Venture Capitalist Guy Horowitz: Some of the Best Founders are Assholes

Is venture capital dead? Not for Guy Horowitz, who boasts 20+ years in the VC ecosystem, holding the title of partner at firms like DTCP, 33N, and ESH.vc. In this episode of Build to Last, we unpack the changing face of early-stage investing and startup funding—from the 2000s hardware boom to the rise of software unicorns, and now the new frontier: AI-first companies. Guy shares battle-tested insights on identifying founder-market fit, navigating VC cycles, and why understanding capital formation is just as important as finding the next big tech innovation.We also dive into the future of work, education, and the middle class. What happens when generative AI and automation replace white-collar jobs faster than traditional schools can adapt? What happens when AI agents arrive at desks, offices, and boardrooms? With three kids of his own, Guy reflects on raising future-proof talent and what young people today really need to succeed in a world defined by machine learning, venture-backed disruption, and rapid technological change. Spoiler: it's not just about coding bootcamps—it's about curiosity, adaptability, and a willingness to learn from people who aren’t like you.Some key takeaways:– How venture capital has changed in the past two decades– Why "great ideas" don’t matter without the right founders– What makes a great startup exit– The question top VCs like Guy Horowitz ask before writing a check– What NOT to say in a pitch meeting– How DTCP became a breakout fund backed by Deutsche Telekom– Why today’s job market is rigged (and how you can stand out anyway)– Whether AI will make human investors obsolete– Why most white-collar jobs are more automatable than we think– Is now a good time to start a fund? Guy’s honest take– Advice for young people unsure about their futureAlso in this episode, we discuss how to identify REAL startup talent (even if they’re mean) and what makes a great VC (beyond capital). Subscribe for more conversations with founders, builders, and leaders.#venturecapital #investing #ai 00:00 Podcast Intro 00:43 How venture capital has changed 01:55 Guy’s early career at Gemini 05:46 Lessons from being cocky too early 09:15 What makes a great VC investor 12:49 How Guy evaluates founders 18:54 What not to say in a pitch 21:38 The story behind DTCP 27:08 Fundraising success and growth 30:11 Is venture capital dead? 36:41 Raising kids in the AI age 43:44 What happens to the middle class?51:12 Advice to young people 52:42 Outro