ABOUT US

 

 

Our Story in Miles

Bossman

Jeremy’s been chasing the horizon since he was 16, when he bought his first bike and rode to Myrtle Beach Bike Week with the directions sharpied on his forearm. Back then everyone called him “Jay,” and yes — high-school Jay thought he was bulletproof.

He went to The University of Akron, joined the Lonestar fraternity, and signed up for the Army Reserves because he “still wasn’t ready for a real job.” That path took him to Bosnia as a firefighter, where he learned grit the kind of hard way most people never experience.

After serving, he moved to Colorado, jumped into real estate, and kept racking up miles — about 600,000 of them over the years. In 2015 he bought Bob’s Hamburg, Akron’s oldest restaurant, and later became the owner of Ohio Championship Wrestling, which is how the “Bossman” name officially stuck.

In 2018 he bought Kim Tam Park at Melanie Springs, kept building community, and stepped even further into service as a Rotarian, Mason, and Springfield Township Trustee. These days, he’s still riding, still building, and still proving that life makes the most sense between the throttle and the next state line.

Favorite Redhead

Jo didn’t pick the name — the name picked her.
Back in her MotorClothes days at Rubber City Harley-Davidson (later Hall of Fame H-D), riders kept coming back asking for “their favorite redhead,” and she ran with it like it was printed on her paycheck.

She was raised on a pig farm in Northwestern Ohio, one of three daughters — no brothers, no shortcuts, and definitely no fear of hard work.
If something needs done, she rolls up her sleeves and gets after it. Always has.

Now she’s the sparkplug of Bossman Rides — running events, filming rides, managing merch, building the website, and keeping the Bossman on task (which should honestly count as cardio).
If you see something organized, posted, branded, or running smoothly… odds are Jo did it with coffee in one hand and just the right amount of attitude in the other.

Bossman Rides

They met years ago at Rubber City Harley-Davidson — he remembers her ass, she remembers his arms, and she still remembers the first shirt he ever bought from her. Life went its separate ways for a while, until the day Jo walked into one of his OCW shows. When he asked for her number, she didn’t hesitate… she put herself in his phone as “Favorite Redhead.” And that was that.

They built the rest of the story on the road. Their first big ride together wasn’t some little weekend trip — he picked her up at the Denver airport, they rode through Colorado, rolled into Sturgis, and rode all the way home. Jeremy brings the veteran grit, the real-road experience, and the kind of stories you only earn by living them. Jo brings the fire, the strategy, the creativity, and the ability to turn chaos into a brand people actually connect with. Somewhere between the miles, the late-night drives, and the laughs, they figured out they make one hell of a team.

Together, they turned those rides into something bigger — filming the road, telling real stories, showing up for veterans, and building a community that feels like family whether you follow from a thousand miles away or show up at Kim Tam Park on a Thursday night for Bossman Rides Bike Night. They ride together, work together, build together — and they’re taking everyone who believes in grit, honor, and brotherhood along for the journey.