One High Roller Turns his Fundraising Into a Four-Event Season 

Most Pelotonia fundraisers ask people to give. 8-Year Rider and Peloton Captain of West Coast Pelotonia Duane Winchester built an entire fundraising season around a different idea: give people something back.  

Duane joined Pelotonia in 2019, raising money by sharing his story as a cancer Survivor with family and friends. He became a High Roller that first year, a distinction reserved for participants who commit to raise $5,000 or more. But it wasn’t until he moved to a Palm Springs, California lifestyle community in 2021 that his fundraising transformed into something else entirely.  

It started small. He joined a member-led cycling club for Sunday rides, and word of his story spread. A pickleball club he’d only just joined redirected $3,000 from an unrelated raffle to his ride, enough to become a High Roller again. That was the spark.   

“That got me thinking,” he said. “What else can I do?”  

What followed was years of experimentation: a neighborhood cycling loop, a yoga event, even a “kamikaze karaoke” night where guests paid to sing, or paid more to make Duane sing instead. Slowly, four events rose to the top.  

A pickleball tournament began as a single day among neighbors, raising about $5,000. The next year, he opened it to outside players and ran it himself — a hectic two days that doubled the total fundraising. By the third year, Duane opened the event to players nationwide. This year, the pickleball tournament raised $23,000. 

The other three events carry their own weight. This year’s bowling night brought in about $8,500, and the art auction raised roughly $7,000. His 30-mile cycling ride through Fox Canyon brought together 25 riders and raised more than $1,500.  

Duane is constantly looking to evolve his events and grow his impact. As an artist, potter, and woodworker, he wants to create enough pieces to stock the art auction himself rather than asking local artists for donations. He’s also working with a local bike shop to help the ride expand.  

In eight years, Duane has raised more than $120,000 for cancer research at the OSUCCC – James, giving back to the place where he received his cancer treatment.   

His next goal is to raise another $100,000 for Pelotonia, but this time in a single year, so more of that impact reaches the researchers and patients who need it now.  

This article appeared in the Summer 2026 issue of the Pelotonia Insider.