Kilwins owner named Illinois Small Business Person of the Year by SBA
Kilwins franchise owner Jacqueline “Jackie” Jackson stood in her Andersonville store near glass cases full of decadent truffles, caramel apples and nut caramel turtles like the ones her late mother loved.
After several rough starts running a string of Kilwins chocolate shops, Jackson’s perseverance was recognized Thursday at an awards ceremony with family, friends and officials.
She was named the Illinois Small Business Person of the Year by the U.S. Small Business Administration (SBA) Great Lakes region. Jackson is a model of “resilience, innovation, and entrepreneurial spirit,” said Geri Aglipay, SBA regional administrator, who presented the award.
From left to right: U.S. Small Business Administration Regional Administrator Geri Aglipay, Kilwins owner Jackie Jackson and Illinois Deputy District Director Mark Ferguson at Kilwins’ Andersonville store, 5224 N. Clark St. Jackson received the SBA’s Illinois Small Business Person of the Year award.
Anthony Vazquez/Sun-Times
Her journey “is not just one of success, but of triumph over adversity, because like many business owners, she has had her share of setbacks that would have made many people give up,” Aglipay said.
In spite of hurdles including store break-ins, the pandemic and personal challenges, “she refused to let her dreams go,” Aglipay said.
Jackson joins previous winners of SBA awards like Ben and Jerry’s, Callaway Golf, Chobani, Dogfish Head Brewery, Stonyfield Farm, Pacifica Beauty, Maui Brewing Co. and Tom’s of Maine — companies that were once small businesses but are now national household brands.
The administration conferred the award during National Small Business Week, in recognition of 33.5 million small businesses across the U.S. that “power our economy and are the backbone of our communities.”
Since 2021, there have been 543,000 new business applications in Illinois, according to the federal agency. Across the country, businesses are starting at rates 65% faster than pre-pandemic levels, said the SBA.
Jackson owns five Chicago area Kilwins, the Michigan-based chocolatier and ice cream shop founded in 1947 that now has outlets in some 26 states.
A native of Brainerd Park, Jackson opened her first Kilwins more than a decade ago in Orland Park. Today, she has two locations downtown, on Michigan Avenue and at Navy Pier, a store in Andersonville, Geneva and Evanston. She expects to open a River North store this month. Her staff has grown from 10 employees to more than 75.
In June, Jackson also plans to open a Fatburger franchise in Chatham. She was part of the team that last year opened a Fatburger in Orland Park at 15110 S. La Grange Road.
To bring the burger chain back to the southwest suburb, she worked with NBA players Anthony Davis Jr., Derrick Rose and Tim Hardaway Jr., as well as Toi Salter, managing partner of A.D.T.J. Development. Rapper Kanye West opened a Fatburger franchise at the same Orland Park location in 2008 but closed it in 2011.
Smell of chocolate
Jackson was a Chicago Public Schools teacher in the 1990s and earned a masters in education from Loyola University Chicago, then became a property investor.
But she fell into a depression after her mother died in 2006. Her interest in real estate dried up. “I had to find something with a sense of passion and purpose,” she said.
During a visit to Fort Lauderdale, Florida, she stumbled on Kilwins. The shop’s sweet aroma reminded her of childhood and her mother.
“She used to love turtle candy,” Jackson said. “I knew if she was still on earth she would love this store.”
She spotted a sign in the shop about opening a Kilwins franchise and immediately looked into bringing the retailer to Chicago. She even visited every Kilwins store near Fort Lauderdale as part of her initial research.
But it was a tough journey. She opened her first Kilwins around 2008 — during the Great Recession — in Orland Park. The business failed even after she mortgaged her house and dipped into her 401(k) retirement fund.
The “timing was wrong,” Jackson said. “I thought my life was over. But I had no choice; I had to keep going.”
She broke her Orland Park lease and opened a store in Old Town. But that store was robbed and after other incidents of crime, she closed the shop in 2013.
Jackson also opened a Kilwins in Hyde Park around 2012. The chocolate company initially didn’t want to set up shop in Hyde Park, since it’s not a tourist destination. And after setbacks with her first two stores, Jackson “knew it would be challenging to get a bank to believe in me.”
She got financial support from Hyde Park’s biggest resident — the University of Chicago, which was pushing a revitalization of 53rd Street by offering commercial space to various shopping and dining tenants. She also borrowed money from her brother, who tapped his retirement fund.
Twelve years later, Kilwins has become a staple of Hyde Park, where she now lives. “The community has been phenomenal,” she said.
A variety of chocolate treats on display at Kilwins’ Andersonville shop at 5224 N. Clark St.
Anthony Vazquez/Sun-Times
Trapped on Michigan Avenue
For a decade, Jackson didn’t take a salary and continued to overcome major challenges like the pandemic. After the pandemic-induced lockdowns, business at her Hyde Park store plummeted 90%.
When protests flared after the murder of George Floyd in 2020, Jackson and her daughter, Janel, now 30, were trapped in the Kilwins’ Michigan Avenue store. The pair “drove downtown around midnight thinking we would do a quick board-up, but it was insane,” Jackson said. It was “very scary, full of active looting and we were trapped the entire night.”
Jackson’s shops weathered the pandemic with financial support from the federal Paycheck Protection Program and Economic Injury Disaster Loan program, as well a grant from the University of Chicago, the city of Chicago and other sources.
But more challenges awaited. In November 2021, her Hyde Park store was damaged after a shooting on 53rd Street, with its windows shattered by bullets. Even though the busy and lucrative holiday season was approaching, Jackson made the difficult decision of closing the store to take care of her mental health in the wake of the latest traumatic experience.
She credits her recovery to community support and customers sending notes of encouragement. “That really inspired me to say, ‘We got to re-open,’” she said.
She renewed the lease on her Hyde Park store and took on renovations, which are periodically required by Kilwins. The shop re-opened in July 2022 and last year, the business won a $250,000 city grant to expand and build an outdoor patio space.
Jackson envisions the new “Chocolate Garden” as a safe haven behind the store that will give the “community a sense of security and space,” she said. It’s slated to open in July with capacity to host around 200 people for events.
Janel Jackson, left, with her mother and Kilwins owner Jackie Jackson, who holds her Illinois Small Business Person of the Year award from the U.S. Small Business Administration.
Anthony Vazquez/Sun-Times
Another bright spot is her daughter’s involvement in the business. Janel Jackson has been working at Kilwins since she was 14 years old and became her mother’s business partner after graduating from college. She also recently graduated from an SBA business development program.
Jackie Jackson said she started therapy after the Hyde Park shooting and learned a new approach to life.
“I have learned to live by faith and not fear. I deeply believe God has protected me and is forever giving me favor,” she said. “My plans are to continue my Kilwins expansion to make a significant impact on communities and families. This is my passion and purpose. It’s been bittersweet.”
Jackson said she continues to grapple with operational struggles such as inflation. Cost of supplies, labor, rent, taxes, construction, electricity and other expenses “are getting totally out of control,” she said. Her chocolate supplier is raising costs by 8%, as rising temperatures and weather conditions have damaged cocoa crops in West Africa, sending prices skyrocketing.
Her advice to other small business owners?
“Things will happen but you got to pick up and keep going. Don’t give up. It’s going to be tough.”
