It’s a perfect summer day in Toronto, a rare respite from the heavy, humid heat typical of the city at this time of year. Tucked away in a pocket of the city’s Leslieville neighbourhood, a photoshoot is about to get underway as a production crew of photographers and editors scurry around, setting up lighting and arranging various backdrops in anticipation of the day’s subject—Oliver El-Khatib, co-founder and CEO of October’s Very Own (OVO).
Dressed in a navy, double-breasted Cucinelli jacket, matching trousers, and a crisp white shirt buttoned to the top with a tie, El-Khatib’s entrance exudes a quiet but marked confidence that commands attention. His attire is a departure from the uniform of his early days, where he spent much of his time slinging streetwear to the city’s style set of artists, entrepreneurs, and creatives looking to make their own mark on the world. This is a more grown-up El-Khatib—one that has traversed life’s hurdles, built a formidable brand, and played a significant role in establishing Canada as a rich source of cultural capital (alongside his co-creators, Drake, Noah “40” Shebib, and the rest of the OVO founding family.) In some ways, Oliver’s sartorial evolution is reflective of his incredible career, from burgeoning creative to modern mogul.
Today, few names have carved a path as dynamic and impactful as El-Khatib. A visionary leader and cultural pioneer, his journey serves as a testament to the boundless possibilities of determination, innovation, and collaboration. Since his early days, El-Khatib has always exhibited a keen knack for anticipating cultural shifts and identifying talent. This foresight laid the foundation for his meteoric rise within the entrepreneurial sphere, building OVO into a portfolio of brands with a global footprint across fashion, music, and more.
What sets El-Khatib apart from his contemporaries is not only his business acumen but his commitment to Canada and the cultivation of new talent. In an exclusive interview with GLORY, Oliver El-Khatib explores his extraordinary entrepreneurial journey, the power of mentorship, and why staying in Canada has always been key to OVO’s success.
Back in 2007, you were asked in an interview about your ultimate goal. You said, “Making a living out of what I love doing. To create and be a part of something with a global influence. To be able to live life exactly the way I feel it should be lived.” Almost 16 years later, what kind of thoughts and feelings do you have when you hear that?
Oliver El-Khatib: It’s fun to hear that because in 2007 I was in my early twenties. At that moment, I really knew that I was going to carve my own path and I managed to find people that were also trying to carve their own paths. It’s crazy how time flies. At that point, industries [in Toronto] weren’t readily available like they were to some of our friends in New York. And if you couldn’t move to New York because you didn’t have the means or you had other responsibilities, what could you do? We decided to build it from home, and we did it together. We wanted Toronto to be a place you had to go to in order to be a part of what’s going on. We wanted that same sense of pride. You have to have a dream and a belief in what you’re going to do. For me, what I have done is make a living out of what I love doing, with the people that I love, and doing it where I’m from.
How have the goal posts changed as you’ve surpassed them?
Oliver El-Khatib: It’s all relative. You accomplish some goals, check some boxes, and then new ones emerge. And then you get older and wiser, and different things become important. The goal posts change for how you define success. For me, health is wealth and happiness is success. It’s your mental health, your physical health, your quality of life—it’s the people around you, what you see, what you hear, what you experience. Prioritizing having a peaceful life is really what allows me to go out there and accomplish more goals than I ever dreamed of attaining. If your life is chaotic and toxic, it’s very difficult to get on to anything outside of that.
As a business owner, you can’t take anything for granted. I think that’s what I embody the most, a sense of grounded humility. You have to stay in the moment and create a culture that’s really about quality of life and loving what you do. To be good at anything, it’s going to take a minimum of 10 years to master it. If you love it, it never feels like work. If you love the people that you work with, it’s an absolute joy that brings meaning and fulfillment. And the byproduct of that will be a successful endeavour.
Are there any misconceptions about the work that you do and the success that you and your team have attained?
