Q
In high school you started your own deejay business, which grew to have 10 employees. I’m wondering where that entrepreneurial spirit came from.
A
It was born from being in a working-class neighborhood [in Omaha, Nebraska] where, if you wanted something, you had to work for it. When I was younger, I bussed tables and worked in the kitchen at Dinker’s Bar and Grill. One of the guys that would come in owned a disc jockey company. When I was 14, I went out with them to help set up. I thought it was really cool. So I convinced my dad to loan me some money to buy a set of speakers and a refurbished Gateway laptop and a mixer. I think it was around 2,200 bucks, and I’m pretty sure he thought he’d never see that money again. About eight or nine weeks after I bought the equipment, I had made enough to pay my father back. And that’s when I realized this can be something pretty cool.
The Hall File
Favorite part about living in Chicago: The diversity of the neighborhoods (“You can go in any one of them and have a different experience each night of the week. I’ve said this before: it’s the greatest city on Earth when it’s not snowing.”)
Favorite vacation spots: Scottsdale, Arizona, and St. Lucia
Favorite Nebraska Golf Course: CapRock Ranch (“I’m fortunate enough to be a member there. It’s a beautiful place in the world, it takes forever to drive there, and your cell phone doesn’t work when you get there, which is part of the allure.”)
Favorite authors: David McCullough, Greg Iles, Michael Lewis
Favorite movies: The Godfather trilogy
Favorite musicians: Bright Eyes, Sturgill Simpson, Dave Matthews
Favorite Chicago restaurant: Piccolo Sogno
Favorite dish at Piccolo Sogno: Linguini with clam sauce
Q
That’s a quick payback.
A
He was eminently impressed—and thoroughly concerned that I got it through illicit means.
Q
Your dad was a state senator in Nebraska, then the state insurance commissioner, and then a CEO of an insurance company. Did you ever have any political aspirations?
A
If I ever did, he would quickly talk me out of them.
Q
Did your father’s political career inspire in you any particular passion for politics?
A
It did, yes, pretty tremendously, actually. I’m a political junkie. He represented a blue-collar district in a part of Omaha that was very diverse. You had a lot of legacy immigrants from the Italian community, the German community, the Irish community, the Czech community, and then couple that with the recent Hispanic immigrants. So he had a very diverse constituent base. It taught me that, despite your differences with somebody else, you can always come to agreement on something.
Q
Did you campaign for your dad?
A
Oh, yeah, we were free labor. We knocked on doors. We built yard signs. He had a political apparatus with my brother, my sister, and my cousins. And my father is one of 15 children. So he had a lot of free labor helping getting him elected a few times.
Q
Tell me about your high school days growing up in Omaha.
A
I went to an all-boys Benedictine boarding school five days a week. You weren’t allowed to skate by. It was pretty formative for me and kind of put me on the path that I eventually landed on today.
Q
Has there been any one aspect of the CEO position that came as the biggest surprise to you?
A
It’s a great question. I’d say the biggest surprise is probably how much of an impact you have, as CEO, on the culture of the firm. Trying to make sure that the culture that we’re setting forth, which is one of respect, accountability, and meritocracy, to make sure that’s permeating throughout the firm.
Q
What three words would your co-workers use to describe your management style?
A
Direct, thoughtful, and passionate.
Q
If you could change one thing about the insurance industry, what would it be?
A
The perception that it’s boring. I think it’s a tremendous home for really smart, driven people. You can have a passion about anything and work in the insurance sector.
Q
What gives you your leader’s edge?
A
I think it’s my knowledge of the industry from a different seat than others. As an advisor to the sector, I got to pick the brains of a lot of CEOs, a lot of leadership teams. That gives me an edge, because I can understand how to approach a problem by recalling how the 50 CEOs I’ve spoken to about it before did.
