Growing up in New York City, Oscar Rachmansky was buying and selling sneakers as early as age 14.
Self-described as a “classic sneaker kid,” Oscar ran around New York City attending sneaker events, oftentimes buying sneakers from retailers and selling them from his phone, via Instagram. He gradually built a network of young New Yorkers who “just liked to buy shoes from him.” Fast forward four years, and what started as a hobby, making him some extra cash as an unemployed high schooler, has morphed into a multi-million dollar business.
Oscar is the founder of OS, Inc., the largest U.S. wholesale platform in the sneaker resale market. OS (FKA OscarSoles) has direct relationships with the largest direct-to-consumer sneaker resale platforms and nearly 1,000 storefronts in the U.S. Headquartered in Secaucus, New Jersey, the company’s business model is a blend of “market-maker” and “wholesale-supplier” in a non-traditional supply chain market.
And he’s just getting started. Recently, he also launched STYR Trade, a digital sneaker exchange.
We sat down with the 22-year-old sneaker entrepreneur to get the backstory and get some insights on how he’s revolutionizing the industry.
Was it a hard decision to leave college to launch OS?
Leaving college was a “phased” dropout. When COVID hit, I moved back to New York City to work on the business full-time, while continuing to take classes virtually at McGill University in Montreal. After one year of running the business, McGill required students to come back in-person full time. I sat down with my parents, showing them the traction we’d made and pointing to the larger market opportunity — the U.S. sneaker resale market is worth $7B and growing fast. With their blessing, I never went back. But as my business grows and expands, I am constantly learning and challenging myself, and I’m grateful to be surrounded by professionals from whom I can learn and grow. So in some ways, these last four years have been the equivalent of getting a business degree in the real world.
What seeded the idea to launch OS?
The business has been an organic evolution. I’ve always had a penchant for trading and selling. When I was four years old, I sold sunflower seeds on the corner in our neighborhood and then I was trading sports cards in elementary school. Both of my grandparents were small business owners so I grew up around entrepreneurs, and I guess it was in my DNA. As a teenager, I became passionate about buying and selling sneakers, and realized the market opportunity was too big to ignore. I operated on my instincts and some “seed” capital from my great-grandmother, who gave me $1,000 for my bar mitzvah. I waited in lines and slept on the streets for new releases. I stockpiled sneakers in our family’s New York City apartment, taking over our living room, much to the chagrin of my parents and little sister. When I started, I didn’t imagine we’d eventually morph into a massive B2B seller — I was going with the flow and following the best opportunities. I find that the most successful founders don’t always know what form their business will take when they start it.
Wait, what does OS stand for?
The name OS is a double entendre. It honors our original name, OscarSoles, while evolving to feel more professional as our business matured. At the same time, OS also stands for “optimized supply,” reflecting our mission to streamline the B2B supply chain for the resale market.
As an entrepreneur, who and what do you draw inspiration from?
It’s a mix. I draw inspiration from my dad,who has been entrepreneurial his entire life. If I didn’t grow up in NYC, I wouldn’t have been exposed to this market in the same way, so I’d say the city itself has inspired me. Truthfully, I take advice from a small handful of mentors. It’s easy to go on Instagram and TikTok, and listen to hundreds of people tell you how to run a business. That’s too distracting. I think we’ve lost the art of putting your head down and disappearing for a few years in-order to build a meaningful and strong operation. In-terms of sneaker business founders, I followed Jaysse Lopez from Urban Necessities and Sean Wotherspoon from Round Two on YouTube as a teenager, two original players who showed me that my hobby could become a business.
You’ve mentioned that you love trading. You recently launched STYR, the first digital trading platform for the sneaker resale market. Tell us more about that.
For years, I wanted to launch a business that truly financialized the sneaker asset class. Starting in 2022 around the NFT craze, there was a phenomenon where people were trading assets digitally, and I wanted to create a marketplace like this for sneakers. I believe we’ve created a simple and efficient platform for people to speculate on sneakers, designed to eliminate the biggest inefficiencies and barriers to growth within the sneaker resale market. We went to market with this product a few months ago, and are very excited. We’d like to see STYR grow into a digital marketplace for all forms of physical assets, including trading cards, memorabilia, and more.
What challenges did you have to overcome in growing the business?
The beginning of 2020 was quite slow for us, and it was compounded during the short-term slow down across all sectors due to COVID. At that time, I do remember feeling discouraged. Thankfully, around summer of 2020, everything kicked off and we found our groove. As the business has grown, I’ve shifted my mindset into a managerial, CEO role rather than a day-to-day operator. That is definitely challenging. We went from a team of three to a team of 25, so there are 25 people depending on us for payroll, which is a huge responsibility that I don’t take lightly. While the pressures are real, I’m actually grateful for the challenges and opportunities because at the end of the day I believe in what we’ve built and the potential ahead of us that we’re tapping into.
OS empowers business owners and young entrepreneurs, helping them scale with a consistent supply source. Can you talk more about this?
Many of our customers are small, independently-owned brick-and-mortar resale shops, who need help scaling their business with a consistent supply source. And we are committed to helping them grow–when tides rise all boats rise. For our vendors, we are a valuable buyer who they know they can trust and grow with. We regularly receive messages thanking us for being a helpful partner. We (OS) want to be a business partner that grows with our vendors.
For many, cool sneakers might feel like a luxury. What’s your relationship to luxury?
I believe in delayed gratification, which is somewhat of a lost art. Most of my financial success has been reinvested back into the businesses. However, I love watches, and try to buy one each year as a birthday present to myself. I hope to make another purchase this year as my birthday rolls around. Finally, I’d like to make some major real estate purchases for my family, like a vacation house for my parents and a home for my grandparents. My family has always been a source of support for me and we’re very close.
You started this business in your teens, and now you’re in your early 20s. What advice would you give to entrepreneurs at this age?
It’s a little paradoxical: Learn as much as you can from others, but stay focused and take everything with a grain of salt. I’d recommend finding two-three people who you rely on for advice, and tune everyone else out. I wouldn’t be where I am today if I didn’t lean on more experienced people for answers, but I pick and choose those people wisely and have learned to trust my instincts. I’m really grateful for what I’ve been able to accomplish and all those around me who’ve provided support and guidance, and I’m excited for what’s ahead and how we’re revolutionizing the industry.
What do you see as the challenges and opportunities for your business in the near future?
A major challenge we’ve been navigating over the past year—and will continue to face—is the evolving resale landscape. Many products are now trading below MSRP, and iconic brands like Nike are seeing their market share challenged by rising competitors like ASICS and New Balance. However, we’ve embraced this challenge as an opportunity by expanding our product catalog to include a broader range of brands and price points.
Our greatest opportunity lies in establishing ourselves as the leading B2B platform for streetwear and sneaker resale. While the DTC segment of resale feels increasingly saturated, the B2B space remains largely untapped and primed for consolidation. With OS and STYR, we’re confident in our ability to emerge as a dominant player in this market.
