Drake’s OVO Faces Fresh Legal Fight Over Investor Payout

BY Erika Marie
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An investor says Drake’s OVO still owes millions and claims it received none of the proceeds from the brand’s recent sale.

A lender says it was left out of OVO’s blockbuster sale despite spending months fighting the company over millions of dollars it claims remain unpaid. A.R.I., the investment firm Applied Real Intelligence, says OVO still owes it millions under financing agreements. It also alleges it received none of the proceeds when Authentic Brands Group and Vince Holding Corp. completed their deal for the Drake-founded lifestyle company in August, even though its dispute with OVO was already before Canadian courts.

A.R.I. financed OVO through convertible notes issued in 2025. In a September statement tied to a 391-page Ontario court filing, A.R.I. said OVO owed C$5,037,977 as of July 31, including interest and other amounts the lender says are required under their agreements. The firm also claims it was never told about negotiations with Authentic and Vince, was not asked for a payoff amount, and learned of the completed transaction after it closed.

“We received no portion of the transaction proceeds,” A.R.I. said. The firm added that it has repeatedly sought information about how its rights were treated during the sale and intends to pursue those answers in court.

Read More: Drake Speaks Out As Authentic Brands Group Buys Majority Stake In OVO Brand

The August 24 transaction gave Authentic a 51 percent stake in OVO’s intellectual property, while Drake retained 44 percent and Vince acquired the remaining five percent. Vince separately took control of OVO’s operating business. According to the transaction documents Vince filed with the SEC, the deal was structured so that defined OVO debt would be repaid before Vince acquired the operating companies.

That does not mean the SEC has accused Drake or OVO of wrongdoing or opened an enforcement case based on the available records. The agency enters the story because Vince is publicly traded and filed the OVO transaction documents with the SEC, creating a public record that can now be compared with A.R.I.’s allegations.

The Court Fight Predates OVO’s Sale

The disagreement began well before Authentic and Vince entered the picture. Billboard Canada reported that OVO sued A.R.I. in Toronto on June 2 after the lender sought an additional make-whole payment after repaying part of its investment. OVO argued that the contractual conditions triggering the fee had not been met.

A.R.I. filed its own case in British Columbia on June 11, arguing the make-whole provision was part of the original financing deal and was intended to guarantee a minimum return if the notes were repaid or terminated before maturity. No court has ruled that A.R.I.’s interpretation is correct.

The lender’s newer filing adds the OVO sale to that existing fight. For now, A.R.I. continues to seek payment and information about the transaction, while the dispute over what OVO still owes remains unresolved in Canadian court.

Read More: DJ Akademiks Finally Gets His OVO Chain From Drake

About The Author
Since 2019, Erika Marie has worked as a journalist for HotNewHipHop, covering music, film, television, art, fashion, politics, and all things regarding entertainment. With 20 years in the industry under her belt, Erika Marie moved from a writer on the graveyard shift at HNHH to becoming the Co-Head of Original Content. She has had the pleasure of sitting down with artists and personalities like DJ Jazzy Jeff, Salt ’N Pepa, Nick Cannon, Rah Digga, Rakim, Rapsody, Ari Lennox, Jacquees, Roxanne Shante, Yo-Yo, Sean Paul, Raven Symoné, Queen Naija, Ryan Destiny, DreamDoll, DaniLeigh, Sean Kingston, Reginae Carter, Jason Lee, Kamaiyah, Rome Flynn, Zonnique, Fantasia, and Just Blaze—just to name a few. In addition to one-on-one chats with influential public figures, Erika Marie also covers content connected to the culture. She’s attended and covered the BET Awards as well as private listening parties, the Rolling Loud festival, and other events that emphasize established and rising talents. Detroit-born and Long Beach (CA)-raised, Erika Marie has eclectic music taste that often helps direct the interests she focuses on here at HNHH. She finds it necessary to report on cultural conversations with respect and honor those on the mic and the hardworking teams that help get them there. Moreover, as an advocate for women, Erika Marie pays particular attention to the impact of femcees. She sits down with rising rappers for HNHH—like Big Jade, Kali, Rubi Rose, Armani Caesar, and Amy Luciani—to gain their perspectives on a fast-paced industry.

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