Joblessness, homelessness, and the pandemic didn’t stop Kalamazoo man from starting his own business

A business that started out of a hotel room is now an online and brick-and-mortar enterprise.
Editor's note: This story is part of Southwest Michigan Second Wave's On the Ground Kalamazoo series.

“Drip” is a good thing. It’s a slang term to compliment a person’s sense of style, as if to say, “She’s cool,” or “He has swag” or “She’s hot.”
Roosevelt Lee-Fleming’s sneakers have always had “drip.” As a teen with little money, he learned to meticulously clean, repair, and paint his sneakers to keep them looking good. Now he does that and more for anyone who wants to keep looking good.
He does that at The Drip Sneakers, a sneaker-restoration business he started in the spring of 2019 but opened as a brick-and-mortar location in May of 2021 at 315 N. Burdick St. in downtown Kalamazoo. The business also sells and trades hard-to-find sneakers and sports jerseys. And it has branched out to sell women’s apparel and other items, primarily online.
“I was just giving myself affirmations – by the second year, two years of me doing this business, I’m going to have a location,” says Lee-Fleming, 41, of Kalamazoo.
That was a lofty goal to set in mid-2020 while doing sneaker repair work out of a hotel room on the west side of Kalamazoo while most people were quarantining at home to avoid COVID-19. At the same time, he was homeless. Lee-Fleming had lost his job as a maintenance engineer in May of 2019 and was unable to find a place he could afford after his apartment lease ended in September of 2019.
The Drip Sneakers cleans, repairs, and restores sneakers. The new business is at 315 N. Burdick St. in downtown Kalamazoo.“All the things I had, I put them in storage, put it in other people’s houses, and prayed over it,” he says.
Times were tough, he says. But he had already decided to go into business for himself.
Jumping into business
“As soon as they (his employers) told me, ‘Hey, we’re not going to bring you back,’ I said, ‘Man, I gotta do something else.’”
So he parlayed skills he had been developing since age 15 into a business that would sustain him as he worked to get back on his feet. Lee-Fleming was not able to afford a $120 pair of Nike Air Jordan sneakers that other kids wanted or had when he was a teen in Benton Harbor.
“Growing up my mom and dad couldn’t or, actually, wouldn’t afford them,” he says with a laugh. “They wouldn’t buy Jordans. That was an unnecessary extra cost, anything like that.”
But he wanted them. So at age 15, he talked his grandmother into giving him $50 for a pair of Air Jordans that a less-fashion-conscious but better-heeled friend was selling for $60. Lee-Fleming worked to get the $10 he needed to pay the difference.
“And when I got that first pair,” he says, “anytime a scuff would come on them, I wiped them off.”
Roosevelt Lee-Fleming began collecting sneakers in high school. He used the proceeds of selling off some of that collection to finance his store, The Drip Sneakers.With artistic skills, he says, he learned how to paint them and he found creative ways to wash and repair them. As expensive new shoes were introduced, he repeated the “ask grandma” pattern.
“I had a collection of about 30 shoes over the years,” he says. “People would always think I had way more just because I always took care of them.” Sneakerheads (people who know, love, and want to wear the latest or rarest sneakers), would appreciate his older shoes “looking like they just came out because of how I painted them and I’m very meticulous with it,” he says.
He sold about two-thirds of that collection to help buy the supplies and inventory he needed to start his business. By doing that, he says he made more than $6,000. “And I reinvested that right back and bought some more shoes.”
It takes a lot of guts to start a business under those circumstances, says Debi Howe, chairperson of Southwest Michigan SCORE. But the business counselor says, “I love people who get it done, who see the opportunity and just do it. He could have said, ‘Poor me. Look at me.’ But he didn’t. He turned it around and said, ‘I’m going to do this.’”
The right thing at the right time
Shoe restoration is a niche business that spins out of the multibillion-dollar U.S. sneaker market. For some, it is an investment. “It’s a micro-niche,” Lee-Fleming says. “A lot of people love sneakers and jerseys and things like that.” Now it is leading him to other online sales.
The bulk of Lee-Fleming’s shoe repair work has been a result of word-of-mouth advertising that started in April of 2019 when a friend did an online posting and raved about the sneakers Lee-Fleming restored.
“He gave me a pair of Air Jordans,” Lee-Fleming says. “He mowed the lawn in them. They had mold in them.”
