Matthew Bermanyesterday +1
20VC with Harry Stebbingsyesterday +4
No Priors: AI, Machine Learning, Tech, & Startupsyesterday +1
Sequoia Capitalyesterday +6
AI Engineeryesterday +1
The Buildersyesterday +4
Everyyesterday +1
Uncapped with Jack Altmanyesterday +1
Chris Williamsonyesterday +2
Cheeky Pintyesterday +1Results
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0:33EN20VC with Harry Stebbings· Mar 17, 2026PodcastAn Investor’s View: Confidence and Doubt in FoundersA brief observation about two apparently opposing mindsets in some successful founders.
0:16EN20VC with Harry Stebbings· Feb 28, 2026PodcastA 20VC Guest Predicts Software Will Need to Serve AI AgentsA brief clip argues that autonomous agents will change how software is designed and purchased.
0:37EN20VC with Harry Stebbings· Dec 16, 2025PodcastA Venture Investor’s Case That Large Funds Can SucceedA short 20VC clip uses one fund’s reported investments to argue that fund size does not determine performance alone.
0:48EN20VC with Harry Stebbings· Nov 18, 2025PodcastAn Anecdote About Persistent Cold EmailA speaker describes repeated outreach and suggests researching personalization with a language model.
0:49EN20VC with Harry Stebbings· Oct 24, 2025PodcastA 20VC Guest’s View of Spotify’s Early AdvantageA short clip argues that geography, licensing and execution helped Spotify gain scale.
0:37EN20VC with Harry Stebbings· Jan 19, 2025PodcastA Short Argument for X’s AI AdvantageA speaker considers distribution and real-time information as potential advantages.
0:34EN20VC with Harry Stebbings· Aug 29, 2024PodcastHow Shopify Lets Employees Allocate CompensationGuest Kaz NejatianKaz Nejatian describes a flexible approach to salary and equity.
0:27EN20VC with Harry Stebbings· Aug 27, 2024PodcastImran Khan on Google’s Early AOL PartnershipA short account of distribution and brand-building.
0:37EN20VC with Harry Stebbings· Jul 18, 2024PodcastPedro Franceschi on Treating Liquidity as a Company MilestoneThe Brex co-founder reflects on tender offers and an IPO.
0:51EN20VC with Harry Stebbings· Feb 23, 2024PodcastDoug Leone’s Interview Question About Self-AwarenessGuest Doug LeoneA personal interviewing practice and its limitations.
0:34EN20VC with Harry Stebbings· Dec 6, 2023PodcastDara Khosrowshahi on Why He Joined UberA conversation with Daniel Ek reframed an offer Dara Khosrowshahi initially wanted to decline.
0:25EN20VC with Harry Stebbings· Nov 27, 2023PodcastA Claim About Fiji Water and Shipping EmissionsGuest Ryan PetersenRyan Petersen compares transport modes without a full lifecycle analysis.
0:34EN20VC with Harry Stebbings· Nov 21, 2023PodcastRyan Petersen on How Funding Can Change SpendingGuest Ryan PetersenA short startup anecdote about a trade-show booth and the effect of a larger bank balance.
0:17EN20VC with Harry Stebbings· Sep 29, 2023PodcastMarc Benioff’s Morning RoutineGuest Marc BenioffThe Salesforce leader describes meditation, family, work and exercise.
0:51EN20VC with Harry Stebbings· Apr 28, 2023PodcastJack Brody on OpenAI’s Technology-First StrategyGuest Jack BrodyA 2023 interview excerpt about developing technology before knowing every use.
0:20EN20VC with Harry Stebbings· Apr 20, 2023PodcastJoost de Valk on WordPress Design: Decisions and OptionsGuest Joost de ValkA short explanation of why useful defaults can make a product easier to use.
0:41EN20VC with Harry Stebbings· Mar 11, 2023PodcastAmjad Masad on Facing Difficult DecisionsThe Replit founder argues that worthwhile outcomes can follow discomfort—and postponing hard decisions can make them harder.
0:42EN20VC with Harry Stebbings· Jan 31, 2023PodcastHenry Schuck on Facing Old Glassdoor Reviews During an IPOGuest Henry SchuckThe founder recalls how he responded when investors asked about negative comments from earlier in his career.
0:52EN20VC with Harry Stebbings· Dec 29, 2022PodcastBen Chestnut on His Children Discovering Mailchimp’s SuccessGuest Ben ChestnutThe Mailchimp co-founder shares a family anecdote about wealth and an unexpected magazine cover.
0:43EN20VC with Harry Stebbings· Dec 22, 2022PodcastBarry McCarthy on Peloton’s Brand and Pandemic GrowthGuest Barry McCarthyA 2022 CEO perspective on customer experience and scale.
0:36EN20VC with Harry Stebbings· Dec 9, 2022PodcastMarty Cagan on Recruiting With a Compelling VisionGuest Marty CaganA short interview excerpt and its context.
2:22EN20VC with Harry Stebbings· Nov 13, 2022PodcastHow Noah Glass Conceived OloGuest Noah GlassA handheld computer, a coffee queue and restaurant experience shaped the idea.
0:33EN20VC with Harry Stebbings· Nov 13, 2022PodcastBrad Gerstner on Choosing Larger OpportunitiesGuest Brad GerstnerThe investor reflects on time spent pursuing ideas with limited potential scale.
0:49EN20VC with Harry Stebbings· Jun 30, 2022PodcastA 2022 Venture Investor’s View of Preparing for a Market DownturnA short 20VC clip discusses changing conditions, liquidity and valuation multiples.