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Written by Mark Wilson for Fast Company. Check out the original article here

“Yesterday, I left my wallet at home,” says Chancelor Bennett, aka Chance the Rapper. It’s 9 p.m. on a fall evening at a Chicago recording studio, and he and his bandmates are packing up for the night. Four days from now, they will put on their biggest show of the year, at the city’s United Center.

Bennett sits next to me in high-waisted track pants and a fitted tee. He admits to feeling a little overwhelmed by having a new baby at home and a new tour to prepare for, and yesterday was proof. He had taken his 4-year-old daughter, Kensli, to Dunkin’ for a rare treat before school. It was the first day all week that he had been able to do morning drop-off, and he’d wanted it to feel special. She picked out a glistening, sprinkle-topped chocolate doughnut, and he realized his pocket was empty.

“It’s just a crazy letdown for a child,” he says, shaking his head, clearly still unable to forgive himself. Luckily, another customer was more than happy to pick up the tab—in exchange for a photo with Chance the Rapper.

The entire span of 2019, in fact, has been rather frenzied for the 26-year-old, who made the unthinkable choice several years ago to eschew record deals and give his music away for free. He’s garnered more than 1.5 billion streams on SoundCloud since 2012, and he’s earned millions of dollars in revenue, through live shows, merchandise, and endorsements instead. Last winter, he filmed six episodes of Rhythm and Flow, a Netflix talent competition that he hosts alongside Cardi B, T.I., and a slew of R&B royalty, which debuted in October. In March, he celebrated his wedding to longtime girlfriend Kirsten Corley, a childhood behavioral therapist and Kensli’s mother. In July, he released The Big Day, his first official full “album” (previously, he had released three “mixtapes”—the last of which snatched three Grammys), which became a Billboard No. 2 hit. He made his feature-film debut in July with a cameo in Disney’s The Lion King remake. In October, he hosted Saturday Night Live for the second time, also serving as musical guest. During all of this, he was also helping to run SocialWorks, the nonprofit he founded in 2016 that works to improve the lives of youth in Chicago through arts education, mental health services, warm-clothing drives, and more. Bennett has donated $2 million of his own money to SocialWorks’ efforts—including $1 million to Chicago Public Schools and $1 million to Chicago mental health initiatives.

In late August, Corley gave birth to the couple’s second daughter, Marli. It was this development that caused Bennett’s already packed schedule to melt down—he felt he couldn’t be a new father and go on tour at the same time. Eleven days after Marli was born, he announced, via Instagram (and a photo of himself with his girls), that he’d be postponing his heavily anticipated, 31-stop North American tour until January.

Yet he kept his promise to Chicago. On September 28, he performed a single show for a crowd of tens of thousands, which featured his brother, Taylor, and Chicago native Kanye West. The decibel level in the United Center, home of the Chicago Bulls, reached levels that rivaled the Michael Jordan era. Chicago was simply another loved one whom Bennett couldn’t disappoint. As he says himself on his 2018 track “I Might Need Security”: “I’m a sign to my city like the Bat-Signal.”

Chicago is a city segregated by a river, which slices it horizontally. Head north, past the old money of Lincoln Park (where the public schools are highly rated); past the Cubs fans at Wrigley Field (which charges some of the highest ticket prices of any MLB stadium); past Edison Park (statistically one of the safest parts of the city, where a disproportionate number of law enforcement officers hole up at night); past the liberal enclave of Evanston (home of Northwestern University); and you’ll reach affluent, 90% white suburbs.

Head south, past the Loop business district, and you’ll start to understand the place from which Bennett draws his inspiration, both musically and civically: the selective-enrollment Jones College Prep (where Bennett went to high school); Harold Washington Library (where he recorded parts of his first mixtape); the White Sox’s Guaranteed Rate Field (which charges among the lowest ticket prices in the MLB, and where Bennett launched SocialWorks while promoting his third mixtape, Coloring Book, in 2016).

