On a sunny March day in his hometown of Chicago, Chance the Rapper makes his way to The DuSable Black History Museum and Education Center for our interview and his SUCCESS photo shoot. Students there on field trips watch with palpable excitement as Chance emerges from his car in his signature snapback with an embroidered “3” on the front and “Chance” on the back.
Chance—full name Chancelor Johnathan Bennett—has been well known in Chicago since he was in high school, then a nascent rapper with a small but loyal following. As that following grew, so did Chance’s fame. And as that fame grew, so did his fortune—which he immediately started giving away, first in a hefty donation to Chicago Public Schools in 2017, then to the county’s mental health services. In 2016, he co-created the Warmest Winter project, which created coats that doubled as sleeping bags for the homeless.
Chance the Rapper never had a Plan B.
Since 2012, when Chance released his first mixtape after graduating from Jones College Prep in 2011, his promise has attracted attention from established artists eager to collaborate. Childish Gambino (Donald Glover), Justin Bieber, John Legend, Shawn Mendes, Megan Thee Stallion, Nicki Minaj, Vic Mensa, Kanye West, Lil Wayne and 2 Chainz are just a fraction of the circle of artists who were quick to jump into the studio with Chance.
Everything was going according to plan—likely because there has only ever been one. “I never had a plan B. Since I was 10 or 11, I knew I wanted to be a rapper…. I was always under the impression that if I had a fallback plan, I would fall back,” Chance says. “Neither of my parents finished college…. College was important, but it wasn’t something that was fully attainable in my mind.”
People had mentioned the idea of Chance following in his father’s footsteps and pursuing a future in politics. (Chance’s father, Ken Williams-Bennett, served as Barack Obama’s state director when the former president was an Illinois senator.) “None of those things ever really interested me,” Chance says. “They actually scared me. The idea of being anything other than a rapper always scared me.”
That one-track mind led Chance from making tracks in his cousin’s recording studio for fun to making mixtapes to hand out in high school. Then came the shows.
How Chance the Rapper defines success
“I made four mixtapes when I was in high school, and I would try to put together shows at different makeshift spaces,” Chance remembers. “I feel like my first big success was the first show I produced. I was a freshman in high school, and I did a show called ‘The Final MCs.’ I was new to the school, didn’t know anyone, and I organized a show with all the rappers and comedians and singers from the school. And I closed out the show. It was cool. It was really cool to be able to gauge my success that way.”
And that’s still how Chance gauges his success. Having finished a big festival in West Africa this January, he says he likes being able to put together safe, exciting events with free tickets: “That’s what gives me the feeling of success.”
Even with those high school highs, Chance had both naysayers and cheerleaders. “There was probably more discouragement than encouragement when I was getting started,” he says. “The way I speak now, people typically tell me that I’m articulating my points and that I am well spoken. And I’ve always been good at reading (not necessarily good at school), so the avenue of rap music wasn’t aligned with how some people saw me. That confused me, because I would think, If you think that I sound smart, doesn’t it make sense for me to have my job be around words?”
But a handful of encouragers he worked with along the way gave Chance the lessons necessary to succeed. He says an after-school program at Chicago’s Harold Washington Library Center gave him the education he needed. The program focused on digital media, crafting and collaboration—and it had an open mic. “That was a really, really big part of me gaining my fanbase…. I learned how to use Pro Tools, how to record myself and how to EQ [equalize] my vocals a little bit from Simeon Viltz and another mentor who passed away, Brother Mike Hawkins,” he says.
Monetizing his music
After mastering the art of making music, though, there was a need to master the art of monetizing it. That’s where his merchandise came in.
“My dad was the one who was really trying to take it seriously and trying to put together my [debut mixtape] 10 Day,” Chance recalls. “He was paying for the CDs that I was burning my music onto. And then I would stand at different popular spots around Chicago… just trying to disperse the music and get it out there. I always felt like the best way to get it to somebody and make sure that they were attached to it—and would really listen to it—was that there couldn’t be a paywall. So, I made sure that I gave the mixtapes away for free. I would start with a conversation and say, ‘Please listen to it. If you like it, send me a message on Facebook or Twitter, and if you don’t like it, send me a message on Facebook or Twitter. But let me know what you think about it.’ I created these real, lasting relationships. There are people who still have those CDs with my handwriting on them.”
Once the music started reaching more and more people through Chance’s grassroots approach, he and his father started arguing about what would come next. You can’t make a living giving music away for free. Especially as an independent artist with mixtapes, streaming-only albums and no studio support.
“What we ended up agreeing on was that merchandise would be the best way to monetize my music. We paid my friend’s older sister who had a printing press to make a bunch of shirts with my Twitter name and some with the name of my latest song. I would sell those at my shows and at the library…. That idea ended up snowballing,” Chance says. “I realized the power of working with other brands and the exposure that comes with that. I realized the importance of branding myself and being able to create something like the ‘3’ hat, which is now synonymous with me. My music is kind of like the commercial for the hat or the T-shirt or a concert ticket or any of the ways that my fanbase can engage with what I make.”
