Fred Wilson on 40 Years in Venture — and Why USV Is Automating Itself
Union Square Ventures
Outro
Episode wrap-up and closing as hosts finish their meal and thank Fred for the conversation.
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 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
This video is produced by USV in partnership with Pod People.
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