Why Billionaires and Bus Riders Give Together in Jackson Hole

For decades, the wealthy have moved to Jackson, Wyo. for the Teton views and the low taxes. That trend has only accelerated with the growth of remote work.

The newcomers’ first philanthropic inclination tends to be supporting environmental charities and the arts, according to Billionaire Wilderness, a 2020 book about the area by a Yale sociologist.

What they often overlook, at least initially, are the social-service nonprofits that help middle- and lower-income people. Resort and construction workers, and even teachers and health-care workers, often can’t afford to pay local rents. Some locals battle depression, a Jackson counselor says, because they’re working two or three jobs in a community where everyone else is in vacation mode. And immigrant workers — roughly a third of the kids in Jackson public schools are Hispanic — are wary of Immigration and Customs Enforcement officers arriving in town from Idaho Falls.

But when the summer tourist season starts to wind down, one event attracts local workers and wealthy transplants in equal measure: Old Bill’s Fun Run.

Old Bill’s might be the nation’s most successful small-town fundraiser.

In an area with glitzy nonprofits, such as the National Museum of Wildlife Art and the $43 million Jackson Hole Land Trust, the early September event helps drive donations and visibility to smaller organizations, including those that aid people who are struggling. Since its inception 30 years ago, it has pulled in more than $300 million for nonprofits and become a model for other small-town community fundraisers in the Mountain West. By identifying donors who are willing to support a general matching fund — meaning those donors don’t control which groups get their funds — the event sparks broad community participation. Some of Jackson’s richest families participate alongside students who show up with loose change. 

“Old Bill’s really shines a light on the needs of our community,” says Laurie Andrews, president of the Community Foundation of Jackson Hole, which organizes the event. “Some people are surprised that we have food-insecure people here, people that don’t have shelter and live in their cars.”

The event matches a percentage of the first $30,000 raised by each of the 240 participating charities, with the size of the match dependent on how much the community foundation can secure from its 96-year-old founder, “Mr. Old Bill,” and fellow co-challengers. (Although his identity is known by some in Jackson, Old Bill has maintained general anonymity for 30 years. Reached through a representative, he declined to talk to the Chronicle.)

The match attracts both charities that want the bonus funds and donors who want to see their gifts to specific charities amplified. Last year’s match was 74 percent. 

Old Bill’s lively “nonprofit village,” with dozens of booths and activities spread across an elementary school field, helps spotlight some of the less-visible charities in Jackson, including Climb Wyoming, which helps single mothers find jobs, and One22 Resource Center, which offers rental assistance and operates a pantry.

Community Foundation of Jackson Hole

The model isn’t dependent on Jackson’s wealth. It’s been successfully replicated in at least three less-affluent towns in the region, including Lander, Wyo; Teton Valley, Idaho; and Red Lodge, Mont.

“Designated gifts are what makes the nonprofit world run — I get that,” Andrews says. “But to me, the co-challengers, and Mr. Old Bill, they’re the ultimate philanthropists. They’re believing in the will of the whole community.”

Connecting Means With Needs

Jodie Louie spent years huddled in her house in Alpine, Wyo., nearly an hour south of Jackson, too crippled by anxiety to seek a job, and supporting her son with government disability checks. In 2021, a friend handed her a flier for a program offered by Climb Wyoming — and she began to turn her life around.

Climb is a statewide organization that helps low-income single mothers gain work skills and find employment. A federal grant launched the charity’s Teton area program more than 20 years ago, but that support lasted just a year. “There was a lot of concern by leadership and the board at the time: ‘How can we keep this going?,’” says Jean Lewis, Climb’s director of advancement. “But the program director got Climb on the docket for Old Bill’s funding, and that partnership is what allowed Climb Wyoming to get established here.”

Donations through Old Bill’s still make up roughly a third of Climb’s local budget. “We’ll have donors who are giving thousands and thousands of dollars, and then we’ll have a donor who gives $5,” Lewis says. “I’ll dig into the details of that $5 donor and find that it’s actually a kid at the school that heard about Climb and wants to see it turn into $7 through the match.”

Climb taught Louie how to use programs like QuickBooks and Excel, and how to dress for office work. The nonprofit also provided both individual and group counseling, as it does for all participants, which helped Louie overcome her anxiety.

