The fire roared in the hearth at Colectivo’s 68th Street cafe in Tosa. Between the crackling pops sounding from the flames, the radiating warmth, and the fragrant smell of coffee hanging in the air, the cafe was the perfect place to be on a cold winter day.
The 20-degree temperature and howling winds would send most people running indoors, but the Milwaukeean I was meeting with that day preferred those conditions. They make for the best waves after all.
Across from me sat Daniel DeWitt, a Wauwatosa native, avid Great Lakes surfer, and founder of High Five Surf, a Milwaukee-based business teaching locals the sport (and art) of freshwater surfing.
I had a lot of questions for Daniel, naturally, because when you see someone braving sub-30-degree temperatures to catch a wave, you kind of want to figure out what in the world they’re thinking. The questions usually sound like: wait, are they surfing out there? How are they doing that on Lake Michigan? Aren’t they freezing their a** off? How do you even get into that?
I learned that what started as a passionate hobby for Daniel bloomed into something much larger than himself. And now, he spends his days taking adventurous locals and visitors out on the frigid waters to show them what makes surfing the Great Lakes so special.
Growing up, Daniel was a fan of skateboarding and watersports, often spending time on Shawano Lake, where his grandparents had a cottage. Outside of that, though, no one in his family was a surfer, and he hadn’t spent much time around Lake Michigan.
His journey to paddling the icy fresh water of the Great Lakes was long and winding, and wouldn’t be put into motion until he happened upon a board while he was living in California.
“What really pushed me into it was going to a rummage sale and seeing a 1980’s colored wetsuit and board. I thought, ‘I gotta get this.’ I tried to teach myself, and it was a disaster. I almost died. I didn’t know anything about the board or surfing and went out in really bad conditions.”
That one, rather traumatic experience would linger. He didn’t touch his board again for years. Not in California and not when he moved back home to Wisconsin. Instead, it sat tucked away in the back of his garage. It wasn’t until 2018, when he watched the Netflix documentary, “Under the Arctic Sky,” that the urge to get back on the board came crashing down on him.
“I googled surfing in Lake Michigan after that, and it was meant to be. I found Lake Effect Surf Shop in Milwaukee, which is now closed, and EOS in Sheboygan and started networking.”
When he wasn’t working his day job in ‘corporate America,’ he found every opportunity to hit the water and every reason to drag family and friends out with him.
“I was not thinking LLC, was not thinking business. I just wanted to share this with my friends, with the world. I just fell in love with surfing and wanted to share it.”
It was a passion that consumed him. Daniel said he often found himself peeking at the beach cameras on his work laptop, and in one extreme instance, he left his job on a Friday afternoon, drove 18 hours through the night to Waco, Texas, hit the wave park where he surfed for just four hours, slept in his car for a bit, then perfectly timed his 18 hour drive back so he got to the office just in time to start work on Monday morning.
In 2019, after a year of working a 9-5 and surfing on the side, Daniel knew a lifestyle change was in order. Instead of working for a large company, he wanted to try to make a living working for himself, with the bonus of surfing around his schedule. He worked odd jobs he could find, started an LLC for handyman services, and secured regular pet care and Rover work that sustained him for the next couple of years.
Then, in 2021, he got the opportunity he’d been looking for. While it didn’t last long, it opened his eyes to the potential market for surf lessons.
“Jake [Besette] from Lake Effect Surf Shop knew I was super into surfing and said why don’t you come be my assistant coach on surf lessons here and there. He would throw me a little money for helping out. I was getting really good feedback, people were saying I was an awesome coach, and asking if I did lessons myself. I asked Jake if he would be okay if I started an LLC for lessons, as long as I didn’t sell gear. Then, in the fall of 2021, I incorporated High 5 Surf.”
The first couple of years of High 5 Surf were mostly part-time as Daniel balanced his other jobs. Then in 2023, he decided to pursue it more seriously. He focused efforts on marketing High 5 Surf, raising awareness for the local surfing community, and – discovering an unfilled gap in the Chicago market – exploring what it would take to bring his skill sets and lessons to the Windy City. While the Chicago market isn’t a high priority for Daniel, he still does a couple of lessons there every year.
Daniel has explored different monetary structures for his surf lessons over the last five years, from barely scraping by at $75 a lesson to a premium model where he charged $250 a lesson. His current model? Community-supported. There is no charge for a lesson, only the option to donate, or as he likes to think of it, “pay it forward’.
“The passion for surfing has stayed with me for the last 5 years, but it’s back even more, like how can I share the gift of surfing with people even more?”
Boards, wetsuits, cameras, everything you need to get out in the water, he provides, but the knowledge around the gear is one of the biggest hurdles he faces. The hesitation people have to get into 30-degree water in the middle of January is more of a mindset challenge than a logistical one.
“A lot of people don’t want to try surfing because they don’t know they can stay warm. With our heated changing stations and the right equipment, you can stay as warm as snowboarding or skiing, which people do all the time in Wisconsin.”
The wind and churning water make our corner of the state a sweet spot for surfing, with Sheboygan and Port Washington serving as regionally recognized hotspots for catching fresh water waves.
While the local surfing community is growing and some days you can find a dozen surfers eyeing the same wave, Daniel said you’re just as likely to find yourself alone on the water, with nothing but your board beneath you.
“Surfing is definitely joy, peace, and fun. Adventure, because it’s not always peaceful. I challenge myself to put myself in some scary, big waves. And I love that too. It’s art, it’s fitness, it’s business now, it’s community, right? It’s so many things.”
Through the surfing community he’s found in Milwaukee, and the greater Midwest, Daniel’s had the opportunity to surf hidden gems on both Lake Michigan and Lake Superior, connect with strangers fueled by a love and respect for the water, and create an appreciation for the sport in the newcomers who now find themselves at the center of someone else’s “are they surfing out there?” question.
When will you try it?
Interview and story by Mikayla Sullivan, the ‘I’ referred to at the beginning of the article.