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Key Takeaways
- Wing It On started by addressing a simple gap in the market.
- Earning nine trophies at the National Buffalo Wing Festival gave the concept proof, not just pride.
- Early success and bootstrapping carried Wing It On far, but franchising too soon exposed gaps in systems and support.
Matt Ensero did not set out to build a wing brand. He was trying to solve a simple problem. He was living in Waterbury, Connecticut, hosting friends on Sundays to watch NFL games, and there were no good chicken wings nearby.
“We were in a wing desert within 30 minutes of my house,” Ensero says.
Driving 40 minutes to a bar meant missing the first quarter. Nobody wanted to do that. So Ensero bought a small fryer, started making wings at home and tested recipes on friends. He wrote everything down and kept refining.
Eventually, one of those friends said what everyone else was thinking. “These wings are really damn good,” Ensero recalls him saying. “They’re better than the ones we’re driving halfway across the state to go pick up.”
That comment turned into a business plan for a quick-service, takeout-focused restaurant concept. When it came time to name and brand the restaurant, Ensero turned to Justin Egan, someone he already knew and trusted from previous work. Sitting in a coffee shop, Ensero talked through the business plan while Egan searched for a name.
“I was on GoDaddy trying to think of every chicken or wing pun on the planet,” Egan says. “WingItOn.com was available. Let’s go.”
The opening did not go smoothly. Wing It On sold out on its first day. Ticket times stretched for hours. Within days, they shut down briefly to regroup and fix the kitchen flow.
The demand was real. The restaurant was profitable within two months, though Ensero was working 80-hour weeks behind the fryer and paying himself nothing.
As the brand grew, Wing It On earned national recognition at the National Buffalo Wing Festival, winning multiple first-place trophies for its traditional buffalo sauces. Competing in Buffalo, New York, against some of the most established wing institutions in the country gave the brand credibility beyond Connecticut.
With momentum building, Wing It On began franchising early. “We probably did it two to three years earlier than we should have,” Ensero says.
They tried to do everything themselves. The concept worked. The system lagged behind. That realization made one thing clear. The next phase would require more than hustle. It led the co-founders to Craveworthy Brands.
Beyond bootstrapping
With the business growing, Ensero and Egan knew the challenge was no longer about food. It was about scale.
They had momentum, franchise interest and national validation from their wins at the National Buffalo Wing Festival. What they did not have was the infrastructure to support growth without exhausting themselves or shortchanging franchisees.
“We got a little too addicted to bootstrapping,” Ensero says.
They were opening one or two stores a year, working 80 to 90 hours a week and trying to support franchisees while wearing every hat themselves. The pace was not sustainable.
The turning point came in Las Vegas at the Restaurant Finance and Development Conference. Ensero traveled there to meet a potential partner, but the meeting fell through. He was standing in a hotel lobby when someone from his PR team urged him to attend a happy hour instead.
There, Ensero met Gregg Majewski. Majewski asked Ensero to tell him his story.
As Ensero walked through the Wing It On journey, Majewski looked up the brand and saw the press around its first-place finishes at the National Buffalo Wing Festival. That detail changed the conversation.
Majewski later visited a Wing It On location, met with Ensero and Egan and tried the food. He liked the product and saw opportunities to strengthen the business.
In early 2023, Wing It On became one of the first brands to join Craveworthy Brands. Craveworthy did not overhaul the concept — the food stayed intact, but the focus was on creating a stronger system.
They refined the logo, adjusted store layouts and interior graphics for multi-unit growth and reorganized the menu to highlight combos, family packs and larger platters to help increase average check values.
“It sounds like minutiae,” Ensero says. “But it all adds up.”
With Craveworthy’s operational playbook in place, Wing It On finally had the support to scale what it had already proven.
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Key Takeaways
- Wing It On started by addressing a simple gap in the market.
- Earning nine trophies at the National Buffalo Wing Festival gave the concept proof, not just pride.
- Early success and bootstrapping carried Wing It On far, but franchising too soon exposed gaps in systems and support.
Matt Ensero did not set out to build a wing brand. He was trying to solve a simple problem. He was living in Waterbury, Connecticut, hosting friends on Sundays to watch NFL games, and there were no good chicken wings nearby.
“We were in a wing desert within 30 minutes of my house,” Ensero says.
