A legal dispute is brewing between Drake’s October’s Very Own (OVO) lifestyle brand and an investment firm which claims the company failed to repay a $5.2 million loan and now owes nearly twice as much.
Florida-based lending company Applied Real Intelligence filed a lawsuit earlier this month in the British Columbia Supreme Court alleging that OVO defaulted on its loan obligations when it refused to pay a series of mounting fees tied to its late repayments.
In court documents obtained by the Star, ARI says Drake’s company repaid the initial amount it owed earlier this year but refuses to pay $4.6 million in default interest, legal fees and other amounts racked up under the terms of the agreement.
None of the allegations have been proven in court. Representatives for Drake did not respond to requests for comment.
OVO, which is incorporated in B.C., was co-founded by Toronto rapper Aubrey Graham and his two business partners, Oliver El-Khatib and Noah Shebib, who grew the brand into a clothing and merchandise force known for its hoodies and hats emblazoned with a trademark owl emblem.
But the lawsuit filed by ARI characterizes OVO as a money-losing operation in recent years. It says that while OVO generated nearly $400 million in revenue from 2019 to 2024, it lost $12 million during the latter part of that period, from 2022 to 2024. The lender says that, in 2024 alone, OVO generated $72 million in revenue but lost $8 million.
Drake has been rebuilding his public image after a widely publicized feud with Los Angeles rapper Kendrick Lamar, during which the two artists exchanged a series of escalating diss tracks in 2024. Last month, Drake surprised fans by releasing three new albums on the same day, including “Iceman,” which spent four consecutive weeks at No. 1 on the Billboard album chart.
Meanwhile, OVO is negotiating the sale of a 50 per cent stake to Authentic Brands Group, which could shore up cash and lead to more licensing deals, according to report in Puck.
The brand development and marketing company, founded by Toronto billionaire Jamie Salter, specializes in intellectual property rights for living celebrities, including David Beckham and Shaquille O’Neal, as well as the commercial and likeness rights for dead celebrities such as Muhammad Ali and Elvis Presley.
