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Michael Osanloo, ’96, took the reins at Portillo’s in 2018—and headed straight for the service counter. He packed the famous Italian beef sandwiches, hand-crafted salads, and presented customers with slices of the Chicago-style fast-casual chain’s famously decadent chocolate cake. After months of stints working in various locations, the CEO felt he could finally “understand what everybody is doing at the restaurant.”

Osanloo took the restaurant public in 2021, a milestone for the chain that started in a trailer in Villa Park, Illinois, in 1963, and now has more than 80 locations across 10 states. Prior to his role at Portillo’s, the attorney turned business executive worked around the globe for P. F. Chang’s, and has held senior roles at Caesars Entertainment and what is now Kraft Heinz Co. 

Osanloo sees Portillo’s as a sleeping giant that’s headed toward a major—920 restaurants major—expansion. For him, it’s just a matter of time before diners from around the country discover their food, just like he once did as a child growing up outside of Chicago.

My entire career trajectory put me in a position to run Portillo’s. I’ve been an attorney, I was a consultant, I ran casinos, and I will always have soy sauce in my blood because of P. F. Chang’s. I’ve seen a lot, and I know how to grow something, but I’m not so jaded that I’m afraid of getting my hands dirty and doing stuff myself. 

The private equity firm that owned Portillo’s reached out.
I took the call because I knew the director and was being polite—but I got more and more intrigued. This is a true Booth thing: sometimes you have to think differently from the norm. I started realizing that Portillo’s is actually a sleeping giant, and the upside potential of this brand is unlike anything else in the restaurant industry. And that’s appealing to me. I’d rather be part of building something amazing than just running something.

The restaurant industry is a game of Whac-a-Mole:
there’s always something going wrong. You have to be comfortable being uncomfortable. As a leader, I strive for perfection, knowing full well you can never really achieve perfection. I know what great looks like, but I’m comfortable knowing that you can’t fix everything at once.

My job is to put my teams in a position where they can be successful.
In turn, their job is to put our frontline team members in a position that they can be successful. Because if they’re happy and successful, the guest is happy, which in turn makes my investors happy, which makes me happy. It’s a beautifully virtuous cycle. But that means that your focus in this cycle is on the front line team members who interact with guests. And it means sometimes subsuming your own ego. 

There’s a universal truth to our food that works in America.
Across most of America, they’d call this a roast beef sandwich with au jus. We happen to call it Italian beef with gravy. But it’s perfectly slow-roasted beef on delicious crusty bread. As human beings, there are times when we want to feel comfort. And Portillo’s is the ultimate comfort food. 

What I loved about my time at Chicago Booth is it teaches you to be a critical thinker.
You just, you can’t beat that. You learn to think for yourself, to use data, and to not get duped by the data. You have this honest embrace of truth in what you’re doing. And then you figure out how to make progress against that to motivate people and galvanize a team. 

“The restaurant industry is a game of Whac-a-Mole: there’s always something going wrong. You have to be comfortable being uncomfortable.”

— Michael Osanloo

Roman Weil [the V. Duane Rath Professor Emeritus of Accounting before his death] got me to be a great student. Weil said, “I believe that one of my jobs here is to weed out admissions mistakes. But because the administration tells me I can only give so many failing grades, I’m going to make sure that I do so.” I found that to be highly motivating.

I use my experience as a LEAD facilitator at Booth constantly.
Back then I was trying to corral and organize all these different personalities, and I still am now. You have all these egos and need to learn how to get people around a common purpose. That’s what a CEO does. For me, the challenge is to get people with diverse and frequently divergent goals excited and motivated. They need to aspire to the same thing.

There are a lot of people who seek to create this separation between work and life.
I kind of define myself by what I do. When you worry about creating separation from work, that suggests to me that you’re not getting joy out of work. So I have phenomenal work-life balance, because work feeds joy into my life. I would not be nearly as good of a father or a husband, or a son or a brother, or a friend if that weren’t true.

Here’s a true story, but nobody believes me.
When I turned 16 and got my driver’s license, I literally went straight to the Portillo’s in Downers Grove. I was scared to try to go through the drive-thru in my parents’ huge Pontiac station wagon, so I picked up my best friend at the time and we went inside to eat. As a 16-year-old kid, that’s what I did to celebrate getting my license. And as a grown man, now I get to run this restaurant company. So that’s a ton of fun.

I strongly encourage people to think for themselves.
If I listened to other people, I would never have gone to Booth. I used to practice law, and everybody said, “You’re an idiot for leaving your great litigator position.” I was a partner at Bain, and when I left—and I took a 70 percent pay cut doing so—people told me I was insane. I’ve made career decisions that people thought were crazy, but I’m super happy where I’ve ended up. So I kind of feel vindicated. There are so many paths in a career and in life, and what other people think you should do is almost never right for you. I listen to other people because I seek input and I want to test my own convictions. But I always do what I think I should.