About 628 articles by Matthew Milner

How To Beat VCs at Their Own Game

Wednesday, August 19, 2026

A few years ago, a buddy of mine from business school invited me to a fancy dinner at his Manhattan brownstone. By the time I finished my first glass of Champagne, I’d met most of the guests — a mix of money managers, venture capitalists, and private equity heavyweights.

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AI Isn’t the Only Game in Town

Wednesday, June 24, 2026

For the last couple years, being an early-stage investor has felt like attending a dinner party where only one guest is allowed to talk. AI says this.

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