Meet Boston’s New Teenage Sneaker Moguls

Damian Mathews, known as Newton Kicks, is closing in on buying himself a car with the money he has made reselling sneakers. / Photo by Pat Piasecki

When Isaiah Singh pulled into the Fall River strip mall at 10 p.m. on a cold Friday night in March, the Expressions sneaker store had long been closed, its lights switched off and doors shuttered. But as he got closer to the entrance, he could make out the figures of two people already standing outside in line, waiting for the doors to open in the morning. The tall, beanpole-thin high school junior from Cambridge stepped out of the car with a lawn chair in hand, popped it open, and took his place behind them—just long enough to raise his arm in the air and snap a timestamped selfie. Armed with proof that he was third in line, he left his chair turned space saver behind, stepped back into the car, and pulled a blanket over himself to keep warm until dawn.

Singh was like a kid on Christmas Eve, anxious for what the morning would bring. It had been more than a year since he’d first laid eyes on the new powder-blue-and-white Air Jordan 1 University Blue high-tops when someone online leaked a mock-up of them in early 2020. He and countless others had been waiting an eternity for the shoe’s release, and now he was mere hours away from drop day.

What a difference a year makes. When Singh first saw images of the shoes online, the pandemic had yet to hit, he was still attending school in-person, and he dreamed of getting the high-tops to put on his own two feet. That was before, thanks to an unprecedented glut of time on his hands, he discovered his entrepreneurial side and launched a life-changing, exhilarating, and remarkably lucrative career reselling sneakers on Instagram. Now he was spending the night in a car in Fall River for the shoes so he could resell them for head-spinning profits on the open market.

Listening to the beats of Drake and Lil’ Jerk reverberating from the radio into the frigid night air, Singh and Sadarius Baker, two of the three members of the sneaker re-selling team known as Skip to My Shoe, or STMS, went over their plan of attack. They strategized which sizes they would each go for based on which they thought would command the highest prices.

High on adrenaline, Singh climbed out of the car at 7 a.m., stretched his lanky frame, and assumed his place in line. When the store opened, Singh’s team immediately scored three pairs. Then Singh got lucky again. While he was walking out of the store, he turned around and noticed a guy having trouble with his credit card. Thinking on his feet, Singh stepped in, paid for the pair the guy was entitled to, handed him $130 in cash for his trouble, and put another shoebox in his bag. On the way home, he grabbed four more pairs the team had won in online raffles, while Jovan Harding, the third member of STMS, picked up another raffle winner in Worcester. “It’s one of the most anticipated shoes, if not the most anticipated, that is going to be released all year,” Singh told me. “And we got 10. This is the perfect day as a reseller.”

By the time the trio behind STMS rendezvoused back in Cambridge that afternoon, there was not a single box of the coveted shoes to be had in retail stores or online, yet there were hordes of people throughout Boston who desperately wanted a pair. Singh and his partners uploaded the sizing info along with images of the shoes onto their Instagram page. Then they sat back and listened to a three-phone orchestra of dings as their Instagram page blew up with offers. Each pair of shoes sold for about $300 above what the team had paid mere hours earlier, Singh said, netting them close to $3,000 in profits. Not a bad day’s work for a teenager.

As it turns out, reselling sneakers is anything but child’s play: It’s a totally legal, booming, multibillion-dollar global industry—some Wall Street analysts now consider the shoes an asset class. The Boston area, meanwhile, has long been an ideal place for sneaker resellers, thanks to its strong sneaker culture (hello, Converse, New Balance, Reebok, and Saucony headquarters), not to mention two world-famous sneaker boutiques, Bodega and Concepts, that enjoy the most elite status Nike confers, known as Tier Zero, meaning they receive the brand’s most exclusive new releases.

Of course, this was all before the pandemic struck, schools shuttered, and legions of teenagers suddenly found themselves bored at home with enormous amounts of free time. That’s when reselling sneakers, already popular, entered the stratosphere.

Throughout the past year, many of us have wondered what teenagers have been doing with their time, stuck in their rooms alone all day and enduring remote school while their parents tried to keep their careers intact from a laptop in the dining room. Well, for many kids throughout region, the answer isn’t drugs or porn or even video games, it’s this: They had their Zoom camera off, their phones in hand, and they were having the time of their lives getting rich flipping kicks.