Oliver El-Khatib: For one, it takes a village. These are not solo endeavors. We have an incredible team. The only thing that maybe gets misconstrued at times is that one person gets all of the credit at any moment for a massive body of work that has taken many incredible minds working in sync for over a decade. It’s one band and one sound, marching in the right direction for a long time that’s probably going to give you the best chance of success.
The thing that I’m probably the most proud of is, obviously Drake is an incredible leader. He has an incredible eye for talent and has been able to surround himself with people of substance that all have really good intentions and real talent. The fact that we’ve all navigated such an incredible journey with so many different potential outcomes, it’s a testament to the group that we work with. The results that have been yielded are really a byproduct of that culture.
You and your team have built up a really impressive empire under the brand that you co-founded with Drake and 40, including OVO the clothing brand, OVO Sound, OVO Fest, and more. What’s the big picture?
Oliver El-Khatib: At the core, OVO is a group of friends, artists, entrepreneurs, and athletes who have come together from our city to pursue one goal, which was a belief in Drake’s talent. OVO was started as an umbrella to catch all of the different endeavours that we were embarking on. The work that Drake and all of us have done in building the culture has laid the groundwork to tell other stories, whether it be in a product space with OVO or identifying new talent and music with OVO Sound. The throughline of it all is presenting it as the most authentic reflection of who we are.
Many have labeled you as a visionary of branding. From your perspective, what are the hallmarks of an exceptional modern brand?
Oliver El-Khatib: The consumer is very smart today. There’s not a lot of room for any kind of business in any industry that doesn’t have a very focused, meaningful intention and is not operating with authenticity or integrity. Those are some of the most important attributes of any company that’s going to have a chance at success.
You’ve got a hand in all aspects of culture, from music to fashion to sports. In what ways do you think of culture as a form of currency in the way that it’s leveraged, traded, and valued?
Oliver El-Khatib: Music and art are for everyone to enjoy and consume. If you’re the casual consumer or listener, then that’s what it’s there for—consumption, whether it’s film, TV, music, or clothing. If you want to be a contributor, then you have to bring something to the table in terms of what new perspective you are adding. I think those are the most important things—to be a contributor to culture and to push things forward.
You’re a captain of industry and community. Is there anything that scares or gives you pause?
Oliver El-Khatib: I try to always remember that where your fear lies is where your task lies. Anything that scares you is often something that you need to reconcile, so I welcome that feeling. I think what I’m really good at is breaking down really big tasks into very small, achievable ones. When you put all those little tasks together and take a step back, you’ll see progress. Beyond that, I think one of the scariest things to do is look within. Nobody’s perfect and we all have our own blind spots. It’s healthy to remember that it’s okay to confront your mistakes and ask for help.
OVO is known for its family, its brotherhood and sisterhood. What’s your philosophy on unearthing and nurturing new talent?
Oliver El-Khatib: As a fan and consumer of music first, I’m always looking for new songs and new artists just to fulfill my own insatiability. Since I was a kid, music is what I gravitated towards, much like style and fashion. The joy of finding new music is so exciting to me and I’ve managed to just stumble upon some extremely talented individuals. You just get a gut feeling when you hear new music that excites you and feels fresh, like nothing that’s out there. Some of my most exciting experiences have been trying to help usher an extremely new sound onto people’s ears that they’re almost not ready for. That’s what I get excited about, shifting people’s ears forward onto new stuff. Personally, I like slow burn music. If I hear it and get it all right away, it’s kind of boring. I need something to really sink my teeth into with some depth.
Mentorship is a big throughline in your career. What kind of mentor do you hope to be for others?
Oliver El-Khatib: I just try to be myself and an example that I didn’t necessarily have growing up. I would love to be in a position to talk about my experiences and just help guide young people to believe in themselves, especially people that come from more of a creative or an entrepreneurial background.
There are so many people that feel like they don’t fit in at school and are not really sure who to look for for mentorship. That’s what I felt when I was as a young person. Now, being able to follow my dreams and make a living out of it, I have a lot of information that would be very useful for the younger version of myself.
