All Articles

The Surprising Path for Startup Investors to Make 10x

Wednesday, September 9, 2026

In the old days, if you’d told me you’d invested in a startup, I’d have asked the obvious question: “When do you think it’ll IPO?” That was the dream. The startup would grow, go public, and your small investment could turn into a big sum.

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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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To Be a Better Startup Investor, Join the Mafia

Thursday, June 25, 2026

Imagine sitting around a table with some of Silicon Valley’s most powerful players — the CEO of OpenAI, a billionaire venture capitalist, the founder of a defense-tech giant. Someone at the table is lying.

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