In 2011, Mikey Trapstar, Lee, and Will—founders of British streetwear brand Trapstar—were asked by Roc Nation’s Jay Brown and Ty Ty to stop by a studio in London. Brown and Ty Ty had just seen Omar Grant, an A&R executive at Roc Nation, wearing a Trapstar hoodie and wanted to know what all the hype was about. “[Brown and Ty Ty] were like, ‘Why is everyone wearing this hoodie? Where is this? Who is this?’” recalls Mikey.

What Mikey didn’t know was that that initial meeting would change his life. “When we got to the studio, they were like, ‘You know why we brought you here. We want to invest,’” he says.

But Mikey is quick to admit he didn’t initially believe Roc Nation really wanted to invest in the brand. “Straight away I was like, ‘Do you know about the brand?’ I knew [Roc Nation] was big and I knew what could happen, but I still had this slight chip on my shoulder,” he says. So he sat with Brown and Ty Ty and gave them a rundown of the brand, showing them YouTube videos of their pop-ups, which they called “Invasions,” and explained all the relevant imagery they used. Roc Nation and Trapstar kept the conversation going for two years, meeting whenever Brown and Ty Ty were in London.

Now Mikey, who’s sitting across from me in Trapstar’s NYC studio on the 39th floor of the Roc Nation offices in Manhattan, says those meetings with Jay Brown and Ty Ty and the early co-signs from Rihanna and Rita Ora were crucial in getting Jay Z’s blessing. “We literally got vetted right there,” he says. Jay Z, who Mikey, Will, and Lee met later, would go on to tell them that he thought they were “fresh” and that he liked their energy.

But don’t get it twisted: Mikey, Will, and Lee had been putting in work long before they were signed to Jay Z’s team.

Back in London, Mikey made T-shirts with a photo he took with his Nokia phone of a painting he bought for his house. The tees, which he gave to his friends and refused to sell, became so popular that people were asking how much money he was making off of them. One of his friends even threatened to copy the shirt if Mikey didn’t start selling it. “That twisted my arm,” says Mikey. “We’ve been bitten for so many things.”

But what really convinced him to start Trapstar was a comment made by Lee’s step father. “We came from a rough area; we kind of had bad reps sometimes. [Lee’s step dad] was like, ‘You all think you’re some sort of fly boys but you’re just trapped… Let’s see you make something of yourselves,’” says Mikey, who responded with: “We may be trapped, but there’s a star trapped in everybody.”

“That drove me,” he adds. “I guess he knew how to push my buttons.”

In the early stages, around 2005/2006, Mikey says no one wanted to stock Trapstar. “They thought we were going to be here today, gone tomorrow.” But what started as an obstacle played out to their advantage. “They just made us go back to our same roots, keep it a little bit more close knit for people who understand who you are and what your brand is about,” he says. Customers needed to contact them via MySpace to place orders. Items were hand-delivered in pizza and detergent boxes (“We always wanted to disguise packaging,” says Mikey). “We sort of had this seen everywhere, found nowhere mentality.”

Trapstar would eventually be stocked at Supra on Portobello Road in London, where they now have a flagship store. “It was like we got signed to a label,” says Mikey. By then, the brand had its own buzz and built its own fanbase. Pop-up shops and in-store events, which they called “Invasions,” in London, Birmingham, Bristol, and Manchester followed. In 2009, Trapstar became one of 12 brands hand-selected to participate in the “Reset” event—a market place where brands sold exclusive, limited edition, and dead stock items—at Nike’s 948 store in Shoreditch, London. “That was the first time we ever got a stampede and it was in front of 11 other brands,” says Mikey. “It was the same day the Yeezys was coming out. There were two queues, so to be second from him and to know how desired those kicks were… We had no marketing budget, no virals, no media showing us love, and we sold out. That’s on YouTube now and I still watch it every now and again.”

All the hard work has since paid off. In the last couple of years, Trapstar has released several collections; designed Rihanna and Eminem’s “Monster” tour merch; made an exclusive collection for London retailer Selfridges, where the brand is now sold; launched its Red Line label; designed a collection with the Hitman video game series; and presented its collaboration with New York artist Haculla during London’s Fashion Week. Not to mention all the co-signs from big name celebrities, such as Future, Fabolous, Chris Brown, Jay Z (of course), Cara Delevingne, Formula One driver Lewis Hamilton, A$AP Rocky, model Jourdan Dunn, Young Jeezy, Victor Cruz, OG Maco, Game of Thrones’ Alfie Allen, and Meek Mill. The list goes on.

So how exactly did a streetwear brand from London catch the attention of Jay Brown and Ty Ty—and Jay Z? We sat down with Mikey and asked him about his journey trying to make it in the fashion industry, and what advice he has for up-and-coming brands and designers. Take notes.

As told to Karizza Sanchez All photos by Andy Hur