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Bridging Cities: Jason Ilstrup, the President of Downtown Madison, Inc

Sep. 9, 2022 at 3:28PM

“Nothing hinges on just one hinge.”

Maybe it’s stating the obvious. But when you are talking to Jason Ilstrup, the door mechanics conjure an image of the state of Wisconsin. And doors, as we all know, need two or three hinges to work.

Milwaukee, Madison, and Green Bay are those hinges—each must play a part for the state to flourish.

Jason is the President of Downtown Madison, Inc. And while his focus is on Madison, he sees immense value in how everyone wins when the population centers of a state are innovating. Wisconsin has made great strides. But why isn’t it doing as well as it could be?

The answer comes from a study conducted by a man named Aaron Oliver. “He’s an economist in Madison who used to be the Wisconsin Department of Commerce Secretary, a super smart guy who was former Director of Economic Development for the city. He's a big thinker,” Jason told me. 

Oliver noticed that Minnesota and Wisconsin were relatively the same states, and Wisconsin was actually a little larger in overall population. Oliver asked himself a fundamental question. 

“Why has Minnesota grown upwards, and Wisconsin has gone upwards but not at the same trajectory?”

Oliver’s conclusion, says Jason, was key to how Wisconsin can grow as a state. “He postulated it was because of density,” says Jason. “About 58% of all Minnesota residents live in the Minneapolis-St. Paul metropolitan area. It's three and a half, almost four million people. Milwaukee is still only a million and a half. Everyone thinks Minneapolis and Milwaukee are the same sizes. They're not even close.”

This is important, says Jason, because with density comes creativity. The power of proximity. People coming together and collaborating. Startup culture thrives. In Minneapolis, that density also led to the rise of major corporations—companies like UnitedHealthcare, Target, Medtronic, and Honeywell (now with headquarters in Charlotte, NC).

Wisconsin, by contrast, doesn’t have the same population density that Minnesota has—it’s more spread out.  “Twenty-seven percent of the state's population is in the Milwaukee metro area. Twelve percent live in Madison, and then Green Bay is five percent,” Jason says.

This gets us to the crux of the matter; a stronger connection between Wisconsin’s two largest population centers—Madison and Milwaukee—needs to be fortified.

“What happens if we could build the connections between the two cities of Madison and Milwaukee? You get 40% of the state's population, and you create this power,” Jason says with visible passion. “Milwaukee is an older, more mature city with great amenities. And then you have the younger upstart Madison economy. They’re 70 miles apart. The cities are growing closer together. You can see it.”

Creating a tighter connection between Madison and Milwaukee is integral to the state's future. Part of strengthening that connection is the Hoan Group, a cadre of young professionals from Madison and Milwaukee headed by Ian Abston. The Hoan Group is a powerful interconnected network dedicated to raising the profile of Wisconsin. Jason is a member and works closely with Ian as part of the Madison faction of the group. Give Jason the opportunity to talk about what’s happening in Madison, and you almost can’t get him to stop.

Ian Abston

Ian Abston

This is a story that, at it’s essence, is all about making friends. It seems simple enough, meeting people, getting to know them, finding common ground, having a few drinks, and exchanging contact information. But the way Ian Abston tells it, if you’re a newbie here in Milwaukee, it is something that’s very difficult to do – and he set out to change that.

“This is a moment of inflection for everybody,” he says. “Madison is the fastest growing city in the state by a long shot. In the census from 2010 to 2020, six of the top 10 fastest growing cities in Wisconsin are in Dane County.

“Madison’s population has grown 17% in 10 years.”

What’s driving that, in Jason’s mind, is Madison transitioning from being a capital town to a capital and university town to now a capital, university, and commercial city. “We've seen significant development, particularly out of a few larger companies. We've always had the bellwethers like Cuna Mutual Group and American Family Insurance. American Family understands that and it's grown in the tech space themselves. But then there’s Epic Systems and Promega. Exact Sciences is growing in leaps and bounds. Even in some of the manufacturing areas with Trek and Sub-Zero. The growth is significant.”

Epic, for example now has 10,000 employees. “They have an incredible campus,” says Jason. Epic is recruiting people from prestigious universities like Stanford and NYU and the same is true for Exact Sciences, which has 6,500 employees. They are competing for talent with the likes of Google and Amazon. This is having a profound effect on Madison’s apartment market.

You're seeing the growth,” says Jason. “Four thousand apartment units are in the development stage right now in the downtown area. This influx of people is in turn having a ripple effect into the buildout of amenities—restaurants, hotels, and venues like The Sylvee. But to me, it's about creating a relationship with Milwaukee because we can take this to the next level.”

Jason sees a future even bigger than Madison and Milwaukee, working together. Put Minneapolis and Chicago in the mix, and he makes no bones about the outcome.

“Those can be the four most vibrant cities in the Midwest.”

The Hoan Group had a virtual presentation during the pandemic that included then Milwaukee Mayor Tom Barrett and Madison Mayor Satya Rhodes-Conway. Jason recounts the call. “It was moderated by Jack Salzwedel, the CEO of American Family. And one of the questions was, what can we do as young leaders to bring the two cities closer together?” Jason remembers Jack’s answer. “He said, whatever your industry is, it could be insurance, healthcare, tech, zoology. Form relationships with your colleagues in the other city, and do work together. And that's how it starts.”