From Left: Jovan Harding, Isaiah Singh, and Sadarius Baker of the Skip to My Shoe Instagram account. / Photo by Pat Piasecki

Every sneaker seller remembers his first time. For 10th grader Gavi Escamilla-Salomon, a quiet yet well-known figure in the local reselling scene, it happened three years ago on a trip to visit his uncle in Texas. By that time, sneakers had already gone from being merely something he put on his feet to the primary way he expressed himself through fashion. So it was with enormous excitement that he tore into the Nike shoebox that his sneakerhead uncle handed him as a gift. That excitement turned to devastation when he saw what was inside: The thin blue pinstripes along the midsole of the navy-and-white low-tops were an instant giveaway, he explains: The shoe was a New York Yankees model, and Red Sox–loving Escamilla-Salomon wouldn’t be caught dead in them.

He managed to thank his uncle, but as soon as Escamilla-Salomon returned home he put them on GOAT, an online platform specializing in sneaker resales. Escamilla-Salomon had nearly forgotten that he’d posted them for auction when one day his phone dinged and he saw a message that read “Congratulations,” informing him someone had bought the shoes. And with that, the businessman inside of Escamilla-Salomon suddenly awoke. “I already had an appreciation for shoes, but, like, the actual shoes themselves,” he says. “But after that first time, I started to realize the value of them and what I could do with it.”

Sneakers themselves have experienced a similar trajectory over the past several decades. In 1985, the first Nike Air Jordans turned what was until then a piece of sporting equipment into a must-have fashion item. As several tragic incidents since then have demonstrated, they also became something some were willing to kill people to steal. By the turn of the
century, sneaker brands such as Nike and Adidas increasingly released collaborations with musicians, celebrities, and haute-couture fashion houses, pushing sneakers into the realm of bona fide luxury goods. (It is quite telling that Concepts in Boston sits on Newbury Street between the Bulgari and Armani stores.) Most recently, sneakers have become a way for some people to earn a fortune.

While reselling has always existed, two big shifts in the industry turned it into the full-blown phenomenon it is today. The first was brands’ decision—principally Adidas and Nike—to adopt a specific business strategy: drop very limited numbers of the most highly sought-after models. Boston financial professional Dylan Dittrich saw so many parallels between the business of sneaker reselling and his day job investing that in 2019 he published a book titled Sneakonomic Growth: Scarcity, Storytelling and the Arrival of Sneakers as an Asset Class. “The brands lean on scarcity to create a halo effect and marketing hype for their other products, not just their limited releases,” he says, adding that the secondary effect of the scarcity is that resellers can sell shoes for much more than their original price.

The second factor was the emergence of sneaker reselling platforms such as GOAT, which launched online in 2015, and StockX, which launched the following year and became a billion-dollar unicorn in 2019. The platforms provide a marketplace for resellers and buyers to transact their deals—for a fee—and even provide authentication services to root out fakes before dispatching sneakers to the buyer. Many resellers prefer to sell directly if they can to avoid the fees, but most of them still use StockX incessantly as a price index. The site provides real-time valuations on what a particular model is going for on the secondary market, and whether the price is trending up or down, much like a stock ticker. Today, according to research from Cowen, a New York–based investment bank, the so-called secondary market for sneakers and streetwear in North America is valued at more than $2 billion and is projected to reach $30 billion globally by 2030.

These platforms, though, tell only part of the reselling story. The rest happens on Instagram. Most people who have never browsed what is known as “sneaker Instagram,” which I’d never done until my 15-year-old daughter became interested in becoming a reseller, are absolutely clueless to the fact that there are thousands upon thousands of accounts that exist where people—most of them boys between 12 and 19 years of age, resellers tell me—are buying, trading, and selling sneakers directly to customers and among one another. Once I went down that rabbit hole, I found a universe so vast, so bottomless, that I was positively amazed it could have been going on right beneath my thumb without my knowledge.

