Within 24 hours of hearing his first song by the Weeknd, in early 2011, Amir "Cash" Esmailian stuffed whatever he could of his Miami apartment into a single suitcase and moved to Toronto. The goal was to get nearer to the guy he says he knew "would change the sound, change the world of music." His plans? He'd figure them out when he got to Canada. His lease? The landlady's problem. His sneaker collection? A small price to pay. Well, actually, that part was heartbreaking. "There were so many Jordans there I wish I could..." Cash, now 33, trails off, shaking his head. "I left everything, bro."

Today, the Iran-born, Ottawa-raised Los Angeles resident co-manages the Weeknd. "There's nothing like him," Cash gushes about the man he knows as Abel Tesfaye. He's also steering the Weeknd's business/cultural empire, XO, which shape-shifts from record label to fashion mark to clique, all while remaining (like Jay Z's Roc and Drake's OVO) a rallying point for fans eager to broadcast their dedication via hand signs, tattoos, and, presumably, the margins of their class notes. Newcomers think XO signifies hugs and kisses. Old heads know it stands for ecstasy and Oxycodone. But to Cash, XO is very simply "family." As for his official title in the business, he's not the LinkedIn type.

"We never operate off titles. I live, breathe, sleep, eat, shit XO," says Cash, as if that suffices as a job description. But it kind of does. When he got to Toronto and befriended Tesfaye, he was at various times his personal assistant, road manager, security guard, fitness trainer, and chauffeur. In 2017, he's a driving force behind the Weeknd's world tour, the release of the debut mixtape of XO singer-producer Nav, the U.S. tour of rapper Belly (cosigned to Roc Nation), a menswear collection with H&M, and an official XO sneaker coming via Puma. Plus he keeps a home studio frequented by the likes of French Montana, Metro Boomin, and Travis Scott. "There's no job for any [XO] guys too big or small," says Cash proudly. "If something spills on the ground, no one's like, 'I'm not gonna pick it up 'cause it's not my job.' Whoever's closest gets it. That's the mentality with us."