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2nd Time Around founder tries a 3rd act with throwback streetwear

Jeff Casler at Thrive Exchange, his new store on Newbury Street.Gretchen Ertl for The Boston Globe

This is Jeffrey Casler’s third time around.

After a seven-year hiatus, the founder and CEO of the 2nd Time Around chain of consignment stores is back at 176 Newbury St., occupying the same location that served as the company’s flagship for over two decades. But instead of preppy Lilly Pulitzer threads, J.Crew cardigans, and coveted Diane von Furstenberg wrap dresses, a distinctly different vibe exists in his newest venture, Thrive Exchange.

The new store’s focus is streetwear, and with racks of mostly 1980s- and ’90s-era clothing, it’s far more of a niche approach to secondhand retail. Casler pays upfront for the items he purchases, such as vintage Air Jordans and throwback Nike windbreakers. And he buys from collectors who are trendsetters on social media, with a portion of the profits going to charity.


Resale is one of fastest-growing sectors in retail, and one that’s rapidly evolving. Casler said he has evolved, along with the industry, since he left 2nd Time Around. He watched last year as the company he built into a national chain imploded after years of mismanagement, with all of its nearly 30 stores abruptly closing, and says the downfall happened, in part, because 2nd Time Around failed to spot the trends he’s now targeting.

“Consignment as we know it is done,” he said.

On the day Newbury Street Thrive Exchange opened last month, the store was packed with teens and twentysomethings grabbing Champion sweat shirts, Supreme hoodies, and Starter jackets as if it were 1994. A Tupac Shakur memorial T-shirt, circa 1996, was selling for $425.

Amber Jackson approached the register with an armful of Kappa zip-up jackets.

“I used to watch the Spice Girls, and this was all Sporty Spice wore,” said Jackson, who had traveled from Connecticut to be at Thrive’s opening.

“This is like a thrift store but just all the good stuff that you’re always looking for,” said Emma Jannino, a freshman at Lesley University.


Customers perused the racks of clothing being sold on consignment in Jeff Casler's new store in April.Gretchen Ertl for The Boston Globe

“There is no store like this on Newbury Street,” said Casler, who opened the outlet as a pop-up but plans to extend his lease through the end of the year. “We’re on trend and setting the trend.”

Sucharita Kodali, a retail analyst with Forrester Research, said Casler’s approach takes advantage of the boost that social-media influencers can give to brands. And it builds on the marketing tactics, like limited-issue releases, that athletic streetwear brands have always used to drive up demand.

“Streetwear is just really hot right now. It is probably one of the few places where younger consumers are spending,” she said.

Casler said the consignment industry has changed dramatically in the four decades since his mother, Dottie, opened the first Second Time Around store in Newton in 1973. (The name was shortened to 2nd Time Around after Casler’s departure.)

“When my mom first started, people were embarrassed to come into the store. They would ask for a different bag,” Casler said.

But Casler believed that fashion’s increasing emphasis on pricey labels would eventually persuade shoppers to turn to resale. He took over the company, opening its Newbury Street flagship in 1990. In its heyday, he’d prowl the aisles of upscale boutiques and department stores, so he knew how to price items for resale when they eventually arrived in his stores. While other retailers struggled through the economic downturn, he profited from a surge in interest in secondhand clothing. By 2009, he had 22 locations nationally and $8 million in annual sales.


Casler, now 54, has lived with multiple sclerosis for three decades, and he said he decided to sell the company to the private equity firm Generation Equity Investors in 2011 to focus on his health. But he couldn’t stay out of the game. Because he’d signed a noncompete clause, he had to head north, to Toronto, where he ran another consignment store, Kind Exchange, for several years.

Casler returned to the Boston area in 2016, opening the first Thrive Exchange in Davis Square. Then, last year, he watched from the outside as 2nd Time Around collapsed, leaving longtime consigners enraged, because many were owed thousands of dollars.

Dudi Luski of Israel checked out a Reebok jacket being sold on consignment at Thrive Market.Gretchen Ertl for The Boston Globe

Talking about the company’s demise for the first time, Casler said he was surprised to see it shift its focus from more accessible clothing to more exclusive brands such as Prada, Hermes, and Chanel. “My vision left and was replaced by an inferior vision,” he said, and “that came to fruition in many different ways.”

When stores began rejecting some of the labels that had been their staples, “it alienated a large majority of the consigners,” he said. Among its missteps: The store’s prices were too high and they carried too few items, and the company opened stores in locations far more extravagant than a clothing reseller could support.

Ultimately, Casler said, 2nd Time Around’s upscale pivot was ill-timed. While full-price retailers across the United States are struggling, off-price and resale stores are actually growing, according to a report released last year by Fung Global Retail & Technology.


“Re-commerce is currently one of the fastest-growing sectors in retail,” according to the report.

Shoppers under 35 — who have a penchant for bargain-hunting, want unique wardrobes, and care more about the environmental impact that secondhand merchandise can help offset — are driving the trend.

A Kurt Cobain t-shirt from 1994 priced at $400 for sale at Thrive Market.Gretchen Ertl for The Boston Globe

Newer websites are also driving secondhand sales: Peer-to-peer marketplaces including Poshmark and sites such as ThredUp and the RealReal have made consigning online far easier and enjoyable than their predecessors. Fung estimated the total market for both brick-and-mortar and online reselling would almost double in five years, from $18 billion in 2016 to $33 billion in 2021.

ThredUp’s own research, published in its annual Resale Report this year, found 44 million women shopped secondhand in 2017, up from 35 million the year before. And 71 percent of its shoppers said they plan to spend more on resale shopping in the next five years.

Casler said he’s not threatened by online consignment, citing the overhead costs it takes to ship, photograph, and warehouse the clothing. He notes that ThredUp has been opening its own stores, and he anticipates that more traditional retailers like Bloomingdale’s or T.J. Maxx will increasingly get into the secondhand game. 

Kodali, at Forrester Research, said that well-curated consigner storefronts can have an edge over online marketplaces. Having an eye for what’s cool is “an art and very difficult to create an algorithm around,” she said, though she questioned how big Casler might be able to build Thrive. “I don’t know how scalable this is.”


But Lauren Beitelspacher, a marketing professor at Babson College, said that Casler’s decision to harness the power of online influencers on social media was a smart strategic move.

“It’s really brilliant. If he’s getting these micro-influencers to vouch for him, that’s unbelievable,”  Beitelspacher said. “A middle-aged man coming from traditional consignment isn’t going to have the same street cred. It shows a tremendous amount of retail insights.”

Casler, for his part, is placing his bets that his long-honed skills for sensing what will sell will continue to attract a new and younger demographic.

“I don’t want to be in the 2nd Time Around business, I want to be in the cool, trendy clothing business,” he said.

Janelle Nanos can be reached at janelle.nanos@globe.com. Follow her on Twitter @janellenanos.