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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.
1:21:52EN20VC with Harry Stebbings· Sep 12, 2026Podcast · 2 speakersMatteo Franceschetti on Eight Sleep, AI Teams and the Cost of AmbitionGuest Matteo Franceschetti · Host Harry StebbingsEight Sleep's CEO discusses customer acquisition, hardware economics, AI-assisted operations and the personal trade-offs behind building a company.
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.
1:20:30EN20VC 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.
1:10:56EN20VC with Harry Stebbings· Mar 14, 2026Podcast · 2 speakersElena Verna on Lovable’s Growth, Trust and Product-Led MarketingGuest Elena Verna · Host Harry StebbingsLovable’s head of growth discusses employee-led social channels, meaningful engagement, pricing and the limits of paid acquisition.
1:25:57EN20VC with Harry Stebbings· Dec 31, 2025Podcast · 2 speakersMatt Fitzpatrick on Enterprise AI, Expert Data and Deploying What WorksGuest Matt Fitzpatrick · Host Harry StebbingsInvisible Technologies’ CEO explains his approach to validating AI deployments, sourcing specialists and building customer-specific workflows.
1:02:16EN20VC with Harry Stebbings· Jul 14, 2025Podcast · 2 speakersVlad Tenev on Robinhood, Tokenized Assets and Building Financial ProductsGuest Vlad Tenev · Host Harry StebbingsThe Robinhood CEO discusses active traders, AI adoption, private-market tokens and the company’s plans for broader financial services.
1:16:43EN20VC with Harry Stebbings· Jun 9, 2025Podcast · 2 speakersMicha Kaufman on AI, Work and Fiverr’s Next ChapterGuest Micha Kaufman · Host Harry StebbingsThe Fiverr CEO discusses adapting to AI, startup competition, creative work and the uncertainty facing leaders.
1:01:21EN20VC with Harry Stebbings· Apr 21, 2025Podcast · 2 speakersJason Wilk on Dave’s Turnaround, Credit and Digital BankingGuest Jason Wilk · Host Harry StebbingsThe Dave founder discusses going public, AI underwriting, customer acquisition and competing to serve consumers with short-term credit.
50:51EN20VC with Harry Stebbings· Oct 11, 2024Podcast · 2 speakersEoghan McCabe on Intercom, AI Adoption and Freedom of SpeechGuest Eoghan McCabe · Host Harry StebbingsThe Intercom CEO discusses customer-support AI, remaining private and founder leadership, then debates political expression and misinformation with Harry Stebbings.
1:09:06EN20VC with Harry Stebbings· Jul 31, 2024Podcast · 2 speakersEthan Mollick on AI Adoption, Education and the Uncertain Path to AGIGuest Ethan Mollick · Host Harry StebbingsThe Wharton professor argues that model progress is only part of the story: organizations, product design and human choices determine how AI changes work and education.
59:47EN20VC with Harry Stebbings· May 22, 2024Podcast · 2 speakersAaron Levie on AI Agents, SaaS Pricing and the Race Between Startups and IncumbentsGuest Aaron Levie · Host Harry StebbingsThe Box CEO considers how AI might change business workflows, employment and software pricing, and why established companies and startups both have a chance.