And it’s not just existing—it’s exploded with popularity since the start of the pandemic. Online sites such as StockX and GOAT reported a significant uptick in activity since the outbreak, with no one, perhaps, benefiting more than teenage resellers—many of whom, including my daughter, got in on the game for the first time over the past year. (Full disclosure: She has resold two pairs of sneakers to STMS and one to Damian Mathews, a.k.a Newton Kicks.) Meanwhile, those who already had a business in the before-times saw their bottom lines soar.

In many ways, it was inevitable. After all, what can you expect from a bunch of teens—at an age when boys (and some girls) tend to become all-consumed by sneakers—who have more time and freedom away from the watchful eyes of their teachers than perhaps at any other moment in modern history? Throw in the fact that millions of Americans received stimulus checks, didn’t spend them on vacations, and were doing most of their shopping online, and you had the perfect recipe for school kids to turn their passion into a money-printing machine.

Escamilla-Salomon went from sneaking his phone out during class to enter a raffle and then trying to contain his excitement when he scored a pair to spending all day alone in his bedroom, freely bouncing between Instagram, sneaker apps, and his Zoom classes without supervision. “I went from selling a couple of pairs a week to selling 20 a week,” he said, insisting his schoolwork hasn’t suffered for it. Remote schooling gave him the freedom to dart out of his house multiple times a day to the steps of a nearby elementary school, where he met his clients, handed them the product, and received a roll of cash before dashing back home in a matter of minutes. His bedroom is evidence of his success: Shoeboxes are crammed in every available square foot of space, including above his dresser, beneath his desk, and under his bed, all alongside his personal collection of about 20 sneakers.

When I asked how much he brings in each month, Escamilla-Salomon would only admit to a few thousand. “I don’t like to talk about exactly how much I make,” he said, adding politely, “My mom taught me not to talk about those things.”

Gavi Escamilla-Salomon, a.k.a. Cambridge Kicks, spent his school year in his bedroom doing Zoom classes while tending to his booming sneaker-resale business. / Photo by Pat Piasecki

In August 2015, while Ryan Waxler, soon to be an eighth grader, was on vacation on Lake Winnipesaukee, he looked down and noticed that his toes were starting to poke through his sneakers. In the Waxler household, that meant it was a moment that comes around only once a year: time to get a new pair of sneakers for $50 or less.

Waxler went to an outlet store to find a pair, but before checking out noticed another pair that he thought might be worth more than their $30 price tag. He bought both, went home, and listed the extra one on eBay. They sold for twice as much, and Waxler was hooked. He spent the remaining weeks of summer making trips back and forth to outlets, once even arranging for a second car to meet him because the 100 pairs of shoes he bought wouldn’t fit in a single vehicle. For the next two years, he ran a booming business reselling 250 outlet shoes a month out of his home in Concord, proving that you don’t need to sell limited releases to make money. In fact, entire segments of resellers move outlet shoes and what are known in reseller lingo as “bricks,” meaning sneakers you can find in retail stores and sell at a small profit. Moving bricks is essentially a low-margin game where the seller makes money based on volume.

After a successful couple of years, Waxler began to grow tired of toiling at the bottom of the resale food chain. “I was kind of fed up with shipping all these pairs out,” he says. “We were always running out of boxes. We’re going to USPS every day, just trying to ship everything out, and it was really stressful and time-consuming.”

Soon, he discovered sneaker Instagram, branded himself as Bullet Kicks, and started trafficking in high-dollar hyped releases. These sneakers are more exclusive, harder to get, and instantly lucrative. Resellers, such as Singh and Escamilla-Salomon, either stand in line, try to get them via raffles on brand and retailer apps, or buy them off other resellers or collectors. When it comes to the online raffles, having the fastest thumbs in the East is often not enough. Many sneaker resellers purchase proxy servers and bots that can hit the raffles faster and more often than any human. As a result, hyped releases can sell out online in a matter of minutes.

Unlike many businesses, reselling sneakers has a relatively low barrier to entry, making it the perfect pursuit for capital-poor and energy-rich teenagers. “You only need around a hundred bucks to start and you literally build up one shoe at a time,” Escamilla-Salomon says. “Knowledge is much more important in this business than money.”

