The Gstaad Guy sits down with Harry Stebbings, founder of 20VC and one of the most prolific investors and podcasters in Europe, to explore what separates the people who say they want it from the people who genuinely cannot do anything else. Harry started a podcast from his bedroom at seventeen with no university and no network, built it into an audience of millions and a fund with around a billion dollars under management, and reflects on a career defined by seeing early that media would become venture capital's real differentiator.
The conversation gets into the specific signals he looks for in founders and why the usual answers about resilience and discipline tell you nothing. Harry is candid about the costs that come with real commitment, from the friends and birthdays missed to the dissatisfaction he thinks founders have to make peace with, and he is clear about where he draws his own line. He makes the case for Europe over the US, explains why he would rather be relevant than rich, and lays out what he believes is coming next with AI. Fast, unguarded, and willing to be challenged on every point, it is a conversation about ambition, honesty, and what you are actually prepared to pay.
Filmed at The Peninsula London.
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(00:00) Intro 🎙️✨
(01:44) Weakness Leaving Your Body 💪🔥
(03:15) If I Were You, I'd Do This 👆💡
(04:21) Insight Developments 🔍📈
(05:10) The Scene In The Social Network 🎬💻
(06:36) Three Ways We Make Money 💰🔑
(09:11) The Signals I Look For 👁️🎯
(10:44) Nobody Great Comes Out Of McKinsey 🏢😏
(12:25) Teach Your Children To Tell Stories 👶📖
(15:08) Fifty Thousand DMs At Two In The Morning 📱😮
(16:22) At Peace With Dissatisfaction 🧘⚖️
(18:33) Found On The Kitchen Floor 🍳😔
(21:20) There Is No Cheat Code 🎮💡
(23:23) The Coffee Bar In Milan ☕🇮🇹
(25:52) Betting A Career On Europe 🇪🇺🎲
(28:41) Why Founders Now Want To Build Here 🏗️🌍
(31:47) A Unicorn Isn't Enough Any More 🦄📈
(32:54) A Hundred Million Beats A Billion 💰⚖️
(35:09) Fame Is The Watch ⌚👀
(36:57) Founder Porn 💻🔥
(40:04) The Parent Problem 👨👩👧💭
(41:26) Four Hobs, Two Burners 🔥⚖️
(43:06) Where AI Actually Is 🤖🔍
(49:55) Build An AI School 🤖🏫
(51:50) Education, Romance, Housing 📚❤️
(55:32) The Friend Zone Is A Lie 💭❌
(58:50) Keep The Main Thing The Main Thing 🎯💡
(1:00:51) À La Poubelle vs. Fantastique 🗑️✨
(1:07:41) A Message For The Twenty Somethings 💌🌟
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