Looking smiley and shaggy-haired in this senior photo at Mount Lebanon High School in Pittsburgh, Mark Cuban had a mind for business that would make for a happy marriage with technology during the dot-com boom. At a time when websites were all selling things, Cuban wanted to create a company where he could stream and listen to sports (specifically college basketball) games over the Internet. This idea evolved into Audionet, and then became Broadcast.com. After selling Broadcast.com to Yahoo! for $5.9 billion, he bought the NBA’s Dallas Mavericks team in 2000 for $285 million.
Did you know: Mark Cuban went seven years without taking a vacation and still eats 7-Eleven hot dogs!