Drake’s lifestyle brand October’s Very Own (OVO) has been hit with a nearly $4 million lawsuit over “multiple loan payment defaults” from earlier this year. Despite the initial loan having been repaid, the lender is now seeking a default penalty fee, as well as legal fees, lender expenses, and other amounts continuing to accrue, pushing the total to well over $4 million.

Florida-based lender Applied Real Intelligence (A.R.I.) claims that OVO defaulted due to late interest payments in early 2026. OVO signed a repayment agreement and wired back the initial $3.7 million principal in May.

But A.R.I. says OVO still owes an additional default penalty fee of roughly $3.8 million ($5.3 million CAD) to protect its minimum negotiated investment return—effectively doubling the total amount of the original loan.

OVO clapped back, initially suing A.R.I. in Toronto on June 2 in a move to legally block the extra fee, arguing that the specific contract clauses that would have necessitated such a fee were never triggered. In response, A.R.I. filed a countersuit in Vancouver on June 11 to forcefully collect the remaining millions.

A.R.I. claims that OVO issued five separate Convertible Promissory Notes to the lender in the aggregate principal amount of $5,234,121.93 between July 14, 2025 and August 5, 2025. Those notes were allegedly five-year convertible debt instruments containing conversion rights, information rights, prepayment restrictions, default remedies, and a contractual Make Whole Fee designed to provide A.R.I. with a negotiated minimum return of the notes were repaid or otherwise terminated prior to maturity.

OVO subsequently defaulted under the notes by failing to make required payments when due and by breaching “additional obligations under the governing financing agreements.” Then, on or around February 27, 2026, A.R.I. delivered a formal notice of default to OVO. The following month, A.R.I. and OVO entered into a formal forbearance agreement, under which A.R.I. agreed to temporarily refrain from exercising its enforcement rights under the financing agreements, conditional upon OVO’s compliance with specified repayment obligations.

A statement from A.R.I. notes that the company “intends to continue pursuing all rights and remedies available under the governing agreements and applicable law.” Neither Drake nor representatives for OVO have spoken publicly on the matter in time for publication.