A popsicle shop grows up

Pete Cooney built his business with popsicle sticks.

In 2014, while working in a corporate finance and accounting role, Cooney was beginning to feel restless. While the then-25-year-old was just getting his feet wet in the “real world” after college, he feared a future where he was just another “cog in the machine.” He wanted to do more.

“I had a good job, but I didn’t love going to work every day,” Cooney told Technical.ly. “I would daydream about what it would be like to own my own business.”

As Cooney climbed the corporate ladder, eventually working his way up to controller at a popular restaurant group, he began toying with the idea of striking out on his own.

But it wasn’t until he was strolling through a farmer’s market one day while on a trip, sampling a funky avocado-flavored popsicle, that his entrepreneurial dreams would come into fruition. In line, he overheard customers talking about similar concepts in North Carolina and New York, and thought: Why not bring that unique popsicle concept back home to Milwaukee?

While still balancing his full-time accountant role, Cooney began whipping up frozen pops in his kitchen, testing out his new flavors on family and friends. The reactions to his new business venture were mixed. Some people were surprised by the sheer departure from his day job; some saw the side hustle as silly; and still others felt like he was on to something big. But they couldn’t deny the tasty pops or Cooney’s imaginative flavor combinations.

“Initially, it was kind of a joke,” Cooney admitted. “But even in those early days, it made people laugh and smile.”

Behind-the-scenes, Cooney was set on turning his popsicle side hustle into a full-fledged business. He secured his business license, a kitchen space, and invested in a push cart with a giant, rainbow umbrella to begin peddling his frozen pops all over the city — officially launching the Pete’s Pops brand.

https://www.instagram.com/p/CVjBkmolF-Z/

In 2016, Cooney entered a small business competition put on by Near West Side Partners, a “Shark Tank”-style live pitch event, where he competed against eight other Milwaukee-area startups. He had placed second at an earlier competition and was determined this time to prove his ground. Cooney ended up taking home the top prize, a $10,000 grant and $25,000 in in-kind services, to bring the business to the central city neighborhood. Eventually, he opened Pete’s Pops’ first brick-and-mortar shop at 3809 W. Vliet St.

It’s been two years since Cooney officially left the corporate finance world to work for Pete’s Pops full-time. Today, Pete’s Pops sells more than 100 flavors of frozen treats at its flagship location on Vliet Street, as well as at stores in Bay View and West Allis.

The company also recently opened a walk-up window in the ticket booth of a presently shuttered antique theater in nearby Whitefish Bay for the summer, and has opened Sneaky Pete’s — which serves boozy pops to the over-21 crowd at Milwaukee Public Market. Between customers at those stops, Pete’s Pops serves up its frozen treats at more than 1,000 mobile events year round, making appearances at street festivals, private events and corporate parties, and it counts nearly 11,000 followers on its brightly hued Instagram.

SPRING OPENING DATES AND HOURS BEGINNING THIS SATURDAY AT WEST ALLIS, BAY VIEW, AND VLIET STREET! 12-6 Saturday and Sunday at all locations. Saturday is also our neighborhood clean up day on Vliet Street. We’d love to see ya. pic.twitter.com/pUfjcOffd3

— Pete's Pops (@PetesPops) April 18, 2022

In the nine years since Cooney first launched the business, Pete’s Pops has practically become a (Milwaukee) household name. The biggest challenge of the past nine years? Transitioning from the hustle and near-burnout of the company’s earliest days, to sustainability.

“In the early days, I was working until midnight, I was working weekends — and that works to get your business off the ground,” he said. “Anyone can kind of hustle their way to success. But I knew if I was going to make it a full-time business, I would need to hire and staff like a business. I couldn’t not have a life and possibly burn out. I personally couldn’t do it all. It was always scary to hire the upper, big positions, but it has paid off. Now, I’m at a stage where people do a better job than me.”

That journey has been tough, but fun throughout.

“There’s a lot of ups and down,” Cooney said. “Some days you can feel like you’re rocking and rolling, but then the next day things can break, people can quit, and thing can not go well. Entrepreneurs and small businesses experience a lot of peaks and valleys, and weathering those and trying to stay consistent is hard, but will serve me well in whatever we’re doing.”

At the heart of the business’ success is its commitment to serving as a positive force in Milwaukee. Whether it’s dropping the price of Pete’s Pops down to a buck to help Milwaukeeans combat the hottest day of summer, hosting a neighborhood cleanup, or hiring underserved youth from the surrounding community, Cooney said he can’t imagine Pete’s Pops without the opportunity to serve others.

“I wanted to be in the Near West Side, and to be a positive anchor in that neighborhood,” he added. “It’s just something that seemed like the path for me and my business. If I am going to spend my life working hard, I want to make sure it’s not just selling something to make money. I want to be a part of a community and make it the best it can be.”

As summer melts away, Cooney appears to be following the positive affirmations inscripted on his popsicle sticks:

“Keep pushing.”

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