It’s not just about work. It’s also about the kind of man that I want to be, my ethics, my principles. Those are all things that come with wisdom. No matter how mature you are as a young person, there’s something about hours in the gym. As you get older and take more trips around the sun, you accrue wisdom. I would love to continue to pass that along.
You’ve chosen to build your empire from home. Why is it important to keep your roots and your foundation in Toronto when you could easily go to another cultural capital?
Oliver El-Khatib: The companies that I admire are Aritzia, Canada Goose, Roots, MLSE, Lululemon. These are Canadian legacy brands that have built their companies from Canada, and they’ve set the precedent for excellence. For us, we have our own culture here, our own nuances, our own point of view, and I’m more interested in developing them and telling that story to the rest of the world.
I would never want to dilute myself or our brand in an attempt to further it by business metrics. It’s more important to be here, doing it our way, with our own POV; that’s what sets us apart. Being everybody else is taken, so you’ve got to be yourself. Our company is Canadian, we’ve got to honour that.
How do you think the Toronto identity, and by extension, the Canadian identity, has changed since you started out on your career path?
Oliver El-Khatib: We have the most multicultural city in the world. It’s really diverse in terms of what it is and is something different to everybody. It’s also a young country, so I think we’re still furthering and solidifying our identity in different spaces. Ten years ago, we were in a different spot within music than we are today. We’ve worked extremely hard in music and are a major influence globally in terms of producers and artists. I think that the producers and the artists here have been the Trojan horse for directors, photographers, creative directors, and stylists. It was a tall task to get people to take Canada seriously, musically, at the beginning. Now, we’re a real player at the table. I would love for us to get to that place with style and fashion.
A lot of the early inspiration on your OVO Blogspot showed a very clear admiration for fashion and style that has really continued to today. Where did your love of fashion and style stem from?
Oliver El-Khatib: It’s something that’s I’ve had since childhood. I was always interested in product and style, and I just followed that intuition. My grandparents were Lebanese and very chic people. Beirut was the Paris of the Middle East in the ’60s. I’ve always admired my grandfather’s joy of dressing and appreciation of style; I think it was just passed on genetically.
How do you think style and fashion are used as vehicles of influence to move culture today?
Oliver El-Khatib: For me, it’s about the people who do really amazing things and then happen to have great style. We live in a world today where people are so obsessed with aesthetics and are more interested in looking like something than being something. I prefer to look for mentors or people that are really furthering some sort of industry or doing something very interesting with their lives. In a sense, it’s about being an industrialist for new industries in our country and our city. Those are the people that I gravitate towards and that’s how I approach things.
For a long time, there’s been this narrative about Canadians being the underdog, of being passive or apologetic—all those stereotypes that come with being in Canada and Canadian. Do you think they still hold true?
Oliver El-Khatib: I think it’s always present, just in the fact that the major market for music, especially, is America. Being an American and having a dream to be in music, you’re already one step ahead of being Canadian. I think it’s brought out this underdog mentality that you have to scrap a lot harder to get noticed. I think it’s made us extremely focused and diligent, and forced us to dig deep to really contribute musically. As a result, I think we’ve all risen to the occasion. I’m very proud of that.
What is your personal Everest? Your greatest ambition for yourself?
Oliver El-Khatib: Health and happiness on a personal level, and then health and happiness of the people around me that I love and care about. I want to help people be the best versions of themselves. I feel a lot of joy from watching people reach their goals. In terms of OVO, it’s about continuing to build a company. It’s about creating new career opportunities and just furthering Canada’s profile in terms of fashion and style.
I think that all the growth of OVO is still in front of us. We have a brand and an incredible perception of scale. Brands like Canada Goose and Lululemon are public companies; their revenues far exceed ours. We have the potential to be part of the next cohort of companies to become Canadian legacy brands. That’s where I’m focused on taking us.
