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Author: Greg Trotter | January 17, 2024

Owner Steven W. likes to test his limits. He's always had a competitive spirit that's seen him participate in various sports at a high level.

Standing at a towering 6' 10", he played basketball, first, at Michigan Tech before finishing his collegiate career at the University of Wisconsin Oshkosh. With shades of Shaq, Steven was an excellent and surprisingly mobile center, and he went on to play professionally in Europe and Australia. 

Though he had a successful basketball career in which he traveled to far flung locales and played with some of the best in the sport, Steven hung up his basketball shoes for good in 2013. Never one to rest on his laurels, he’s since sought a new outlet in the form of competitive cycling.


Steven’s adventurousness may have something to do with his roots. Growing up near Gallup, New Mexico, his childhood was spent along the storied Route 66, one of the original roads built as part of the U.S. highway system and a stretch that John Steinbeck once dubbed the “mother road” because of its promise of escape and freedom.

It’s fitting that this highway connects the Midwest to the West Coast. Steven’s family is originally from Michigan, not too far from the highway’s point of origin in Chicago’s Loop. No matter how far away Steven traveled, the Midwest always seemed to beckon.

During his sophomore year of high school, Steven’s parents, both of whom are pharmacists, got jobs in Michigan’s Upper Peninsula, and the family traded in desert vistas for the wooded landscape of Marquette, Michigan, a place to which he would return yet again many years later.

When he was younger, Steven, like most kids, spent a lot of time on his bike pedaling around town to and from friend’s houses. However, the idea of taking cycling seriously is a more recent one.

Biking began as a way for Steven to spend time with his brother. After moving back to the U.S. and settling with his wife in Milwaukee, the brothers began cycling around the Brew City as well as Chicago and Michigan.

Steven notes that cycling has provided him with a great way to bond with his brother. It’s also both a competitive outlet and an activity in which he can take some time to himself. As he explains, “It’s a great way to get outside, explore nature, and see places that a lot of people can’t get to [any other way]...It brings me a lot of joy, and it’s a passion that I can dedicate [myself to].”


Another aspect of cycling that appeals to Steven is the culture. Here, he sees an important connection between his passion for cycling and his love of watches. Both of these pursuits have introduced him to thriving communities of like-minded individuals.

He points out that, like the growing group of Oak & Oscar Owners, “cycling, especially in the gravel and endurance scene, is very community driven. I’m always drawn to connecting with genuinely good people.”

Steven owns several Oak & Oscar timepieces, including a Sandford, a navy Jackson chronograph (which he wore on his wedding day), a grey Humboldt 12-HR, and a white Olmsted. Steven points out that “Oak & Oscar is doing things other brands aren’t doing.” He adds that Oak & Oscar is constantly pushing the limits of watchmaking in similar fashion to the ways in which competitive cyclists are always trying to push their physical boundaries.

“Biking and watches are two things I’m super passionate about, and they’ve both allowed me to see places I’d never thought I’d go and meet some amazing people, with many becoming lifelong friends.”


After a time, the brothers decided to push the envelope a bit, and they competed in their first race in February 2018. Of course, Steven didn’t ease into competitive cycling. His first race, the “Polar Roll”, was a 15-to-30-mile snow bike race that was grueling and cold.

The description of the event indicates that the weather is “unpredictable and dangerous” and that participants should “prepare for the worst.” Cyclists braved frigid temperatures and wooded trails with no aid stations or other official support. The Polar Roll Field Manual states, “You are on your own. No one is out there to save you. You are responsible for your choices.”

In short, the race gave Steven exactly what he was looking for–a way to expand his boundaries and test his mettle. Despite the tough conditions, he and his brother found the experience incredibly rewarding, and they couldn’t wait to register for their next race.


Now living in Michigan’s Upper Peninsula with his wife, he has to be deliberate about his training. During the winter months, that means fat snow tires, warm weather gear, and a thick, bushy beard. It also means engaging in some in-door training with his dog and training partner, Teddy.

Steven’s Finnish heritage comes into play here, too. As he explains, his grandfather built his own sauna by hand from the ground up. During childhood visits to his grandfather’s home, he and his brother became well acquainted with the therapeutic benefits of the sauna, and it’s since become a critical part of his training and recovery.

Alternating between the hot steam of the sauna and cold rolls in the snow helps him stay ready for the variable conditions he may encounter on race days. And, perhaps more importantly, the practice connects him with his past. 


During a typical cycling season which spans roughly from March to October, Steven competes in a race per month. That means he’s always preparing for the next one, and training is no easy feat. “The last one to two years, I’ve done more of these races, and I’ve wanted to be a little bit more competitive. Your body can always do more if you push it. You just have to trust your training.”

He adds that, “There are times where you probably want to quit, but you have to make that decision: do I keep going and try and push through or do I pull out? I think the more and more I push myself in training with longer rides, the more confident I feel when I get to the race…”

In April 2023, Steven competed in the 62-mile Barry-Roubaix gravel road race. Occuring on the third Saturday in April in Hastings, Michigan, the Barry-Roubaix is one of the world’s most popular gravel road races.

Throughout the course of the race, Steven biked up a whopping 4,000 feet of ascent and pedaled over pavement, rocks, sand, and mud.

His ability to complete tougher, longer races and to traverse more demanding terrain is a testament to the dedication he puts into his training. Nothing feels better than seeing the culmination of all your hard work.

As Steven puts it, “A lot of it is about pushing yourself, seeing how far you can go, but ultimately finishing what you start. When you do get to that point of finishing the race and achieving a goal that you set for yourself, it’s very rewarding, and you know that you’ve completed something that you’ve dedicated time to achieving.”

Steven has no plans to stop anytime soon. In March 2024, he’ll be competing in the 100-mile Mid South race in Oklahoma, one of the world’s largest gravel road races.


Are you an Owner? Do you have a story? Of course you do! We’re always looking to meet our Owners and share their adventures on our site and with our fans. Send us a message and let us know you’d be willing to chat with us about you and your adventures, and we’ll do the rest.