Keep going, and you’ll reach Hyde Park (the predominantly black intellectual stomping grounds of the Obamas and also, incidentally, where Bennett, at age 9, first heard a track by Kanye West on the radio, which inspired him to buy College Dropout, the first rap album he ever listened to) and eventually the heart of the South Side, an area most Americans know only as a gun violence caricature.

Abutting this part of Chicago is a middle-class neighborhood called Chatham, where Bennett was born. He is among the fourth generation of Bennetts to have lived on the same block, and his music, friends, family, and Christian faith remain rooted here. It’s for this reason that he runs his business differently from perhaps any major entertainer working today. Bennett has no Hollywood agent or manager on retainer. There’s no slick branding agency or publicity firm out there procuring megadeals. His music and social good operations are purposefully intertwined, in an organic way that eschews org charts. “We really are a mom-and-pop-type shop. We just operate on a large scale,” says Colleen Mares, his day-to-day manager, who booked one of Bennett’s earliest shows, in 2013.

One team member happens to be Bennett’s actual pop. Ken Bennett is a veteran of the Chicago political world who served two mayors and helped organize Barack Obama’s unsuccessful 2000 congressional race, along with his history-making 2008 presidential run. Ken is now a board member at SocialWorks and treats his son’s career like that of a political candidate’s. He found Bennett his primary career manager, Pat Corcoran, who’d been working with some South Side rappers, in 2013.

Most of the roughly 10 people who work on Bennett’s mini label are native Chicagoans who have been with him since around that time, including his lighting designer, live video producer, and the artist who does branding and merchandising for both the label and SocialWorks. Bennett’s closest childhood friend, Justin Cunningham, is now the executive director of SocialWorks. Reese White, a friend from middle school, sits on SocialWorks’ board and helps with marketing. Essence Smith, whom Bennett and Cunningham met during homeroom orientation their freshman year of high school, is SocialWorks’ director of operations and communications. These are “people I trust very much,” Bennett says. “It’s not like we’re coworkers. It’s more like . . . just an easy conversation.”

Bennett and I climb into the back of a comically large SUV, and he slides his Nintendo Switch aside for me to take a seat. As we make our way south from the studio to his new condo downtown, we talk about Cunningham, who has been instrumental in keeping Bennett on task for as long as the two have known each other.

“From grade school [on], he was the only kid who would give me a pencil, because I came to school every day without a pencil. I would come to school every day without lunch,” says Bennett. “I just wasn’t very organized is the best way to put it—even to this day.”

Bennett did so poorly in his first 10 weeks of high school that he was almost kicked out. By the end of his first quarter, he was failing six out of seven courses. To stay in, he embraced a rigorous schedule, ditching electives, stacking two biology classes in the same day, and enrolling in summer school. Still, Bennett says, he secretly paid Cunningham to do his summer-school work.

When Bennett was a junior, his father took a yearlong job in Washington, D.C., working at the Department of Labor under President Obama. Bennett, Taylor, and his mother, Lisa (formerly a community relations liaison for the attorney general of Illinois), stayed in Chicago. By the time Ken returned, Bennett was beyond disciplining. “Having that amount of time without a strict dad, just, like, hanging out—and everybody is starting to buy guns, get into drugs, have sex, grow, and make their decisions. . . . I was running it up.”

Cunningham and Smith went off to college. Bennett, who wouldn’t graduate from high school with the rest of his class, didn’t. “It was a weird space for me,” Bennett says, recalling how it felt to have his friends move on while he stagnated, dreaming of a career in rap that felt far from attainable. “So when I didn’t go to school or get a job, obviously, [my dad] kicked me out,” says Bennett, who spent the next year couch surfing at friends’ places.

