The first day Kareem Edwards arrived at DePauw University in 2003, he was two weeks early, homesick, and quietly wondering whether he’d made a mistake. A kid from Far Rockaway, Queens, raised by a first-generation Trinidadian-American mother who believed in preparation over daydreaming, he had earned his place there through a Posse Foundation scholarship and sheer will.
When the rest of the freshman class finally moved in, he spotted a young woman across the dorm with her family and told his friends he was going to marry her someday. He didn’t even know her name yet. Two decades later, that woman Janelle is his wife, his business partner in spirit, and the person who ultimately pushed him to stop playing it safe.
A résumé that read like a highlight reel
After graduating with a degree in mathematics, Edwards headed to New York and started climbing. He landed on Wall Street, then moved to Lehman Brothers, navigating the firm’s historic 2008 collapse and emerging on the other side with sharper instincts and a growing sense that success and fulfillment weren’t the same thing.
By his early thirties, he was featured on the cover of Crain’s Chicago Business as one of the city’s first 20 in Their 20s. From the outside, everything looked exactly as it should. On the inside, he was already asking a harder question what would it feel like to actually love the work?
That question sent him to the University of Michigan’s Ross School of Business, where he graduated in 2015 and was named a Top MBA to Watch by Poets & Quants. He went on to lead a breakthrough innovation team at Kraft Heinz, helping launch Just Crack an Egg, which Nielsen recognized as a top new product. Then came Google.
The decision that changed everything
Around 2015 and 2016, Edwards began researching franchise opportunities with the same discipline he had applied to every career move before it. He evaluated laundromats, Subway, and McDonald’s. Chick-fil-A kept rising to the top and not because of the chicken sandwiches.
The brand’s local owner-operator model stood apart. There are no absentee multi-location owners. Operators are embedded in their neighborhoods, present in their stores and personally accountable for everything that happens inside. For Edwards, that structure aligned with something deeper than business strategy. He wanted to be visible, to be present, and to watch change happen in real time.
The application process also required Janelle to interview multiple times, a detail that stuck with him. He had grown up without his father and had no intention of his own children saying the same. The fact that Chick-fil-A wanted to know the whole family before handing over a location told him everything he needed to know about the company’s values.
Before fully committing, he spent nights working Chick-fil-A counters after his Google shifts, testing whether the day to day reality matched what he had imagined. It did. He saved money, prayed, and made the leap.
Building something real in the South Loop
The South Loop location at 1106 S. Clinton St. opened in January 2021, in the middle of a global pandemic, with a team of nearly 100 people depending on him to hold things together. Edwards became Chicago’s first and only Black Chick-fil-A owner-operator, stepping into a role that required far more than any MBA had prepared him for.
On any given day, he could find himself functioning as a counselor, a father figure, a babysitter, or a makeshift health resource for members of his team. He built systems, practiced grace, and kept showing up.
Rooted in the community
Eight blocks from the store sits Just Roots Chicago, an urban farming nonprofit serving displaced community members in the area. Edwards and his family got to know the organization and its director personally. When a Chick-fil-A corporate grant opportunity arose, he put the nonprofit forward without hesitation.
That instinct to invest back into the neighborhood reflects how he was raised and what he wanted ownership to mean. His mentors throughout his career have largely been Black women, a fact he carries openly and has worked to mirror in how he leads his own team.
Saturday mornings, Tokyo, and what it all means
On Saturday mornings, Edwards sets the store aside. Swim lessons and ballet come first. His longtime college friend Charles Kuykendoll, who grew up on Chicago’s west side, has been alongside him for years through every grind and pivot. Last spring break they took their families to Dubai. This year, Tokyo.
For a kid from Far Rockaway who arrived at college two weeks early and barely knew anyone, that life built brick by brick, bet by bet is the whole point.
