On a sunny March day in his hometown of Chicago, Probability the Rapper makes his strategy to The DuSable Black Historical past Museum and Training Heart for our interview and his SUCCESS photograph shoot. College students there on subject journeys watch with palpable pleasure as Probability emerges from his automobile in his signature snapback with an embroidered “3” on the entrance and “Probability” on the again.

Probability—full title Chancelor Johnathan Bennett—has been well-known in Chicago since he was in highschool, then a nascent rapper with a small however loyal following. As that following grew, so did Probability’s fame. And as that fame grew, so did his fortune—which he instantly began giving freely, first in a hefty donation to Chicago Public Faculties in 2017, then to the county’s psychological well being providers. In 2016, he co-created the Warmest Winter challenge, which created coats that doubled as sleeping luggage for the homeless.

Probability the Rapper by no means had a Plan B.

Since 2012, when Probability launched his first mixtape after graduating from Jones School Prep in 2011, his promise has attracted consideration from established artists desirous to collaborate. Infantile Gambino (Donald Glover), Justin Bieber, John Legend, Shawn Mendes, Megan Thee Stallion, Nicki Minaj, Vic Mensa, Kanye West, Lil Wayne and a couple of Chainz are only a fraction of the circle of artists who have been fast to leap into the studio with Probability.

The whole lot was going in accordance with plan—doubtless as a result of there has solely ever been one. “I by no means had a plan B. Since I used to be 10 or 11, I knew I wished to be a rapper…. I used to be at all times beneath the impression that if I had a fallback plan, I might fall again,” Probability says. “Neither of my mother and father completed faculty…. School was necessary, nevertheless it wasn’t one thing that was absolutely attainable in my thoughts.” 

Individuals had talked about the concept of Probability following in his father’s footsteps and pursuing a future in politics. (Probability’s father, Ken Williams-Bennett, served as Barack Obama’s state director when the previous president was an Illinois senator.) “None of these issues ever actually me,” Probability says. “They really scared me. The concept of being something apart from a rapper at all times scared me.”

That one-track thoughts led Probability from making tracks in his cousin’s recording studio for enjoyable to creating mixtapes handy out in highschool. Then got here the exhibits.

How Probability the Rapper defines success

“I made 4 mixtapes after I was in highschool, and I might attempt to put collectively exhibits at totally different makeshift areas,” Probability remembers. “I really feel like my first massive success was the primary present I produced. I used to be a freshman in highschool, and I did a present referred to as ‘The Remaining MCs.’ I used to be new to the varsity, didn’t know anybody, and I organized a present with all of the rappers and comedians and singers from the varsity. And I closed out the present. It was cool. It was actually cool to give you the chance to gauge my success that means.”

And that’s nonetheless how Probability gauges his success. Having completed an enormous competition in West Africa this January, he says he likes with the ability to put collectively secure, thrilling occasions with free tickets: “That’s what provides me the sensation of success.”

Even with these highschool highs, Probability had each naysayers and cheerleaders. “There was in all probability extra discouragement than encouragement after I was getting began,” he says. “The way in which I converse now, individuals sometimes inform me that I’m articulating my factors and that I’m nicely spoken. And I’ve at all times been good at studying (not essentially good at college), so the avenue of rap music wasn’t aligned with how some individuals noticed me. That confused me, as a result of I might assume, When you assume that I sound sensible, doesn’t it make sense for me to have my job be round phrases?”

However a handful of encouragers he labored with alongside the way in which gave Probability the teachings essential to succeed. He says an after-school program at Chicago’s Harold Washington Library Heart gave him the training he wanted. This system centered on digital media, crafting and collaboration—and it had an open mic. “That was a extremely, actually massive a part of me gaining my fanbase…. I realized use Professional Instruments, document myself and EQ [equalize] my vocals a bit of bit from Simeon Viltz and one other mentor who handed away, Brother Mike Hawkins,” he says.

Monetizing his music

After mastering the artwork of constructing music, although, there was a have to grasp the artwork of monetizing it. That’s the place his merchandise got here in.

“My dad was the one who was actually attempting to take it severely and attempting to place collectively my [debut mixtape] 10 Day,” Probability remembers. “He was paying for the CDs that I used to be burning my music onto. After which I might stand at totally different fashionable spots round Chicago… simply attempting to disperse the music and get it on the market. I at all times felt like the easiest way to get it to any individual and ensure that they have been connected to it—and would actually hearken to it—was that there couldn’t be a paywall. So, I made positive that I gave the mixtapes away at no cost. I might begin with a dialog and say, ‘Please hearken to it. When you prefer it, ship me a message on Fb or Twitter, and if you happen to don’t prefer it, ship me a message on Fb or Twitter. However let me know what you concentrate on it.’ I created these actual, lasting relationships. There are individuals who nonetheless have these CDs with my handwriting on them.”

As soon as the music began reaching increasingly more individuals by means of Probability’s grassroots strategy, he and his father began arguing about what would come subsequent. You possibly can’t make a residing giving music away at no cost. Particularly as an unbiased artist with mixtapes, streaming-only albums and no studio help.

“What we ended up agreeing on was that merchandise can be the easiest way to monetize my music. We paid my good friend’s older sister who had a printing press to make a bunch of shirts with my Twitter title and a few with the title of my newest music. I might promote these at my exhibits and on the library…. That concept ended up snowballing,” Probability says. “I spotted the ability of working with different manufacturers and the publicity that comes with that. I spotted the significance of branding myself and with the ability to create one thing just like the ‘3’ hat, which is now synonymous with me. My music is type of just like the industrial for the hat or the T-shirt or a live performance ticket or any of the ways in which my fanbase can have interaction with what I make.”

