Whenever an idea pops into Oscar Rachmansky’s head, he whips out a notebook or whatever scrap of paper is closest and writes it down. It’s a habit you might expect from a Gen Xer or elder millennial clinging to analog comfort. Rachmansky is neither.
He’s 24, and the company he founded about five years ago generated $40 million in sales revenue in 2025 (confirmed from documents reviewed by Business Insider).
Going against the grain is kind of Rachmansky’s thing.
When he was 4, he opened a sunflower seed stand while the other kids sold lemonade. As a teenager, he dropped out of college to pursue a business opportunity that he’s since developed into a multimillion-dollar company.
Rachmansky launched OS Group in 2019, before he’d turned 20. The company is a B2B wholesaler of branded footwear and streetwear that he bootstrapped from the ground up, he said.
What started with sneaker sales out of his bedroom has turned into a team of 30 employees distributing about 25,000 items a month from a large New Jersey warehouse. Rachmansky says he always thought he’d run his own business someday. He just didn’t expect it to involve so many sneakers.
The business opportunity that no one saw
Bryan Toro
Growing up, Rachmansky was a sports kid who imagined himself running a sports agency one day. “I certainly wasn’t at all interested in fashion, sneakers, or anything of the sort,” he told Business Insider.
Still, he began buying and selling sneakers in high school as a side hustle. As he learned the resale market, one thing stood out. “No one was paying attention to the B2B side of this industry,” he said. “And that’s what powers the entire market.”
He launched his B2B company shortly after enrolling at McGill University. His first resale client quickly revealed how fragmented the supply chain was, with retailers jumping through hoops just to source inventory, he said. The inefficiency was obvious. So was the scale.
Then COVID-19 hit. The resale market froze. Rachmansky said he wasn’t making any money and briefly considered walking away. “I was like, well, maybe it wasn’t meant to be, maybe I should just keep studying and figure out what happens.”
College, however, never felt like the long-term plan. Within his first month at McGill, he said he opened his notebook and wrote a prediction: “This is going to be my first and last year of college.”
By 2021, the business had gone from cold to hot. Pandemic-era supply-chain disruptions created one of the lowest sneaker production years in recent memory. At the same time, resale prices for brands like Nike, Jordan, and Adidas soared to two or three times retail.
Rachmansky dropped out of McGill and reinvested the roughly $30,000 he’d earned from his sneaker side hustle into expanding OscarSoles — now OS Group. “I knew that the industry was growing, and I just wanted to go all in,” he said.
From humble beginnings to multimillions
Bryan Toro
At first, the company operated with more hustle than infrastructure.
“The first warehouse that we had, we didn’t even have offices,” said Isaac Murov, one of OS Group’s original employees, who joined the company in 2021. “We actually made cubicles out of Nike Air Force boxes, so we could have a little bit of privacy,” he added.
Murov met Rachmansky through a mutual friend, and the two hit it off quickly. “He was always a very bright individual, and I think I gravitated toward him for that exact reason,” Murov said.
Even as the resale market cooled after the pandemic, OS Group continued to grow. Rachmansky credits his team above all else. “We’ve been really, really intentional with our hiring,” he said, focusing on people with good attitudes who are coachable and fast.
That growth came with its own learning curve, though. For the first several years, Rachmansky said, he worked 15-hour days. “I’ve always kind of associated output with input — more hours equals better output,” he said. Eventually, however, he learned that working harder wasn’t always the same as working smarter. An early focus on hiring people who added value and growth to the team helped him see that.
The company’s hustle culture was also shaped early on by Rachmansky’s willingness to do whatever the job required. “He always led by example,” Murov said. “Whether that was hacking boxes in the back, he was never really above that.”
Today, Rachmansky wants to take OS Group beyond footwear and past pure transaction volume. His goal is to turn the company into a long-term operating partner, offering services like financing, logistics, and software using the infrastructure OS Group has already built internally. “We really see ourselves as growing into a real operating partner for this industry,” he said, with the ambition of building “the entire B2B ecosystem.”
Rachmansky no longer works 15-hour days and says he has a better work-life balance. “A fear that motivates me is not being able to do everything that I want to do with my life,” Rachmansky said, adding that he hopes to travel more in the future. “My dream day 10 years from now is probably waking up somewhere that I wasn’t the week before.”
