Kilwins owner named Illinois Small Business Person of the Year by SBA

Kilwins franchise owner Jacqueline “Jackie” Jackson stood in her Andersonville store near display cases filled with decadent truffles, caramel apples and nutty caramel turtles like the ones her late mother loved.

After several rocky 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 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 entrepreneurship,” said Geri Aglipay, SBA regional administrator, who presented the award.

Anthony Vazquez/Sun-Times

His journey “is not just one of success, but one of triumph over adversity, because like many entrepreneurs, he has had his share of setbacks that would make many people give up,” Aglipay said.

Despite obstacles that include store violations, the pandemic and personal challenges, he “refused to let go of his dreams,” Aglipay said.

Jackson joins previous SBA award winners such as 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 presented the award during National Small Business Week, in recognition of the 33.5 million small businesses in the US. USA who “drive 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 65% faster than pre-pandemic levels, the SBA said.

Jackson owns five Chicago-area Kilwins, the Michigan-based chocolate and ice cream shop founded in 1947 that now has outlets in about 26 states.

A native of Brainerd Park, Jackson opened her first Kilwins more than a decade ago in Orland Park. Today, it has two downtown locations on Michigan Avenue and Navy Pier, a store in Andersonville, Geneva and Evanston. She hopes to open a River North store this month. Its 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, he worked with NBA players Anthony Davis Jr., Derrick Rose and Tim Hardaway Jr., as well as Toi Salter, managing partner of ADTJ Development. Rapper Kanye West opened a Fatburger franchise in the same Orland Park location in 2008 but closed it in 2011.

I smell like chocolate

Jackson was a Chicago Public Schools teacher in the 1990s and earned a master’s degree in education from Loyola University Chicago, then became a real estate investor.

But he fell into a depression after his mother died in 2006. His interest in real estate dried up. “I had to find something with passion and purpose,” he said.

During a visit to Fort Lauderdale, Florida, he stumbled upon Kilwins. The sweet aroma of the store reminded him of childhood and his mother.

“They used to have turtle candy,” Jackson said. “I knew if I was still on earth I would love this store.”

She saw a sign in the store about a Kilwins franchise opening and immediately sought to bring the retailer to Chicago. He even visited every Kilwins store near Fort Lauderdale as part of his 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 home 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 move on.”

She broke her Orland Park lease and opened a store in Old Town. But that store was robbed and after other criminal incidents, she closed the store in 2013.

Jackson also opened a Kilwins in Hyde Park around 2012. The chocolate company initially did not want to set up shop in Hyde Park, as it is not a tourist destination. And after setbacks with his first two stores, Jackson “knew it would be a challenge to get a bank to believe in me.”

He obtained financial support from Hyde Park’s largest resident, the University of Chicago, which was pushing for the revitalization of 53rd Street by offering commercial space to various store and restaurant tenants. He also borrowed money from his brother, who tapped into his retirement fund.

Twelve years later, Kilwins has become a staple of Hyde Park, where he now lives. “The community has been phenomenal,” he said.

Anthony Vazquez/Sun-Times

Stuck on Michigan Ave

For a decade, Jackson didn’t take a paycheck and continued to overcome major challenges like the pandemic. After the pandemic-induced lockdowns, business at its Hyde Park store fell by 90%.

When protests broke out after the killing of George Floyd in 2020, Jackson and his daughter, Janel, now 30, were trapped in the Kilwins’ Michigan Avenue store. The couple “drove downtown around midnight thinking we’d do a quick board, but it was crazy,” Jackson said. It was “very scary, full of active looting and we were stuck all night.”

The Jackson stores weathered the pandemic with financial support from the federal Paycheck Protection Program and the Economic Disaster Loan Program, as well as a grant from the University of Chicago, the City of Chicago and other sources.

But more challenges awaited. In November 2021, his Hyde Park store was damaged after a shooting on 53rd Street, with its windows shattered by bullets. Even as the busy and lucrative holiday season approached, Jackson made the difficult decision to close up shop to take care of his mental health in the wake of the latest traumatic experience.

He credits his recovery to community support and customers sending notes of encouragement. “That really inspired me to say, ‘We have to reopen,'” he said.

She renewed the lease on her Hyde Park store and took on renewals, which are periodically required by Kilwins. The store reopened in July 2022 and last year, the company won a $250,000 city grant to expand and build an outdoor space.

Jackson envisions the new “Chocolate Garden” as a safe haven behind the store that will give the “community a sense of safety and space,” he said. Its opening is scheduled for July and it has the capacity to host around 200 people for events.

Anthony Vazquez/Sun-Times

Another positive point is the involvement of his daughter in the business. Janel Jackson has worked at Kilwins since she was 14 and became her mother’s business partner after graduating from college. He also recently graduated from an SBA business development program.

Jackie Jackson said she began therapy after the Hyde Park shooting and learned a new approach to life.

“I learned to live by faith and not by fear. I deeply believe that God has protected me and always favors me,” he said. “My plans are to continue my expansion of Kilwins to make a significant impact on communities and families. This is my passion and purpose. It was bittersweet.”

Jackson said it continues to grapple with operational struggles such as inflation. The cost of supplies, labor, rent, taxes, construction, electricity and other expenses “are getting totally out of control,” he said. Its chocolate supplier is raising costs by 8% as rising temperatures and weather conditions have damaged cocoa crops in West Africa, sending prices soaring.

Your advice to other small business owners?

“Things will happen but you have to pick yourself up and keep going. Don’t give up. It’s going to be hard.”