Sheboygan County has some pretty spectacular entrepreneurs, and we’ve had a blast on our social media connecting with some of them personally.

It’s astounding to see how small businesses find their niche and thrive in Sheboygan County. But even more, it’s just inspiring to see the passion in the people behind them.

Let’s revisit five of those entrepreneurs.


Anthony Flores Fitness

Anthony Flores knows firsthand what makes fitness important and effective – in his own fitness journey, he saw change was not only necessary for his health but also possible.

“Our motto ‘Easy Day’ is a mindset – the time in the gym is the hardest part of the day, so we can handle anything the day holds after that,” he states. But the best part is, at AFF, the hardest part of the day is also fun.

AFF was started about 3 years ago. Anthony had been working at a factory as he worked on his own fitness and helped others, when a friend pointed out he had what it took to become a personal trainer. He got certification and did just that at the Sports Core, then as an on-site help at Bemis manufacturing. It was after that he decided he wanted to offer personal coaching outside larger corporations. He saw Sheboygan County had a need for personal trainers, and stepped up to fill that need.

So why Sheboygan County? “Partly because I already lived here,” Anthony laughs, but then continued, “Sheboygan County is Someplace Better because we have the Malibu of the Midwest. You can’t beat the location; people take it for granted. Lots of great small businesses are here to explore, too.”

Small Town Big Family

“Sheboygan County is someplace better because the mindset of entrepreneurship is ingrained in our towns and the community is supportive,” Jon Prigge of Small Town Big Family says. And he knows firsthand – this Elkhart Lake small business was born out of a season of loss.

Started in 2016, Jon and his partner, Jennifer Liermann, wanted to start a hat company that represented the heart of Elkhart Lake and the community. They had just witnessed several losses of dear people in the community, and in the wake of that intense grief, they were inspired by how the community rallied around the families with sincerity and sacrifice in an outpouring of support.

“Deep down, we’re all from a small town,” the tagline goes, and that sense of community is emulated in their products. Featuring graphics of local natural resources like Elkhart Lake and Lake Michigan, their hats, shirts, bandanas, and more bring that serene quiet to everyday life.


The business was met with a warm reception. Prigge began selling out of a backpack, but has since moved to farmers markets, began getting purchases internationally, and now is in the process of opening storefronts in Elkhart and Colorado.

But it goes beyond their brand. STBF partners with other businesses to represent and support them, as well as gives back to the community – most notably in their turtle-themed products, The Wendall Line, when purchased helps ALS research, to which the community lost a close family member.

The goal is to make products with meaning that make you feel like part of a family. And STBF does just that. Sheboygan County is someplace better because it has small towns that make you part of a big family.⠀

The Paddock Club

Elkhart Lake, a small town in the northwest part of Sheboygan County, boasts the Paddock Club – a restaurant with heart, intention, and the occasional live music, opened 12 years ago by sisters Cheri Has and Lynn Chisholm. (Lynn also owns Polly Popcorn down the street from the Paddock Club!)

Boasting a chic environment, homemade pasta, locally-sourced ingredients, and in-house crafted drinks and dishes, this cozy location offers a perfect date night spot. But, it’s also a favorite of the families in the community.

“Sheboygan County, and Elkhart Lake in particular, is someplace better because it’s a small community and everyone takes care of each other. Even between restaurants, we help each other out,” Becca S, the manager and hostess says. And it’s evident – as people walk in, they’re greeted by name, kids included. The Paddock Club marries elegance in food and environment with familiarity in its culture. Original Brunswick bar, 1890s⠀

A couple neat things to note – the bar is an original Brunswick bar from the 1890s. Tuesdays are the favorite days to come because they feature a small plates menu. And once in a while, live jazz will happen on Fridays – it’s a pleasant surprise you don’t want to miss.⠀


Harry’s Prohibition Bistro

Sheboygan County is someplace better because it has places with experiences that make you forget where you are. Harry’s Prohibition Bistro on the Sheboygan Riverfront is one of those places.⁠

If you want authenticity in recipe and atmosphere, you’ll find it here. Decor reminiscent of the prohibition fill the walls with the staff donned to match. And, the pizza is Vera Pizza Napoletana – a title earned by having a truly-true-to-Naples pizza, making this a rare gem not only in the county but the country!⁠

The brothers who own and operate the restaurant moved here from just north of Greece in 1994. Why Sheboygan County? “Sheboygan County is thriving in industry, and it’s one of the best places to raise a family,” says Avni “Al” Latifi, one of the founders of the restaurant.⁠

The idea for the restaurant was born in their own backyard, quite literally – the brothers built a pizza oven, making their pizzas for the neighbors, and the rest is history. The Bistro opened its doors in 2013 and has surpassed expectations ever since.⁠

“The crust is a canvas and the ingredients make the painting,” says Al. And now, they’ve expanded their gallery to include Roman style pizzas on Tuesday nights only!⁠

“We’re a family business and we truly take pride in seeing satisfied, happy, laughing customers leaving our doors.” And they succeed – there’s this unmistakable air of a family bond and everyone leaves with a smile on their face.⁠

“Sheboygan County is #SomeplaceBetter because it is so diverse, and the people know good food. This place has it all and endless opportunity.” – Al Latifi⁠

The Fig & The Pheasant

Sheboygan County is Someplace Better because it hosts places that marry tradition with innovation, and epicure with fun. The Fig & Pheasant is one of those places – previously known as 52 Stafford, its new owners, Patrick and Ronna O’Toole, have brought this beloved location to the next level in quality and experience.

Combining the positive symbol of a fig with the creativity represented by the pheasant, their revisited Irish menu adds a level of extraordinary to flavors you may know and love.

Every Wednesday night, too, you can come to hear delightful Irish music performed live!

But this modern twist on tradition carefully preserves tradition – the downtown Plymouth restaurant is housed in the oldest known hotel in Wisconsin and has been cherished by the community over the years. Now owned by Patrick and Ronna, chefs who originate from San Francisco and have been from Norway to a Dubai, with heritage just a few generations back in Ireland, the history and tradition is honored while bringing in a new season allowing it to flourish. With everything for drinks and food made with real ingredients in house, the menu boasts a quality and care only Sheboygan County knows.

“Sheboygan County is someplace better because kids can be raised in a small town environment, with a safe community, and wonderful seasons,” says Patrick. “The schools are wonderful and there are opportunities for children. The environment is also gorgeous,” Ronna adds.

There is much more to say, but we encourage you to come and hear their incredible stories yourself.

Who’s an entrepreneur in Sheboygan County that’s inspired you? Tell us.
Looking to become an entrepreneur? See why Sheboygan County is the place to do it.