Mark Cuban's career is the epitome of success: He worked his way up and now owns the Dallas Mavericks, invests in successful businesses as a shark on ABC's "Shark Tank" and has a net worth of $3.77 billion.
But, before he became a billionaire, Cuban's rides included a 1966 Buick LeSabre and a Fiat X1/9 with a hole in the floorboard.
"I didn't have a car that cost more than $200 until I was 25, I think," he told Money in a recent interview. "It was crazy."
Cuban's insistence on driving clunkers stemmed from his desire to reach financial independence at an early age, a goal inspired by Paul Terhorst's "Cashing in on the American Dream: How to Retire at 35."