10. Jordan Belfort
Jordan was once a multi-millionaire reaping massive success as a stockbroker.
Belfort was making an estimated $250 Million a year when he was 25 years old thanks to his stock broking firm, the Stratton Oakmont.
The money dried up, though, after Jordan was found guilty of money laundering and fraud.
He had to pay back at least $100 million in ill-gotten gains.