About half of Climb’s clients are from Jackson, but it’s a hard place for working people to live — rents there can consume 50 percent of an employee’s paycheck. The other half, including Louie, commute from less-expensive towns.

Eight months after starting with Climb, Louie got a full-time administrative job, with benefits, at the hospital in Jackson. The commute takes about an hour each way by bus, but the hospital picks up the tab, and she enjoys listening to music and books. Her pay helps support her mother, who lives with her, and her adult son, who just moved back home.

Louie has become an advocate for Climb. She spreads the word about the nonprofit at the hospital, and she and her mother sometimes make the drive up to Jackson in early September to participate in the 1K walk at Old Bill’s.

“I absolutely love my job,” Louie says. “I still have my bouts of anxiety, but it’s nothing like it was. A huge part of it was the encouragement I got through Climb.”

Courtesy of Climb Wyoming

For charities focused on social services, Old Bill’s is often their first connection point with rich new homeowners in Jackson.

For years, a small group of wealthy locals helped support the work of Mental Health & Recovery Services of Jackson Hole, which provides services regardless of ability to pay, says the charity’s executive director, Deidre Ashley. But many of those supporters have died or moved away, and the newcomers with wealth didn’t immediately get involved at the same level.

With state funding stagnant or declining, the nonprofit has become ever more reliant on philanthropy, which now makes up about a quarter of its $4.5 million budget.

“There’s no real glitter in what we do,” Ashley says. “It’s hard for us to get in front of the new people coming into town. Old Bill’s has been super helpful in providing a stage for that.”

Spreading the Wealth

The idea for a fundraiser for nonprofits led by the community foundation came to Old Bill in 1996 when he was out on a run. 

Clare Payne Symmons, who became the community foundation’s first full-time leader around the time the run started, says she and the board had to meet individually with Jackson nonprofits to persuade them to sign on.

“The hardest part was not organizing the event,” Symmons says. “It was convincing the nonprofits in the community to tell their donors to not give to them, but to this upstart community foundation.”

The pitch worked and Old Bill’s was a hit from the start.

Last year, Old Bill’s raised a record $26.1 million for 240 charities. Among the crowd favorites is the Teton County Search and Rescue Foundation, which raises about a third of its $1.5 million budget through Old Bill’s. Its executive director, Keegan Young, moved to Jackson three years ago after working for the Tulsa Area United Way, which serves a region with more than 1 million people, earlier in his career. Old Bill’s brings in about as much money as his former employer raises in a year.

“I’m amazed that a town of 10,000 — a county of 23,000 — can do something like this,” Young says.

It’s hardly surprising that nonprofits and local donors to individual charities are flocking to Old Bill’s, where there’s free money on the table. What’s more interesting is the motivations of the people who put up the match.

Mr. Old Bill now contributes $1 million per year, and together with his wife, who has passed away, has donated $17 million since the event’s inception. More than 100 Jackson residents and businesses contributed $25,000 or more as “co-challengers” last year, yielding a matching pool of $6.6 million.

In an era when critics see philanthropy as yet another means for the ultra-wealthy to exert control, the donors providing the match are instead elevating the impact of everyday donations, especially to Jackson’s smallest charities, and gaining a greater understanding of people throughout the community.

Carrie Kirkpatrick, a self-discovery coach, has been a challenger since 2012 and currently gives $25,000 per year to the matching fund. “This is a very non-ego-based event,” she says.

Kirkpatrick’s father, Foster Friess, who died in 2021, was a larger-than-life presence in Jackson. He didn’t give to Old Bill’s, Fitzpatrick says, but he celebrated his 70^th birthday with a lavish bash at the Four Seasons highlighted by a surprise donation of $70,000 to the preferred charity of every one of the more than 100 couples in attendance.

The event seems similar to Old Bill’s in some ways, Kirkpatrick says, but Friess, an early backer of conservative activist Charlie Kirk and a strong advocate for limited government, also had a secondary reason for requiring guests to send in their charities.

“It was partly to create that whole hype and feel,” she says, “but there was also dual purpose in that, ‘I really need to know where this money’s going, so it’s not against what I want.’”