A few days before Bennett’s United Center concert, Ken Bennett sits in a nearly empty stadium on the suburban DeKalb campus of Northern Illinois University. Bennett and his band have set up a stage mimicking the United Center’s, complete with 30-foot screens and strobe lights, and the bass floods my body as they perform and tweak songs until they get them right. Ken sits with his head tilted back, eyes closed in a relaxed micro nap. He’ll rouse himself later, bobbing his head to the music, as Bennett and Taylor perform “Roo” onstage. The lyrics credit Ken for instilling a bond between the brothers but also address the hole that opened when he left for that year.

Bennett may have been a terrible student, but he still learned a lot during his high school years. Through Chicago Public Library’s YouMedia studio, a creative media lab at Harold Washington Library, he honed his musicianship and recorded an album. A mentor named “Brother Mike” Hawkins ran a weekly open mic night for Chicago schoolkids. The rules were simple: Three minutes onstage, and no racism or sexism. Hundreds of teens would show up, so not everyone could perform. Somehow, though, Bennett’s name would consistently float to the top of the list.

“I remember, I had the song ‘Brain Cells’ . . . and I would perform [it] every week. And at one point, Brother Mike came to me and was like, ‘Yo, if you perform that song again next week, I’m not going to let you perform [anymore],’ ” Bennett recalls, lying on the concrete arena floor and using his denim jacket as a pillow. As the setting sun shines through the building’s lone set of windows behind us, he cheerfully admits he’s half asleep. “A lot of people have different theories about how I came up . . . but truthfully, the lessons that I learned and the fans that I gained all came from when I was doing open mic.”

During that uneasy year after high school, Bennett says, he was out one night in tony Lincoln Park with his older friend and aspiring rapper Rodney Kyles, when a “big-ass fight” broke out. Kyles was stabbed by an unidentified man who would never be caught. That evening, from the hospital where his friend died, Bennett phoned his father.

“It was the first time I had called him in a long time. He picked me up, and I came back home, and I just stayed there. And then I lived there,” says Bennett. Not long after that, Ken quoted a line from Bennett’s idol, Kanye West: “Told my mama I was on the come up / She said ‘you going to school I’ll give you a summer / . . . Ten years later she driving a Hummer.” It was Ken’s way of giving Bennett his blessing—and a year’s deadline—to become Chance the Rapper. And he’d help.

Before Bennett’s first mixtape was even complete, Ken persuaded a popular apparel store to agree to hold a listening party, because he knew that’s where lots of young rappers, including Bennett, hung out. He printed pluggers, the little handouts used by politicians, and drove Bennett and Taylor, who is three years younger, to some of the city’s biggest and most prestigious local high schools to promote the show. “And then hella people came,” says Bennett, “like 200 to 300 people showed up.” After Ken brought manager Pat Corcoran into the fold, Bennett’s mixtape 10 Day caught the attention of actor and musician Donald Glover (aka Childish Gambino), and Bennett became the opening act for some of Glover’s 2013 tour. Bennett’s career was clearly accelerating, and Ken had one key piece of advice.“He was like, ‘Hire your friends,’ ” recalls Bennett. “ ’There’s no reason your friends should be working for people other than you, for less than they’re worth.”

So when Bennett needed a personal assistant, he called Smith, who deferred law school to join him. When he wanted to do some social good projects, he called Cunningham, who balanced the work with college. When Brother Mike died, in 2014, at age 38, Bennett was shaken. He and Cunningham—along with local poet Malcolm London—relaunched the neighborhood program as Open Mike, with the same three-minute limit and other rules, and Bennett began to host the event in 2015. That year, Kanye West and Kendrick Lamar each made appearances. Also that year, Bennett and Cunningham launched a coat drive.

Bennett says that the urge to give back to the community didn’t come upon him suddenly; he had always felt a certain “weight” of responsibility. “[It’s] just how I was raised and my faith. It’s the exact opposite of impostor syndrome. It’s like, I walk outside sometimes and I feel like I have an abundance, and so I feel like I need to share it and serve in all [the] ways that I can find,” he says. “It just feels like that’s who I am—and not in a way that’s cocky [but just that] I’m supposed to share things.”

