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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.
39:36EN
No Priors: AI, Machine Learning, Tech, & Startups· Dec 14, 2023Podcast · 2 speakersThe Most Underestimated AI Buyer Is the Shop on the CornerHost Sarah Guo, Elad GilFormer Square CEO Alyssa Henry tells No Priors that generative AI is unlocking work small merchants always needed and never paid anyone to do.
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Cognitive Revolution "How AI Changes Everything"· May 4, 2023PodcastTrying ChatGPT is not the same as using itHost Nathan LabenzRachel Woods of The AI Exchange tells Nathan Labenz what she learned from more than a hundred company calls: start inside the business, skip the annual tool contract, and expect to be using only a sliver of what the models can already do.
1:38:45EN
Lenny's PodcastPodcastWhen Coding Stops Being the Bottleneck: Inside Anthropic's Claude Code and Cowork TeamsHost Lenny RachitskyFiona Fung, who leads the teams behind Claude Code and Cowork, describes how an engineering org that ships roughly eight times more code manages quality, hiring, metrics and culture.