Currently, Bennett is working on a new album, a follow-up to 2015’s Broad Shoulders. Last month, he released a song with Stro and Jordan Bratton, “New York Nights,” and played his biggest headlining show to date in his hometown. “A lot of my music that I write is based on futuristic things that happen to me,” he says. “It’s hard to be honest with yourself as a person, but I’m very, very honest when I write my music, and maybe that’s why I see the future unfold after I release the track.”

AGE: 20.

HOMETOWN: Chicago, Illinois.

CURRENT LOCATION: Chicago, Illinois. I wouldn’t have it any other way. I know where everything is. [laughs] It’s just where I fit. It built me as a person. I wouldn’t be the same person I am today without the city of Chicago.

MUSICAL BACKGROUND: I never took music lessons or anything like that. Chance took some piano lessons as a kid, but me, it’s always been natural. It’s been something that comes to me. I’ve loved it since I was a child. My family loves music and we’ve always played music, from Jay Z to Coldplay to Erykah Badu. I grew up in a household where music was very much a backbone of our childhood.

DEBUT PERFORMANCE: The first time I ever had a show was with a pretty big group. I was nervous. I couldn’t afford to practice somewhere that had a microphone, so I’d been performing my vocals with a remote in my hand. I had my friend as a hypeman playing the instrumentals in the background. I was the first opener and there were about 30 people there—not too many.

A RAPID RISE: By my senior year in high school, I was selling out venues that held about 500, 600 people. I decided to run with it and go after it. It wasn’t just my parents, it was me too. I never wanted to wake up one day and go, “What if I had gotten on Sway and done the 10 Fingers of Death? What if I dropped an album that was premiered by Rolling Stone when I was 19, 20 years old? What if I was one of the most streamed Soundcloud exclusive artists?”

MUSICAL MANIFESTO: I make music to bring people together. I’ve known that since a young age. There’s a lot of people that make music to be relevant. There’s a lot of people that make music for money. There’s a lot of people that make music for fame. None of those things have ever been a variable for me in terms of writing music. I’ve always wanted to make timeless music. I made a tweet and I’ll never forget it, I said I’d make timeless music for funerals and weddings and I’m not ashamed of it. I want people to share an experience so when they look back in 30 years, they don’t mind that they paid a dollar for it, or got it for free, or had to go on these sites and look it up—when they hear that music, they remember a specific experience and what it was like at that moment in time.