Can we find you here at Motel Bar often?

I’m here probably once a week, I eat here a lot. They’ve got a great southwestern chicken salad that is pretty solid. That, plus french fries, is my staple.

What is your typical day like since you’ve taken over as CEO of Groupon?

My day starts early. I’m up around 5 o’clock and at the office somewhere around 6. Sometimes I’ll work out it in the mornings [but other than that] I’m working non-stop, eating fast. Lunch is typically like 12 minutes and then I’m leaving here around 6 or 6:30 p.m. so it’s 12 power hours and then I’m home. 

Do you find it easy to turn off work mode when you’re at home with your family?

You know, I used to be great at shutting down my brain but it’s getting a little harder these days. I used to be so good at it that I would leave work and I wouldn’t even open up my email. I wouldn’t look at my iPhone—back then Blackberry—and I wouldn’t work on the weekends, I was totally shut down. These days it’s hard to shut down because we have 11,000 employees in 48 countries so something’s happening somewhere all of the time.

Are you enjoying being able to focus on only one thing or do you miss being able to spend more time on your other companies?

I’m enjoying focusing on one thing far more than I would have thought. Before I started this [role as CEO of Groupon], I had built this whole world upon focusing on a lot of companies at one time. Between the companies that Brad [Keywell] and I had started and Lightbank we probably had 60 or 70 companies that we were in some way, shape or form growing and I was really loving that. Then my family and I left for a few months to go to Asia, we took our kids out of school and just spent two months traveling. When I came back it was [as CEO of] Groupon and it’s weird because I’m actually enjoying the singularity of just being focused on one thing and trying to do it really well. It’s hard to think about what life is going to be like after this because the only thing I’m thinking about is how this company can become as good as it possibly could be and how we can make it truly one of the greatest e-commerce businesses in the world.

You once said that you became fascinated with money at a young age.

Yeah, I was probably fascinated with money by a young age … I teach at the University of Chicago and I tell this to our students sometimes and it’s that business is a little tricky. If I were to say to you, “I want to be the best doctor in the world,” the measurement of that would be how many lives you have saved or if you invented a cure for a disease. If I say, “I want to be the best lawyer in the world,” the measurement might be how many cases you have won or if you’ve become the head partner in the biggest firm. In business the metric is the money thing, you’re measured by profits. You’re measured by money and wealth and all of that stuff … So early on when you’re an entrepreneur and you get into business and you’re working really hard, if you want to be great at what you do in your business, you want to make a ton of money.

Is that still what drives you?

At some point if you’re lucky and you’re successful that doesn’t become your primary focus because you can only spend so much. At some point you’re kind of like, “Okay, I have more than I could possibly need.” In fact at some point you start thinking about giving it away, you know? You spend as much time making it as you do giving it away so these days it’s definitely less [focused on] that. For me it’s much more of, I feel like I have a chance to build something or help build something that really is going to change the world in a long-lasting way and I just want to see that happen.

After you finally felt like you had made it, what was one of the first things you splurged on?

The very first time I made a bunch of money was with my first company that I started in 2001, InnerWorkings. We sold a bunch of that [company] in 2005 and then took it public in 2006 … That was the first time I flew private, I think I bought a NetJets share and that was life-changing. It’s a life-changing event when you take your first trip flying private.

Why do you think Groupon gets such harsh criticism?

I think that people in America are fascinated when something out of nowhere becomes incredibly successful. They’re fascinated both in the rise and in the fall and then the rise again, that is just part of our DNA. Even with Facebook and its IPO there was a sentiment out there that they got too big too quick. “Was it really worth it?” and, “Is it overvalued and overplayed?” There was all of this negativity and at first with Facebook, by the way, there was all of this positive press. Then there was all of this negative press and now there’s a lot of positive press again so I think you get that same cyclicality. Amazon had it, Facebook had it, certainly Groupon had it. It’s not uncommon to want to build somebody up and tear them down and then build them up [again], that’s part of the media in this day and age. Someone made this great comment once and it was that no one wants to read about planes landing, it’s boring. You read about plane crashes as sad as that is because planes landing are not that exciting. So I think that people and the media tend to over-exaggerate both the highs and the lows.

What is one thing you’re especially tired of hearing in the media?

The only thing I get that’s hard in my current role in particular is people don’t realize that Groupon is only 4 years old and that the business model is still being built, it’s not like this is a company like General Electric that has been baking in the oven for 100 years. So a lot of times I wish people both internally and externally would have a little more patience because even though it’s a company that will do billions and billions of dollars in sales, it’s still a four-year-old startup.

Do you make it a point to stay out of the press?

In my world it’s impossible to stay out of the press because Groupon is a very public company and it’s just impossible. When I’m not in this capacity, I work really hard at staying out of the press because you want some things to be private.

What do you think the biggest misconception the media has about you?

Well, I think Andrew [Mason] got it much worse than even I do now … My first technology company was a startup that I had in 1999 when I was probably 28 years old. In those days people wrote emails really freely so I think probably the single biggest misconception is certainly some of the press that has been written about things I said or did in the late ‘90s that is way over-exaggerated and incomplete and inaccurate … Anything that is sensational gets printed over and over and over again so I think there are some misconceptions about that era. The people who were a part of building the technology companies of the late ‘90s, none of us saw the rise up and none of us saw the fall down. Even with guys like Mark Cuban, who had a company back then and sold it to Yahoo, you couldn’t time it. It was such an insane period of time. There was such a frenzy around technology and then in 2000 when the bubble burst there was such a frenzy against technology. There was a lot of inaccurate media from over that period of time.

