From the very first step you take into Stride Chicago, you are immediately struck by the store’s cleanliness: the gray tiled floor is polished, the hoodies—hanging on a rack in the middle of the store—are vibrant, and the massive shoe shelf on the far left wall seems to neatly overflow with over 100 right-foot shoes. The atmosphere is quiet, calm, and cozy which gives the store an air of familiarity. Yet what makes Stride Chicago truly stand out is that it is owned and managed by two teenage boys.
Created in the winter of 2024 with $500 and ten pairs of sneakers, New Trier High School juniors Aaron Ryba and Drew Steckler began Stride Chicago on Instagram as an online trading and reselling sneaker business. In November 2025, Ryba cosigned on a lease with his mother to buy property (or “brick and mortar,” as Ryba put it) in Skokie, Illinois. Now, every Monday through Friday, Ryba and Steckler leave New Trier High School and immediately drive the 11 minutes to Stride Chicago. There, they work for three hours on weekdays and eight hours on weekends selling shoes, filming Instagram-style advertisements, and cleaning newly-traded sneakers. By putting their all into Stride Chicago, Ryba and Steckler are growing a successful business with 350 pairs of sneakers, cheap competitive prices, and an Instagram account of a little over 1000 followers.
Ryba’s journey to starting Stride Chicago began when he was a camp counselor, and his subsequent realization that he preferred business.
“I didn’t enjoy working for someone,” Ryba recalls. “I always liked being able to create my own path.”
Ryba and Steckler began their entrepreneurial journey selling clothes; however, one day they bought and sold a pair of Why So Sad? Nike SB sneakers and made a profit. They quickly realized the great potential in the sneaker business.
“We realized sneakers make us tons of money,” Steckler recalls. “So then you turn that one pair [of sneakers] into three, and then it [keeps] on going from there.”
Ryba and Steckler, who met during eighth grade, were friends prior to starting a business, which has led the two to rarely disagree as business partners. Instead, Ryba and Steckler often try to compromise on tough decisions, such as whether they should buy sneakers from an out-of-state supplier or not.
“We both have a final goal, which is [to] be as successful as we can,” Ryba says. “Any disagreement blocks us from that.”
Steckler, who currently owns 20 pairs of sneakers, has always loved sneakers—his favorite is the Air Jordan 1 Lows X Travis Scott.
“Seeing tons of shoes always was an interest of mine,” Steckler says. “So when we kept selling them, it was very fun, and I really enjoyed it.”
Steckler explained that Ryba handles Stride Chicago’s finances while he works on both advertising (via Instagram posts and reels) and buying sneakers.
“I do more of upfront work, and he’s more behind the scenes,” Steckler says. “But [Ryba] does a lot of work for our spreadsheets which keeps us up and ready to go.”
For Steckler, determining sneakers’ authenticity is his specialty.
“It’s like a sense,” Steckler says. “It’s like the back of my hand. Whenever I feel a shoe, I know if it’s real or not.”
Starting out mostly on Instagram, Ryba and Steckler eventually decided to invest in a storefront to expand their reach. Ryba’s mother, who co-signed the property lease (minors cannot sign leases), was initially hesitant, but eventually cosigned because she trusted Ryba’s dedication to the business.
“I showed her how many pairs we have, what it is, [and] what it could be,” Ryba recalls. “I don’t know if it was really my explaining [that convinced her, but actually] my drive that she saw [is what caused her to] really trust me.”
This drive has guided Ryba in all of his decisions.
“I always try 100% on everything,” Ryba says. “I don’t like to leave stuff on the table. Things left on the table is like money out of my pocket for the business or [an] opportunity that wasn’t achieved.”
Growing up with a family knowledgeable in business, with ventures in stocks, real estate, vending, and entrepreneurship (his grandfather, for example, owns Little Red Hen in Glencoe), Ryba’s grandfather, father and uncle taught him business tactics which he uses for running Stride Chicago. While Ryba took Introduction to Business during his freshman year, he found his family’s advice most useful. Even then, Ryba says the bulk of his learning of how to run a successful business came from first-hand experience.
“They would teach me that you need to have your finger on the pulse,” Ryba recalls. “You can’t let your money go where you’re not, and you have to always be on top of everything.”
Ryba explained that he sometimes uses his parents’ accountant and lawyer for help, but the majority of Stride Chicago is controlled by him and Steckler. Ryba and Steckler are ultimately making all of the decisions.
“[My parents] are always a good backboard of support,” Steckler says.
Once Ryba and Steckler bought the storefront on Nov. 24, 2025 which used to be a haircut shop and had been vacant for seven years, they had a lot of work to do. The storefront was initially visually unappealing, so Ryba and Steckler spent their Thanksgiving break remodeling and improving it—Ryba even went in on Thanksgiving Day.
“We saw the vision,” Ryba recalls. “We signed the lease while it was Thanksgiving break, so every day of Thanksgiving break, I was at the store painting the walls—cleaning everything. We put up a mural. We had to do a lot of things, but it looks really good now.”
Even customers used to acknowledge the storefront’s flaws. For Ryba and Steckler, fixing up the store was a priority.
“People were like ‘oh, you guys gotta fix that,’” Steckler recalls. “Now no one says anything anymore. It’s great.”
Stride Chicago attracts not just people from the North Shore, but also sneakerheads from Chicago and Wisconsin. All of this, Steckler explained, is due to Stride Chicago’s authenticity and prices.
“All our shoes are real, which is really hard to find these days,” Steckler says. “And we have the best prices. No one can match the prices that we have. And that’s why people keep coming back because the prices you find online are so much more than we have for them in store.”
Ryba explains that if they were to buy a pair of sneakers for their retail price of $150, then they would sell them for $190. They also have a $50 and under table at Stride Chicago for customers on a tighter budget.
“At the very start, we didn’t really sell to personal buyers, like people that would put them on foot,” Ryba says. “We would mostly sell to resellers, so we had less margins. Now that we have a store, there’s all these people, like personal buyers coming in, so we can charge more money.”
Ten years from now, Ryba hopes that Stride Chicago will still be running.
“Hopefully, we are still in business,” Ryba says. “Hopefully we move stores to a bigger, nicer spot, and have a few employees—maybe another shop.”
By creating Stride Chicago, Ryba and Steckler have both grown as leaders and entrepreneurs—no matter what the future holds.
“I know more about business, especially talking to people,” Steckler says. “I could talk to more people without being nervous or stuff like that. So that builds your character in a good way.”
For Ryba, who eventually wishes to work in real estate development, he feels more confident.
“I’m proceeding in life,” Ryba says. “I’m taking another step forward. I’m not stuck doing the same thing. I’m not stationary.”