AND NELSON IS the perfect ringleader. With his friendly drawl, athletic six-two frame, and a knit hat pulled over his unruly red hair, the native Californian comes off more like a liftie than a former derivatives specialist worth around $100 million.

Originally from the Bay Area, Nelson grew up skiing in Squaw Valley, raced in high school, and competed for the University of Colorado ski team, pitching in to help the Buffaloes win three national championships before he graduated, in 1980. "He did a very good job on the B team," says Bill Marolt, who was Nelson's coach in Boulder before moving on to become the president and CEO of the United States Ski and Snowboard Association.

Good, but not good enough, Nelson was passed over for a spot on the national team, so he went into investment banking, spending two decades logging 80-hour weeks, first in London and, eventually, Hong Kong. To stay sane, he ran ultramarathons and summited Aconcagua and Mount McKinley.

In 2001, Nelson jumped into the soft embrace of his bank account and moved to Sun Valley, where he built a 9,000-square-foot bachelor palace complete with amphitheater, indoor climbing gym, and a 75-foot lap pool. On average, he skied 180 days per year and dabbled in various sports like rock climbing, fly-fishing, and bird hunting.

"People like to call me the ‘banker gone wild,' " he says, "but I worked unbelievably hard for 20 years. It was time for something completely different."

When "completely different" started to feel like more of the same, Nelson turned philanthropic. He became a foundation board member for the USSA and, later, the Winter Special Olympics. Awash in the facts and figures of his favorite sport, Nelson saw a "weird lack of opportunities" for professional ski racers in the U.S. In 2005, hoping to create something more frequent than the X Games and less starchy than the World Cup, he gathered his Idaho buddies—former college roommate Steve Brown and former U.S. Ski Team members Reggie and Zach Crist—to brainstorm. Two years later he and Brown launched the tour.

"I don't even expect to break even until year three," Nelson says. "I'm committed that far, at least....[The goal is] to build a company that will make an impact. To do that, we've got to get noticed."

One way to get noticed is by mainstreaming events like skiercross—racing head to head on a jump-and-berm-laden course—which will debut as an Olympic sport in Vancouver in 2010. (Boardercross debuted at the 2006 Turin Olympics.) According to Marolt, tour competitions will "very likely factor into" whatever points system the International Ski Federation comes up with to qualify athletes for Vancouver skiercross teams. Nelson takes this role seriously, spending at least $65,000 per tour stop on the cross and halfpipe courses alone.

Meanwhile, the tour is infusing new life into ski resorts, where visitor numbers nationwide have flatlined at 55.5 million for the past ten years.

"Kipp has shown a lot of foresight in taking his show on the road," says David Perry, senior VP of Aspen Skiing Company. "He's exactly on the right track."