Oliver El-Khatib is the founder of OVO (October’s Very Own), co-manager of Drake and a self-made legend in his own right. But besides those few facts, not much else is known about the man many call Oliver North.

“For me, it’s more about a way of thinking. There’s a basic philosophy that can be applied to anything in life,” says the jack-of-all-trades who doesn’t just dabble in, but rather innovates in the realms of design, music, fashion and urban lifestyle. “I wanted to make a living doing what I love doing, no matter what.”

A humble and underwhelming statement for the immeasurable success Oliver has found and the dynamic his brand has made to shift the state of popular culture.

Despite the renowned OVO name, Oliver remains private. His face is only seen on basketball court sidelines and Instagram, a feat near impossible for a man of his calibre. However, Oliver opened up in a rare keynote address moderated by the Remix Project’s Gavin Sheppard to close out the fifth year of the North By Northeast (NXNE) Interactive conference in front of a packed auditorium of up-and-coming creatives thirsting for knowledge, or maybe just a story or two about Drake.

He started at the beginning.

“Skateboarding was probably the real introduction to what was happening in other cities. Keep in mind, there was no Internet. I’m from the generation of having to listen to 88.1 FM on Saturday to see what they’re playing on the radio,” he says.

After grinding all week with odd jobs to earn $25, a young Oliver would hit up record stores like Toronto’s Play De Record to cop a few projects. He would study and analyze the craft from the artists and production to every word and name on the LP’s liner notes. He is a true self-taught student of the game. Throughout the keynote, there was never any form of entitlement for any success as he chalks it up to the people in his corner.

It is no secret that OVO is an authentic team, each member with his own level of notoriety, all intertwined in Drake’s career, making cameos in the bars of Drizzy records and photos he posts. Wherever he goes, his team goes.

Oliver took attendees back with him explaining how he met the crew. Oliver and 40 met in grade nine home room and immediately hit it off as friends, forming a DJ group, The Lebanon Dons, while he met Drake at Lounge, a store/hub in Toronto where he worked, fashion being his first area of expertise.

When it came time to make music with Drizzy at the forefront, OVO was formed.

“We started as a blog. My job was to blog. Besides setting up the infrastructure and the template for what OVO would become, I think my initial role was being someone to creatively make Drake feel safe in that regard. With OVO, him and I set out to create this backbone. We kind of knew that no matter how big his career would get, we wanted to offset that with something that only reminded us of what we set out to do. There would always be this contrast of the high level of trying to get as big as possible, but we’re going to have this ground level energy that’s untainted, that’s not for sale, that’s uncompromised behind us,” he says.

“I have partners in what I do that make all of this possible, who are all geniuses in their respective spaces. We are competitive internally and I think that we have a great team and we have people experts and it’s a circle of trust. We hold each other to standards that I think are insane and we’re all very ambitious. Half of it is your outward mission to put on for the city and half of it is just internally. We set out to do this together,” he says.

As an advocate of not only his team and of the talent he affiliates with, Oliver is also a huge supporter of city he’s from, evident in the way he speaks, his attitude and his creative vision.

“We’re a young city. We live in a city that’s pretty much ungoverned artistically. We take liberties that in another city you wouldn’t think to do. There’s no way of doing things. Everybody is doing something brand new. I think a lot of the time it sounds so different that it’s almost harsh. The line between genius and trash. That’s way more interesting than, ‘yeah, that was good.’ I’m so into music that I lived to be challenged by it.”

Whether it was the stories, the history, or his tips on branding that fed the curiousness of each attendee, the universal message of the intimate keynote was really to continue to prove that everything Oliver does is for his team and for the 6.

Words By. Samantha O’Connor + Event Photos By. Adrian McKenzie + Main Photo Courtesy of Zach Gold