DJ Steph Floss started running to help two friends. In 2014, the DJ for the Cavaliers, Browns and Z 107.9 was looking for ways to be philanthropic in Cleveland. A few months before the Cleveland Marathon, Floss’ friend Mick Mumford had a cancer recurrence. Another friend’s mother was dealing with cancer around the same time. He wanted to use his platform to help. “Cancer victims need things,” Floss says. “They need treatment and research, and hospital bills aren’t the cheapest.” Then, a lightbulb went off one day when he picked a friend up from the airport.
“She was limping and walking crazy,” he says. “She said ‘I just ran a half marathon yesterday.’ I said ‘Yo, if you could run a half marathon, I can run a half marathon.’” This was March — not enough time for Floss to start running and complete a half marathon in May. But he found a “couch to 5K” app and trained himself to run the race. Inspired by the rapper/producer Diddy’s ‘Diddy Runs The City’ event from 2003, he started a GoFundMe to raise money for his friends.
“He ran the New York Marathon and had never run before and people watched him train and everybody was into it,” Floss says. “I wanted to do that locally. So I framed it as me running a 5K to raise 5K.” Floss finished the 5K — and raised the money. “[Running] didn’t suck as bad as I thought,” he says. “Once I start something new, I get really excited. Once I get in it, I’m really in it.”
After he finished that first race, Floss met and saw people just like him, who had just started running and wanted to keep going. So he kept going, too.
The next week, he launched Run With The Winners: a running club for runners like him — “not necessarily the fastest, just interested.” The name is inspired by a company named Roll With The Winners, a brand Floss had ties to.
“The next Saturday after the Cleveland Marathon was our first group run,” he says, “and there were like seven of us. I still have the picture.”
Floss credits his following for helping Run With The Winners grow. His DJing with the Cavs and his affiliation with LeBron James, he says, gave him a platform to give back in ways most people can’t.
“I definitely used that when I started running to promote Run With The Winners,” he says. LeBron even attended an event in Toronto in 2014 along with Tristan Thompson and some other Cavs players.
Hitting Its Stride
Today, Run With the Winners is a fixture in the Cleveland running community. The group has two weekly runs — one on Tuesday nights starting at North High Brewing Co. in Ohio City and another on Saturdays at rotating locations. It has a prescence at nearly every race in Cleveland.
“If you didn’t know who we were,” Gockowski says, “you’d still know that we are something special.”
That includes the 2023 Cleveland Marathon on May 20-21. Floss is doing the challenge series and will run either the 5K or the 10K on Saturday and the half marathon on Sunday.
“I love that it’s more family and friends than anything else,” he says.
Run With The Winners is purposefully inclusive — all paces are welcome. Adam Gockowski, a Run With The Winners member since 2019, said the vibe matches what Floss brings to DJing at a Cavs game or a club downtown: energetic and positive.
“It’s a diverse group,” he says. “We come from different aspects of life, but we gel. We aren’t a cookie cutter group who all match in personality types and performance types.”
Floss hopes to engage even more Black Clevelanders. On Juneteenth each year, Run With The Winners hosts the Runteenth event to encourage Black runners to join. Floss started the event in 2020 after Ahmaud Arbery was murdered while running. This run, Floss says, is about helping Black runners feel more comfortable and safe.
“We are adamant about getting more Black runners to join the running group,” Floss says.
Floss can’t make every run due to his demanding schedule — his regulars and his partner Kat Ferenz step in if he can’t be there — but the activity has become a vital part of his life.
“I do it for myself. I love to run now,” he says. “But mostly I do it for everybody else that comes and runs.”
Get ahead of the weekend by signing up for our free weekly “In the CLE” newsletter — your guide to fun throughout The Land. Arriving in your inbox every Wednesday, this weekend to-do list fills you in on everything from concerts to museum exhibits — and more. Click here to subscribe.