Sweet Success: Kilwins Owner Named Illinois Small Business Person of the Year

This Mother’s Day weekend, the Chicago Defender celebrates dynamic Black women excelling in their careers while guiding and nurturing their families.

I knew I wanted to do something with entrepreneurship, but I didn’t know what it would be. – Jacqueline “Jackie” Jackson

Walking into Kilwins in Andersonville is like entering a wonderland of sweetness. As soon as you open the door, the air is filled with the delightful aroma of chocolate, caramel and vanilla, instantly awakening the senses and inducing pure excitement. Ice cream is also served in the cozy space, where every sweet craving is effortlessly satisfied.

Recently, Geri Aglipay, the Regional Administrator for the U.S. Small Business Administration Great Lakes region, presented the Illinois Small Business Person of the Year award to Jacqueline Jackson, owner of Kilwins, at a brief ceremony at the store. 

As a Chicagoan and a Black woman entrepreneur, Ms. Jackson was honored for embodying excellence, innovation and an entrepreneurial ethos.

Thriving and Emerging

During the event, attendees gathered around to listen to notable speakers, including Aglipay, Jackie Jackson and her daughter Janel, Illinois Deputy District Director Mark Ferguson, Outreach and Illinois District Office Marketing Specialist Peggy Rayson, Alderwoman Leni Manaa-Hoppenworth of the 48th ward, Chamber of Commerce staff, and a multitude of family, friends, mentors and classmates from the T.H.R.I.V.E. Emerging Leaders Reimagined program that Janel attended to further her business legacy.

Following the speeches and the award presentation to Jacqueline, everyone enjoyed complimentary ice cream, fudge and candy samples. 

Building on America’s Small Business Boom’

U.S. Small Business Administration Regional Administrator Geri Aglipay, Kilwins owner Jackie Jackson, and Illinois Deputy District Director Mark Ferguson

During National Small Business Week, the SBA highlights President Biden’s dedication to creating a fairer business environment for small enterprises in Illinois and nationwide. This year’s NSBW theme, “Building on America’s Small Business Boom,” highlights the remarkable surge of 17 million small business applications since Biden assumed office.

Ferguson added, “The SBA offers many resources, including over 40 Small Business Development Centers, SCORE, and various resource partners. Our resource partners are invaluable, providing essential guidance to entrepreneurs. We assist them to the best of our ability, stepping in when necessary to give more direction. Whether refining a business plan or navigating the process of securing a loan or contract, we offer guidance to ensure their success.”

Small businesses like Jackie’s and Janel’s Kilwins location exemplify this vision. Janel herself participated in the T.H.R.I.V.E. graduation program, highlighting the impact of initiatives in empowering entrepreneurs.

Aglipay said,  “You can visit sba.gov to access resources tailored to your needs. The first step is to connect with us. We are committed to equity, particularly for historically marginalized communities lacking financial, knowledge, and social capital access. By working together, SBA wants to build generational wealth and ensure an inclusive, competitive, and equitable economy.”

The 2024 SBA T.H.R.I.V.E. Emerging Leaders Reimagined program is open for applications until May 10. This program empowers applicants with skills to overcome obstacles hindering business growth. Through this enterprise, the program helps participants elevate their leadership skills, gain MBA-level insights, receive tailored business guidance while forging valuable connections with fellow entrepreneurs, consultants, and experts.

A Mother-Daughter Duo Builds a Legacy

Jacqueline Jackie Jackson and her daughter Janel Jackson

After losing her mother in 2006, Jackson found solace after taking a trip that landed her in a shop of ice cream treats from her childhood. She felt her mother’s memory and spirit around her for motivation. This poignant memory inspired her to launch the first Kilwins ice cream and fudge shops in Chicago. From there, she became instrumental in introducing the franchise to neighborhoods like Hyde Park, aiming to spread joy and tradition.

Jackson’s determination remained steadfast despite enduring challenges such as robberies and the upheaval from the COVID-19 pandemic. Her vision expanded beyond mere business success: she aimed to foster growth in underserved communities across Chicago. Over the years, her efforts have borne fruit, with seven flourishing stores in Illinois.

From humble beginnings in 2012 with a single store and ten employees, Jackson’s enterprise has blossomed, now providing employment opportunities for over 75 individuals. Her journey epitomizes resilience, community investment and the power of cherished memories to inspire meaningful change.

Starting at Kilwins at just 14 years old, Jackson’s daughter Janel has evolved into her mother’s business partner. Along her journey, she has grown within the company and developed a strong business mindset.

“I had to recognize that I possessed valuable business knowledge and could contribute meaningfully to her endeavors. It took effort to break free from negative thinking patterns and insecurities,” said Janel. 

“Fortunately, I found the opportunity to learn and grow through programs like the SBA program. By seeking knowledge and support, I gradually rebuilt my confidence and became a more effective asset to my mother’s business and personal growth.” 

The Next Chapter in Jacqueline Jackson’s Journey

In June, Jackson is poised to broaden her entrepreneurial horizons by launching a “Fatburger” franchise in Chatham. Additionally, Jackson is committed to nurturing her team’s growth, empowering them to forge their own paths. She eagerly anticipates sharing in their moments of success.

Jackson aims for her team to extend beyond being employees. She envisions them as future partners. 

“Some of my team members have been with me since they were 16 and continue to grow alongside me. As I approach retirement, I intend to ensure they have a stake in the business, granting them equity and ownership.”

“I recall how my mother, even in her absence, influenced families by empowering them to achieve milestones like buying their first homes or cars,” said Jackson. 

“Now, I find similar fulfillment in guiding my team through significant moments in their lives, whether it’s negotiating a fair deal on a car or addressing financial concerns. They’re like family to me, and I’m committed to their growth and well-being.”

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