Having played in a legion of bands before creating Into It. Over It. in 2007, what made you want to go out on your own?

It’s nice having that complete control. After years of being in bands where I had to sacrifice that or be held up on decision-making or not be able to take all of the opportunities that I wanted to because of someone else in the group, now I can just make my own decisions and go with it and if I think something is right I can do it. This year it’s a little different since I have the band [performing with me] but they trust what I have in mind and are behind me 100 percent as far as what I think is smart for everyone.

In your experience, what have caused the biggest issues with bandmates in the past?

All of the disagreements that I’ve ever been in with bands have been generally based around what the band should do, if we should go on tour or not go on tour, if we should put a record out or not put a record out. It’s never been so much about the songwriting but that might be because I’ve always taken major control over that aspect. I don’t know if I work well with others. [Laughs] Maybe that’s the common theme for most solo artists, it’s that they don’t work well with other people. They want that control and that’s why they eventually go solo.

What are the highs and lows of this business?

The lows are when you are on tour. It’s the day in, day out repetition. There is a lot of feeling lonely and wishing you could be home. You’re exhausted, you’re sick, you’re all of these things. But beyond that it’s mostly highs, man. I’m 30 years old and had desk jobs for years. I’ve had stupid retail jobs, I was a marketing manager, I was a ditch digger; I’ve done it all. The last five years have been great. If I have anything to complain about that’s really just me being a total dick because there really isn’t much to complain about.

Living in Chicago, what was it like having the opportunity to play at Lollapalooza? 

It was cool feeling like we were the band that was representing rock bands in Chicago. We were the only rock band from here that got to play so we were honored to be able to showcase our city pretty well.

Many dream of becoming a successful musician. What should they be prepared for?

It has been long and difficult journey but in the most rewarding way. You put in a ton of work and you sacrifice everything for the opportunity to be able to do something cool and maybe it will work and maybe it won’t but that’s part of the risk. If you don’t take that risk, you don’t get any of the reward. That to me was the biggest thing. I started out playing around here in living rooms and since then I’ve been just recording tons of songs and working day in, day out only focusing on music. I haven’t done anything but work on music for the last six years.

When will you know you’ve made it as an artist?

My idea of success is when I can go into a restaurant and I don’t have to look at how much the food costs to order what I want to eat. That’s my idea of success. Once I can do that, I’ve made it and I’m doing okay.

One song you’d like to never hear again?

That “Happy” song by Pharrell.

How would you describe your relationship with your fans?

Into It. Over It. started so small, it started as a DIY grassroots project so I know most of the people who come to our shows. When we go back to the same cities I recognize a lot of the same people coming back and a lot of the relationships I have with our fans are on a first-name basis and are very personal. I try to talk with them about things that aren’t music-related. We met some people at Lolla this weekend who were our neighbors and I was like, “We should get a drink, we live in the same neighborhood.” It’s like that, way more personal and way less of a division between the band and fans.

Who was the first person to believe in you?

My mom. Not my dad. [Laughs] Definitely my mom. I had a lot of friends who did too but she was always there. I think she knew while my friends were always kind of skeptical. I did a tour where I had to be on a bus and my dad had to drive me up and drop me off to the start of the tour. So he drives me up and when he rounds the corner he sees the bus that all of the bands were riding on and he was so proud. He was taking all of these photos and sending them to his work buddies and stuff. Since then my dad has totally given me the sign of approval. But yeah, it was definitely my mom [in the beginning].

Was your family in the audience at the Grove Stage?

A lot of friends were there but none of my family. My family is all in New Jersey and Philadelphia where I grew up. That’s where they all have stayed but I’ve been living here for seven years. They were all watching the livestream at home. My mom was sending me text messages asking me if I had a cold. Which, I did. She could tell!

If you were able to pick the brain of one of the artists at Lolla this year, what would you want to learn?

I would want to ask the guys in Outkast how they come up with new ideas and how they stay focused, motivated and inspired. Life gets in the way and often times you find yourself finding it more difficult to stay focused on one thing. For me, I know that if I don’t do one thing at a time I completely lose it. Recently I’ve been coming into situations where I’ve had to do more than one project at a time and my brain is all over the place. So I’d be interested in asking them how they’ve been able to do that, whether it’s with acting, writing, producing or recording.

In your opinion, best Lolla acts this year?

The one band I was really looking forward to watching was Interpol. That was really my favorite performance of the weekend. I got to see a little bit of Lorde and a little bit of Bombay Bicycle Club but really we were running around enjoying downtown … We were kind of making it a stay-cation. We never really hang out downtown so with the festival being down there all weekend we got to do all of these things we normally don’t get to do because we are always hanging around Wicker Park or Logan Square.

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

Barack Obama. But I don’t want to talk about anything. I just want to sit in silence, smoke a cigarette, have a whiskey and that’s it. Just sit quietly and hang. And it’s not even because he is the President, he just seems like a chill dude. There are other chill dudes, Dave Grohl, same thing. Ringo Starr, I feel like that would be a really good drink.

KIRSTEN MICCOLI/A DRINK WITH at BOILER ROOM

Click here to see 2014 Lollapalooza performance