Union Square Ventures

Fred Wilson co-founded Union Square Ventures in 2004 after his first firm was wiped out in the dot-com crash. In the two decades since, USV has backed Twitter, Etsy, Coinbase, Kickstarter, and MongoDB — and Fred has spent most of his career in the same neighborhood.USV General Partners Fred Wilson and Michael Mignano walk that neighborhood together: from Union Square Park to the USV office, up to the rooftop, and into Leon's. The conversation covers the original USV thesis, the Coinbase investment, Fred's concerns about the AI kill zone, how USV built AI agents that are starting to replace its own partners, the New York Knicks, and what 40 years in venture has actually taught him.What we get into:3:22 - That time Fred one-shotted Mike on Twitter6:01 -  Pre-Internet VC in NYC9:50 - Early Internet Investing and Raising for Flatiron Partners11:59 - The Dot-com Crash Killed Fred’s First Firm14:28 - Fred’s Grudge Against Coffee Shop16:35 - How to Pick the Right Team at Right Time 18:28 - AVC blog, Gawker’s Nick Denton, TypePad.com20:44 - Jim Kramer invented Tweeting21:46 - Why Fred Bet on Twitter Early23:39 - Building Agents on Claude Code and Tasklet26:20 - Claude Mythos and Doomerism27:27 - The Original USV Thesis29:19 - Network Effects and Brad’s Thesis31:29 - Coinbase: Thesis, Investment, Outcome33:18 - Investing in Decentralized AI34:59 - Open Source AI36:55 - AI Kill Zone: Legal AI is Dead, Energy Investments42:37 - USV Agents Will Replace Its Partners47:00 - Are VC’s building themselves out of a job?48:30 - Leon’s, NYC’s New Tech Watering Hole50:52 - Generative Art 53:18 - SOLIENNE: AI Artist trained by Kristi Coronado54:25 - What About AI Scares Fred55:40 - Societal Backlash to AI 58:10 - Advice to Early Career VCs: There’s More Risk in Not Doing Deals1:00:48 - Fred’s Biggest Regrets: Saying No Because of Price1:04:17 - Fred’s Bold Prediction for the Knicks and the MetsThis video is produced by USV in partnership with Pod People.Show Links:The Aspirational Investor: Taming the Markets to Achieve Your Life's Goals – A Practical Framework for Managing Wealth and Risk USV Blog: Four Futures SOLIENNE: AI Artist trained by Kristi Coronado