Skaters sometimes get the bad rap of simply being some stoned dudes hanging around a parking lot trying to land the perfect ollie or kick flip. But that's not the case with these next five guys, who all leapt from being pro skaters to full-blown entrepreneurs (or, in one case, the other way around). Not only did they make their names, and their fortunes, by doing what they love, but they've managed to maintain their authenticity in both the half-pipe and the boardroom.