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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.
1:00:08EN20VC 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.
1:25:00EN20VC with Harry Stebbings· Jun 13, 2026Podcast · 2 speakersMatan 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 with Harry Stebbings· Jun 11, 2026Podcast · 3 speakers20VC 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 with Harry Stebbings· Jun 4, 2026Podcast · 3 speakers20VC 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.
1:14:12EN20VC with Harry Stebbings· Jun 1, 2026Podcast · 2 speakersBrendan 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.
1:27:44EN20VC 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.
1:27:17EN20VC with Harry Stebbings· May 21, 2026Podcast · 3 speakersAI 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.
1:20:30EN20VC with Harry Stebbings· May 4, 2026Podcast · 2 speakersTobi 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.
1:20:29EN20VC with Harry Stebbings· Apr 27, 2026Podcast · 2 speakersAdam 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.
48:49EN20VC with Harry Stebbings· Apr 25, 2026Podcast · 2 speakersAmjad 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.
54:54EN20VC with Harry Stebbings· Apr 20, 2026Podcast · 2 speakersAaron 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.
1:16:32EN20VC with Harry Stebbings· Mar 30, 2026Podcast · 2 speakersMarc 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.
1:17:50EN20VC with Harry Stebbings· Mar 19, 2026Podcast · 3 speakersNvidia’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.
1:21:20EN20VC with Harry Stebbings· Mar 12, 2026Podcast · 3 speakersAnthropic’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.
1:25:26EN20VC with Harry Stebbings· Mar 5, 2026Podcast · 3 speakersAnthropic, 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.
1:14:16EN20VC with Harry Stebbings· Mar 2, 2026Podcast · 2 speakersEran 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.
1:00:33EN20VC 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.
1:21:53EN20VC 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.
1:29:46EN20VC with Harry Stebbings· Feb 16, 2026Podcast · 2 speakersKlarna CEO Sebastian Siemiatkowski on AI, Software and the Future of BankingGuest Sebastian Siemiatkowski · Host Harry StebbingsThe Klarna cofounder explains his predictions about software switching costs, customer service and a digital financial assistant, while discussing the pressures of building a public company.
1:06:37EN20VC with Harry Stebbings· Jan 26, 2026Podcast · 2 speakersLegora CEO Max Junestrand on Legal AI, Growth and CompetitionGuest Max Junestrand · Host Harry StebbingsThe founder discusses enterprise adoption, model choices and pricing, as well as his predictions for legal work and the structure of the market.
2:20:35EN
Cognitive Revolution "How AI Changes Everything"· Sep 28, 2025PodcastChatGPT Is a Thousand Days Old. Emad Mostaque Says We Have About a Thousand Left.Host Nathan LabenzThe Stability AI founder’s new economics argues that when intelligence is abundant, scarcity-based money and GDP stop making sense.
1:59:55ENCognitive Revolution "How AI Changes Everything"· Jan 8, 2025PodcastMost People Would Quit Tomorrow: Nathan Labenz Maps AI Utopia and DoomHost Nathan LabenzIn part two of a Cognitive Revolution AMA, Nathan Labenz answers listener questions on abundance, superintelligence, p(doom), machine consciousness, and what to do this week.
1:50:09ENCognitive Revolution "How AI Changes Everything"· Feb 27, 2024PodcastNine Hundred Occupations, Twenty Years, and Still No AI RevolutionHost Nathan LabenzEconomist Robin Hanson tells Cognitive Revolution why each new AI demo looks like the last one, and why wages and headcount are the tests that matter.Load moreShowing 24 of 27