This might be the coolest space we’ve ever seen. 

The idea is to make it feel like anything but a retail store, make it feel fun and different and make customers think they didn’t even know it was here. That’s part of why we’re in this Western edge of River North. We’re very convenient to everything but we’re not above, like, Hubbard Inn. You can park on the street here really easily but if you go five blocks this way or that way you can’t park anywhere … I think you’ll see everything we’ve done is an attempt to make it feel not only better than any store you’ve ever seen but also better than any office. If you walk into a Chanel, or even the new Burberry store on Michigan Avenue, that store is for tourists. It’s people that are in town for a conference or from Des Moines and want to spend money on something where this is something that’s really about having a club. It’s cool, it’s fun, it’s different.

Men will never have a reason to say they don’t like shopping with a full bar and Peroni on draft. 

People are much less likely to be rude or frustrated when they’re having a drink. Wait, this is classic. Here is my sales staff, trying to wend their way through the halls with all of these clothes and then oh, there’s their wine! Not saying we’re alcoholics but that’s why we’re always working, right?

Offering such a high-end experience, will customers be paying high-end prices?

Yeah and that’s a problem for us. The expense thing is hard, you can’t solve that problem because we can’t provide all of this without having a full price transaction. We still lose money every month, we’re not profitable. But if I go out to dinner or if I go out on a date, say I go to Maude’s, it’s 200 bucks! But it’s a great restaurant, you can’t get Maude’s on sale. It’s all about the experience.

That’s what makes it worth it.

That’s the hope! But it is expensive, it is. It’s sort of like when you go to a good club, you have a great time but then you’re thinking, “Ugh, I dropped a lot of money… but we had a great time!”

What made you want to make Trunk Club a Chicago-based startup?

I just wanted to live here. I’ve run companies in San Francisco and New York but hey, California’s a terrible place to do business and in New York people are just not nice. A good salesperson here makes $80,000 and when you make 80 grand in Chicago, you’re livin’ well. In New York you’re sharing a one bedroom in Brooklyn and you’re just marginalized, it sucks.

Does your apartment have the same kind of vibe?

A lot of this in here is my furniture so a lot of the stuff you see is stuff I’ve collected over the years. I live in a really nice building at Erie and Rush. It’s a rental and I’ve lived there for a couple of years and it’s nice but it’s not the hedge fund, panty-dropping, “Oh my gosh you must be an important man,” kind of apartment. It’s just a nice two-bedroom with a pretty cool view but a lot of effort went into it. People joke because my closet is not that big, they always think that because I have a shirt sponsor and I get a lot of free clothes that I have four walk-in closets but the truth is there’s two guys here that are my same size and I just give them everything. 

Do you have any hobbies outside of work?

I joke that I only like to work and workout. I play on two hockey teams at Johnny’s right in the West Loop which is fun. I always say that my personal style is a Toronto NHL player, or something like that. I try.

Go-to spots for a good meal?

I go to Nellcôte all of the time, we’re friends with the guys that own that place. I also really like Maude’s. I think Brendan Sodikoff does a really good job. I went to their new place, the diner Au Cheval, and it’s awesome. I had such a great experience. I’m a huge fan of Lan’s on Sedgwick just south of North Ave. That’s my go-to Chinese spot.

What is your typical day like?

I work from home in the morning. I have a nice gym in my building so I usually swim for a workout in the morning. I have a Trader Joe’s in the building so I always have fresh fruit and stuff. Then I walk to work and get in around 10 a.m. having already taken care of a lot of things from home.

Do you cook?

I do. I make this bachelor’s version of chili that’s incredible but it’s not really chili because it doesn’t have meat. It’s salsa, tuna fish, fat-free cottage cheese, tomato sauce and sautéed cherry tomatoes. It sounds terrible but it’s incredible. I’ve been making this for 10 years and everyone I’ve ever had try it, every friend or girlfriend becomes hooked on it, they love it. The key ingredients are the fat-free cottage cheese, which just adds protein, and the salsa. It tastes incredible.

One book you’ve read that made an impact?