Focusing on what he loves to find success
It wasn’t just Chance’s own brand that landed him on the Forbes 30 Under 30: Music list in 2015 and the Forbes Celebrity 100 list in 2017. (His estimated earnings in 2017 were $33 million.) It was all the brands that came calling: Red Bull, H&M, MySpace, Nike, Doritos, Kit Kat, Dockers, Ben & Jerry’s and, most recently, NBC’s The Voice.
Only in his 20s, Chance had already accomplished major goals he’d set for himself, including hosting and performing on Saturday Night Live and winning Grammys.
The goal of becoming a millionaire wasn’t on Chance’s list, but it happened anyway. “I’ve never really ever judged my successes by how much money I had or how much money I made…. There’s never been a moment where I looked at my bank account and felt bigger. That’s just never how I felt,” he says.
In fact, Chance is happiest on stage, where the revenue, by comparison, is somewhat paltry. “I’m very much into performing. That’s my favorite part of making music. I love to write, and I love to record,” he says, “but I really love to actually play at a concert or a festival. And, so, I just accepted that I’d make little to no money playing shows, because I wanted the exposure and because I love the feeling of being onstage. Once you get to a point where you’re opening for major acts—like Donald Glover [Childish Gambino] or Mac Miller [who passed away in 2018] or Eminem—I got paid $1,500 a night. And I had to pay for my own bus, food and lodging.”
Chance the Rapper: an independent artist
And while—on an album’s liner notes—collaborations with other artists may look like a coterie of friends happily singing together, Chance thinks they can present other challenges. “It can be a tough thing, as an artist, to collaborate. It either means that you couldn’t finish the song, or you made it and were inspired by another artist, and then you have to convince them to get on board. To try to create that magic again is difficult sometimes,” he adds.
Then, there’s the issue of sharing the revenue. If one person writes and sings the song, they keep the profits. But, just like sharing in any other industry, the more people on a song, the smaller everyone’s paychecks are.
“The cool thing about collaborating with me, versus collaborating with artists that are on a record label, is that beyond the 50% royalty split between masters and publishing, there’s also a 50% split between the label and the artist on that master royalty,” Chance explains. “For me, if I do a song, I’m my own label…. So, if you ask me for 15% of the artist net, you’re getting 15% of 50%. As opposed to 15% of 15%.”
One potential downside of being an independent artist, although it’s not one Chance ever criticizes, is that with self-releasing music comes self-promotion. Take music videos, for example. That’s usually a record label expense. But when there’s no label, the production costs come out of Chance’s pocket.
“I pay for my own videos…. It’s good to be able to create those experiences for everyone around me. None of us had been to Venice, none of us had been to La Biennale di Venezia,” he said of his video for The Highs & The Lows, shot in Italy and France. “Those experiences make you a better artist. They make you a better person. And being in control of that—being able to decide when I want to take that on, what my budget is for my song, my video or my album art—is an autonomy and agency that I would never want to give up.”
Paving the way for like-minded artists
Likely because Chance’s eyes are wide open when it comes to the most troublesome side of the music business. “[The music industry] is not designed for the benefit of the people who produce the work. The idea of somebody who isn’t you owning your masters is a crazy thought. The reason why that was initially the case was because labels had cornered the market on the printing presses of vinyl,” Chance explains. “Now, there are not a lot of mechanical copies being made. But a label is still contractually owning the voices of people who spent their whole lives honing their craft and becoming great writers, great vocalists and superstars.”
While most artists accept the fact that the music industry can be fickle, Chance isn’t one of them. His peers are signed to record labels, but Chance’s insistence on maintaining his independence has paved the way for other like-minded artists. And it’s earned him a serious cache of awards and nominations. Among them are the three Grammys he won in 2017, breaking records by being the first streaming-only artist to win best new artist, best rap album for Coloring Book and best rap performance for the song No Problem. (There’s some poetic justice in winning a Grammy for a song about being chased by record labels.)
How Chance the Rapper pays it forward
Chance kicked off 2023 by organizing a free music festival in Ghana for around 52,000 people, and he’s planning an encore performance in 2024 in Jamaica. “When I believe in something strongly, I do my research on it and try to be as vocal about it as possible,” he says. “There are times when you have to insert yourself in the situation to create the change that you want to see.”
For Chance, part of that change comes through his nonprofit organization SocialWorks, which “aims to empower the youth through the arts, education and civic engagement,” according to their website, and raises funds to support its five community initiatives.
“It’s a heavy responsibility to be endowed with being a good person,” Chance says when discussing his ongoing philanthropy. “But it comes from the inside, so there’s nothing you can do about it other than stay on your path.”
This article originally appeared in the July/August 2023 issue of SUCCESS magazine. Photos by Nick Onken.