Specializing in what he loves to seek out success

It wasn’t simply Probability’s personal model that landed him on the Forbes 30 Beneath 30: Music record in 2015 and the Forbes Movie star 100 record in 2017. (His estimated earnings in 2017 have been $33 million.) It was all of the manufacturers that got here calling: Purple Bull, H&M, MySpace, Nike, Doritos, Package Kat, Dockers, Ben & Jerry’s and, most not too long ago, NBC’s The Voice.

Solely in his 20s, Probability had already completed main objectives he’d set for himself, together with internet hosting and performing on Saturday Night time Stay and profitable Grammys.

The purpose of turning into a millionaire wasn’t on Probability’s record, nevertheless it occurred anyway. “I’ve by no means actually ever judged my successes by how a lot cash I had or how a lot cash I made…. There’s by no means been a second the place I checked out my checking account and felt larger. That’s simply by no means how I felt,” he says.

Actually, Probability is happiest on stage, the place the income, by comparability, is considerably paltry. “I’m very a lot into performing. That’s my favourite a part of making music. I really like to write down, and I like to document,” he says, “however I actually love to really play at a live performance or a competition. And, so, I simply accepted that I’d make little to no cash taking part in exhibits, as a result of I wished the publicity and since I really like the sensation of being onstage. When you get to a degree the place you’re opening for main acts—like Donald Glover [Childish Gambino] or Mac Miller [who passed away in 2018] or Eminem—I obtained paid $1,500 an evening. And I needed to pay for my very own bus, meals and lodging.”

Probability the Rapper: an unbiased artist

And whereas—on an album’s liner notes—collaborations with different artists could appear to be a coterie of buddies fortunately singing collectively, Probability thinks they’ll current different challenges. “It may be a troublesome factor, as an artist, to collaborate. It both signifies that you couldn’t end the music, otherwise you made it and have been impressed by one other artist, after which you need to persuade them to get on board. To attempt to create that magic once more is troublesome generally,” he provides.

Then, there’s the problem of sharing the income. If one particular person writes and sings the music, they maintain the income. However, identical to sharing in every other trade, the extra individuals on a music, the smaller everybody’s paychecks are.

“The cool factor about collaborating with me, versus collaborating with artists which are on a document label, is that past the 50% royalty break up between masters and publishing, there’s additionally a 50% break up between the label and the artist on that grasp royalty,” Probability explains. “For me, if I do a music, I’m my very own label…. So, if you happen to ask me for 15% of the artist web, you’re getting 15% of fifty%. Versus 15% of 15%.”

One potential draw back of being an unbiased artist, though it’s not one Probability ever criticizes, is that with self-releasing music comes self-promotion. Take music movies, for instance. That’s normally a document label expense. However when there’s no label, the manufacturing prices come out of Probability’s pocket.

“I pay for my very own movies…. It’s good to have the ability to create these experiences for everybody round me. None of us had been to Venice, none of us had been to La Biennale di Venezia,” he mentioned of his video for The Highs & The Lows, shot in Italy and France. “These experiences make you a greater artist. They make you a greater particular person. And being in charge of that—with the ability to determine after I wish to take that on, what my price range is for my music, my video or my album artwork—is an autonomy and company that I might by no means wish to hand over.”

Paving the way in which for like-minded artists

Possible as a result of Probability’s eyes are large open in relation to essentially the most troublesome aspect of the music enterprise. “[The music industry] shouldn’t be designed for the good thing about the individuals who produce the work. The concept of any individual who isn’t you proudly owning your masters is a loopy thought. The rationale why that was initially the case was as a result of labels had cornered the market on the printing presses of vinyl,” Probability explains. “Now, there aren’t plenty of mechanical copies being made. However a label remains to be contractually proudly owning the voices of people that spent their complete lives honing their craft and turning into nice writers, nice vocalists and superstars.”

Whereas most artists settle for the truth that the music trade could be fickle, Probability isn’t certainly one of them. His friends are signed to document labels, however Probability’s insistence on sustaining his independence has paved the way in which for different like-minded artists. And it’s earned him a severe cache of awards and nominations. Amongst them are the three Grammys he received in 2017, breaking data by being the primary streaming-only artist to win greatest new artist, greatest rap album for Coloring Ebook and greatest rap efficiency for the music No Downside. (There’s some poetic justice in profitable a Grammy for a music about being chased by document labels.)

How Probability the Rapper pays it ahead

Probability kicked off 2023 by organizing a free music competition in Ghana for round 52,000 individuals, and he’s planning an encore efficiency in 2024 in Jamaica. “Once I consider in one thing strongly, I do my analysis on it and attempt to be as vocal about it as attainable,” he says. “There are occasions when you need to insert your self within the state of affairs to create the change that you just wish to see.”

For Probability, a part of that change comes by means of his nonprofit group SocialWorks, which “goals to empower the youth by means of the humanities, training and civic engagement,” in accordance with their web site, and raises funds to help its 5 group initiatives.

“It’s a heavy duty to be endowed with being an excellent particular person,” Probability says when discussing his ongoing philanthropy. “However it comes from the within, so there’s nothing you are able to do about it apart from keep in your path.”

This text initially appeared within the July/August 2023 concern of SUCCESS journal. Photographs by Nick Onken.