Tony Acosta and Drew Steckler met over a pair of Nike Dunks.
Both teenage “sneakerheads,” Steckler, a 16-year-old New Trier High School junior, answered a listing Acosta, an 18-year-old Niles North senior, posted online last year for the basketball shoe and negotiated the sale down to $45.
Pretty soon, the two were selling sneakers to each other on a regular basis with Steckler sometimes offloading 50-100 pairs, or $2,000 worth of shoes, to Acosta at a time.
Now they, along with another friend, Aaron Ryba, have become business partners. The trio opened Stride Chicago at 3558 Dempster St. in Skokie in November.
With more than 400 shoes in stock, Steckler said the boutique storefront is a one-of-a-kind in the area, because, if “the price is right,” they purchase just about any sneaker customers bring in, and their inventory has no fixed price tags; they like to haggle and offer deals well below the market rate.
The store is open 4-7 p.m. Monday through Friday — when the young entrepreneurs get out of school — and 11 a.m.-7 p.m. Saturdays and Sundays.
Acosta admitted he needed to be talked into walking away from his individual operation buying and reselling sneakers online, but Steckler’s salesman skills meant he “was good at convincing.”
The two built a friendship and grew to trust each other over the course of their many transactions in 2025, especially as both were no stranger to being scammed by other sneaker sellers, they said.
Steckler said he became hooked on sneakers after his mom bought him his first pair in 2021. Once he lost interest in building his personal collection and decided to sell the shoes he had, Steckler realized he could make good money and meet interesting people trading sneakers.
It became his “dream” to own his own sneaker store, one like the shops his parents brought him to in the city, Steckler said. He found a rundown, long-vacant former barbershop located on a main drag next to Skokie’s acclaimed New York Bagel & Bialy deli, and the teens signed a lease.
They gave themselves just 10 days to get ready — painting the walls, replacing ceiling tiles and renting a truck to haul in a display case — before they opened on Nov. 30, 2025.
Acosta said much of the preparation was accomplished by his girlfriend Bella Albanese, who also helps lace and inventory the shoes, and whom he met in part thanks to a conversation over her sneakers.
The result since opening has been successful so far, Steckler said, as customers are coming in, and they are building up their brand by making videos on social media — something they couldn’t really accomplish when they only sold shoes through apps and websites.
While the teens are younger than the majority of their customers, Acosta said that hasn’t stopped them from connecting over their shared love of sneakers. Already experienced, the teens know what the hottest shoes cost and can guarantee authenticity — they know how to spot the fakes.
That sets them apart from other sneaker sellers who sometimes try to “get people,” Acosta said.
A recent customer was hesitant about buying a shoe for their child and so they knocked down the price to make them happy. Another customer, a local father, hung around after a sale to talk about shoes.
“Sometimes it’s not even about the money, I just love the sales part of it, meeting people, selling something, giving someone a good product and something they’re satisfied with,” Acosta said. “It’s about what sneakers is — it’s a community and people come and talk about it.”
Some sneakerheads may be interested to know the teens just sold a $2,200 pair of limited release “Purple Lobster” Nikes, and their display case holds a $1,000 pair of used Travis Scott x Air Jordans they’re offering for $380. But a rack near the front door also holds sneakers worth $50 and under.
Steckler said his parents didn’t even know about the sneaker resale hustle when he got started, and he and Acosta both said their families and friends were “shocked” when they actually opened a physical shop.
The teens said they still have a lot of work to do, including mounting a sign over their entrance. But for now, they’re just excited about expanding and distinguishing their niche as a hub for “authentic shoes at better prices.”
Steckler affirmed he wants them to be “that first thought in mind when someone thinks of a sneaker store.”
“I think taking risks is the most important thing you can do, especially when you’re young. It’s all about taking risks,” Acosta added.
“If you fail, then OK, then you go back to whatever you were doing before and believing in yourself and taking chances and I think we both know how to do that,” Acosta said.
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