At Old Bill’s, Kirkpatrick says, the focus remains firmly on nonprofits supported by the community, regardless of their focus. 

“For many people, it’s the happiest day of the year,” says Kirkpatrick, who served on the community foundation’s board for nine years, including a stint as chair. “There’s a vibe, an energy — it’s a celebration of my and your individual passions, whether you are choosing to walk with the library foundation or with Climb Wyoming.”

Margot Snowdon, a 48-year Jackson resident who first came for the skiing, scenery, and wildlife, now focuses her giving on human-service nonprofits such as One22, where she often spends Friday afternoons working at the pantry. Snowdon and her husband, Yves Desgouttes, give $35,000 per year to the Old Bill’s matching fund.

“It’s the idea of being willing to support things that are unknown,” Snowdon says. “I know the names of the organizations, but I don’t always know what they do, or their executive director, or how tight their budgets might be — and I don’t need to. I want to support the community.”

The matching fund has multiple uses. It not only provides the match but also covers the costs of the event (participating nonprofits keep costs down by supplying most of the 350 volunteers who help with the event). Twenty percent of the match pool goes into a community-grants fund distributed throughout the year by the community foundation.

Community Foundation of Jackson Hole

Snowdon, who along with her extended family oversees a left-leaning national grant maker, the Hill-Snowdon Foundation, has served on the local committee that distributes the community grants. The experience gave her greater respect for conservatives also serving on the committee.

“The people I profoundly disagreed with had some good ideas,” Snowdon says. “Let’s just say my eyes were opened.”

A Model on the Move

Other communities are also raising funds and awareness of local nonprofits in their town by borrowing the model of Old Bill’s.

Charities just over Teton Pass, in Teton County, Idaho, used to participate in Old Bill’s before the 2007 creation of the Community Foundation of Teton Valley. That foundation’s version of Old Bill’s, a July fun run in Driggs called the Tin Cup Challenge, now raises about $4 million per year for local charities.

The Annual Fun Run for Charities, in Red Lodge, Mont., raised $470,000 in 2025. Started by the Red Lodge Area Community Foundation after a wealthy resident learned about the concept from Jackson friends, the event has produced $4.9 million for the local nonprofit community in the past 22 years.

In Lander, Wyo, a town of 7,400 three hours east of Jackson, the Lander Community Foundation adopted the Old Bill’s model in 2011. Its event, called Challenge for Charities, is tied to a half-marathon on the Fourth of July and now raises an average of more than $1 million per year for more than 50 local nonprofits.

Michelle Escudero helped bring the model to Lander after running in Old Bill’s. She and her husband, Scott Kane, have contributed to the Lander matching fund since it started.

“We understand that out of those 53 organizations, there might be some that we’re not crazy about, right?” Escudero says. “But we also understand that this is a way to support the community at a very broad level and it’s meaningful.”

Long-Term Growth 

Back in Jackson, the community foundation continues to find donors to support the general match at Old Bill’s. That means the event will likely continue to grow even when its 96-year-old founder is gone.

This fall, the cross-country runners from Jackson Hole High School will again line up against energetic fifth-graders and middle-aged plodders for the mad start of an event that’s about much more than running. Many nonprofit leaders will opt for the untimed walk instead, a chance to network with prospective donors and one another.

The timing is key. Expensive Jackson homes sit empty much of the year, but absentee owners arrive in droves in August and early September. It’s what many consider the best season in Jackson, when the aspen are beginning to change and the wildlife-art museum hosts a popular show.

One22 is among the charities that will be looking to make as many new friends as possible on the day of the run. The nonprofit, which runs the Jackson Cupboard, provides rental assistance, and serves as a key resource supporting the Latino community in Jackson, raises more than 12 percent of its $4 million annual budget through Old Bill’s.

“The money we raise through Old Bill’s would be impossible to replace through year-end fundraising because so many of the major donors aren’t here in December,” says Sharel Lund, One22’s executive director.  “It can be out of sight, out of mind.”

“When those folks are here is when they care about what’s here.”

Reporting for this article was underwritten by a Lilly Endowment grant to enhance public understanding of philanthropy. The Chronicle is solely responsible for the content. See more about the Chronicle, the grant, how our foundation-supported journalism works, and our gift-acceptance policy.