Carmen Rossi, J.D. ’12, expects sleepless nights.

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He anticipates problems, stressful days. Like the eye of a storm, he sits calmly at the center, and he would not have it any other way.

To him, life’s all about curiosity, risk. It’s about survival and taking care of those around him.

“Every day, it seems, is one of the most stressful days of my life,” said Rossi, who now owns at least 40 businesses, a number that grows regularly. “Rarely is the problem too big. It’s difficult to get me excited.”

Rossi has gone by many titles—businessman, restaurant owner, lawyer, clerk, real estate developer, commissioner, board member, instructor and more. But the most fitting label is entrepreneur.

He has had failures and successes. When he hits a brick wall, he finds a way.

“I don’t know if I could give one singular example where I got from A to Z without having to meander around or through or over a brick wall. Usually, it’s dozens of brick walls,” he said. “To me, that is just part of the process.”

‘The Perfect Fit’

Carmen Rossi and President Biden

Rossi’s days are long and always have been. Even in college, he’d squeeze in as many productive hours as possible.

The Frankfort, Illinois, native, now living in Chicago, earned his juris doctorate degree from NIU’s College of Law in 2012. He chose NIU to be near Chicago, but outside the major metropolitan area.

Upon arriving in DeKalb, he’d already started several small businesses and earned both bachelor’s and master’s degrees from the University of Illinois, Urbana-Champaign.

He liked the intimacy at NIU, the smaller class sizes and easy access to professors, who put in three hours outside the classroom for every hour inside.

“It was the perfect fit for me,” he remembered. “I was close enough to the city to engage, but far enough not to get swallowed up in the Chicago nightlife, with which I had become familiar.”

The locale kept him from immersing himself too heavily in his businesses. He could focus on his studies. He soon joined several student organizations and became president of the Student Bar Association, while working as an intern with the Will County States Attorney’s Office

Living on campus, Rossi grew close to his roommates and classmates, often hanging out at Molly’s. There was a sense of camaraderie—of being in it together.

He looks back on those days with nostalgia.

“You don’t get those times back ever again.”

Prepared for Whatever Hits

Rossi’s entrepreneurial spirit thrived in his teens as a student at the University of Illinois, said Chris Bader, his business partner and one of his best friends.

The two first met working at a campus bar.

“I just saw blonde highlights and wondered, ‘Why does he have his hair like that?’” Bader joked.

They often thought of promotions the bar owners didn’t have in mind, Bader said, and pursued them.

“As we got to know each other, we always had something going on when it came to business,” Bader remembered.

He later remembers once introducing Rossi as a lawyer. Afterward, his friend corrected him.

“Please don’t do that,” Rossi told Bader. “I’m not going to be just a lawyer.”

“He was very adamant from the beginning,” Bader said. “He was going to be an entrepreneur.”

Upon law school graduation, Rossi worked for a civil law firm in Joliet, mainly on appellate court drafting.

He’d knock out his day job deadlines and use the rest of his 18-hour day to focus on his side businesses—employing college students to paint, sell event tickets, build furniture and other ventures.

Living on Ramen noodles in college, he’d saved up some money.

“My leap was to take that money and do something loud,” he said.

He had no real background in hospitality management or culinary arts when he and Bader decided in 2013 to invest in the Hubbard Inn, a restaurant in the competitive River North neighborhood of Chicago.

Living with his parents in Frankfort at the time, Rossi commuted to the downtown business.

The restaurant succeeded, he said, “which is great, because it could have gone the other way.”

“If it had gone the other way, that’s okay,” he quickly added. “That’s business.”

“It is too often when a major decision has to be made, the result of which is out of your control, and it could go one of two ways,” he said. “Whatever the circumstances, you have to be prepared for whichever result hits you or lands at your feet.”

A Network of Support

He knew long ago what he knows and teaches now as an adjunct professor at the University of Illinois Urbana-Champaign—It often comes down to networking.

“When it comes to being an entrepreneur, so often in many industries—not all, but many—your network is one of the strongest assets you actually have,” he said.

Carmen Rossi and President Obama

And one thing Rossi has definitely done is network.

He’s lunched with President Joe Biden, had dinner with both Bill and Hillary Clinton and attended President Barack Obama’s holiday party at the White House. His Instagram account at @c_rossgo features photos of him with Chance the Rapper, Chicago Mayor Lori Lightfoot and other dignitaries and celebrities.