Bennett and Cunningham dubbed their effort Warmest Winter, and were able to purchase 1,175 new coats for homeless people after raising $117,517 in the first year (the program now distributes donated outerwear). Cunningham recalls having “a good, old-fashioned heart-to-heart” with Bennett afterward: “[It was like], We want to keep doing this . . . how can we do it better?” A nonprofit to wrap all this work up in seemed to be in order, but what would that even look like? Would Bennett just pump money into a foundation—like many celebrities do? Or would this be something else, an outgrowth of the local community?

Bennett, Cunningham, and Smith became equal partners in the new venture, which devotes only 10% of funding to operating expenses and today encompasses four main initiatives: education (providing arts grants for dozens of Chicago public schools), mental health (offering funding for six local healthcare facilities), aid for homeless people (Warmest Winter is now an annual tradition), and a summer camp (Kids of the Kingdom is a Christian-focused camp founded by Bennett’s great-grandmother). Ken Bennett is also on the board, and his connections in Chicago politics help ensure that the group can get the right people on the phone in order to get things done. In September, SocialWorks expanded beyond Chicago for the first time, launching an Open Mike in Las Vegas.

Their secret to accomplishing so much despite Bennett’s hectic schedule lies in 17 years of personal history. Bennett knew that his friends were hardworking, studious, and efficient. Plus, “we’re friends, so you know when it’s a good time to talk about something serious, or when it’s music time,” says Smith. “And it’s not like I’m going to be bothering him. It’s stuff he’s passionate about.” The team collaborates via group chat. Bennett weighs in on all topics, but, as he puts it, often serves “as a lightning rod” to bring in money and volunteers. As it turns out, many people, and many brands, want to collaborate with Bennett the artist and Bennett the philanthropist. They may not even see a distinction.

For instance, when the athletic-wear company Champion sent Bennett some free clothing samples, he started wearing them, simply because he likes to be comfortable. Then he kept wearing them, along with other items from the brand. His team spotted an opportunity for the nonprofit. “If he’s going to be wearing all this stuff, let’s see if we can help out SocialWorks in some way,” Mares says. Although Bennett isn’t paid by Champion to wear the label, Champion is a sponsor of SocialWorks, donating merchandise, supporting live activations, and hosting a design contest that raised money for Chicago Public Schools. (Manny Martinez, founder of the American Branding Agency, which has represented Champion for the past 15 years in the youth culture world, calls Bennett “the Muhammad Ali of hip-hop.”) Bennett’s team evaluates each potential deal in this manner. If a company has the marketing budget to hire Bennett, it will likely have the corporate social responsibility dollars to help SocialWorks.

“We think about bartering. We’re not just like, Hey, cut [us] a check,” says Mares of Bennett’s brand partnerships. “A lot of times we just throw the ask out: ‘Would you bump up the money if some of it went to SocialWorks? Or throw in a component that somehow benefits [them]?’ In a positive way, we try to use Chance’s leverage to benefit the work the nonprofit does.”

In addition to Bennett’s $2 million, SocialWorks has been funded by $6 million from corporations that include Google, Lyft, and Champion (none of which sponsor Bennett directly), and the organization forges other kinds of affiliations when appropriate. (Warmest Winter, for instance, is now run in partnership with well-known local philanthropist Michael Airhart.) Bennett is highly disciplined with his music—he makes decisive edits to the tracks during rehearsals to get them just right—but with SocialWorks, he’s accommodating. “I really like to help people, and I really like to feel happy,” he says with a slight smile. “So, in a certain context I’m the best at saying no, but in other cases, yeah, I’m not the ‘no’ guy.”

