T-Pain
T-Pain almost lost it all at the peak of his career. He once had $40 million in his bank account, but due to a series of bad investments, he lost it all. However, this taught him how to manage his money, and now he is doing significantly better than before.
Dennis Rodman
Dennis Rodman just might be one of the greatest basketball players who ever lived, but once he stopped playing, Rodman became unable to support his lifestyle. In 2012, Rodman was forced to file bankruptcy because he owed $800,000. In recent years, Rodman has earned plenty of cash doing documentaries, interviews, and building up his personality as an entertainer.
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