Instant Entrepreneur

When Jason Fry won the Florida Lottery in late 2007, he did exactly what you'd expect a lotto winner to do: He started spending it.

He bought a new Cadillac Escalade and a few weeks later ferried his buddies in a limousine bus to the Citrus Bowl in Orlando, where he had purchased a section of tickets on the 50-yard line to watch the University of Florida play the University of Michigan in football.

Fry, who played professional football for a short time in Canada, even spent some of the money on golf lessons with the hopes of hitting the professional circuit. “I spent four to six months hanging out and relaxing,” he says.