Peter Thiel sold 20 million shares of Facebook, just months after its IPO—but they'd be worth nearly $15 billion more if he had held on

Peter Thiel holds hundred dollars bills as he speaks (Credit: Eva Marie Uzcategui/Bloomberg via Getty Images)

• Billionaire Peter Thiel was Facebook’s first outside investor, but he may now have regrets for how soon he cashed out. Just months after the tech company’s IPO, he sold millions of shares for $20 each for a sum of $400 million; with the stock now worth 37 times more, he could have been $15 billion richer today.

Investing is a game of risk and reward. Get it right, and you could build a billion-dollar fortune. Get it wrong, and it might all go up in smoke.