CHICAGO — Entrepreneurs see the world through a different lens. Some might say they look through rose-colored glasses, but the truth is, they filter everything through their vision of the endgame.
“One thing that happens with entrepreneurial endeavors is that no one really talks about the tough parts,” said Stephanie Hart, founder and owner of Brown Sugar Bakery in Chicago. “We just always see the finished product.”
By that logic, bakers and entrepreneurs have a lot in common. And perhaps that’s what has driven Stephanie to build Brown Sugar from a small storefront on Chicago’s South Side into a brand with a reputation worthy of lyrics in a Taylor Swift song.
Stephanie opened Brown Sugar Bakery in 2002 when she chose to pursue baking over the corporate lifestyle and walked away from a career in technology.
“I did have that traditional entrepreneurial dream, to track into corporate and do something big in technology,” Stephanie said. “In the ’80s and ’90s, that was the big thing, and I was part of that explosion.”
By the turn of the century, she was tired of pursuing something that she realized might not be her dream after all.
At some point during her business travels, she couldn’t quite satisfy her craving for a sweet treat, so she tried her hand at making cake herself. In the kitchen, Stephanie discovered she could combine her technical skills with a craft that brought her joy.
“I realized that baking met my inner personality of needing things to be exact,” she said. “I’m a mathematician. I like science. I like things that are steady and consistent. With baking, you can build on that foundation and fix the things that aren’t working. The most creativity in baking is figuring out how to keep it the same, and that appealed to me.”
From there, it was a pursuit of happiness.
“I really just wanted to do something that would make people happy,” she said. “When I put a piece of cake in someone’s mouth, it can literally make them happy right at that moment. You can see it on their face.”
But every bakery owner knows that, beyond the joy, tough times often await.
“What happens to many bakers is that we don’t plan for the future, and we don’t have an escape pod,” Stephanie said. “We just bake until we can’t bake anymore.”
To make it through, the entrepreneurial baker needs one important trait to go the distance. More than grit, determination and pure passion, they need stubbornness.
That’s something that Stephanie herself admits she has in spades. It’s what’s gotten her through the times when business was slow, and she didn’t know if she could make rent or keep the lights on. It kept her going when she was eliminated from a Food Network competition and when the staff had to field hate-filled phone calls.
“[Stubbornness] is just part of my personality,” Stephanie said. “When I look back on it all, a normal person probably would have quit, but I guess I have a high tolerance for pain. This is what I set out to do, and I wasn’t going to stop. For entrepreneurs, you need insane persistence and pain tolerance.”
It’s what led to a James Beard Award nomination, notoriety in the worlds of entertainment and politics, a foray into manufacturing at scale, and the acquisition of another longtime Chicago-area cake brand. And she got there one cake at a time.
“I’ve been working to get beyond one cake at time for a long time,” Stephanie said, celebrating the automation she’s invested in for her first manufacturing facility. “It’s always been my goal to make more cakes.”
This story has been adapted from the March | Q1 2024 Craft to Crumb mini-mag. Read the full story in the digital issue here.


