Curt Schillling
Curt Schilling made a name for himself as a pitcher for the Boston Red Sox and for pitching 7 innings to help the Red Sox tie the series against the New York Yankees at 3-3, all the while wearing a bloody sock. His efforts forced a game 7, where the Red Sox made history by becoming the first in MLB history to come back from a 3-0 deficit to win the ALCS Championship that year.
Curt also founded Green Monster Games in 2006, which was later renamed to 38 studios. He hoped to create titles that rivaled those produced and developed by EA Sports and Activision. His investment never really panned out, though, and three months after releasing Kingdoms of Amalur: Reckoning, the only game the studio ever developed and released, Schilling was forced to fire all his employees and close down the studio, causing Schilling to lose much of the $50 million he invested.