When I give talks about entrepreneurship I often reference a book called “Stumbling on Happiness” written by a Harvard psychology professor [Daniel Gilbert]. He basically explains that in human nature we’re not good at knowing what’s going to make us happy. And that’s true, right? I mean, 50 percent of marriages end in divorce but everyone still gets married because they think it’s going to make them happy. A lot of people work in finance and make a ton of money and think that’s going to give them happiness but then they still aren’t happy and don’t know why. Then you go to places like Vietnam where there’s 80 million people trying to live in this beautiful sliver of a country in Southeast Asia and people have nothing but they’re running around happy as hell … I’m just a normal guy, a hockey-playing meathead from the Midwest who happens to like clothes. Prior to this I worked on Wall Street, I went to Stanford for business school and I love the fact that I have a buddy in town right now and he’s like, “This is ridiculous, this is your job?” because most of my peers would never have guessed I would have done this with my career.

What was it like working on Wall Street?

It’s really not that different than the Loop. I think that when you work in Manhattan, if you work in finance you’re in a sea of people doing work who are very competent, very driven and very ambitious. The things that I liked about it were how much you can learn and how interesting and diverse the work force is. The things I didn’t like about it are that it’s really a cynical world. I find New York and London to be two of the darkest, most cynical places. Even though they’re famous cities, people are angry and their food sucks and everything’s expensive; it’s a tough scene. One of the things I like about Chicago is that you’ll go to R.J. Grunts and see a bunch of people coming in after work, hangin’ out, havin’ dinner and chatting with friends. People are happy! This is a happier town, it’s a friendlier town. It’s the Midwestern values and that’s how I wanted our corporate culture to feel and that’s why I wanted the business to be based here.

Do you have any vices?

I like to play craps. I like to throw dice in Vegas. I do occasionally stay out very late clubbing and dancing. I really like the Underground actually. I like the people there, I like the staff there. I like the fact that I can go there year after year and it’s still fun. I also like the fact that unlike Studio Paris, which I think does a great job, the Underground serves to someone who just wants to be in a club with good music. I don’t need to be in “the” place.

Favorite place for a power lunch?

I’m an investor in Protein Bar so I go there all of the time. I love Matt [Matros], Matt’s awesome. That guy works hard and does such a great job. We go to Karyn’s all of the time too because I try to eat vegan. I’m mostly vegan at least for breakfast and lunch but for dinner it’s harder because I spend so much time traveling. When I’m at home I make a vegetable fruit shake every single day. If until 7 p.m. all you put into your body is vegetables and maybe some quinoa that’s not so bad.

You have a girlfriend, how did you two meet?

I met her at a Trunk Club party. She was just really easy to talk to and we have a lot in common so we became friends before we started dating, which is a great situation. We’ve been dating about four months.

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

David Geffen. He came to Stanford once and spoke to the business school and I asked him, “What’s the best party you’ve ever been to and what’s the best concert you’ve ever been to?” He gave an unbelievably cool answer and said, “That’s the first good question I’ve gotten today! The best party was Studio 54 in the ’70s,” he said it was basically a decade-long party and it was insane. Then best concert he said he had been to was Crosby, Stills and Nash the week before Woodstock.

What’s the best party you have ever been to?

Setting aside friends’ weddings, Café de La Musique New Years Eve in Florianópolis, Brazil. It was insane, I’ve never seen anything like it before. Everything was just perfect. Amazing crowd, no pretension, no bullsh-t, just great people and phenomenal music. People had such a good time, it was just very memorable. It was 500 bucks just to get in and we were all thinking, “This is probably stupid, right? We’re going to totally regret paying this much,” and then it made sense because there was over one bottle of champagne per person, tons of staff, incredible food and it went from 7 p.m. to 6 a.m.

And the best concert?

I saw Foster the People on the Monday night after they won the Grammy last year. AG throws a small show for the largest vendors in Vegas and they’re amazing in concert. I also saw Arcade Fire in Berkeley a couple years ago and that was also incredible.

 KIRSTEN MICCOLI PHOTOGRAPHY