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Mystic ― Bill Middleton says there was never an “ah-hah moment” when he realized he’d rather be an entrepreneur than a financial adviser. But over the past six years, the 57-year-old Stonington resident has gradually reinvented himself and the Mystic restaurant scene along with it.

First, in August 2016 while still working at his firm Sound Portfolio Advisors as a financial adviser handling millions of dollars in investments, he created The Jealous Monk at Olde Mistick Village. Then in December 2019 came Rio Salado across the street, and later the add-on Rio Rapido takeout Mexican establishment and the El Sueño speakeasy.

Two years ago, in May 2021, he finished converting the former M Bar near downtown Mystic into Taquerio, a casual eatery in a former gas station. Then, just last December, the Italian-themed Andiamo sprang up where a Friendly’s ice cream shop had held sway for decades.

And, by next year sometime, he hopes to put the finishing touches on a remodeled Exit 90 hotel with 56 rooms to be called The Commodore where a former Roadway Inn once stood. He likes the idea of having a standalone, non-branded hotel near the highway and the Mystic River where people might be able to park and either walk to Mystic or perhaps take a boat trip to the village from a dock that could be installed nearby.

“We always look at what’s not here,” Middleton said. “It’s not like I came up with this grand master plan. It just sort of happened organically as opportunities arose.”

Middleton, a former philosophy major at the University of Pittsburgh, says he has a deep understanding of the hospitality industry based on some of his earliest career experiences running a microbrewery while still in college and afterward landing with Rockefeller Resort Management. There he worked with Laurance Rockefeller to create some of the first eco-friendly resorts in the world, including in St. Croix, Jackson Hole, Wyo., Woodstock, Vt., and Hawaii.

He mingled with some of the top chefs and hoteliers in the world at the time, but was “always the finance guy,” he said. Now, he has put his worldwide contacts into use by creating brand-new restaurant experiences in Mystic, where he currently owns 45,000 square feet of space while employing about 120 people.

He says he’s currently the largest seller of craft beer in Connecticut. Yet few people who go to his restaurants would know him on sight.

“I’m not a ‘stand at the front door, kiss babies’ guy,” Middleton said.

He stops in regularly, of course, but remains largely behind the scenes, troubleshooting business issues and talking with employees about how to make improvements.

“I’m not afraid to put a tool belt on or work a jackhammer,” he said, referencing some of his hands-on work to finish Andiamo.

Tall and broad-shouldered, with a frame one might associate with a rugby player or football linebacker, he comes across as friendly and open, yet a bit of a business wonk, talking about crunching numbers but also the importance of developing a good culture. He said the goal is to produce an identical and perfect meal every time.

“It’s a virtuous cycle. If you can attract better employees, you get better customers,” he said. “And great employees want to work with great employees.”

Middleton encourages employees to write up notes at the end of their shifts highlighting problems and victories so he can address issues before they flare up. New employees take quizzes and go through role playing games, and he has books of standard processes and procedures they need to live by, but they also receive good pay and are eligible for medical benefits.

“People like to work in a well-managed environment,” he said. “It all comes back to that culture, and you have to build that culture.”

Bruce Flax, president of the Greater Mystic Chamber of Commerce, marveled at Middleton’s ability to create so many jobs while being very generous to the community, including putting up foreign restaurant workers last summer in his motel. He said the chamber has held events at all of Middleton’s restaurants, including a grand opening with the Ocean Community Chamber of Commerce at Andiamo scheduled 3 p.m. Tuesday.

“The variety and breadth of the restaurants he has created - each has its own unique ambiance,” Flax said in a phone interview Thursday. “People don’t realize how complex it is to run one restaurant, never mind four.”

Dan Meiser, who runs a group of restaurants under the umbrella of the 85th Day Food Community that includes Oyster Club, called Middleton a longtime friend and great asset to the Mystic business community.

“His restaurants are a wonderful addition to the casual dining scene for locals and tourists alike,” he said in an email.

Middleton, whose restaurants operate under the umbrella of his company Cannonball Management Inc., said he has sketched out a plan for just about every potential restaurant site in Mystic at one time or another. But he took his first chance on the large former Ten Clams and Newport Creamery building where The Jealous Monk now stands. The concept, he said, was to create a uniquely European beer hall or pub for the public to use as a local gathering place to exchange ideas.

The Jealous Monk didn’t explode onto the restaurant scene right away but has gradually developed a loyal following, attracting a lot of groups, including retirement parties, weddings and wedding receptions. It’s a place where a group of 40 could walk in without worrying that they would be overwhelming the kitchen or waitstaff.

“It always takes a little while for a place to get its own feel,” Middleton said. “It’s an iterative process. You can’t force things on people.”

Middleton sees Exit 90 as a great central meeting location, close enough to Providence, Hartford and New Haven that people can meet in Mystic as a midway destination.

So his next project was even more ambitious, taking the 7,500-square-foot Boathouse restaurant space on Coogan Boulevard and converting it into a high-end Mexican restaurant in a floor-to-ceiling rebuild. The concept included a huge prep kitchen that he said rivals anything you would see at local casinos.

It remained to be seen if people from New England would accept a gourmet Mexican restaurant, but it worked. Mobs congregated there during the height of the tourist season, and locals loved it as well.

“We want to hold our own with any restaurant in New York or Boston - we’re just trying to get to that level,” Middleton said.

And that brings the level of the entire restaurant scene in Mystic up a notch, a scene that already includes iconic names such as Oyster Club, Steak Loft and Bravo Bravo and the well-known restaurateurs Dan Meiser, Carol Kanabis and Jon Kodama.

“In some ways, we’ve become New England’s dining destination,” Middleton said.

And that makes the idea of competition not a big issue in Middleton’s mind.

“We’re all on the same side here; we all face the same challenges and issues,” he said. “I can’t think of anyone doing a penny less in revenue because a new restaurant opens.”

Middleton faces his challenges with a well-tuned team that includes executive chef Ken Arnone and chief operating officer Michael Corso, who is also listed as co-principal of Rio Salada LLC. His project and operations manager is Paul Jordan.

Together, they have faced all the highs and lows of the restaurant world over the past few years, including the closure of The Jealous Monk and Rio Salado for several months during COVID. By his own account, the closures were worrisome but manageable given Middleton’s experience facing clients in the midst of 2008’s financial meltdown.

“I’m old. I’ve seen this before. It’s not my first ‘end of the world,”’ he smiled.

His next project may prove to be his most ambitious as he works to transform a mid-1960s motel into a more upscale property with outdoor fire pits and games as well as a pool and a bar/lounge that will give it a midcentury feel.

Middleton said the same property, which he purchased according to land records for nearly $3.7 million (beating out McDonald’s, he points out), includes 2 acres of vacant land that he has not yet decided how to utilize.

Through it all, Middleton seems to revel in assembling all the chess pieces and making the killer move. Yet with characteristic self effacement, he claims to be lazy, enjoying the simplicity of having all his properties within a mile or so.

“I went from complex, high-value decisions (as a financial adviser) to less complex, low-value decisions with more creativity but a lot of responsibility,” he said.

It was the same combination of low-key confidence and a mind for details that helped him ably steer the ship when the Stonington Village Improvement Association asked him to help plan out the James Merrill House project 20 years ago and when he headed the Mystic Art Association’s restoration of the former Emporium building on Water Street in Mystic a decade ago.

“It’s not about me; it’s not about my ego. It’s really about keeping the trains running,“ he said. “My main job is to attract, retain and motivate people.”

l.howard@theday.com