Oscar Rachmansky Built $40M Sneaker Business by 25

Oscar Rachmansky demonstrated business instincts from an early age. At four years old, he opened a sunflower seed stand while other children sold lemonade. This early venture foreshadowed a career built on identifying overlooked market opportunities.

Rachmansky grew up as a sports kid who initially envisioned running a sports agency. He had no interest in fashion or sneakers, stating, "I certainly wasn't at all interested in fashion, sneakers, or anything of the sort." Despite this, he began buying and selling sneakers in high school as a side hustle.

During his first month at McGill University, Rachmansky wrote a prediction in his notebook: "This is going to be my first and last year of college." He dropped out to pursue a business opportunity that he developed into a multimillion-dollar company.

The business opportunity emerged when Rachmansky noticed a critical gap in the market. While learning the resale market, he observed that "No one was paying attention to the B2B side of this industry." He recognized that the B2B sector powers the entire market.

He launched his B2B company shortly after enrolling at McGill. His first resale client revealed how fragmented the supply chain was, with retailers struggling to source inventory. The inefficiency was obvious, and so was the scale of the opportunity.

When COVID-19 hit, the resale market froze. Rachmansky wasn't making money and briefly considered walking away. He thought, "well, maybe it wasn't meant to be, maybe I should just keep studying and figure out what happens."

By 2021, the business had transformed. Pandemic-era supply-chain disruptions created one of the lowest sneaker production years in recent memory. Simultaneously, resale prices for brands like Nike, Jordan, and Adidas soared to two or three times retail value.

Rachmansky dropped out of McGill and reinvested roughly $30,000 from his sneaker side hustle into expanding OscarSoles, which later became OS Group. "I knew that the industry was growing, and I just wanted to go all in," he said.

The company launched in 2019, before Rachmansky turned 20. He bootstrapped the B2B wholesaler of branded footwear and streetwear from the ground up. What started with sneaker sales out of his bedroom evolved into a team of 30 employees.

Operations moved to a large New Jersey warehouse distributing about 25,000 items per month. Early infrastructure was minimal. Isaac Murov, one of OS Group's original employees who joined in 2021, recalled, "The first warehouse that we had, we didn't even have offices." The team improvised: "We actually made cubicles out of Nike Air Force boxes, so we could have a little bit of privacy."

Murov, who met Rachmansky through a mutual friend, described him as "always a very bright individual." He noted that Rachmansky "always led by example" and was "never really above" doing any job required, including "hacking boxes in the back."

Even as the resale market cooled after the pandemic, OS Group continued to grow. Rachmansky credits his team above all else, noting they have been "really, really intentional with our hiring." The company focuses on recruiting people with good attitudes who are coachable and fast.

Growth came with a learning curve. For the first several years, Rachmansky worked 15-hour days. "I've always kind of associated output with input — more hours equals better output," he said. Eventually, he learned that working harder isn't always the same as working smarter. An early focus on hiring people who added value helped him see this distinction.

Today, Rachmansky no longer works 15-hour days and has achieved better work-life balance. His goal is to take OS Group beyond footwear and pure transaction volume. He aims to turn the company into a long-term operating partner offering services like financing, logistics, and software using infrastructure already built internally.

"We really see ourselves as growing into a real operating partner for this industry," Rachmansky said, with the ambition of building "the entire B2B ecosystem."

Regarding personal motivation, Rachmansky said, "A fear that motivates me is not being able to do everything that I want to do with my life." He hopes to travel more, stating, "My dream day 10 years from now is probably waking up somewhere that I wasn't the week before."