The night of the United Center concert, Bennett’s presence is everywhere. Throughout the day, he’d been tweeting announcements about free tickets he’d left around the city like a real-life Willy Wonka: at the DuSable Museum of African American History, Coleman Ribs restaurant, and the National Teachers Academy. A sign over the I-90 expressway acknowledges the concert with a play on Bennett’s lyrics: “Get a sober angel to drive and there’s no problem.” Bennett performs “Hot Shower” with the Chicago Bulls’ mascot, Benny the Bull. During a late verse of “All We Got,” an unmistakable auto-tuned voice emanates from stage left, and Kanye West trots out to join Bennett in finishing the refrain “We know, we know we got it.” On the concert floor, I’m almost lifted off my feet as the crowd rushes the stage.

This evening, Bennett feels like Chicago itself—the unelected mayor of the city. For years, Bennett has actually teased the idea of making that relationship more official (in a 2015 track, he said: “They screaming Chano for mayor / I’m thinking maybe I should”), and after his $1 million donation to Chicago Public Schools in 2017, his fans started a petition for him to run.

But in 2018, after Mayor Rahm Emanuel stepped down, Bennett backed two separate candidates for the job instead, first donating $400,000 to a young policy consultant named Amara Enyia, and then, after she couldn’t muster enough votes in the primaries, advocating for Toni Preckwinkle (whom his father was working for). Both lost. Is Bennett reconsidering a campaign?

“I don’t know,” he says. Running for office is one thing, but when it comes to actual governing, “the decisions are always either reformist at the most, or maybe conservative, but they’re never radical. And I feel like if I was in that position, I’d just lose my mind understanding how many things are wrong and being a part of that shit.” Not only does he agree with the sentiment that governing is like trying to turn a very big ship—it’s inherently slow, but “the ship itself is flawed,” he says, getting a bit more passionate. “It’s a slave ship, in reality, and it’s a huge caste system within it and it is sinking. So trying to guide it somewhere is whack. We should be trying to get lifeboats or something like that.”

If Bennett’s future isn’t in politics, it could be in publishing. In the track “I Might Need Security,” released before this latest album, Bennett revealed that he had purchased 15-year-old city blog The Chicagoist for an undisclosed amount in 2018: “I bought The Chicagoist just to run you racist bitches out of business / Speaking of racist, fuck your microaggressions / I’ll make you fix your words like a typo suggestion.” He was likely directing his ire at several parties: then Governor Bruce Rauner, who had seriously cut funding to Chicago’s public schools; the Chicago Sun-Times, which had called Bennett a deadbeat dad in an editorial; and Cubs owner Joe Ricketts, who had last operated The Chicagoist and had folded his family’s local media properties when the staffs unionized. (The Fast Company editorial staff is represented by the Writers Guild of America, East.)

To many, this was a shock. Not just that he’d purchased a news site, but that he was claiming he’d control its voice. “A lot of people . . . thought that I was saying, ‘I’m a tyrant.’ ” That’s not the case, he promises. The Chicagoist will relaunch as an app he’s helping to design. It will be a utility, he says, focused less on crime reports or news from City Hall and more on food and culture. “Just creating a city-level directory for everything, and making it more interactive, is my main goal,” he says. Once the platform is built, Bennett plans to bow out, giving an editor complete independence.

But Bennett bristles at the way people reacted, pointing out how common it is for successful black entertainers to receive criticism when they try to change lanes (witness Jay-Z’s purchase of the Brooklyn Nets or just about every business Oprah has pursued). And besides, the former Chicagoist owners “weren’t doing that great of a job!” he says.

Indeed, publishing may seem like a surprising turn for Chance the Rapper, but he’s beginning to look at his career in the longer term and embrace the amorphous archetype of his own future. “I don’t ever say it, but I’m kind of like a child star. I made a lot of decisions around the ages of 17 and 18 that impacted me for the rest of my life.” He hit his career milestones early. “I wanted to be on SNL, I wanted to go to the MTV Video Music Awards. I wanted to meet Kanye West,” he says. “But then it’s like, life goes on, and you have to form new goals. So now, I want to have a certain number of kids. I want to be happily married. I want my kids to have a good, easy time in school. I want my parents to live a long time. It’s more intangible things.”

And doughnuts.