A few years back, a promising British heptathlete named Jessica Ennis-Hill was hungry for a competitive edge. Sidelined from the 2008 Olympics, due to injury, and forced to take a hiatus from competing, her prospects for the London Games were dimming.

Enter Barrie Wells. The grandson of a world-record holder in the pole vault, Wells had made a fortune in insurance and was looking for ways to give it away. Seeing potential, he agreed to pay for new equipment and the travel expenses of her trusted physical therapist. Ennis-Hill, who went on to win gold in London, is one of 18 athletes the philanthropist has helped fund. “I said to them, I want to be on your journey,” he says.

As athletes take to the ice and slopes in Pyeongchang this week, chances are that it took them more than courage and skill to get there. Spiraling training costs have led athletes to seek funding from all kinds of sources. It’s a need that’s increasingly being met by deep-pocketed individuals who’ve made supporting Olympians into a sort of charitable hobby—one that comes with the potential for vicarious Olympic glory.

Billionaire investor Tony Pritzker began funding top skiers through the U.S. Ski & Snowboard Foundation more than a decade ago, after he became casually acquainted with a few of its executives. While hosting dinners for them at his Deer Valley, Utah, ski house, he got to know some of the athletes they brought along and was fascinated by the athletes’ stories and diverse backgrounds.

“Almost all of the athletes and their families have made great sacrifices to compete at a world-class level,” says Pritzker. “To me, their dedication is so admirable and worthy of support. I have seven kids. These athletes are great role models for mine.”

Every February, Pritzker organizes an informal gathering of a couple of dozen friends he calls “the Icemen.” Each chips in $10,000 for U.S. Ski & Snowboard and spends the day skiing with former Olympians such as Picabo Street and Phil Mahre. Pritzker and his family also attended the 2010 games in Vancouver as a guest of the association, getting the chance to experience the adrenaline first-hand. When the athletes finished competing, they hit the slopes together.

“It was really cool to be able to just ride up the chair with them,” he says. “And ask questions: Were you nervous? How did you get here? Each one of their stories is so moving.”

Private donors are particularly crucial in the U.S., whose Olympic teams receive no government dollars, which is “completely opposite from all our competitors,” says Trisha Worthington, the chief development officer of U.S. Ski & Snowboard’s fundraising arm. With an endowment of $36 million, the foundation raises money year-round to help athletes defray expenses that range from airline tickets to virtual-reality-enhanced training.

U.S. Ski & Snowboard receives almost as much from individuals donors as it does from corporate sponsors. To court contributors, the foundation hosts black-tie galas and offers coveted perks in exchange for donations, including a select number of Gold Passes that grant unlimited access to 250 American ski resorts. For $360,000 per person, donors can tag along with Team USA to the Olympics or World Championships, as Pritzker did at Vancouver. There are close to 70 such VIPs with the team in Pyeongchang.

U.S. tax laws preclude writing off donations to individual athletes, but Worthington says she still encourages them to get to know individual backers.

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