Slumped in the back corner on the main floor of East Room, a members-only communal office space in Toronto’s Riverdale neighborhood, La Mar Taylor is glued to his phone. Taylor, who now lives in L.A., had planned on only visiting family and friends while he was in town. But right now, the creative director for Grammy award-winner The Weeknd is planning several projects for artists under the singer’s XO record label. “It always comes together in the last minute,” says Taylor.

The 26-year-old, who’s dressed in a black Puma tracksuit and matching sneakers, met The Weeknd (“Abel,” to him) the first day of their freshman year of high school in Scarborough, a suburban district of Toronto. “We had the same business class and I remember it vividly,” he says, laughing. “I was wearing a pink polo and he had a baby blue du-rag on. We were just cracking jokes at each other.” Taylor and The Weeknd shared interests in music and creative photography, and quickly formed a bond.

At 18, he and The Weeknd dropped out of high school together, and moved into a one-bedroom apartment in downtown Toronto with their friend Hyghly Alleyne. At that point, The Weeknd was already dabbling in music and Taylor was developing his skills in photography. Taylor had planned on becoming a nurse, and he admits he was hesitant to drop out at first. But he eventually surrendered to The Weeknd’s persuasion. “We wanted to live the lifestyle 24/7,” he says. “No ifs, ands, or buts. It just got to the point where we were like, ‘We can’t fucking hop on the train at 1:30a.m. trying to catch the last one to go back home [to Scarborough] and then do the same thing all over the next day. If we really wanted to live our dreams, we felt like we had to live the lifestyle non-stop.”