Minneapolis vintage streetwear seller wants bigger piece of billion-dollar secondhand industry

Three years ago, Jake Webb paid $4,000 for four vintage T-shirts he purchased online.

Soon after opening the package, he realized three of the items were fake. It was the first time in 13 years as a vintage clothing reseller that Webb found himself scammed out of thousands of dollars.

"You're just looking at pictures on a resell app and trusting the buyer is selling what they're actually taking a picture of," he said.

From that incident, Webb created a solution for other resellers and fans of secondhand, vintage clothing and accessories: an app that uses artificially intelligent photo scanning to verify items' authenticity.

Thrift MRKT — which is set to launch next year — will serve as an online marketplace that handles the exchange between sellers and buyers, Webb said. It also provides price verification, so buyers aren't overpaying.

He and his co-founders recently secured $2.5 million in seed capital from a private investor to build the platform, said Webb, who's managing the business from ad agency Mono's headquarters in Minneapolis' Uptown, where he's an entrepreneur in residence.

Through the app, people will be able to sell T-shirts, handbags, hats, shoes and other accessories. Items sold on the app will initially be streetwear apparel, but Webb and his co-founders see potential in using the technology to verify other styles of clothing and accessories.

It's a platform Webb and his co-founders believe has potential to grow significantly within the booming global secondhand market.

By 2026, the secondhand apparel market will double in size and outpace the overall apparel market threefold, reaching $82 billion in sales in the U.S. alone, according to a 2022 resale industry report by thredUP, a California online resale platform. By the end of next year, 50% of total secondhand dollars are expected to come from online transactions.

Webb's infatuation with thrift shopping started soon after he graduated from Tuskegee University in 2011, when his father gave him a 1997 Minnesota Gophers Big Ten Conference championship hat discovered in a local secondhand store.

Admirers of the vintage hat constantly asked where Webb found it. Their curiosity was his motivation to discover other hidden treasures in thrift stores across the Twin Cities. In the years that followed, Webb spent his free time sifting through tubs and piles of clothing at thrift stores, searching for valuable — but easily overlooked — vintage items.

Webb's reputation and following as a reseller of vintage streetwear and sneakers led to him opening the Kings of Vintage retail store on W. 28th Street and Hennepin Avenue in 2018.

One of those earlier followers and customers was Kasey Lamba, a North Dakota State University student who learned of Webb's pop-ups while visiting friends attending the University of Minnesota's Twin Cities campus.

"I just thought it was the coolest thing in the world," he said. "From my perspective, that's when the Minneapolis vintage streetwear scene blew up."

Soon, visiting Webb's store became Lamba's sole reason for visiting Minneapolis, either to buy or sell items to Webb. Mostly, he wanted to see what new items Webb had found, whether they represented Black culture or African American history, or "the really nostalgic '90s clothing and streetwear that people want to this day," Lamba said.

"I just wanted to gather inspiration," said Lamba, who now lives in Minneapolis and operates his own vintage resale pop-up store, 4DaLo Bodega. "Even if I wasn't going to buy it, it gave me an idea of what kind of stuff to look for."

A year into the storefront business, though, someone robbed the Kings of Vintage and made off with big-ticket items worth $25,000. Webb couldn't recover from the losses and closed the store.

Bhrandon Beasley, a friend and classmate of Webb's at Tuskegee, was Webb's business partner for the store. When Webb said he was working on a new venture at the intersection of technology and vintage retail, Beasley agreed to join as chief financial and chief operating officer.

"This could be game-changing," he said. "We figured out the solution for an issue with profiting, thriving businesses. They need just a little tinkering."

Celester Webb, Webb's father and a former Minneapolis firefighter, said his son has always been an entrepreneur. Unbeknownst to him, he sparked a hobby that became Webb's livelihood.

"Every parent wants their child to find the American dream," the elder Webb said. "I always wanted him to help people. His app is helping people. He figured out a way to help people and be a resource."

Targeted users of the app are buyers and sellers of vintage urban streetwear, specifically items that were created in the '90s and depict pop culture and hip-hop music. Only items authenticated through a two-step verification system will make it onto the Thrift MRKT app, Webb said.

The image verification software authenticates five checkpoints: the tags, the fabric and material, stitching, graphic designs and any copyrighted design details, like a logo.

On the app, sellers use an authenticator button to upload images of items. Once purchased, the seller mails the item to Thrift MRKT's authentication center, where it will be automated by the AI technology and verified by an expert. The company then ships the items to the buyer if it is, indeed, authentic.

Webb likens the process to how a person deposits checks on mobile banking apps by scanning images of the front and back using a smartphone camera.

Thrift MRKT charges a 7% service fee and $2 authentication fee, Webb said.

A generational shift toward resale has made it more mainstream, said Sarah Broadwater, director of marketing at Plymouth-based Winmark Corp., the franchiser of secondhand retailers like Plato's Closet, Once Upon a Child and Style Encore. The company's 2022 survey of 2,000 shoppers revealed three out of four were comfortable buying secondhand items, with two out of three stating more than half of their belongings were preowned.

"We're seeing a shift in cultural attitudes toward resale as it gains prevalence in the overarching retail landscape," said Broadwater, whose company has a network of 1,300 stores across North America. "These factors — combined with economic uncertainty and an increased focus on sustainable living — contribute to consumers' increasing movement toward resale."

Webb said this is an opportune time for Thrift MRKT to dive into the resale industry, given its platform appeals to the shopping habits of Gen Zers and millennials, who are more likely to wear premium items only once or twice before cashing in on its valuable condition and reselling it.

According to thredUP, 62% of Gen Zers and millennials look for secondhand items before purchasing a new item, while 46% of people in those age groups consider the resale value of an apparel item before purchasing it.

"As long as that cycle continues, we have users on both ends, buyers and sellers," Webb said.