Gupta was into clothes even as a teenager. “I wore J.Crew and Diesel back in high school,” he says. “As I got older, I was more into A.P.C. and Lanvin.” By the time Gupta was at Yale, sites like Mr Porter and Gilt Man were in their infancy, but he sought out like-minded shoppers on chat rooms and message boards. It was here that men talked openly about their clothing obsessions and bought and sold their one-of-a-kind finds. “I bought some A.P.C. denim at great prices,” says Gupta. “And this was right after college, so I had no money.”
Once he saw the active audience, he wanted to create a marketplace to serve these members. So he coded Grailed, using the chat rooms as focus groups.
“It was by the people for the people,” Gupta says. “I announced its launch on Reddit. For the first six months, it was me in my bedroom working on this and talking to the people on the forum. They would give feedback and say, ‘I wish I had a wish list or a shopping cart,’ and I would spend time making those features.”
Today, the New York–based Grailed lists nearly 50,000 items on its site a month. The site attracts sneakerheads and celebrities, suburban dads and Brooklyn hipsters who love Raf Simons, Vetements, Hood By Air, and Acne Studios. The company doesn’t carry inventory, instead hosting a network of over 20,000 users who buy and sell their own luxury goods, setting prices significantly lower than what’s at retail. The goods are both new and used, but if used, they’re still in pristine condition.
“One of the great parts about Grailed is that you’re experimenting with used stuff,” says Gupta. “Maybe it would be a frivolous purchase if you bought it new.” On Grailed, he says, “You don’t have to spend a ton of money,” and if you’re not happy with a purchase, “You can just resell what you just bought.”
Gupta has noted how men’s shopping has evolved since the time he was browsing chat rooms. “Before, it wasn’t considered manly,” he says. “Now rappers and celebs are noticeably into fashion. More men are spending dollars on fashion. Department stores are putting more time into their men’s selections. It’s okay for guys to care more about fashion.”
And for Gupta, that’s one wake-up call he’s happy to hear.