Sky Dayton looks more Fight Club than your average CEO. Indulging his passion for surfing, the founder of wireless ISP Boingo has suffered a forehead gash that required 30 stitches and, most recently, a bashed nose from smashing into his board as he surfaced. "If you're in front of the surf when a wave comes, you're hosed," says Dayton, 32, who also founded ISP EarthLink and co-founded the start-up incubator ECompanies. "It's like being in a washing machine."

Despite the possibility of living out a rinse and spin cycle, Dayton steals away from his 65-employee, Santa Monica-based company several times a week to surf in Malibu, the Channel Islands, and Santa Barbara on one of his six Channel Islands boards. He's also chased waves in Fiji and Baja. True to his Internet soul, he tracks the best ones at surfline.com. And true to his entrepreneurial soul, he's advising Surfparks, a start-up that's designing pools with perfect eight-foot waves. Still, Dayton won't be spending much time in chlorinated water -- he's too much of a purist.

"I was looking down the face of the wave, and it started to 'wall' in front of me," says Dayton, an avid snowboarder and dirt biker as well.

"I remember laughing for five minutes. I couldn't stop."