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If Sean Williams had to ballpark it, he would guess that he's owned over 4,000 sneakers in his lifetime. However, Williams is so much more than a sneaker enthusiast. Working in the field for 20 years, Williams is behind a lot of firsts for the industry, including founding the inaugural sneaker podcast, Obsessive Sneaker Disorder, launching America’s first sneaker and culture academy, SOLEcial Studies Community Academy and—most recently—creating Time Out Market New York, Dumbo's first-ever merch shop, Time Out Swag. We caught up with the sneakerhead to learn about his addiction to shoes, when his love for kicks first started, how he knew it could be a business and what kind of specialty swag he is selling at the Market.
You fell in love with sneakers when you were 13. What was it about the sneaker industry that drew you in?
I've always seen sneakers as a story in every box. Storytelling has always been my north star for a lot of things in my life. Over the years, as my relationship switched from consumer to industry professional, I became even more enamored with the stories and the business side of sneakers.
Do you remember your first pair?
I was 13 years old in 1984 when I begged [my mom] for them. It was a pair of sneakers from Puma, the model is called the Basket. So basically, my late mother is the enabler for my 40-year-long love affair with sneakers.
When did you know that you could make this a career?
It took a long time for me to actually begin working in the industry professionally. It's been 20 years now, as of 2026, but it was a gradual progression to actually being a sneaker industry professional. The realization came through small situations that led to the big picture—it was very organic.
You founded Obsessive Sneaker Disorder, the longest-running sneaker culture talk show and podcast with Dee Wells. What started this journey?
Obsessive Sneaker Disorder (OSD) is really the official coming-out party for us as footwear industry professionals. OSD is the very first sneaker podcast in the industry. It opened the doors to what everyone now calls "Sneaker Media." In addition to the podcast, we're consultants for sportswear and retail brands around the world. We're also sneaker exhibition curators. Our exhibitions have been seen by over 13 million people in the last 12 years.
You also founded SOLEcial Studies Community Academy (SSCA), America's first sneaker business and culture academy. Tell us about its creation and its mission.
We realized that the brands only spoke to women and people of color through the lens of a consumer. But the major issue involved the lack of education about the sneaker industry. It was like people thought new sneakers just magically appeared on the walls every week. Someone needed to educate and empower people to take on that mission. We accepted that mission.
Since starting the program in June of 2011, we've had thousands of students all over the world. In July of 2023, we officially opened the SOLEcial Studies CommUNITY Academy in the DUMBO section of Brooklyn, my native borough. We're actually neighbors to Time Out Market.
Any idea of how many shoes you own at the moment?
There are two answers to that question. Over the last 40 years, I've owned over 4,000 pairs and counting. Currently, I have about 400 pairs that I use for teaching and sneaker exhibitions. I also have a small allotment of sneakers that I wear daily, maybe about 100 pairs.
What do people get wrong about the sneaker industry?
We'd have to do a completely separate interview just for that answer. But to give you one of the most prevalent answers, it would be the myth that all sneakers only cost a few dollars to make, but the makers all inflate the cost without justification. That myth crosses into almost every major metropolis on Earth.
How did you get involved with Time Out Market?
All the credit goes to Andrew Denno and Arenn Evans. Andrew recognized a revenue stream Time Out Market was missing in Brooklyn. Having merch in the same space where people eat, drink and enjoy other events and attractions just made good business sense. Arenn came up with the right designs that he knew would resonate with both natives and tourists alike, and then the three of us put our brains and expertise to work on building out the entire merchandise experience.
What kind of items can people find at the Time Out Swag Shop?
The Time Out Swag Shop sells T-shirts, hoodies, tote bags and beanies. We'll also offer some light sneaker customization options—sneaker charms, Time Out Market shoe laces and Time Out Market sneaker decals. Customers can add those items to their sneakers themselves, or, for a small fee, we can customize their sneakers while they enjoy the food and amenities at the Market.
Time Out Swag Shop is open Wednesday through Sun from 11am to 6pm.