Orlando Bravo

The first billionaire from Puerto Rico is a leading

Wall Street dealmaker. His private equity firm, Thoma Bravo, has done some 230 software deals worth more than $68 billion since 2003 and now oversees a portfolio of 35 software companies that generate roughly $10 billion in annual revenue. Bravo’s ticket out of Puerto Rico was tennis: As a teenager he roomed with Jim Courier at Nick Bollettieri’s esteemed tennis academy in Florida and was then recruited to play for Brown University.