The smell of pot wafts in through the glass doors. Nav crosses our view on his way to the pool house, a cozy, amenities-riddled white-on-white hut that's about the size of my apartment (which, painfully, is four blocks from here). Cash says his "guys" like to work there because it harks back to the bedrooms and basements they first recorded in, "in the trap." He calls it Birdhouse Studio because—again, painfully—it reminds him "of a little birdhouse," he says. "It's like, if we don't keep working hard, we're gonna end up right back over there." He chuckles, while I cry inside.

When I ask him how he discovered Nav (born Navraj Goraya), another Toronto talent, Cash just says, "I'm always in the loop with everything going on in that city. The local guys can always get a hold of me. I'm there day one to give them advice and opportunities without asking for anything." The real answer is that Cash heard Nav's SoundCloud breakthrough, "Take Me Simple," called him up ("Obviously he knew who I was," Cash adds), then booked Nav a flight to L.A., where "he fell in perfectly." In February, XO and Republic co-released Nav's self-titled mixtape, which notched a respectable No. 24 on the Billboard 200 (No. 4 on Canadian Albums) fueled by single "Some Way," wherein featured guest the Weeknd, who's dating Selena Gomez, seems to take shots at his famous girlfriend's ex-boyfriend Justin Bieber (Tesfaye is also cosigned to XO and Republic). Nav is now wrapping an album with Metro Boomin, and performed his first show ever at Coachella in April.

All of that speaks to the power of the XO cosign — which is, ultimately, the power of the Weeknd. Nav is a good producer with a reliable knack for mixing goopy New Age synths with icily clacking trap percussion, but as a vocalist he's been criticized by many for being lazy and juvenile, which extends from his use of the N-word to overly Auto-Tuned punchlines like, "I think my nuts look better on her face." The Weeknd, by contrast, is a deus ex machina, the answer to a dozen lingering questions about how R&B and rap interface with pop culture at large (EDM, Hollywood, style, celebrity, drugs, sex, black identity, Michael Jackson's sonic legacy). Cash has to know all this, that the source of XO's strength is the Weeknd himself. Maybe that's why he reportedly keeps Tesfaye's old, signature Basquiat-ish dreadlock in a safe.

"I do have the hair," Cash confirms. "It's stored well, secure, with 300 armed guards and its own condo in Toronto." That last bit was a joke—probably. But if you can overlook the creepiness of the situation, it's kinda sweet. Cash is clearly a sincere, sentimental dude. His eye-contact is strong, he divides his social circle into "big brothers" and "little brothers," and then there's the wrestling memorabilia distributed throughout his home. The largest concentration is in his office: a dozen shining championship belts, each on its own shelf bearing letters like WWE, WCW, and NXT alongside images of eagles, globes, and eagles on top of globes. But his personal connection to wrestling isn't typical for a wealthy, well-connected fan. "I learned how to speak English watching WWE," he explains. "That's why I'm so loyal to it. Sometimes, if I can't sleep, I'll put on the WWE network and watch reruns because it puts me in a good place. It reminds me of watching it with my dad on the bed."