Results
93 articlesSort
1:15:42EN
20VC with Harry Stebbings· Sep 28, 2026Podcast · 2 speakersAlex Mashrabov on Higgsfield's AI Video Business, Model Costs and GrowthGuest Alex Mashrabov · Host Harry StebbingsHiggsfield's founder explains the search for product-market fit, how he calculates annualized revenue and why creative workflows matter more than chasing model benchmarks.
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.
1:16:00EN20VC 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.
1:09:44EN20VC with Harry Stebbings· Aug 17, 2026Podcast · 2 speakersAndrew Macdonald on Uber’s Membership Strategy, Autonomy and AIGuest Andrew Macdonald · Host Harry StebbingsUber’s president and COO discusses marketplace incentives, autonomous vehicles, the company’s China exit and the challenge of measuring AI’s value.
1:04:36EN20VC with Harry Stebbings· Jul 13, 2026Podcast · 2 speakersWix CEO Avishai Abrahami on Base44, AI and Building for Small BusinessesGuest Avishai Abrahami · Host Harry StebbingsThe Wix co-founder discusses AI-assisted application building, software economics, customer support and leadership through market uncertainty.
54:29EN20VC with Harry Stebbings· Jun 27, 2026Podcast · 2 speakersfomo CEO Paul Erlanger on Social Trading, Fundraising and Product GrowthGuest Paul Erlanger · Host Harry StebbingsErlanger discusses building a trading app, raising from angels and venture firms, and combining social features with financial products.
1:03:40EN20VC with Harry Stebbings· Apr 4, 2026Podcast · 2 speakersAndrew Dudum on Hims & Hers, Preventive Care and Building a Public CompanyGuest Andrew Dudum · Host Harry StebbingsThe Hims & Hers CEO discusses management, healthcare distribution, marketing and expansion. His medical and commercial claims are presented as his views, not independently verified evidence.
1:12:41EN20VC with Harry Stebbings· Apr 2, 2026Podcast · 3 speakersAI Security, Revenue Claims and Wearable Economics: A 20VC Investor RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate AI product strategy, security spending, startup valuations and the durability of consumer subscriptions. Their discussion includes reported developments and unverified estimates, as well as O’Driscoll’s disclosure of an indirect Oura investment.
1:18:06EN20VC with Harry Stebbings· Mar 16, 2026Podcast · 2 speakersGokul Rajaram on Software Moats, AI Products and Venture ReturnsGuest Gokul Rajaram · Host Harry StebbingsThe operator and investor explains his eight-part framework for software defensibility and debates how AI changes product strategy, growth and venture investing. His company assessments and forecasts are opinions, and he has investments or board roles in several businesses discussed.
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.
1:03:18EN20VC 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.
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.
1:21:57EN20VC with Harry Stebbings· Dec 18, 2025Podcast · 3 speakersCursor, Figma and the Race to Build Across AI WorkflowsGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll discuss venture scale, software convergence and the risks of growth valuations.
1:18:29EN20VC with Harry Stebbings· Nov 24, 2025Podcast · 2 speakersBase44 Founder Maor Shlomo on AI App Building and CompetitionGuest Maor Shlomo · Host Harry StebbingsShlomo explains why he joined Wix, how he thinks about app-builder defensibility and why the future of software remains contested.
1:17:11EN20VC with Harry Stebbings· Nov 13, 2025Podcast · 3 speakersAI Defensibility, Venture Risk and the Difficulty of Timing a ShortGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Jason Lemkin and Rory O’Driscoll debate fast-moving AI markets, investment risk and how founders approach fundraising.
1:22:04EN20VC with Harry Stebbings· Sep 8, 2025Podcast · 2 speakersElevenLabs CEO Mati Staniszewski on Voice AI, Growth and Building from EuropeGuest Mati Staniszewski · Host Harry StebbingsStaniszewski discusses the company’s origins in dubbing, its financing and reported ARR, and the challenges of scaling voice products.
1:14:08EN20VC with Harry Stebbings· Aug 18, 2025Podcast · 2 speakersLovable CEO Anton Osika on AI App Building, Economics and SecurityGuest Anton Osika · Host Harry StebbingsOsika discusses Lovable’s reported growth, model costs and product strategy while Stebbings challenges its defensibility and security.
1:56:42EN20VC with Harry Stebbings· May 19, 2025Podcast · 2 speakersDuolingo’s Severin Hacker on AI Tutors, Learning and Building a CompanyGuest Severin Hacker · Host Harry StebbingsThe co-founder explains how Duolingo uses AI, where he sees limits in current tools and why his forecasts about education and work remain uncertain.
56:42EN20VC with Harry Stebbings· Mar 17, 2025Podcast · 2 speakersYamini Rangan on HubSpot, AI and Competing in the MidmarketGuest Yamini Rangan · Host Harry StebbingsThe HubSpot CEO discusses founder transitions, product-led growth, AI pricing and serving larger customers without abandoning smaller ones.
49:39EN20VC with Harry Stebbings· Mar 5, 2025Podcast · 2 speakersAnton Osika on Lovable’s Launch, Early Retention and Building AI Products in EuropeGuest Anton Osika · Host Harry StebbingsThe Lovable co-founder explains the transition from an open-source experiment to a fast-growing app builder, and discusses hiring, fundraising and the limits of early retention data.
1:02:41EN20VC with Harry Stebbings· Mar 3, 2025Podcast · 2 speakersMike Krieger on AI Products, Model Competition and the Future of CodingGuest Mike Krieger · Host Harry StebbingsAnthropic’s chief product officer explains how he thinks about product design, model differentiation and the limits of current AI tools.
1:20:53EN20VC with Harry Stebbings· Feb 14, 2025Podcast · 2 speakersSolly Solomou on Building LADbible, Social Media and Expanding to the USGuest Solly Solomou · Host Harry StebbingsThe founder recounts buying a Facebook page, creating a media business and learning to lead through rapid change.
1:15:33EN20VC with Harry Stebbings· Feb 12, 2025Podcast · 2 speakersFabien Pinckaers on Odoo’s Business Model, Culture and CompetitionGuest Fabien Pinckaers · Host Harry StebbingsThe Odoo founder discusses open core, pricing, ownership and his approach to building an integrated business software suite.
55:38EN20VC with Harry Stebbings· Feb 10, 2025Podcast · 2 speakersSridhar Ramaswamy on Snowflake, AI Competition and Leading Through ChangeGuest Sridhar Ramaswamy · Host Harry StebbingsThe Snowflake CEO discusses the overlap between models and applications, the importance of distribution, and how leaders can manage difficult transitions.Load moreShowing 24 of 93