4. Curt Schilling.
Source: Iconosquare
A former pitching great, is best known for pitching seven innings for the Boston Red Sox in an American League Championship Series game while wearing a bloody sock, but not many may know he spent $50 million on a video game company. The great led his team to tie the series at three games apiece, after trailing 3-0. The Red Sox eventually beat the Yankees in that Series and won the World Series as well. The company he invested in tried to compete with giants EA and Activision. Instead, it went broke and laid off all its employees.