Do you still talk to Andrew Mason?

He’s done what I think is a very good job of distancing himself from all of us and from Groupon. Not because he doesn’t want to stay in contact with a thousand people here but more because when he left, he made it clear—and he made it clear publicly so there’s no great story here—that he just needed to disconnect. It was the kind of thing where he was either all-in or all-out but he couldn’t be half in and half out. He really just needed to move on. He spent four years of his life and this was all he thought about, all he did, it was all-consuming and he needed to just detox from it. So he’s detoxing.

After all of the years you and Brad Keywell have worked together, is it easy for you two to spend time together as friends or does the conversation often find its way back to business?

Yeah, we hang out a lot. Our families are close friends and we live near each other so we hang out all of the time and don’t talk business. We actually don’t talk a ton of business outside of work. When he and I do talk business even within work it’s like two 12-year-olds tweeting or texting … We have really, really short blasts of catching each other up like, “Did you call him?” and, “Did you do this?” or, “What about that?” It’s really fast so it’s not like we’re sitting down having 30-minute conversations like, “What industry should we go into next?”

Do you guys ever get into disagreements or by this point is it a well-oiled machine?

You know, early on [we had disagreements]. Twenty years ago when we had no money and life was tough and every day you felt like you were fighting for your survival, the tension was high but these days [we don’t]. Also in the old days we used to do the same thing and I think we’ve gotten good over the past six or seven years at not doing the same thing. I’m running Groupon, he’s running Lightbank and there’s almost no overlap.

Can you see yourself ever wanting to slow down?

When I was at Lightbank before I took this job and I was traveling for a couple of months it was great. I would definitely like to do more of that and when this Groupon gig is over I’m sure I will.

What do you consider your strongest quality to be?

I try to be pretty driven to succeed, I don’t want to give up. I try not to quit and not to walk away from hard problems. I try to be pretty logical and not get too worked up or too emotional. I try to be pretty rational by principle and I try to do the right thing. At every turn it’s pretty easy to do the wrong thing and it’s hard to do the right thing so you have to try to do the right thing.

After 16 years of marriage and three kids, ages 8 to 14, how do you juggle the roles of husband, father and CEO?

What’s made my personal life work is that I don’t let my business life climb into it. Typically for the first 15, 20 years of my business career and really up until the last few months, if you talk to all of the guys who work with me they would tell you, “I can’t call him at night,” or, “Don’t email him at night. Don’t call him on the weekend.” You have to turn it off and if you don’t turn it off you don’t have any balance. It’s not so much that I’m husband of the year or father of the year and that’s why I turn it off, although I hope to be good at both of those things, I really turn it off because business is not easy so you have to find a way to clear your head. I find that if you’re constantly thinking it’s almost like studying, if you’re studying over and over again you actually do worse on the test. At some point you just have to stop and relax and clear your mind and it’s the same thing in business. If you don’t take a break then it’s tough.

What was it about your wife, Elizabeth, that sealed the deal?

We were friends before we got engaged and married. I knew almost immediately at the time we became friends. I was in Wisconsin and when I moved to Chicago I didn’t really know that many people here but I knew her and we started hanging out. I knew almost immediately that I liked her and then it took me about a year or two to convince her to go out with me.

First thing you do every morning and last thing you do at night?

The first thing I do in the morning is work out or stretch, one of those two. That’s what comes with being 44 … And the last thing I do at night is I put my kids to bed every night. I put them to bed and then sadly I pass out not long after that.

Do you buy Groupons?

I buy a lot of Groupons! Yeah, I buy a ton of ‘em. I’m a huge Groupon Goods fanatic.

Last meal you cooked for yourself?

Kraft Macaroni and Cheese!

Last song you downloaded?

“Wake Me Up” by Avicii. I downloaded that three days ago.

Last book you’ve read?

I am a horrible reader. The thing is I read for a living, I read 300 emails a day and I’m constantly printing emails that I don’t get a chance to read during the day and reading them at night or on the weekend. And these emails are dense, it’s not like people are writing one word emails so for me reading a book is not relaxing. For me watching a movie is relaxing.

Favorite movie or TV show?

I watch a ton of sci-fi so anything sci-fi is fantastic. I’m a big “Star Trek” guy. I don’t watch a lot of TV but I recently just watched season one and two of “Homeland” and it was awesome.

What’s one app that you’re always using?

I’m a huge weather guy because I fly all of the time but I don’t love flying. I used to hate it but now I don’t just because I have to be flying constantly. So I’m always looking at the weather and constantly trying to figure out where a thunderstorm is and if I’m flying through them or around them or whatever.

Having grown up in the suburbs of Detroit, are you a Red Wings or Blackhawks fan?

It’s very hard to lose your roots. I will tell you, when the Blackhawks play the Wings I’m conflicted. I’m a Blackhawks fan now and my kids love the Hawks but it’s tough, I’m torn.

If you could have a drink with anyone, who would it be?

I’ve been fortunate that in my life I’ve been able to meet insane people and of all of the insane people I’ve met, a good chunk are the most interesting people in the world. The one that I really found to be the most iconic was Bruce Springsteen. Being with Bruce Springsteen you feel like you’re not really with Bruce Springsteen but that you’re with somebody who is playing Bruce Springsteen. He’s that iconic and also awesome and a totally great guy so that was pretty cool. If I could spend a night with somebody living, I would want to spend a night with Bruce.

Who’s the coolest person you have in your phone?

I have unbelievable people in my phone. Let’s put it this way, you would want my phone!

KIRSTEN MICCOLI PHOTOGRAPHY