Although it sells and restores lots of men’s sneakers, women are the best customers for The Drip Sneakers. It also sells unique women’s apparel.However, Lee-Fleming was able to restore them well enough to allow his friend to resell them for $500. And the interest his friend’s social media post generated inspired him to create a webpage that he dubbed “The Drip Sneakers.” That page, TheDripSneakers.com, has been joined by a site on Facebook (The Drip Sneakers LLC) and Instagram (@thedripkzoo).
In the months since his business started, buying and re-selling hard-to-find and collectible basketball shoes and sports team jerseys has become a major focus for Lee-Fleming. It has grown to account for about 70 percent of his sales. And online sales of unique women’s apparel has become a growing part of the balance of his business, which is thus far a two-man operation. Lee-Fleming has an assistant to help with most aspects of his operation.
“This is a business where if you have the right thing at the right time, people will come from afar,” he says. He’s had buyers from as far away as Canada and Pennsylvania.
In the meantime, “Women are the premier shoppers for The Drip Sneakers because when they come, they not only shop for themselves,” Lee-Fleming says, “they tend to remember themselves, their children, and their men. And usually all at once. Men, we tend to say, ‘Let me get something for when I go out tonight or let me get something for my girl. It’s her birthday. … Women tend to put it all together.”
When he was young, his grandmother helped finance Roosevelt Lee-Fleming's collection of sneakers. Now he has turned what he learned as a collector into a business.So he is growing a clothing boutique at his location that he hopes to have fully stocked by the first week of December. The Drip Sneakers presently uses about 650 square feet of space at its North Burdick Street location. That is the total area of three small offices that previously housed former Michigan State Rep. Jon Hoadley. A storefront office space there continues to be the local office of Michigan Rep Julie Rogers.
Some particulars
At The Drip Sneakers, Lee-Fleming charges $25 for normal sneaker cleaning, and $40 to $80 to clean, repair, reglue, paint or do other work on a pair of shoes. He strives to do whatever is necessary within three days of receiving anyone’s shoes.
“Even when people tell you to take your time,” he says, “I keep them no longer than three days. I know they can’t wait to get their shoes back.”
For sneakerheads, Lee-Fleming says the most popular shoe in his collection was a Volt neon green pair of Nike Air Foamposites. They were released in 2012. Also known as Penny Hardaway’s (for the hoops star for whom they were designed), they are now worth about $520. Lee-Fleming also sold a pair of Jordan 1 Bred sneakers for $400. That shoe was released in 2005 and according to one online source, a pair would now be worth about $1,100.
The pride of the shoes he is now selling is the Maya Moore Jordan 1 and the Maya Moore Jordan 10, each named for retired WNBA basketball star and social activist Moore. The rare shoes are expected to sell for $400 to $500.
On the streets
From September of 2019 to September of 2020 Lee-Fleming was homeless.
“I built my business through COVID and homelessness,” he says. He also continued to raise his young son, LeAngelo, now about 3 and one-half years.
“I stayed in hotels and I had some homeless nights outside — where I would let my baby sleep,” he says. “I’d go to the park. He would sleep at night and I would stay up.”
Roosevelt Lee-Fleming learned to clean and restore sneakers as a teen. He keeps a colorful array of shoelaces as part of that.Lee-Fleming described himself as a single father after he parted ways with his son’s mother, a former girlfriend. But fearing he might lose parental rights, he didn’t tell her how tenuous his living situation was.
“She didn’t really necessarily know because when I had him, I had him,” Lee-Fleming says. “Part of my thing is like ‘No complaints.’ And then I didn’t want to lose him. That was a big thing for me. … So at that point, I was in the mindset to do whatever I could to be the best dad.”
He received unemployment benefit payments. He used about half of a $3,000 federal income tax return to pay his bills and the other half to invest in his business. After months of staying with friends and sporadically living on the streets — occasionally at Bronson Park — he was able to rent a hotel room for weeks at a time. Last fall he was able to find a full-time place to live.
Lee-Fleming says the experience has given him a soft spot in his heart for people living on the streets. “Anyone can become homeless,” he says. “But a lot of people don’t have the mindset to come out of it.”
Of the mental state of long-term homeless people, he says, “There’s a brokenness to it” and there is the feeling that no one cares about you. He says he thanks God for giving him the skills and knowledge, as well as his son as motivation, to do the things he is doing now.
Roosevelt Lee-Fleming stands in the hallway of some of the space used by The Drip Sneakers at 315 N. Burdick St. in downtown Kalamazoo.His son’s mother is now very much involved in their son’s life. He says, “We co-parent.”