Escamilla-Salomon says he doesn’t really like to read, yet next to his bed are three books on sneakers. Resellers say they also watch YouTube tutorials specific to different segments of the secondary market. They join “cook groups,” which are group chats on Discord or Slack—some of which charge monthly membership fees—where novices can get one-on-one advice from pros and everyone benefits from updates on drops, industry tips, and access to bots.

Many say they’ve learned from their rookie mistakes and losses and, over time, have learned to read the market and know what to buy and—perhaps even more important—when to sell. Damian Mathews, a 17-year-old high school senior known in the reselling community as Newton Kicks on Instagram, worked his way up during the pandemic to a point where he had enough capital that he could hold sneakers and let them appreciate like a good investment. “Once you kind of get past that point of needing to flip fast, then you’re golden to hang on to a shoe that you think is a little undervalued,” he says.

While almost anyone can play the sneaker resale game, making it to the highest echelon requires a lot more than knowledge or even capital: It requires highly placed contacts in the industry and a stable of big-spending customers. This is exactly where Waxler, the onetime outlet king from Concord, found himself by the time he was a junior in high school. After transitioning to hyped releases, he was able to buy shoes until he had worked his way into the rarefied territory of what is known in the sneaker world as “grails”—the most exclusive, sought-after, and expensive sneakers on earth.

In July 2019, the summer before his senior year, Waxler was back on Lake Winnipesaukee tearing it up on his Jet Ski, jumping over the wake of a ferry, when he heard his phone ringing from inside his waterproof pouch. He took his hand off the gas, slowing down until he was floating in the middle of the lake, and answered the call. It was a reseller from L.A. telling him he had a buyer for one of the two pairs of Nike Mags, the sneaker from Back to the Future II, that Waxler had recently posted on his Bullet Kicks Instagram page. As he bobbed on the lake, the waves splashing over his Jet Ski, Waxler and the buyer went back and forth over a price, eventually landing on $9,500. “I was so excited I almost dropped my phone in the water,” Waxler says.

His sales that month totaled $150,000, of which $30,000 was profit (“not a great margin,” he admits). Later that year, he sold another pair of Nike Mags for $11,500. It was his best year as a reseller in terms of earnings, although he said he also had a lot of “expenses,” too. “I like to go out to dinner,” he explains. “My favorite restaurant is Mastro’s in Boston, and that runs up a nice price tag.” When I asked how much he’d made that year, he hedged. “You can make multiple hundreds of thousands a year, and it’s not insanely hard,” Waxler said. “I’m not the biggest seller out there. I know there’s bigger than me. I know people make millions.”

When Waxler and I spoke, he told me that while the Mags may have been the most expensive shoes he ever sold, they were not the most expensive he has owned. Then he reached down and pulled out a pair of gray, red, and black Jordan high-tops with a bunch of small red-and-white words emblazoned across the top portion of the upper and explained to my untrained eyes what exactly I was looking at.

The sneaker was part of an extremely limited run of an Air Jordan collaboration with the rapper Eminem. There were only 313 of them ever produced—a nod to the Detroit area code—and StockX considers them to be one of the rarest Jordan shoes in existence, capable of fetching anywhere from $3,000 to $12,000. There were some sample pairs produced ahead of the limited run, Waxler explains, and as far as he knows there are only two of them in existence—one of which is in Eminem’s closet. The other one, which has never been worn, is the one Waxler was turning around and palming in his hands. “For the right buyer I think this will go for upward of $20,000 or $30,000,” he told me, adding, “And I am in no rush to sell.”

Bodega, a world-famous sneaker store. / Photo by Jared Kuzia

On a Saturday morning, exactly two weeks after the Air Jordan 1 University Blues came out, a new Yeezy—the coveted sneaker-brand collaboration between Kanye West and Adidas—was set to drop at 10 a.m. The Adidas x Concepts store on Newbury—just a block away from the main Concepts store—was offering its supply of the sneaker on a first-come, first-served basis. Not long before it opened, a crowd of more than 60 fashionably shod people stood in a line that snaked down the street.

