These days, Oliver’s main project is OVO’s fashion line. OVO collaborated with brands like Canada Goose and Roots Canada on designs for high-end coats and jackets in 2011, the same year they sold their first in-house product: T-shirts featuring the owl logo. Now, the company is producing a wider line: hats, graphic tees, and sweatshirts, but also towels, tracksuits, tote bags, and, more recently, cut-and-sew button-ups. Product drops follow their own schedule, with limited runs of new designs arriving every month or two. “I’m really proud of where the brand is at today,” says Oliver. “The clothing business is a tough business to go into and have success. It’s something that takes a long time, and it’s an immense amount of work—you’re working 16, 18 months out.”

As they take on the logistics of making clothes, Oliver emphasizes that OVO remains a “mom-and-pop” operation, owned by itself. “If there is any idea that this is some massive corporate entity that’s worth billions of dollars, then that’s a misconception,” he says, laughing. “There’s a few of us putting our blood, sweat, and tears into this 24/7. It’s a lifestyle. It’s not a job that we all go home from. It’s something that we’ve put our own time and money and equity into, and we’re building it with hammers and nails.”

OVO products are sold through a minimalist e-shop and at a meticulous brick-and-mortar store in Little Portugal, a slowly gentrifying strip of quickly gentrifying Toronto. “This seemed like a place that was going to be sustainable for us,” Oliver says of the store’s location. “We’re a destination, so it wasn’t going to matter if we were in a central or upscale area.” A year after its doors opened, it’s not unusual to see kids lined up outside to cop new hats or just catch a glimpse of OVO crew members through the glass storefront. Oliver calls the shop OVO’s “tangible access point” and says he’s “100 percent” involved with its design and staffing. “Who’s working in the store? What music is playing in the store? What’s the vibe in the store? What’s the temperament in the store? That’s a complete extension of our brand. It’s very, very important for people to be able to go there and see what it is,” he says.

The shop is an exercise in clever marketing and offers an additional income stream—hats are priced at $45 CAD and a full tracksuit can run you as much as $300—but it’s also a symbol of OVO’s devotion to Toronto and their desire to change the city’s cultural landscape. Growing up, Oliver says he “never really saw a clear path” for himself in school, and struggled to find mentorship or entry points into Canada’s limited creative industries. Now that he’s made himself successful in a creative role that bridges music and fashion, he sees the store as a way to celebrate kids like his younger self, who have “incredible work ethic, incredible ideas, and an incredible amount of passion.” He envisions the space as a place where creatives can “come together and meet other people like them,” and where eventually those meetings will result in “something new.”

Ten years ago, Oliver might have left Toronto for New York, L.A., or London to find work and build a life. Today, OVO’s example has arguably made it more appealing for young people to stay put, and the store is a symbol of possibility and pride. “We’re from a city where I’m not sure if we’ve fully embraced our identity as creative people yet,” Oliver says. “If there’s anything that we want to put forth, it’s just to have some patriotism for what we’re doing here and to look within for talent and for inspiration.” This vision has earned him fans of his own; in a YouTube video scrutinizing OVO’s Spring 2015 products, a young reviewer says, “Oliver, I look up to him so much. More than I look up to Drake, honestly.”

For years, Drake, 40, and Oliver’s stated goal has been to make the city proud. And now that together they’ve sold millions of records and built an undeniable brand, the city is proud—rallying behind the Raptors (Drake serves as the NBA team’s global ambassador) and calling itself The 6 (a nickname popularized by Drake in the past year, drawn from Toronto’s 416 and 647 area codes). The annual OVO Fest now features an educational seminar (OVO Summit) and a community basketball championship (OVO Bounce), events that tease the kind of programming OVO might support in Toronto down the line. But to expand their offerings, Drake must continue to thrive—if he crumbles, everything could crumble with him. “Drake has to stay touring and keep the machine running so that we can help the city. I want to start setting up more speaking engagements, community programs with music programming,” 40 explains. “If he just stops everything he’s doing, what happens next?”

