Cyclist Kevin Bupp of 72-Hours to Key West Discusses Bike Charity Rides

Cyclist Kevin Bupp Discusses Charity Rides on One Community blog

Matt Scarborough recently invited Kevin Bupp to speak with him on the One Community podcast. 

Bupp is a local real estate investor, cyclist, and one of the founders of the 72 Hours to Key West Charity Ride which has been going for 13 years. Scarborough and Bupp talk on this episode of One Community about cycling, how to fit in hobbies and work around family life, and what it takes to start and run a successful charity ride event. 

“I always enjoyed being on two wheels and the freedom it provided,” Bupp said about his early days riding bikes as a kid. He wasn’t a competitive cyclist but used his bike to get from one place to another growing up in Harrisburg, PA. 

It wasn’t until he met his wife, a serious runner, that he took up running too. From there the two began competing in triathlons which meant getting more serious about biking. “I found that love I had as a kid of getting out on my bike and riding for hours,” Bupp said. 

One of the great things about the biking community is how many ways there are to enjoy cycling. While Scarborough enjoys mountain biking, Bupp is primarily a road biker.  

“I love being able to get on my bike from my garage and go ride,” Bupp says. “It changes the dynamic and excitement when I have to load it up into a vehicle and travel a couple hours. On top of that I have young kids. I try to work in my riding to where it doesn’t interfere with family time.” For Bupp, this means fitting his long rides in first thing in the morning so his family is just starting their days as he’s coming home.

Between his work at Sunrise Capital where Bupp’s company invests in manufactured housing communities and parking garages in several states, going on regular rides, running the 72 Hours in Key West charity ride, and spending time with his wife and kids, a lot of Bupp’s time is spoken for. But spending quality time with his kids is important to him. “They money doesn’t matter after we’re gone,” Bupp told Scarborough during their conversation. What families remember is the time you did—or didn’t—spend with them.

72-Hours to Key West Charity Bike Ride

When Bupp was struggling to find ways to give back to charity after the 2008 financial crash, he realized that one thing he did have was his “two legs.” Despite never organizing a charity ride before, Bupp isn’t one to think small. “I didn’t want your normal 50-mile charity ride. I wanted something that would attract folks from across the country.” The first year of 72 Hours to Key West—a 280-mile ride from Fort Myers to Key West—only brought in $300 in donations. The most recent ride raised $75,000. Proceeds go to the Tiny Hands Foundation which gives out school supplies, holiday meal baskets, and more and Starting Right, an initiative in Tampa that helps homeless youth.  

Kevin Bupp’s Tips for starting a charity ride

  • Consider the length of the ride: As a father and businessman, Bupp wanted to make 72 Hours to Key West something people could do in a weekend because he knows how hard it can be to take more time away from family and other obligations. He knew that roughly 100 miles a day was a good amount and looked at the map to see what rides might be in the ballpark of 250-300 miles. That’s what led him to pick Fort Myers (an easy location for people to travel to) to Key West. 

  • Make the ride a destination: There’s just something more romantic about the idea of biking the Florida Keys than a random stretch of 280 miles. It’s the kind of thing that can feel like a bucket list item even if riders have never heard about it before. People now sign up from across the United States (even as far as Washington state) and come in from out of the country to do the ride.

  • Don’t be afraid to keep it small: Bupp caps the number of riders at 75, enough to bring in a donation and be fun but not so many that it’s overwhelming for the chosen route and planning hotels and transportation

  • Make it fun for volunteers: 72 Hours to Key West started with a core group of volunteers who have kept coming back to help make the event a success year after year. They organize lodging for riders and make sure everyone gets to the starting line. Having the same people want to come back and help plan the ride puts less on Bupp to organize.

  • Word of mouth is your best advertising: While signups through Facebook ads and similar result in about a dozen sign ups a year, most of the early riders were friends of Bupp’s from cycling or running events he’d done in the past. Now people tell their friends looking for a fun ride about 72 Hours to Key West. It helps keep the ride going and makes it so people signing up know what they’re in for and have a good time. 

For the annual charity ride initiated by Scarborough Bicycle Accident Law, check out the Parkinson’s Awareness Ride at Suncoast Trail and put it on your radar for next April.

Cyclist Kevin Bupp is one of the founders of the 72 Hours to Key West Charity Ride which has been going for 13 years. Matt Scarborough and Bupp talk on this episode of One Community about cycling, how to fit in hobbies and work around family life, and what it takes to start and run a successful charity ride event.

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