Fred Wilson is one of the greatest VCs of all time. He is also my new partner at @USV and I'm lucky to say that. We've known each other for years, but becoming partners felt like a reason to get to know him even better. So a few weeks ago, we walked around Union Square and caught up about what @fredwilson has learned over nearly 40 years of VC, how AI may be making the profession obsolete, how to build an investment thesis, why he believes the Knicks will win the NBA title this year, and a few of his long held grudges. Here's a video of that conversation, set at Union Square, Madman Espresso, the USV office, and Leon's on Broadway. Chapters: 3:22 - That time Fred wrecked Mike on Twitter 6:01 - Pre-Internet VC in NYC 9:50 - Early Internet Investing and Raising for Flatiron Partners 11:59 - The Dot-com Crash Killed Fred’s First Firm 14:28 - Fred’s Grudge Against Coffee Shop 16:35 - How to Pick the Right Team at Right Time 18:28 - AVC blog, Gawker’s Nick Denton, TypePad.com 20:44 - Jim Kramer invented Tweeting 21:46 - Why Fred Bet on Twitter Early 23:39 - Building Agents on Claude Code and Tasklet 26:20 - Claude Mythos and Doomerism 27:27 - The Original USV Thesis 29:19 - Network Effects and Brad’s Thesis 31:29 - Coinbase: Thesis, Investment, Outcome 33:18 - Investing in Decentralized AI 34:59 - Open Source AI 36:55 - AI Kill Zone: Legal AI is Dead, Energy Investments 42:37 - USV Agents Will Replace Its Partners 47:00 - Are VC’s building themselves out of a job? 48:30 - Leon’s, NYC’s New Tech Watering Hole 50:52 - Generative Art 53:18 - SOLIENNE: AI Artist trained by Kristi Coronado 54:25 - What About AI Scares Fred 55:40 - Societal Backlash to AI 58:10 - Advice to Early Career VCs: There’s More Risk in Not Doing Deals 1:00:48 - Fred’s Biggest Regrets: Saying No Because of Price 1:04:17 - Fred’s Bold Prediction for the Knicks and the Mets
