If you hit up any of Milwaukee’s many festivals this summer, chances are you’ll spot a pink cart on the back of a pink bicycle, topped with a pink and blue umbrella. Behind that cart, chances are you’ll find Sam Wisneski, the co-owner of Chillwaukee, slinging frozen pops and shaved ice made with vegan, gluten-free, all-natural flavors.
“The best part of the business is being able to provide the customers with such an awesome, delicious treat, especially on a hot day,” said Wisneski. “It’s really fun when the kids are so excited. Kids just light up when they see our bicycle.”
Wisneski and his wife, Alyssa, who met at UWM and are both UWM graduates, purchased the Chillwaukee company in 2023. Chillwaukee dishes up frozen treats in flavors ranging from strawberry mango to sea salt chocolate to pumpkin pie, and you can find them at festivals and farmers’ markets across Minnesota, Wisconsin, and Illinois.
Here are three things you need to know about Sam Wisneski and Chillwaukee.
1. Before Chillwaukee, things came in a Sweet Little Box.
Chillwaukee is not Wisneski’s only business, nor is it his first one.
Wisneski graduated from UWM with his bachelor’s degree in 2019 and immediately embarked on his master’s degree. But then, the COVID-19 pandemic hit. Wisneski and his wife grew bored during lockdown, so they decided to start a business. They realized how many people had turned to crafting and DIY projects to fill their time during quarantines, so the couple decided to start selling supplies to help budding creatives. They packed up “sweet little boxes” – in fact, the Wisneskis named their company Sweet Little Box Co. – full of products they made themselves such as candles, soaps, and scrubs, and began selling them online.
“Overnight, it exploded,” said Wisneski. “Literally, we posted our first gift boxes and the next day, we had 50 orders.”
Today, Sweet Little Box Co is still going strong, with two warehouse spaces devoted to its inventory. A large part of their business is corporate gifting; the Wisneskis just finished a 350-gift box order for the Professional Golf Association’s (PGA) employees across the country. The business also provides income outside of summer when the couple can’t run Chillwaukee’s bikes.
While they were proud of founding Sweet Little Box Co, Wisneski and his wife were missing face-to-face customer interactions. So, when the opportunity arose in 2023, the couple got into the ice pop business.
2. Wisneski built on Chillwaukee’s success by staying true to its principles.
Chillwaukee was established in 2017 by another couple, who created the ice pop recipes as well as the company’s trademark pink bicycle and umbrellas – a solid branding base to build on, Wisneski said. Taking over a business that already had a devoted following in the city was with its own set of pressures, especially since Chillwaukee’s claim to fame is vegan, gluten-free, delicious desserts.
“Our customers really held us to that,” said Wisneski. “The moment that is most fun for me is when someone gets to enjoy a sweet treat who otherwise wouldn’t be able to enjoy (because of dietary restrictions).”
Even so, Wisneski is aware that the “vegan” label might put some customers off; the dairy substitutes used in ice cream aren’t to everyone’s taste. Still, he joked, “It’s not that hard to make a vegan popsicle.” And when the ice pop recipes do call for a bit of cream, he can personally guarantee that the company’s proprietary blend of oat milk, coconut milk, and rice milk adds a delicious bit of flavor. He recommends the chocolate-dipped peanut butter banana pop.
In the three seasons they’ve been operating, Chillwaukee has expanded its festival footprint, increased its bike fleet, gained a trailer, hired more staff, and added new flavors. They cater private events (about 35% of the company’s business comes from catering) in addition to working festivals in multiple states. You can also find them at the farmer’s markets in Shorewood, Greenfield, West Allis, and Milwaukee, among others.
The company produces approximately 700 pops per day at its kitchen in St. Francis, Wisconsin, and can stock up to 500 pops in each bicycle cooler. Some days, that’s not enough.
“A huge pet peeve of mine is selling out,” Wisneski said with a laugh. “That means we could have sold more.”
This year, Chillwaukee is adding something new to the menu: Shaved ice made with natural flavors, thanks to syrups that the company crafts in-house.
3. UWM helped him find success.
Wisneski chose to attend UWM because he fell in love with Milwaukee and wanted to go to college in the city. He majored in Journalism, Advertising, and Media Studies (JAMS) because he’s a naturally curious person. JAMS allowed him to try new things and talk to people from all walks of life. He followed up his bachelor’s degree with a master’s in media studies.
One of the most useful things he learned was how to ask questions.
“Because of journalism, I was trained to give in to my curiosity and dig deeper and ask questions. I think the most direct application would be for when I’m finding out about events – I am sending emails to companies, to festivals, to any kind of event where people gather. I do a load of research to find out how we can work together. That is the same as in journalism when you’re approaching a source for stories,” he said.
He also appreciates the writing skills he gained at UWM – skills he now uses to draft emails, create content for his websites, write descriptions of flavors, and craft his menus. And the organization and time management skills he learned while working on his master’s thesis have come in handy, too.
“I wish more folks in the College of Letters & Science … went on to be entrepreneurs,” he added. “It’s creative, art-focused, media-focused students who can start businesses because they have that creativity.”
By Sarah Vickery, College of Letters & Science