Turns out Musk is also a YOLO fanatic—going from earning $20 million to becoming the world's richest man, all thanks to YOLO moves. 1. Founded Zip2, sold it, pocketed $22 million 2. YOLO'd into PayPal, got acquired by eBay, walked away with $170 million 3. As the sole investor, started SpaceX, then YOLO'd his entire fortune into Tesla two years later—this time he almost went bankrupt He said: 'I’ve always been eager to push my chips back onto the table.'