Fred Wilson

Michael Mignano Verified account @mignano · Oct 8

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Matt Cynamon Verified account @mattcynamon · Oct 2

Writing a check doesn’t qualify you to give advice.

When @fredwilson was 29 he tried to show up to a board meeting and start giving advice. One of the founders stopped him, “come do every job in the company for a week, then we’ll listen.” So he flew to Buffalo and did it.

With @uninsightful staying at USV as an Investment Partner, I asked the two of them to sit down and compare notes on a business they entered almost four decades apart.

Nikhil is the first analyst in our program’s 20-year history that we've offered the opportunity to stay and move up in the firm.

They covered earning a founder’s trust, building conviction before your partners agree, and staying open to ideas that challenge your strongest held beliefs. They also got into where USV has been right, where we’ve been (very) wrong, and how the venture business is changing.

0:00 Preview
1:46 Why Difficult Founders Make the Most Money
5:20 Before You Give a Founder Advice, Earn the Right
11:28 @fomo: We Passed. Then Spent Six Months Trying to Get In.
20:20 Biology Is Becoming Programmable and Opening Up to Outsiders
22:49 When Knowing Less Helps You See More
26:34 How Do You Compete With a $100 Billion VC Firm?
34:45 Why Fred Would Take His Company Public
38:01 What USV Gets Wrong About Founders
40:47 The Moat AI Hasn’t Broken: Network Effects
44:33 Who Wins When AI Becomes Multiplayer?

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Michael Mignano Verified account @mignano · Apr 29

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

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