Harding, of the STMS trio, kept warm in his gray Canada Goose jacket but felt tired, having arrived at 10 p.m. the night before to secure the sixth place in line. In that position, he felt assured he’d get a pair in a smaller size, which fetch the highest price in the secondary market because Yeezys are thought to look better on smaller feet.

Right behind him were four equally haggard-looking 13-year-olds from Medford sitting on a low wall and resting their heads in their hands. They had been there since 5 a.m. They told me they started reselling during the pandemic because they like sneakers and there’s money to be made, but mostly, one of them said, “because it gave us something to do during corona.”

About midway through the line was Singh, looking fresh and awake in his black sweatpants, black jacket, and black pair of Nike VaporMaxes after arriving at a decent hour that morning with Baker. Farther back still were two more 13-year-olds from Newton. “We have been doing this for only two months and we have already made $3.2K,” one of them told me before the other passed me their card.

By the time the Adidas x Concepts store finally threw open its doors at 10 a.m., many of the resellers in line were already busy on their phones trying to secure another shoe—the Air Jordan 3 Georgetown—that was dropping that same instant in an online raffle. One young reseller in the line was simultaneously working two phones, one in each hand.

Slowly, the security guard began signaling with his hand to those at the head of the line, beckoning them inside the sleek, dimly lit store that sent thumping rap music pouring into the street. When I asked the security guard how long it could take to get through the line—or through the supply, whichever came first—he told me it could take until 1 p.m. “Sometimes they get in here and their card gets declined,” he said, shaking his head. “Sometimes they pay in nickels and someone has to count it.”

Not even the security guard was privy to how many pairs were on hand that day, and no one in the store would say. That meant the fates of those in the back half of the line were uncertain. All that was clear on that bright Saturday morning was what is always the case these days: There would be legions of sneaker fans and regular customers at home who desperately wanted one of these new, limited-run Yeezy Boost 350 Ash Pearls and would not be able to get a pair. Unless, that is, they wanted to buy from a reseller.

While resellers are happy making money and many buyers are equally content, not everyone is a fan of the current sneaker economics. After all, the growing resale phenomenon means that there are more people in line—and arriving much earlier—for these events than there used to be years ago. It is also impossible for a human to compete in a raffle with resellers’ bots. This has created an enormous amount of frustration among sneaker fans, says Matt Powell, senior industry adviser for sports at the NPD Group. He claims that retailers and sneaker brands take bot defense seriously, but that it’s akin to a never-ending arms race. “Every time someone comes up with a new methodology,” he says, “a new way of transaction, someone figures out a way to do an end-run around it.”

While frustrated sneaker fans are clamoring for more to be done to restrict resellers, brands are in a tight spot. On the one hand, Sneakonomics author Dittrich says, they “want to ensure that they are not pushing loyal customers past the point of no return.” On the other, he says, the hype reselling creates has been “tremendously beneficial to the brands.”

Not everyone, however, is so sympathetic to the fans’ complaints. Yuming Wu, the founder of Sneaker News—who has resold sneakers in the past—says he has little patience for all the bellyaching. “I’m one of the guys that’s deepest in this industry. And there’s a lot of times that I can’t get a pair of sneakers, because it just doesn’t work out that way. That’s how life goes. You can’t have everything. If you can, then what’s the point? There’s no more fun in it.”

Every reseller I talked to told me that while they’re certainly out to make money, the sneaker game for them is about much more: the friends they make and then continue to see Saturday after Saturday in the line for a drop; the customers they see jumping up and down with excitement; the fun of the hunt; and, most of all, their profound, unwavering love of the sneakers themselves. “You can’t do it just for the money,” one of the Medford 13-year-olds waiting for a Yeezy told me emphatically. “You have to do it for the sneakers.”

In a world where the usual ways of securing a financial future are no longer working for so many young people, it’s hard to knock the next generation of adults for building booming businesses, one shoe at a time, before they are even old enough to vote. Oliver Mak, the cofounder of Bodega, says that his store strives to create a level playing field for everyone who wants the sneakers they sell. Still, he appreciates reselling. “It gives someone the opportunity to become a self-sustained businessperson on their own,” Mak says, adding, “It is what you have to do to survive in America. The next generation, the one younger than us, knows that there’s no regular way of making it anymore, there’s no opportunity for normal.”

