Ex-banker sold on Detroit

Starting Corktown business took solid plan, leap of faith

Brian J. O'Connor / The Detroit News

In his old job as a Chicago banker, Ryan Cooley worked with a lot of numbers.
But somehow, things just didn't add up.

As a vice president working with commercial lending, he put a sharp pencil to the paperwork on the deals real estate developers and builders brought to him.

But often, he says, it looked like the folks on the other side of his desk were having all the fun.

"I saw that there were a lot of different ways I could be successful in real estate. The banking part, I didn't find it as challenging," says Cooley, 30. "I'd rather be out there and be creative and be my own boss. That was the driving force."

That force led him to open O'Connor Real Estate, a third-generation offshoot of his grandfather's real estate practice, handling redevelopment projects, home sales and other real estate deals in Detroit's Corktown neighborhood, situated between the moldering Tiger Stadium and the looted Michigan Central Depot.

Where he came from: After finishing high school in Marysville, a town of less than 10,000 near Port Huron off the knuckle of the Lower Peninsula's thumb, Cooley headed to Chicago for school. An internship turned into a job with a firm that made senior housing loans across the country.

He moved up to banking and specialized in handling loans for real estate projects, financing apartment or condominium deals, purchases of vacant land and industrial properties.

He liked the urban setting, and both he and his wife, Meghan McEwen, had good careers going.

What changed: The Cooley family, it turns out, has deep roots in real estate. Ryan's grandfather, Francis O'Connor, sold real estate in Marysville and the company is still in business there. Ryan's brother, Phil, had the same familial urge, and the two had looked at Chicago properties where Phil could open a bar and restaurant.

Instead, the Windy City lost out to Motown, when Phil bought and restored a Corktown property to open the acclaimed Slows Bar BQ on Michigan Avenue. It didn't take long for Ryan to follow.

He considered heading back to Marysville to work in real estate, but decided he liked urban settings. Plus, Detroit's vintage but vacant buildings offered more chances to be creative, find good deals and make an impact.

"The idea of having these older kinds of buildings and rescuing them, it's something that you just can't build from scratch any longer," Cooley says. Plus, the price was right. "The first building was $45,000. You just couldn't find anything like that in another urban setting."

Moment of truth: It was trips to visit his brother's Corktown project that got Cooley hooked on the idea of making his move in Detroit. His father was from Detroit, and they had visited for concerts and ballgames when Cooley was a boy.

"But I didn't realize until my brother moved here how many young people wanted to live downtown," Cooley recalls. "Every time I'd come to town, every place would be packed with pretty young people. It made me realize that we wouldn't be the only ones trying to do something here."

Stumbling blocks: The decision to open up a Detroit branch of his family real estate business wasn't an impulsive one, Cooley says. He and his wife both knew it would mean a change in their lifestyles, especially since she decided to make the change from working for such big-name firms as Oprah Winfrey's Harpo Productions and the Leo Burnett USA ad agency. While the lower cost of real estate in Detroit helped, they still had to prepare.

"We spent a solid three years planning, and a year and a half doing some heavy-duty saving so we could make the move," he says.

Detroit's slow real estate market hasn't made things easy, but Cooley saw that going in, and hasn't planned on generating big instant cash flows or quick flips.

Another issue has been the demand to find projects that come with hefty tax breaks, and the paperwork and review process that comes with them.

"In another market you don't have those issues and you can start your construction quicker," he explains.

Still, his banking expertise makes it possible to put together deals that work and to attract the right financing. The restaurant is doing well, and Cooley has three commercial buildings finished. He's also got a project in the Eastern Market and just bought another two Corktown properties.

Words of wisdom: Moving to Detroit to launch a new venture brings some baggage, Cooley notes.

"There are times where there's going to be a lot of people being negative about the city," he allows, "and you just can't let that deter you."

Besides a thick skin, patience is another necessity.

"I think there are endless opportunities here, but if you really think you're going to jump into real estate and make a ton of money quickly, you're not doing it for the right reasons. I didn't move here to come in for a few years and then head out of town."

The satisfaction of the projects he's working on comes from the impact he sees them have on the neighborhood, Cooley adds.

"In other urban areas you can't make a dent; people don't even notice. But even just this block -- to see how much it's changed since we've done three buildings, to see the activity that it's supporting -- it's fun to be part of that."

You can reach Brian O'Connor at (313) 222-2145 or boconnor@detnews.com.