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EMERGING ENTREPRENEURS: From cyclist to landscaper, Sylvester makes a change

Bay Port High School junior recently started his own landscaping company

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July 11, 2023

NORTHEAST WISCONSIN – Knowing a change is needed and taking the steps to make that change are two completely different things.

At just 17 years old, Bay Port High School junior Cohen Sylvester, a once budding cyclist with dreams of riding in the professional peloton someday, did just that.

Needing a change from cycling 300-400 miles per week and the nerves that go along with it – all while balancing school, work and life – the young entrepreneur said he had enough of life on the road and the rigors of training.

“I needed to pivot because I wasn’t having fun anymore,” he said. “A lot of people don’t realize the difficulties that come with wanting to turn professional or what it’s like to be a professional. Especially with pro cycling, there’s not much involved in making it big. Half of the guys out there aren’t making enough money to earn a living.”

Sylvester said the time it takes to train was part of his decision to switch things up, but there was more to it.

Cohen Sylvester

“There’s a lot of risks (in professional cycling) for little reward,” he said. “Fortunately, I’ve never had a serious crash – I feel lucky about that. I still love cycling but want to do it for fitness and fun. I did a century (100 miles) with my dad a few weeks ago. It was fun to go with him at a chill pace. It was probably the most fun I’ve had on a bike since last fall.”

Cognizant that a change was needed but not wanting to sit idle, Sylvester started his own landscaping company – Sylvester’s Lawn Care Service.

“I switched up my life quickly,” he said.

A leap of faith
Spending thousands of dollars on a road bike has been commonplace for Sylvester, however, a bike doesn’t come in handy as a landscaper. 

He needed different equipment – and lots of it, something Sylvester said he had to invest in.

“I used my savings to buy a (used) truck, a trailer, a zero-turn mower, a push mower, a blower and a weed whacker,” he said. “I had no customers and no accounts… The big initial investment was expensive, and I still need to get some more big-ticket items.”

Sylvester said he already has a few bigger jobs lined up.

“I couldn’t be happier with how things are going,” he said.

Sylvester said his parents have been “very supportive” of his decision.

“I’ve always been my own kid,” he said. “My parents have been great. At first, they said, ‘(Adapt Cycling) is a great opportunity, so maybe you should reconsider staying with it.’ But, they are supportive of the change.”

Sylvester said his long-term goal is to be a “big landscaping company.”

“There’s a demand for those,” he said. “I’d like to have employees, a warehouse, etc. That’ll be down the road – hopefully. I’m not quite ready for that yet.”

Switching things up
After switching to outdoor labor about a month ago, Sylvester, who had previously worked at Broken Spoke Bike Studio in Downtown Green Bay, said “I’m having fun again.”

“I like labor, working hard, being outside and getting my hands dirty,” he said. “I don’t claim to be an expert landscaper, but I’ll figure things out, get the job done and know it will look good. I don’t get scared of things, even if I don’t know what I’m doing. I know as I get more experienced, I’ll learn more.” 

Sylvester said he had been thinking about doing something different for quite a while, but he also loved his job at Broken Spoke, which he had for about three years.

“A week after deciding not to be on the team anymore, I put my two-week notice in at Broken Spoke,” he said. “I’m grateful for having worked there – it taught me customer service, how to run a business, etc. I knew I wanted to do something now to set me up for my future. I’ve always had an interest in landscaping.”

Sylvester said right now, his main form of advertising for Sylvester’s Lawn Care Service is word of mouth.

“I’ve used social media, but I’ve also knocked on doors, used door hangers and business cards,” he said. “I’ve done some jobs for cheaper simply to get customers and get my foot in the door.”

A needed change
Sylvester said he began riding with an elite junior road racing team last year called Adapt Cycling – a 501(c)(3) nonprofit, developmental Wisconsin-based cycling team.

Cohen Sylvester, front, decided to put his cycling dreams aside to start his own landscaping business. Submitted Photo

“Our schedule was packed,” he said. “I went to Arizona in February and then Georgia for three weeks in April. I was a bit burned out going into (the training) because I rode so much during the winter – I was very strict, oftentimes spending hours on my (indoor) trainer. In Georgia, we were doing back-to-back days of 100 miles with 10,000-plus feet of climbing.”

Sylvester said he was tired mentally.

“It was hard balancing school, work and training,” he said.

Although training sometimes meant missing school time, Sylvester said he still received good grades but admitted it affected him somewhat.

“It messed me up a little bit, but I still got mostly B’s,” he said.

Once he decided to take a break, Sylvester said “it was a process stepping back from the team.”

“When I got back from Georgia, I settled back into life and began thinking more about my future,” he said. “Don’t get me wrong – getting to that level, telling people I was a junior pro and traveling all over was sweet, but in reality, sometimes it sucked.”

Sylvester comes from an athletic background – both of his older brothers played college football at Division II University of Minnesota-Duluth.

“Now I ride to have fun and don’t feel like I have to ride,” he said. “The second I stopped racing on the team, all the pressure went off – I’ve been way happier. I need to find that joy again. I still see myself getting back into racing at some point – maybe on the mountain bike. I do have a few other road events planned this summer, too.” 

For now, Sylvester said he’s excited about seeing growth in his landscaping business.

“I’m not quite sure about college yet,” he said. “If I do go, it would be for business. If I go somewhere for college, that’s at least two years of me not making money – and the time. I’m not opposed to it because there would be a benefit, but there would also be a loss in time.”

Time will tell.

One thing is for sure – the high school junior will give Sylvester’s Lawn Care Service his all.

More information on Sylvester’s Lawn Care Service can be found on Instagram, through email ( or by calling/texting (920) 404-5082.

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