S.04 - EP. 04

Carmen Rossi: So You Want to Build a Hospitality Empire?

40 min
Oct 7th, 2025
Carmen Rossi, Owner of 8 Hospitality, gets real about the hustle of building successful restaurants, bouncing back from failure, and why community is everything.

 

Carmen Rossi is a man of many talents. He’s a lawyer, an entrepreneur, and an active member of his Chicago community. In an alternate universe, he might even have been a professional baseball player.

 

“When you get into your athletic years, you want to be shortstop for the Yankees, right? But once I gave up on baseball, which was after practice one,” Carmen reminisces, “Yeah, I sort of pivoted.”

The pivot turned out to be a good one. Today, Carmen is the mastermind between the 8 Hospitality restaurant group. With local staples like Joy District and Hubbard Inn among nearly a dozen other nightlife hotspots, Carmen’s restaurants are a fixture in Chicago’s buzzy food scene. During our most recent episode of So You Want to Run a Restaurant, hosts Claudia Saric and Spencer Michiel welcomed Carmen Rossi for a discussion on the entrepreneurial side of running a restaurant. 

 

5 Big Takeaways From Our Chat with Carmen Rossi

 

 

Carmen’s restaurants are massively successful. And yet, Carmen admits, he has never actually worked in a restaurant. So what exactly drew him to this very challenging business? And what are the secrets behind his incredible success (aside from the fact that he gives a great interview)?

 

We asked him about all of this and more. Below are a few of our favorite moments from our conversation with Carmen. 

 

1. Do It For the Love of the Game

 

So how did Carmen’s pivot from baseball take him into the world of restaurant ownership? He cites an “overplayed but hyper-important quip – do what you love if you can.”

 

We speak to a lot of chefs and family business owners – people who have basically grown up in the restaurant business. They often say the same thing. Do what you love. And many express that love through cooking. This was not an option for Carmen. 

 

 “I'm not a chef. It’s actually embarrassing now, but I've never cooked eggs,” he tells us. However, says Carmen, “I love the job creation, the idea of hospitality, [and the] community element.” He ultimately found that the best way to express that feeling was to launch a restaurant. 

 

2. Create That Sense of Community

 

The community element that Carmen mentions isn’t just nice to have. It’s really the whole point. You have to create that kind of environment if you want to turn customers into regulars. “Bringing a new customer in the door is a major accomplishment,” says Carmen. “But the asterisk is the repeat business, getting them to come back after their first experience. That takes a sense of community. And that excites me.”

 

That’s why Carmen pours more than just his business savvy into his growing restaurant group. When it comes to running his restaurants, he says, “I live here. I'm not only putting a product onto the internet and being experienced globally. If you have a brick and mortar store, you’re a family restaurant.”

 

Carmen relishes in being able to curate spaces that create a sense of family for his employees and a sense of community for his guests. Both have rewarded him by keeping his restaurants staffed and his dining rooms full. 

 

3. Assembling Your Team

 

Naturally, creating that kind of space requires the talent and contributions of a dedicated staff. Carmen acknowledges that kitchens and dining rooms can be intense, high-pressure places to work. He expresses admiration for the people that keep his restaurants running smoothly everyday. But he also notes that it’s extremely important from a leadership perspective to make sure people are placed in the roles that give them the best chance to succeed. 

 

“I'll stick with the baseball analogy,” says Carmen. “You're putting together a team, and there are role players, and then there are some players you can put in six different positions.”

 

“The really big challenge though,” says Carmen, is the “ability to recruit players that work well together.” 

 

4. Give People A Reason To Leave the House

 

These days, restaurants aren’t just competing with one another for business. In reality, our whole industry is competing with the rising impulse for consumers to simply stay home on a Saturday night. “You can go on an app and they'll deliver the burger to you,” says Carmen, “and you could stay in your pajamas watching whatever Netflix series episode you're on.”

 

This is exactly why so many industry leaders are talking about customer experience these days. Consumers are watching their money closely as everyday costs continue to rise. Restaurants have to offer a compelling value proposition if we want consumers to put that money toward a date night, a brunch with friends, or even just a pint at the bar.  “So if I'm going to get you out of your house to eat the thing that you want,” says Carmen, “we’ve got to make this special. If it's not going to be fun, or if it's not going to be unique, you’ll stay home.”

 

Obviously this starts with great food and great service, but Carmen notes that the pressure is on restaurants to distinguish themselves “because this isn't just a measure of taking your order and bringing you your food. There is more. And where do we see it? We see it in the design. We see it in the decor. We see it on the plate.” Yes, it is about making the experience unique, interesting, and memorable. But most importantly, it’s about giving your customers something they can’t get while sitting on the couch at home. 

 

5. Learn to “Fail Forward”

 

Sometimes, you can do every single thing right and still fail. This is a tough business. Carmen’s success didn’t come without struggle. 8 Hospitality may be sitting atop a portfolio of beloved neighborhood spots, but Carmen notes that some concepts simply don’t pan out. And when it happens, it’s a gut punch. 

 

“I've met with the neighborhood association. I've  scheduled a meeting with the alderman. I understand what other businesses are coming in that haven't been announced yet,” says Carmen. “I talk about due diligence – we've done it, and here's what I've landed on. And sometimes it doesn't work, and you have to accept that.”

 

Of course, accepting failure is not the same thing as liking it, which is why Carmen turned around and responded to every defeat with another swing for the fences. Carmen stresses the importance of rebounding from your setbacks and staying faithful to your own ideas.

 

The Secret Ingredient to Carmen’s Success

 

“One huge word circled 10 times,” says Carmen. Resilience! I think as we're making our chili, that's got to be one of our big ingredients.”

 

Absolutely! Another key ingredient? Staying informed on everything that’s happening in our industry.

 

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