This is Working for Me Savoring the Challenge

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.