For the past two years, property developer Matt Rogatz made a weekly five-hour round trip from his home in northern Chicago to Green Lake, Wisconsin — population 1,005.

Before that, the only thing he knew about the small town was that his high school buddy had family there, he said.

But after a 30-year career in industrial real estate, completing more than 400 transactions totaling more than $750 million, Rogatz said he hit a wall, which prompted a midlife crisis.

“I was looking for my next industrial property and couldn’t find anything of value,” Rogatz told CNBC Travel. “My life was kind of on autopilot. I wasn’t growing as an individual. A lot of people at that point might retire, but I’m not that kind of guy.”

Rogatz said there was “no way” he wanted to get into the hospitality industry. He had no idea how to run a hotel and had been put off by horror stories about bad hotel guests, he said. Plus, he had heard the restaurant business was notorious for theft, he said.

But an internet search in early 2021 completely changed his mind, he said.

One day while on his computer, Rogatz saw that a small hotel — the Green Lake Inn — was for sale. The 17-room property, set on 1.5 acres of land, is minutes from the small town’s “downtown” area, and most importantly, just around the corner from the 7.3-mile-long lake, which is said to be the deepest in Wisconsin.

Rogatz took the gamble, thinking that in the worst-case scenario, he could use the inn for private getaways and invite extended family on vacation. He spent the next few months refurbishing the inn — which he described as “well maintained, but very outdated.”

That worst-case scenario didn’t happen— in fact, the opposite did, he said.

“The timing was right as it was after Covid, and people started wanting to do things again,” Rogatz recalled.  “I was like, ‘Wow, I’m on to something.’ I made some decent money that first year.”

His next purchase was The Manor, a grand waterside villa and guest house with its own boat dock, formerly known as The Angel Inn.

The elderly couple that had run it as a bed and breakfast wanted to retire to spend more time with their grandchildren. Rogatz gave the seven-bedroom, seven-bathroom property a complete face-lift, replacing its dark color scheme and 1970s carpets, linen and furniture with modern finishings and windows that maximized its lakeside views.

Rogatz’s entrepreneurial mind began whirring, and immediately he saw the potential in creating wedding packages incorporating both properties — the Green Lake Inn as a wedding venue, and The Manor for extra guest accommodations. He even purchased a minibus to shuttle guests between venues.

Then, like a Monopoly player on a winning streak, when the local spa, Élan Brio, hit the market, Rogatz scooped up that property too. It meant he could add hair and beauty treatments for weddings, which included dips in the spa’s saltwater pools.

Adding the Goose Blind bar and restaurant and partnering with local golf courses sealed the deal for vacation packages for fishermen and golfers in the area.  

“I’ve had groups of 24 guys stay at our hotel. We shuttle them to the golf course, then to the Goose Blind, and they love it. Then we shuttle them back. They don’t have to worry about drinking and driving. We put everything together for them so they just pay one fee,” Rogatz said.

The inn also has outlets where fisherman can charge their boats, he said. “And we have boat parking, which a lot of hotels don’t have,” he added.  

Two years —  and five properties — later, Rogatz has a full-fledged tourism operation on his hands — Our Green Lake — which cost him nearly $4 million to buy, and several million more for refurbishments, he said.

Attracting more tourists to Green Lake has become a personal mission, said Rogatz — especially among those who regularly visit another Wisconsin town called Lake Geneva, which he called the default getaway for Chicago residents.

“It’s crazy expensive, and it’s packed. It’s not even fun, because there are so many boats. But Green Lake is just that bit further away from Chicago, so it’s not really on the radar for a lot of Chicago people,” said Rogatz.

He plans to change that by marketing to adventure sports groups in Chicago, and by building relationships in different cities to promote Our Green Lake. The usually quiet winter months — when average temperatures are below freezing — aren’t even a barrier, he said. Ever optimistic and opportunistic, Rogatz plans to entertain visitors with activities like ice sailing, ice fishing, curling and even dog sledding, he said.

Rogatz said his latest purchase — Green Lake’s three-story former jail — will provide indoor activities in the winter too, such as boutiques and a flea market, as well as cooking and mixology classes.

He’s already turned the first floor, which had a kitchen, into a 40-seat breakfast venue called the Terrace Cafe. The second floor, where the jail cells used to be, is proving a little trickier, he said.

The third floor is being used for a monthly bingo night, which Rogatz has agreed will continue if he can use it for other events the rest of the time, such as laser tag and obstacle courses.

Rather than see Green Lake’s vacant properties as a red flag, Rogatz views them as an opportunity to create a “renaissance” for the town.

He said he and other investors who bought local golf courses, cafes, hotels and bowling alleys have brought a new energy to Green Lake. Rogatz said he now serves as an advisor on the Green Lake Economic Development Committee.

While some locals have expressed concerns about their hidden gem becoming as busy as Lake Geneva, the Green Lake Area Chamber of Commerce is happy for the town to be “put on the map,” especially during the winter, said Lisa Meier, the chamber’s executive director.

“Matt’s investments will help uplift our charming community to be recognized as a year-round destination,” said Meier.

For Rogatz, it’s become his personal mission to see Green Lake thrive.

“You come to Green Lake, and you instantaneously take a breath,” he said. “You feel good. You’re relaxed. You feel all the stress of the city leaving you.”