Mathews, who in a good month makes between $10,000 to $12,000 in profit, says reselling has been his best education this past year. “I was learning more from reselling than I was in school. Even though that’s, like, not necessarily a good message,” he says with a laugh. “But I felt like what I was teaching myself in terms of being entrepreneurial and selling was more useful for life than finding x in an equation.” At first, his mother, Olivia Mathews, had a lot of questions and concerns. Was it legal? Was it safe? Who was he hanging out with? Now that she knows it is legal and has seen her son become part of a community, pay taxes, and invest in a Roth IRA , she no longer has those worries. What’s more, she no longer has the mother of all mothers’ worries, either. “I have no doubt,” she tells me, “that my son will be able to support himself as an adult.”

On a cold Sunday in March, moms driving SUVs pulled into a parking lot across the street from an AMC movie theater in Framingham and helped their sons and friends unload and set up folding tables to arrange a display of sneakers. Resellers old enough to drive themselves were tailgating, their kicks spilling out from their cars. Within an hour there were more than a dozen cars in the lot and twice as many kids milling about under the intense sunlight that provided some comfort from the icy wind whipping across the open expanse of asphalt.

About an hour after the meetup started, Singh and his STMS partners, Baker and Harding, rolled in and made their way around, looking over the sneakers. Baker approached a reseller, asked him the price on a shoe, whipped out his phone to check its current quote on StockX, and haggled a little, eventually closing the deal. Singh hung back quietly, his hands in his pockets, and told me he was waiting for Newton Kicks to show up, because they had agreed to do a deal there that day.

The whole scene had a collegial feel to it. Many of the resellers knew one another—at least on Instagram—and had done business before. Still, there are plenty of conflicts that arise within the reselling community. Nearly every sneaker reseller I talked to told me about sellers who try to pass off fakes as real, or people who either fail to pay or fail to deliver shoes that have already been paid for. However, considering the age bracket, these situations don’t usually end too badly. A pair of resellers told me they’d both seen skirmishes that ended in a similar manner: one reseller threatened to tell the other reseller’s parents what they had done.

That is not to say, however, that sneaker deals never end in violence. One reseller told me that there is a particular group of Boston resellers who arrange meet-ups, only to beat up the kids selling the sneakers and steal their merchandise. In some cases, he said, this group has tried to run over resellers with their car. He told me of a 15-year-old friend—the story was first reported by Patch—who was beaten and robbed in front of his home in Peabody by a gang of six who had made online arrangements with him to purchase sneakers. In late March, a 19-year-old man was shot and killed in Cambridge. Police were still investigating the case at press time, but his mother told reporters that she believes her son was killed while selling a pair of sneakers.

A pair of police cars did show up at the parking lot in Framingham that Sunday, though they weren’t responding to any signs of trouble at the sneaker meet-up. “It’s like a car show for sneakers,” one of the officers remarked, astounded as he took in the scene. Another officer announced to the crowd that the parking lot was private property and that they all would have to move elsewhere, before offering an apology. “I really like sneakers and I really like people trying to have a nice day,” he said, throwing his arms in the air.

The resellers were not content to cancel their event; it seemed nothing could stand in the way of the deals that they all still hoped to make. A few of them gathered, consulted their phones, and made a quick plan to reconvene in another lot several miles away, posting the location on Instagram. A train of cars pulled out of the lot, some driven by kids and some by moms, and soon the crowd set up shop in the small lot of a Friends Meeting House across from some horse pastures.

Soon after that, Mathews, who’d caught on to the change in plans, arrived at the new location, ready to make a deal. When Singh handed over a pair of Air Jordan x Union LA 4s, Mathews opened the box, looked them over, pulled out his phone, and transferred Singh $800 on Zelle. Deal closed.

Singh had bought the shoes off another reseller just a few days earlier for $680, making an easy $120 on the deal. A few weeks later, I asked Mathews about the Union 4s. He told me he was still holding them, confident that they will easily be worth a grand come fall.