3. Chamillionaire – Houston Home Turned Worthless
Chamillionaire made a name for himself as an underground rapper in Houston before taking the national hip-hop scene by storm with his hit single “Ridin’” in 2005. “Ridin’” reached #1 on the Billboard 100 and won Best Rap Video at the 2006 MTV Video Music Awards. He hasn’t been able to achieve any comparable mainstream success since, but Chamillionaire did invest in a string of successful auto dealerships and start his own record label – Chamillitary Entertainment.
In 2010, however, Chamillionaire was forced to default on his 7,500 square foot Houston mansion. The rapper says that the $2 million home became worthless, and he had to eat the loss. Unlike other stars on this list, it might be wise to trust Chamillionaire’s judgement. This year, he was named “Entrepreneur-in-Residence” at Los Angeles-based venture capital firm Upfront Ventures. Only time will tell if a Chabillionaire name change is in order.
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