Union Square Ventures Fred Wilson on 40 Years in Venture — and Why USV Is Automating Itself
26 snips
Apr 29, 2026 
Fred Wilson, veteran venture capitalist who backed Twitter, Coinbase and Etsy, shares reflections from 40 years in investing. He recounts early internet wins and the dot‑com crash. He discusses building AI agents that are already automating firm tasks, tensions between open and closed AI, sector risks like the AI kill zone, and why human relationships still matter in venture.
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How A Viral UX Mistake Led To A Partnership
- Fred Wilson first met a future founder via a viral Twitter UX issue when Anchor auto-tweeted without clear consent and he publicly called them out.
- The founder cold-emailed afterward, fixed the UX, and later became a USV portfolio founder, turning a public reprimand into a relationship.
Flatiron's Crash Became The Foundation For USV
- Fred's Flatiron Partners made money during the internet boom but then the dot-com crash blew up much of the portfolio, forcing the firm to wind down.
- That failure taught lessons they codified when founding USV, shaping what they'd avoid next time.
Fred Built A Chief Investment Officer Agent For His Family
- Fred built personal agents for his family's chief investment officer using Tasklet and Cloud Code to read Ashton's book and tailor investments to goals, needs, and values.
- He keeps private data local and worries about locking agent access for security.
