AI and the Work of BuildingGuest Marc Andreessen · Host Harry StebbingsThe a16z co-founder discusses founder selection, venture economics, AI and why his firm has no current need to go public.
1:17:50ENNvidia’s AI Spending Outlook, Anduril’s Army Contract and the Venture Math Behind Big BetsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate infrastructure spending, AI-driven organizational change and the challenge of investing in huge markets.
1:21:20ENAnthropic’s Pentagon Dispute, AI Infrastructure and the Venture Investors’ Market DebateGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate an unresolved government dispute, the economics of compute, junior hiring and software valuations.
1:29:32ENDylan Patel on AI Agents, Military Use, Jobs, and the Race for ComputeMatthew Berman, Dylan Patel · Forward FutureThe SemiAnalysis founder discusses how AI agents are changing his business, the controversy over military use, and the economic and geopolitical stakes of frontier models.
1:25:26ENAnthropic, Block and Cursor: A 20VC Roundtable on AI and SoftwareGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate government oversight of AI, software valuations, layoffs and coding tools. Their financial figures and predictions are estimates or reported claims, not independently verified results.
1:14:16ENEran Zinman on Monday.com’s AI Pivot, Pricing and Software MarketsGuest Eran Zinman · Host Harry StebbingsThe Monday.com CEO discusses AI-built software, agent workflows, sales automation and leading a public company through a difficult market.
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.
1:21:53ENCitrini’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.
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