now in Glastonbury, Judy’s early life was marked by both athleticism and a severe eating disorder.
A Rocky Start and a New Beginning
“I was in and out of hospitals for about 10 years dealing with the eating disorder,” Flynn shared. “But alongside that, I was always an athlete—running marathons, cycling, powerlifting. I knew a lot about nutrition, the good and the bad.” Despite the challenges, Judy’s love for fitness and nutrition led her to create a quick and efficient way to fuel her body post-workout: protein shakes.
Her professional life, however, followed a different path. After working in corporate finance for several years, Judy married a fellow financial advisor, had two children, and stayed at home to raise them. Following a divorce, she found herself starting from scratch.
“Walking away with two kids and a couple hundred dollars, I had to rebuild,” she recalled. “I got back into finance, but quickly realized it wasn’t where I wanted to be anymore.”
The Leap Into Entrepreneurship
The turning point came when Judy found herself impulsively renting a small retail space in Wethersfield. What started as an off-hand comment from her hairdresser turned into a new business venture.
“He said to me, ‘You don’t seem like your usual happy, laid-back self,’ and I admitted that I wasn’t enjoying my corporate career,” Flynn said. “Then he said, ‘You should do something about that.’ And that's when the idea hit me.”
With no formal business plan and limited resources, Judy rented a 650-square-foot retail space once occupied by a CrossFit supplement store that was closing down.
“I didn’t know exactly what I was going to do with the space, but I knew there was a fitness audience coming in and out, and no one was offering protein shakes in the way I wanted them,” she said. “I figured, why not just do it?”
Within a week, she bought a used fridge and freezer, painted the walls, and set up shop with only one drink size—a large, 32-ounce shake. She didn’t market or network; she simply opened the doors.
“I didn’t have savings, just an income,” Flynn said. “I applied for loans at three different banks, and within 24 hours, I had micro-loans approved. The next day, I quit my corporate finance job.”
The Name and the Food Truck
The Fresh Monkee was born almost by accident. “The name came from my obsession with buying stuffed monkeys for my son,” she explained. “I thought, ‘Monkeys are cute. People like monkeys.’ It just popped into my head.”
After a quick online search revealed that "The Fresh Monkee" with a single "E" was already taken, Judy added a second E and the brand was set. “It was a name that felt right.”
A year after opening, Flynn expanded into the food truck business, transforming a yellow school bus into a mobile kitchen. “I had no idea what I was doing, but I learned quickly,” she said. “It was a blind experience—like the blind leading the blind.”
Overcoming Struggles with Humor and Resilience
The road to success, however, was far from easy. Flynn often laughs at some of the early struggles she faced. “There was one day in Wethersfield, the line was out the door, and I was working at the food truck. I got a call that one of my employees had turned on the blender without the lid. The place was covered in protein shakes—people, ceilings, you name it!”
Other challenges were less comical but no less taxing. “There were plumbing issues, frozen pipes, and constant breakdowns,” Flynn said. “But after all these years, I’ve become ‘Bob the Builder.’ Now I know how to fix plumbing, blenders, you name it.”
Despite these setbacks, the business grew. Within months, customers were lining up for shakes, and Flynn was hiring staff. “The first real success came a few months after opening. It was just crazy—people were coming in nonstop,” she said. “We went from one store to five stores and a food truck. It wasn’t planned, it just happened.”
The Fresh Monkee's Expansion and Franchising Journey
What started with a single store in Wethersfield soon grew into a multi-location business. But growing beyond Connecticut required a new approach: franchising.
“People started messaging us from out of state—Florida, Texas, California—saying they missed The Fresh Monkee and we should expand,” Flynn explained. “So I started researching how to franchise.”
After a failed attempt to secure a private equity partner, Flynn turned to franchising as a way to scale without risking too much of her business. “I wasn’t ready initially, but after learning more, I realized that franchising was the way forward,” she said. “We’re now in 11 states, and expansion is happening quickly.”
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udy Flynn's journey to founding The Fresh Monkee—a successful chain of smoothie and protein shake shops in Connecticut—was anything but conventional. Raised in Wethersfield, Connecticut, and living
"I really think that's why we've grown so much is because I listen to staff and their guidance, because they are the ones who are on the front line at all times."
Advice for Aspiring Entrepreneurs
Looking back on her unconventional path, Flynn offers advice for aspiring entrepreneurs: “There's no way that anyone opens a small business and everything goes smoothly. That just doesn't happen. So the choice of how you respond to problems is super important because if you expect everything to go smoothly, you're going to quit as soon as something bad happens, as soon as you have to take on debt to pay something, as soon as your key staff person leaves unexpectedly, whatever it is. You can't have thin skin and survive small business. I just don't think that's possible.
To me, I think small business owners are the pinnacle of being willing to take a risk. But our way is not always the correct way. So you have to be open to suggestions. Customers are going to have suggestions, staff are going to have suggestions. And if you're one of those people that has a really big ego or whatever, where your way is the only way, your business may never grow. Especially if you're not in the business working every day and your staff is, you have to be willing to hear what they're saying to you. Like, Judy, this doesn't make sense because of X, Y, Z. I really think that's why we've grown so much is because I'm willing to listen to staff and their guidance, because they are the ones who are on the front line at all times. The staff are the ones dealing with everything every day. So they really know from a procedural or functional aspect something that doesn't make sense.”
The Role of Staff in Building Success
Despite the rapid growth, Flynn credits much of the success of The Fresh Monkee to her staff. “They’re the faces of the business. They are the ones who keep it running day-to-day,” she said. “I’ve had some employees with me for five years, even up to ten. I’m so proud of them.”
She’s also learned that empowering her staff and listening to their feedback has been crucial. “Mistakes will happen. They always do. But I don’t micromanage,” she said. “If someone messes up, we talk about it and figure out how to avoid it next time.”
Flynn’s journey is a testament to resilience, adaptability, and the willingness to take risks. “It’s not about making the perfect decision every time,” she said. “It’s about moving forward and learning as you go.”
As The Fresh Monkee looks to expand beyond Connecticut and into the national market, Flynn’s story serves as an inspiration to small business owners everywhere who are navigating their own unpredictable journeys.
