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 Social Works 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 Social Works.
Bennett’s closest childhood friend, Justin Cunningham, is
now the executive director of Social Works. Reese White,
a friend from middle school, sits on Social Works’ board
and helps with marketing. Essence Smith, whom Bennett
and Cunningham met during homeroom orientation their
freshman year of high school, is Social Works’ 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 orga-
nized 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 elec-
tives, stacking two biology classes in the same day, and
enrolling in summer school. Still, Bennett says, he se-
cretly 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.
Time he gets up
“Today I woke up at 4.
I have a fresh baby,
so I wake up real
early. [Otherwise I’m
up] by 7 or 7: 30.
I’ve got to take my
daughter to school in
the morning. And
I just wake up early.
I don’t know why.”
The days are long for Chancelor Bennett.
First thing he does
in the morning
“I talk to my wife.
Usually, we wake up
How he handles
“I’m in the business of
having to use social
media, and I’m of the
generation that re-
ally, like, made social
media what it is. So
it’s something I’m on
all day. All the time. I
think it’s definitely un-
healthy, for sure!
It’s just the reality of
Last thing he does
Time he goes
and 2 a.m.