Age: 86
Sonic Automotive
Fortune 500 rank: 307
O. Bruton Smith's path on the fast-track to racing fame was unlikely: he grew up in a poor farming family, never went to college, and got his start in the business while also working as a car salesman.
Today, Smith's Speedway Motorsports operates eight racetracks and hosts major NASCAR events. Smith is famous for pioneering the luxury, lighted tracks that helped fuel the sport's wild popularity. He also has his hand in a variety of other industries and is the head of Sonic Automotive, which operates more than 100 car dealerships.
Smith's business success is likely thanks to his penchant for driving an incredibly hard bargain. Reports from his early days at the Charlotte Motor Speedway have it that when he had a pay dispute with workers, he showed up to the construction site with a posse and a shotgun. (The work got done.) Since then, he's been known for bringing a similar -- if less violent -- passion to boardroom negotiations.
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