Former Chicago Mayor Rahm Emanuel appointed Rossi to serve on the Commission on Chicago Landmarks, and he’s a member of the Illinois Economic Development board, appointed by the governor.

He’s also a member of both the Illinois Restaurant Association and the Chicagoland Chamber of Commerce PAC, and on the board of INTERSECT Illinois, a one-stop resource for doing business in Illinois.

“Whereas a lot of people want to perhaps keep regulatory bodies or politicians out of the equation because there’s red tape created, I look at local officials and civic leaders as shareholders in anything we do,” he said.

He puts himself out there.

Don’t be bashful, and don’t worry about a lack of response, Rossi said.

“I used to send 100 notes before I got a response,” he said. “It didn’t bother me. It was just the law of numbers. You might have to send out your resume 100 times before you get a response. The probability increases with every one you send…

“A lot of times, you’ll be very surprised at who answers the phone or responds.”

‘He Really Cares’

It’s also important to be in it for the right reasons, Rossi said.

With some business ventures, breaking even can be a core goal for a period of time in order to meet longer-term objectives.

“It’d be easy to roll your eyes at this comment, but I won’t often make a decision for profit,” he said. “If you do a good business and you make a positive impact, the likelihood of profit is at least present.”

Rossi gets paid last. If you’re part of his team, he’ll drop everything when you need him. And, if you’re in his network, he has your back.

“No one really knows how good of a friend he is,” Bader said. “At the end of the day, he’s the kind of friend you’re going to have for the rest of your life. No one really knows how much he really cares.”

From friends to those in his network, Rossi said he feels rewarded being able to positively impact those around him.

“I think that has been apparent in my wanting to position myself as a positive civic member in our community,” he said. “I can appreciate having a reputation for building quality spaces, providing jobs and paying millions in taxes… and I like that. I’m proud of those numbers.”

‘Not Always Sunny’

They are numbers that have grown steadily since Rossi’s DeKalb days.

Within several years of his first restaurant, Rossi’s restaurant holdings grew to 13. More restaurants followed and remain today, including the Hubbard Inn, which, he says is “still kicking it through COVID.” (Rossi recently opened another Hubbard Inn in a unique location at Midway Airport.)

Today, Rossi and Bader employ hundreds through 8 Hospitality Group, a restaurant, hospitality-development and management company they founded that specializes in food and beverage, marketing, branding, promotions, public relations and operations.

The pandemic has been a struggle for the industry.

“I did the COVID dance for sure, furloughed hundreds of employees,” Rossi said this past May. “I’ve had as many as 900 employees. Now we’re just beginning to get a fraction of that amount back to work.

“I still have venues that haven’t been open since March 15, 2020,” Rossi said in May. “That’s just been a new challenge. It speaks to the understanding that there will be good days and bad days. It’s going to rain. It’s not always sunny.”

‘Say Yes to Everything’

In 2014, he started Chicago Knight Life to offer meals and companionship to clients of Chicago-based charities. He encourages his employees to volunteer, although they don’t need much encouragement.

“There’s never a [volunteer] sign-up sheet that doesn’t have a waitlist,” he said. “I’ve got amazing young people who will sit and dialogue and engage or will cook. I have so many kitchens in the city, it’s easy to put food together and provide warm meals.”

All that, and Rossi still practices law in his own firm, City Lake Law in Chicago, focusing on government administrative law and in concert with lobbying. He does work in varying capacity for many of the city’s major music festivals and numerous developers.

“The law is obviously a big part of my life,” said Rossi, who dreamed of becoming a lawyer even as a child.

Today, his law degree gives him the credibility and confidence to understand complicated transactional documents, he said.

His entrepreneurial spirit keeps him restless.

“To this day, I’m single. I don’t have an immediate family of my own, and I’m still moderately young-ish, so I have a very aggressive attitude toward growth expansion and operation,” he said.

His most recent ventures involve a dispensary in downtown Chicago and the recent passing of signature opportunities in the gaming industry.

He’s also invested in start-ups, such as a company called Upkey, which connects students with internships and career preparation resources.

So many opportunities have come from unexpected places, he said, from meetings filling his calendar, whether he has time for them or not.

He says, “It’s very hard to get me to say no. I want to say yes to everything.”