Drake’s October’s Very Own secures investment from A.R.I.

Canadian lifestyle brand October’s Very Own (OVO), founded by Aubrey ‘Drake’ Graham, Oliver El-Khatib, and Noah ‘40’ Shebib, has received a capital injection from US-based investment firm Applied Real Intelligence (A.R.I.) to support the brand’s global expansion plans.

In a statement, A.R.I., which specialises in growth financing for category-defining, innovative companies, said OVO represents the “next generation of Canadian entrepreneurship,” and with global demand for culturally authentic brands high at the moment, that “timing couldn’t be better for OVO”.

Dr. Zack Ellison, founder and managing general partner at A.R.I., said: “Recently, Human Made, the streetwear brand partially owned by Pharrell Williams, went public at nearly 500 million US dollars and was reportedly 60 times oversubscribed. It’s a clear signal that investors see tremendous value in brands that blend creativity, community, and cultural credibility.

“OVO is uniquely positioned within that movement, combining global influence across fashion, music, sports, and a cultural and lifestyle presence that sets it apart.”

A.R.I. backs Canadian fashion and lifestyle brand OVO

Founded in Toronto in 2008, October’s Very Own began as a music collective before evolving into a vertically integrated lifestyle company, and has become one of Canada’s most successful cultural exports. Offering premium apparel and accessories, the brand has become known for its distinctive owl logo and black-and-gold aesthetic, as well as its collaboration with Nike (Jordan Brand), Timberland, the NBA, NFL, MLB, NHL, Fanatics, Disney, Warner Bros. (Looney Tunes), and The Simpsons.

The Canadian lifestyle brand is currently led by chief executive Derek ‘Drex’ Jancar, who was brought on to scale OVO’s global e-commerce business, expand premier partnerships, and grow its physical retail footprint, building on the creative foundation established by Drake, El-Khatib, and Shebib.

The brand operates 12 flagship stores, including in Toronto, Mississauga, Ottawa, Calgary, and British Columbia in Canada, along with international locations in Los Angeles, New York, and Las Vegas in the US, and London in the UK, as well as having a worldwide e-commerce presence.

Ellison added: “Drake, Oliver, and 40 created something culturally unparalleled, and Drex is now scaling that vision with remarkable discipline and strategic clarity. It’s a rare combination, and one that A.R.I. is proud to support.”

Celebrity-led brands continue to grow

The investment comes as celebrity-led brands continue to hit record valuations worldwide, such as Kim Kardashian’s shapewear, underwear, and swimwear brand Skims being valued at five billion US dollars in a Goldman Sachs–led round joined by BDT and MSD Partners, and Hailey Bieber’s beauty brand being acquired by E.l.f. Beauty for one billion US dollars, five times the brand’s trailing revenue.

Other celebrity-led brands achieving growth and expanding includes Rihanna’s Fenty, which now offers lingerie and loungewear, as well as a full beauty, skin, hair and fragrance offering, and actress and singer Selena Gomez recently reach a valuation of 2.7 billion US dollars for her Rare Beauty brand, and singer Jessica Simpson continues to have one of the most successful celebrity fashion lines, with reports suggesting the line generated around one billion US dollars in annual revenue in 2025.

A.R.I. believes that OVO is set for global domination as it blends artistry and cultural credibility, much like other brands in the streetwear landscape, such as Supreme, Kith, Stüssy, Off-White, Human Made, and Bape, while also expanding its reach within the sports, lifestyle, and performance categories.

OVO is looking to define its place in global streetwear with capital injection

OVO is also uniquely placed due to its influential collaborations in Canada and internationally, which bridge fashion, sports, and entertainment, including with the NBA team Toronto Raptors, MLB team Toronto Blue Jays, and NHL team the Toronto Maple Leafs, alongside other Canadian collaborations with the Canadian Football League, Canada Skateboard, Canada Goose, and Roots. The brand also has ties with sports stars Wayne Gretzky, William Nylander, and Georges St-Pierre.

Recent partnerships include PlayStation, Chelsea Football Club, Red Bull Racing, Callaway, Vessel Golf Bags, and Hockey Canada ahead of the Winter Olympics.

Ellison added: “A critical part of A.R.I.’s investment process is evaluating staying power. OVO isn’t a moment; it’s a long-term movement. Very few brands have sustained OVO’s level of credibility and consistency across both creative and commercial dimensions. It is extraordinary, and it’s exactly the profile we seek in our investments.

“OVO has become a symbol of Canadian creativity and excellence. Just as Drake elevated the visibility of Canadian music worldwide, OVO is elevating Canadian culture in global streetwear.” Financial terms of the investment were not disclosed.