Do you believe there is a common thread in the mentality of all entrepreneurs?

I don’t think there is one.

Interesting.

Well, I don’t know. I think before working in startups I would have thought there were standard cliché answers about aversion to risk or other slightly crazy things but now from being in the startup space and meeting a ton of entrepreneurs, everyone is completely different and completely individual depending on whether they’re in the enterprise space or consumer space. I love the analogy that entrepreneurs would rather work 80 hours a week for themselves than 40 for someone else. The unfortunate reality is that most of us fail so some people’s mentalities are probably positioned much better than others for being successful in this kind of career path.

Do you still get excited when you notice your Belly iPad set up in small businesses around the city?

It is cool! People get annoyed because I’ll walk in and start showing cashiers how the different functionalities work and their stats, all sorts of stuff. Besides going into businesses, when I meet people and they take out their keys to show me their Belly card or take out their phone and slide to the app, that doesn’t get old.

How many iPad boxes would you guess are stacked around here at the Belly headquarters?

Well, we’ve got 6,000 locations up and running so there are more than 6,000 boxes up here.

What have you learned most from your first go at being a founder and CEO?

Get comfortable with discomfort. I think you have to be incredibly comfortable with a level of uncertainty. Chaos causes panic but uncertainty is something you have to have a level of tolerance for. Even when things are going well there are always, always problems so I think as a founder you either accept that, get comfortable with it and deal with things head–on or the problems will continue to build and the end result will be failure. As an entrepreneur you don’t have a boss or someone else to fall back on, you sink or swim. So jump the f-ck in and figure it out!

You’ve learned from the best: Eric Lefkofsky, Brad Keywell and Paul Lee. What are some key take-aways from those guys?

From the Lightbank guys? Well, I certainly learned how to deal with discomfort. Brad Keywell wrote an article in the Wall Street Journal this week and said something to the effect of, “a good board member will piss you off,” and I think he speaks from experience because that certainly has happened in our case. They’re incredibly successful guys, they’ve started three companies that they have taken public so they know what it takes to build a successful company and they don’t have any real tolerance for mediocrity or for being average. They push hard and make you recognize that you want to be better, that your goal is never really high enough and in order to get there it takes a lot of hard work.

Making the Techweek100 list doesn’t come easy. What rookie mistakes do you see made by those aspiring to get to where you are?

I am a rookie! I’ve been in startups for a long time but with Belly this is the first time I’ve been a founder so I would never profess to have the advice or the answers. That being said, I think there are things that I’ve learned with this company. Some mistakes I’ve seen others make are that people vastly overvalue an idea. They don’t understand that success and entrepreneurship and starting a business has nothing to do with an idea, it all has to do with execution. Most successful startups today aren’t revolutionary concepts. I mean, we’re a digital loyalty product. It’s not like loyalty is a new concept, it’s about execution. I think people think a startup is sitting in a room talking about ideas and drawing different designs when early on people should be actively selling as much as possible. Always be selling and pitching. You will learn a lot about what people will like, won’t like, what they’ll buy and what they won’t buy if you’re proactively selling as much as possible.

Why Chicago?

I grew up in the Bay Area, my first startup was there but I’ve been in Chicago seven years now and I think it’d be a lie if I said I stayed for a lot of other reasons besides for meeting a girl who is much prettier than me. I’ve really come to love Chicago. I think it’s off base when people try to make comparisons between Chicago and Silicon Valley or the L.A. and New York startup scene. Chicago is not there yet but I think you can build a great company anywhere, anyone saying anything else is making an excuse. There are a lot of benefits to starting a company in Chicago. The Chicago tech community is not only growing but everyone within it is incredibly supportive and incredibly helpful. People have a real genuine interest here and besides, being in the Midwest people are just f-ckin’ nicer. People genuinely want Chicago tech to be successful so they’re willing to help. There are a lot of resources, a lot of mentoring, a lot of introductions so the ecosystem here is phenomenal.

When is the last time you were in a suit and tie?

I wear jackets every once and awhile but mostly just t-shirts. I was kicked out of an event recently for wearing jeans and a blazer. They loaned me slacks so I was wearing black pinstripe pants with cowboy boots, it was awkward. But that kinda counts! And then for a wedding. But professionally? Not ever.

Where can we find you hanging out when you take time to relax?

Being that I started a loyalty company, I’m typically at the same places often. I’m a creature of habit. I’m not the “unlock the city, discover new places” kind of guy. You’re not going to find me clubbing with bottle service. I live in Lakeview so I hang out mostly around the Lakeview area and I go to the same spots over and over.

Are you a Chicago sports fan?

I’m a die-hard 49ers fan.

So the beard isn’t for the Stanley Cup?

This isn’t for this year’s cup, it was for the cup like nine years ago. I think I’ve had this since the ’90s. My wife and I made some trade-offs so I’ll root for the Cubs and the Blackhawks but I’m die hard for the Niners. Last time I shaved my face was for my first job interview out of college at my first startup. I got the job and I haven’t shaved since.

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

Oh, man. I’d probably start with Julius Caesar, some crazy tyrant. It would probably have to be wine I guess, I think that’s all they had back then. Maybe some barley. We’d eat some olives together on just a big f-ckin’ throne or watch a gladiator event. As for someone alive, probably Bill Clinton. He seems like he’d have a good time!

We didn’t bring the Batch 19 for nothing. Time to see what your beer pong game is like.

I tell my team I typically like people who hate losing more than they like winning so you’ll probably start to see that come out.

ALINA TSVOR PHOTOGRAPHY