Grailed's staff.

“I see too many tweets about kids getting their phone taken away because they are using Grailed,” said Arun Gupta, a lanky 29-year-old who speaks as if he’s being timed for speed.

Gupta, who studied physics at Yale, is the chief executive officer and cofounder of Grailed, the men’s resale site that launched in 2014.

Last week, Grailed’s Twitter mentions were particularly pointed. The e-commerce site released an update to its iPhone mobile app and there were a few glitches. Users were upset about a missing “back” and “done” button, the inability to add pictures to a listing and not being able to send messages to other users.

App glitches that prevent customers from purchasing or selling product are a problem, but the mentions, which ranged from obnoxious to highly concerned, were indicative of Grailed’s connection to its user, who is typically male, between ages 17 and 35 and has a penchant for streetwear and high-end designers. The site isn’t as omnipresent as, say, Instagram, but it’s quickly become a resource and daily attraction for a demographic that most retailers and brands are trying to win over.

Grailed, which is a term used to describe a highly sought-after item — derived from holy grail — combines the utility of eBay with the engagement of message boards. The site is divided by core, which is basic product; hype, which is just-released product, and grail, which is hard to find, expensive product. Its 750,000 users are able to buy and sell new and used items. Grailed makes money from the 6 percent commission it collects from each sale and users populate the site with 150,000 items each month. Gupta didn’t want to speak about profitability, but said the business is self-sustaining and isn’t looking to raise any money. Thrive Capital, which has invested in Warby Parker and Glossier, was a seed investor.

According to Gupta, Grailed has won over this customer with the three c’s — content, community and curation — and each “c” creates a loop that’s hard for clothing enthusiasts to escape. Customers are learning about brands on Grailed, shopping from these brands on Grailed and selling them on Grailed. The team has tapped into Millennials’ need to promote rare purchases on Instagram, their entrepreneurial spirit and their fickleness. As soon as they are over a product, they can sell it and buy something else.

“People are trying to figure out what their personal style is. It’s all a journey,” said Gupta. “Grailed is a great avenue for you to recycle your pieces. Someone can say, ‘I love this leather jacket and it’s still great, but it’s not my style anymore. Let me offload it to someone for a fair price, then I can take that money and experiment more with my style.’”

Gupta has a very altruistic view of what Grailed is offering. Its tagline is “fire for all,” which means affordable access to designer pieces. For example, a pair of Balmain biker jeans sold for $370, but they typically retail for around $1,000. On the other end of the spectrum, the company benefits from the exorbitant resale prices for limited product. But the team has positioned the site to be democratic and inclusive.

“Grailed is not a site for hypebeasts,” said Jake Metzger, Grailed’s director of marketing. “The focus is to serve all communities and all ages.”

The most popular line on the site is Supreme, but brands including Adidas, Nike, Vetements, Balenciaga, Rick Owens, Raf Simons, Gucci, Billionaire Boys Club, Enfants Riches Déprimés and Palm Angels are also trending.

“We are a reflection of the market,” said Metzger.

He was referring to the brands that do well on the site, but Grailed is also a reflection of how people are shopping now. The online resale market has boomed, with sites such as Vestiaire Collective, The Real Real, Depop and Thredup, which launched a luxury site called Luxe earlier this year, doing well. This growing market has contributed to the demise of 2nd Time Around, the fashion consignment retailer that closed all 20 of its stores in April. According to a study completed by Thredup/Fung Global Technology, the apparel resale sector is expected to grow 13 percent to $33 billion in 2021, from $18 billion in 2016, and e-commerce sites are driving this growth.

Brands selling new merchandise are starting to capitalize on these platforms and secondhand resale sites are attempting to align more with fashion. In September, eBay unveiled a partnership with Spring, a luxury shopping app, to give the eBay customer access to new product from brands including Chloé, David Yurman and Rag & Bone, which currently sell on Spring. Stella McCartney has teamed with The Real Real to promote luxury consignment. Both companies plan to host in-store panel discussions with experts about the circular economy and a Stella McCartney pop-up shop will open at The Real Real’s concept store in November.

Grailed has also started to catch the attention of designers. Helmut Lang launched its Re-Edition collection, a re-release of 15 of the designer’s most iconic and memorable garments, on Grailed in September, and Robert Geller turned to the retailer to release his “Immigrant” T-shirt on the site in March. Fear of God’s Jerry Lorenzo dropped a capsule of  T-shirts exclusively with the online marketplace, and Grailed has also collaborated with Can’t Skate, a New York-based skate line, on product.

“When you bring the idea of Grailed to a designer or brand that isn’t aware, then they get very curious. They want to know what their stuff is selling for and what people are saying about it,” said Lawrence Schlossman, Grailed’s brand director. “With Robert, he thought it was a great way to directly reach a specific consumer and his fans.”

The men’s streetwear customer is accustomed to buying and selling new items, specifically sneakers, but according to Metzger, getting this customer to be comfortable with used and archival apparel has required some smart marketing and merchandising.

“We have re-branded the narrative around used clothing and made it cool and even aspirational,” said Metzger. “That’s allowed us to attract new types of users who would have not considered buying something used in the past, but now it has a different connotation.”

Grailed has been able to do this by associating with influencers such as Nick Wooster, Lorenzo and Luka Sabbat, who have each had Grailed shopping events that feature pieces from their own collection and items they select from the site. Grailed also styled rapper Playboi Carti for his “Magnolia” music video.

Then there’s its content, which sits under Dry Clean Only, and is spearheaded by Schlossman, who came from Four Pins, a Complex-owned site that was known for its comedic take on streetwear. Schlossman said the Grailed user is looking for less humor and more education from the content. For example, the site features a story on the history of Arc’teryx Veilance and a post detailing how Gap ruled the Nineties.

“It’s not about patronizing our reader,” said Schlossman. “It’s about talking to them as the enthusiasts and experts they already are.”

Merging content with commerce has become a thing for publications and e-commerce sites. Sometimes it works — see Mr Porter — sometimes it doesn’t — see the second iteration of It works for Grailed because the content is baked into the shopping experience and stokes a fire for its users who view the acquisition of clothing as a serious hobby. The strongest example of that is The Grailed 100, an annual event the site has done for the past two years that highlights 100 of the most coveted pieces the site has obtained from users and other sources. Grailed shoots each item and offers backstory on why the piece is important.

The team is hoping the formula they’ve created for Grailed will work for Heroine, its women’s site that launched this week and is being led by Kristen Dempsey, who has a background in costume design and used to work with Comme des Garçons on the Dover Street Market store in New York. The site sells brands including Céline, Givenchy and Ann Demeulemeester. Dempsey is hoping to differentiate it from other resale sites with community and content.

“Women want something that reflects what they are interested in,” she said. “I think they want to be in a community of other users who have the same ethics and interests as them rather than a site that’s made by a corporation just feeding them with a certain type of supply.”

Next up for Grailed is continuing to improve the user experience and growing its community while still remaining focused on its audience, which Schlossman thinks more retailers should consider.

“My advice would be to get as specialized as possible,” said Schlossman. “If I had a store I’d cater to a specific lane of enthusiasts who want to give you their money if you offer the right product. People should try to be laser-focused.”

More from WWD:

The Real Real, Stella McCartney Team to Embrace Circular Economy

Tough Retail Environment Claims 2nd Time Around Units

Ebay Partners With Spring to Boost Fashion Category

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