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.

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