He's the man who put skateboarding on the map. He's the first to land a 900 (two and a half full rotations). He's also among the richest pitchmen in any sport. And, in a sport that's especially youth-oriented, Tony Hawk, a 40-something father of four, still connects with his audience by staying true to who he is.

Moving easily between the ramp and the boardroom, Tony currently runs one of the most acclaimed action sports companies, a clothing line, and video game series bearing his name that has...