Bootstrapping to business-savvy: Relationships are everything


CHICAGO — It wasn’t all that long ago that Stephanie Hart, owner of Chicago-based Brown Sugar Bakery, was living month-to-month with her ingredient procurement and other resources. It’s not an unfamiliar story to many independent bakery owners.

So, how did she make the leap from her first little shop on Chicago’s South Side to having a second location at the iconic Navy Pier and creating product at scale for both locations, as well as direct-to-consumer?

It wasn’t easy, but she had a little help.

“I started by baking one cake at a time,” Hart said. “I’d buy what I needed for today, make it, sell it and go back to the store.”

As the business grew, Hart found herself driving from Chicago to Indiana several times a week to meet with her Dawn Foods representative.

“That’s how I financed my business,” she said. “I bootstrapped beyond compare.”

At that time, the original Brown Sugar Bakery took up 700 sq. ft. Today, the flagship bakery on 75th Street is just a few doors down from that original location. Only now, the team works seven days a week in more than 2,000 sq. ft. of space to stay ahead of orders.

Working ahead has been one of the biggest lessons Hart has learned in producing at scale, especially after opening the second location.

“When you open up one store and then another, and there are bakers at each location, it can be a nightmare,” Hart said. “That’s when you have to start thinking differently.”

While the 75th Street bakery is closed to the public on Mondays, it’s constantly in production to supply the Navy Pier location as well as wholesale accounts and online orders for its signature layer cakes, cupcakes, cheesecakes and other items.

“All of our wholesale orders go out on Sundays and Mondays,” Hart said.

As the business has grown, so has her relationship with Dawn Foods, thanks to the efforts of Dawn CEO Carrie Jones Barber.

“I had gone from coming to Indiana twice a week buying ingredients a few bags at a time, to spending six figures,” Hart said. “I was a little bakery who was all-in.”

As Jones Barber stepped into her leadership role, she recognized Brown Sugar’s significant growth and personally stepped in and got to know Hart.

“She shook things up,” Hart said. “She shook up the old school and brought in a new school way of thinking where we’re developing partnerships.”

Since then, their partnership has blossomed.

“That’s been our relationship ever since,” she said. “They’ve been extremely supportive of me and led me into areas I previously couldn’t get into.”

Three years ago, Hart bought a 10,000-sq.-ft. candy factory with the primary intent to increase her bakery production. While the facility helped in that regard, Hart also added specialty candies and ice cream to her product line.

Hart welcomes other bakers and entrepreneurs to visit her bakery to ideate, share best practices and learn from one another. After 21 years running Brown Sugar Bakery, Hart hopes that her journey from a bootstrapping entrepreneur to a successful business owner and James Beard Award nominee can help other bootstrapping bakers find success as well.

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