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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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