Silicon Zombies
Legendary VCs Share Their Biggest Investment Regrets.
Two of the biggest names in venture capital sat down with us and didn't hold back — not on their wins, and definitely not on the deals that got away. We're talking Uber, Twitter, and a handful of others that would've made their fund several times over if they'd just said yes.They also break down how secondary markets actually work (hint: it's basically the used car lot of startup equity), how private companies like SpaceX and Anthropic get priced when there's no public market to check against, and why they'd both tell most people thinking about becoming a VC to just... not.If you've ever wondered what it's like to watch a deal you passed on turn into a 4,000x return, or you're trying to figure out how the private markets actually value companies, this one's worth the full watch.⏰ Timestamps00:00 – Intro01:28 – Welcome to the Zombies02:42 – Meet the Guests05:58 – The Real Work Starts After the First Check09:42 – What Is a Secondary Market?10:54 – Is Secondary Just Legalized Insider Trading?12:36 – The Used Car Market for Startup Equity13:39 – Why So Few Companies Go Public Anymore14:32 – Talking Anthropic, SpaceX & OpenAI15:35 – How Private Markets Actually Price a Company16:45 – SpaceX's Valuation Explosion21:27 – VCs Talking Geopolitics27:20 – Bringing Venture Access to Everyday Investors29:43 – Their Biggest Regrets: The Deals They Passed On32:06 – Missing Uber, Twitter & More33:50 – When a Good Deal Goes Bad36:56 – Data Centers: Picks, Shovels & Power38:19 – "Don't Become a VC"39:35 – Thoughts on One-Person, Vibe-Coded Startups42:25 – Advice for First-Time LPs44:33 – The Reverse Apple Hire Problem45:57 – Accelerators vs. Venture Studios49:54 – How Do You Build a Moat in AI? About Silicon Zombies:Silicon Zombies is a Top 5% global podcast for AI, Venture Capital & Tech Innovation. Straight from the heart of Silicon Valley, we bring you weekly deep-dives with elite AI engineers, VCs, and longevity innovators shaping the next decade. We cut through the hype vs. reality of emerging tech, SaaS, biohacking, and startup investing — no fluff, just real insight. Whether you're a founder building your network, an engineer chasing technical depth, or simply staying ahead of the curve, we bridge the gap. Insider access to the world's brightest tech minds. Weekly live streams with a global community across 100+ countries. Connect with Us:Instagram: @siliconzombiesX (Twitter): @siliconzombiesTikTok: @siliconzombiesSubscribe so you don't miss the conversations defining what comes next.
