Canadian lifestyle and clothing label October’s Very Own (OVO), co-founded by rapper Drake, is facing a lawsuit alleging partial debt repayment and breach of contract. The allegations come from ARI OVO Growth Capital. The company said that after previous attempts to resolve the legal issues, it now wants to enforce its rights and protect its investors.
The investment firm has commenced proceedings in the Supreme Court of British Columbia. She is seeking repayment of approximately $4.6 million for amounts owed, contractual late payment interest, legal fees and other expenses.
ARI entered into a financing agreement with OVO in early 2025. Funds were provided through separate transactions, including a senior secured credit facility and convertible notes. The firm said it initially viewed the globally recognized brand as an attractive credit opportunity with significant shareholder value potential.
OVO was founded in 2008 by Aubrey ‘Drake’ Graham, Oliver El-Khatib and Noah ’40’ Shebib. It is currently led by Chief Executive Officer (CEO) Derek ‘Drex’ Jancar. The brand is in the premium lifestyle and luxury streetwear segment and has become known for its activities in fashion, music and sports.
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However, in February 2026, OVO was said to have breached the applicable agreements by failing to repay its debts on time. ARI said it was working on an out-of-court solution. Finally, a deferment agreement was reached in which OVO recognized the validity of the unconditional payment obligations.
In a statement, the firm said it has “worked extensively with OVO in a formal restructuring process and has given the company considerable time and flexibility to resolve the situation out of court.”
In May, ARI said it received a transfer of around $3.8 million from a third-party account. This was part of the $4.6 million owed. However, according to the statement of claim, OVO is said to take the position that no further payments are outstanding.
Concerns about the agreement grew when ARI learned of OVO’s alleged efforts to secure $30 million in equity financing. These funds could be used to repay approximately $10 million in debt, according to ARI. The company is also believed to have recorded cumulative losses of approximately $12 million between 2022 and 2024.
ARI also referred to a current report from the media platform Puck. It said OVO was considering a transaction with US-based Authentic Brands Group, which was said to be considering acquiring a 50% stake. The investment firm said such discussions should have been disclosed as part of the contractual agreement.
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