Now Downtown Madison, Inc. (DMI) and Milwaukee Downtown have a Madison + Milwaukee Downtown Exchange, a quarterly series where they get together and talk about joint issues together. “We're literally bringing these two associations together.” Some of the most important people representing the two cities are in the room, and progress seems inevitable.

Connecting Madison and Milwaukee. Connecting people and ideas. Connecting like-minded people working toward the same goal. Connecting seems to be Jason’s superpower.

His career trajectory has played out like a series of unlikely connections and career changes. His worldview comes from a varied background that includes the Peace Corps, the hotel industry, and earning a law degree.

Jason grew up in Minnesota. He studied political science at Boston University. He had every intention of starting a career in politics. After a short stint as Campaign Manager for Martin Sabo’s congressional bid in Minnesota, Jason took the left turn to beat all left turns.

He went and joined the Peace Corps.

“I was in Niger, West Africa. A dollar a day would be a lot of money for these folks. I lived in a small village right at the border of Nigeria. It was about eight good car hours ride away from the Capitol.” Jason’s first assignment was as a Natural Resource Management Volunteer, “in the bush,” as he calls it.

“There was no running water, no electricity. An hour car ride away from a phone. Hot desert. One hundred and twenty degrees. I got malaria, dengue fever, all of it. But it was an amazing experience.”

In Jason’s third year, he became a leader to the volunteers in the area. 

And while in Maradi, he was stationed with a few Americans (“A few of us and a few missionaries”). There was a guy from LaCrosse, Wisconsin, there who married a Nigerian. He was a former Peace Corps volunteer himself. “They built a little small hotel in Maradi, and the ex-pats would all stay there,” Jason remembers. “It was a great little hotel.” It was Jason’s and the other volunteers’ one respite; it had air conditioning, cold beer, cable TV, and pizza.

At that hotel—simply called Guesthouse—Jason fell in love with the hotel industry.

Jason seemed a lock for entering the hotel industry. Instead, surprisingly, he decided to enter law school. And while law school was a great challenge, he really didn’t love it. “I never wanted to be a lawyer,” he said. “I never really practiced law. I took the bar. I think I've signed one or two legal documents. My wife is an actual attorney.”

His wife, who he met during his stint as a congressional aide for Congressman Martin Sabo in Minneapolis, turned out to be the reason Jason ended up in Madison. “She was interested in going to law school. She was born and raised in Madison. And we got to know each other because she was interested in law.”

But he stayed in Minneapolis when she headed to Madison to go to school. Still, they kept in touch.

Congressman Sabo retired, and Jason lost his job. His girlfriend-now-wife told him, “Either shit or get off the pot.” At the time, Jason was about to take a job as State Director for another Minnesota politician named Amy Klobuchar. “Amy Klobuchar still tells this joke about a potential employee who chose another woman over working for me.”

“I went to Madison, and it was the greatest thing I did. I fell in love with my wife, and I fell in love with the city.”

In Madison, he took a job in politics and, out of the blue, one day did something he never thought he would do. “I just didn't like my job, and I quit. I’d never done that in my life.”

In a moment of self-reflection, Jason asked himself what he wanted to do. “I thought back to hotels, and I said, I want to own my own little boutique hotel; I want to do what my friends back in Niger did.” But he knew no bank was just going to loan him the money to start a hotel -- so he decided he would work his way up.

He applied and became a bellman at the Madison Concourse hotel. But when his wife got a job as a prosecutor under John Chisholm, they packed up and moved to Milwaukee. It turned out to be a very fortuitous move. “I got super lucky,” he says. “I went to a job fair at the Iron Horse Hotel before it opened and somehow got on the opening team. And the rest was history. It was boutique hotel of the year for two years in a row. And I was part of the team.”

He then got an offer for a job to open a hotel in Madison called HotelRED, and it was perfect. “We weren't necessarily looking to get back to Madison, but my wife’s family was still there, and it worked. I managed the hotel for six and a half years. And then I left in 2018 to start my current job with Downtown Madison, Inc.”

Jason may just have the only resume that includes politics, law, hospitality, and the Peace Corps.

And now, with the Downtown Madison Association, he seems to have found a home.

“I usually take 40 to 50 meetings a week,” Jason tells me when I ask about what it’s like leading Downtown Madison. “Every day is different.” The goals never change, whether it’s coffee meetings, a forum, or a neighborhood business association meeting, the goals never change. “We do three things,” Jason tells me stayed in Minneapolis e. “We do community building. We're a nonprofit membership organization with about 450 members, and every one of those members’ employees are our members. Nonprofits, for-profits, small businesses, and large businesses. We run about 100 events a year.”

“We do policy, a ton of advocacy work, which is my main work. We advocate on behalf of our members, mainly in local government. And then, we do policy research. So, we have an agreement with the Lafollette School of Public Affairs at UW. That's where we get our policy research.”

In the job, Jason, as is his nature, knows how important it is to establish strong connections. Surrounding himself with smart people seems to be his superpower. “I know deeply about nothing,” he says with equal parts self-deprecation and total confidence. “But I know people that do. And so, if you strip everything I just said away, it's about connection. And we make the connections—that's really what we do. And then who knows where those connections go? You just hope they go for good.”

“It's an exciting job right now in Madison. Because the city really is growing. Dramatically.”

Jason will continue to make connections in any way he can. The greatest of which is building in his mind the most important one—between Madison and Milwaukee.

About the author

Nicholas Pipitone

Co-founder, Editor-in-Chief,