On the Edge: The Art of Risking Everything

by Nate Silver

Successful risk-takers take a raise-or-fold attitude toward life. They abhor mediocrity and they know when to quit.

“I always say expected value is the probability of success times the degree of impact. That math works easily, but people are very uncomfortable in the low-probability domains,” said Vinod Khosla,

Josh Wolfe, of Lux Capital, is fond of the phrase “chips on shoulders put chips in pockets.”

According to PitchBook, just 2 percent of VC funding in the United States goes to female-only founders or founding teams. Another 16.5 percent goes to women who are paired with men. The latter figure has increased in recent years, but the former one hasn’t.

Finally, there is reciprocity. This is the most Riverian principle of all, since it flows directly from game theory. Treat other people as intelligent and capable of reasonable strategic behavior. The world is dynamic, and although people may not be strictly rational, they’re usually smart about adapting to their situation and achieving the things that matter most to them. Play the long game.