Making another strong comeback
Lee-Fleming’s family relocated to Washington state when he was age 5. But he spent time living there and in Michigan. After high school, he hung out with some friends he had known for years, although he knew they sold drugs. He was with them when they were caught with drugs trying to return to Michigan from Chicago and were arrested on federal drug charges.
Believing that he would be set free based on his otherwise clean record (which included college courses he took in Washington en route to a career in music and the arts) and what he believed was his minimal involvement with the drugs, he was shocked when his two friends testified against him and he received the stiffest punishment of the three. They received three- and four-year prison terms. He served nearly 10 years of a 12-year sentence before being released just before his 28th birthday.
Since then, Lee-Fleming has talked about business and entrepreneurship with students at Kalamazoo Central and Loy Norrix high schools as well as Hillside Middle School. He reserved a talk about his arrest and years in prison for 14- to 16-year-olds involved in Prevention Works, a program that tries to educate and engage at-risk youngsters and put them on track to make good decisions in life. The nonprofit organization is located at 309 N. Burdick St., next door to Drip Sneakers.
Roosevelt Lee-Fleming became used to juggling problems as he started his Kalamazoo business, The Drip Sneakers. Trendy sneakers were something his parents wouldn’t pay for when he was a teen.While showing them how to clean shoes this past summer, Lee-Fleming told them the story of a naive teenager named Tyrone who got involved with the wrong crowd, made mistakes, went to prison, and struggled to get his life on track. At the end, he told them he was “Tyrone” and they were stunned by how far he has come.
“He decided to tell his own story once and not use his name,” says Molly Trueblood, associate director of Community Impact for the United Way of the Battle Creek and Kalamazoo Region. “He just told the story and the kids were really inspired. They were like, ‘Well, that person really overcame some stuff.’ And he said, ‘Yeah, that was me.’ and that really surprised them.”
Lee-Fleming has gone on to become a member of the United Way’s Small Business Cabinet, helping the organization’s Business Grant Review Committee make decisions about contributions to small businesses.
“He is really passionate about his work but also about giving back to the community,” Trueblood says. I don’t think that I’ve ever met anybody so dedicated to passing on what he’s learned, passing on the resources that he’s gained to kids, and to young people — teaching them to do shoe restorations while he’s trying to run his business.”
Roosevelt Lee-Fleming of Kalamazoo holds one of the sneakers that have been the focus of his business, The Drip Sneakers LLC.Lee-Fleming says he wanted to leave the students with the idea that there are people who don’t care and who are waiting for them to mess up. But “these people (at Prevention Works and other organizations) that are here right now, that they (the students) don’t want to listen to, that they want to talk back to — care about y'all more than y'all realize.”
Trueblood says, “He cares about his community. And he always brings a smile and a laugh to everyone he engages with, everybody he meets.”
Some lessons learned
Lee-Fleming says prison taught him not to let anyone else control his future.
“For one thing, it just helps me to be my own man, to make my own decisions,” he says. “No one can pressure me into nothing. And that’s a thing. A lot of the world seems to need someone to tell them what to do, or how to live, or how to be. I had so much of that. I couldn’t control people telling me what to do and where to go. And it drove me crazy.”
He says he knew that was not his destiny.
Lee-Fleming says he was grounded in the business world by his mother, who he saw operate a licensed daycare center, then return to college to become a teacher. Although he wanted to work in music as a songwriter, she implored him to take college-level business courses after his early graduation from high school.
“I was always about music and the arts and my mom was like, ‘Nope, you need business. That’s what’s going to get you ahead,’” Lee-Fleming says. “So I was like, ‘Alright.’”
During the next few years, he says he does not know into what areas his business may expand although he expects to be very successful. He is sure that he will hire and train another person to do shoe restoration work, perhaps one of the young people he met this past summer. He says he is happy to be building a business that will ultimately benefit his son and he is thrilled that the business has given him a platform to talk to young people.
“He is one of those people who – this is going to sound kind of silly – but who takes lemons and makes them into lemonade,” Howe says. “And even further, he gives everybody a drink of the lemonade.”
Lee-Fleming says he wants to learn to be a good chief executive officer because “And then I want to do it differently. I want to do it my own way because I think there’s a certain level of compassion that’s missing from higher levels of business.”

Photos by Fran Dwight. See more of her work here.
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Al Jones is a freelance writer who has worked for many years as a reporter, editor, and columnist. He is the Project Editor for On the Ground Kalamazoo.