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Drake’s business ventures outside rap span clothing, a record label, esports, entertainment production and whiskey. His role differs in each: he co-founded OVO and OVO Sound, joined 100 Thieves as a co-owner, and is associated with DreamCrew and Virginia Black. The available evidence is strongest for the first three—and OVO’s ownership structure changed in August 2026.
At a glance: Drake’s five ventures
| Venture | Business | Drake’s documented role |
|---|---|---|
| October’s Very Own (OVO) | Apparel and lifestyle | Co-founder; owns 44% of the intellectual property after the 2026 transaction |
| OVO Sound | Record label | Founder, with Noah “40” Shebib and Oliver El-Khatib |
| 100 Thieves | Esports, gaming and apparel | Co-led a 2018 Series A funding round and joined as co-owner and strategic advisor; stake size not disclosed |
| DreamCrew | Production and entertainment | Associated with the company on his official site; exact ownership and current operations are not established |
| Virginia Black | Whiskey | Associated with a past whiskey venture; ownership and current status are not established |
1. October’s Very Own (OVO): apparel and lifestyle
October’s Very Own, commonly called OVO, is the Toronto-founded lifestyle brand Drake co-founded with Oliver El-Khatib and Noah “40” Shebib. Its business includes premium apparel and accessories, sold through retail stores and e-commerce. At the time of Vince Holding Corp.’s August 27, 2026 announcement, OVO operated 12 stores across Canada, the United States and the United Kingdom.
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The transaction announced that Authentic Brands Group owns 51% of OVO’s intellectual property, Drake owns 44%, and Vince Holding Corp. owns 5%. Vince acquired OVO’s operating business and became its core apparel and retail licensee. So Drake is a co-founder and substantial IP owner, but the announcement does not describe him as the sole owner or operator.
Drake described the brand’s origins in the announcement: “We’re just a couple kids from Toronto who started something we believed in, here we are 20 years later, same kids with bigger dreams. Authentic and VNCE are the perfect partners to help us continue to grow.” Source: Vince Holding Corp., August 27, 2026.
#1 Best Overall
2. OVO Sound: a separate record-label business
OVO Sound is a record label, distinct from the OVO clothing and lifestyle brand. Drake founded it with Noah “40” Shebib and Oliver El-Khatib. Its official site lists artists including PARTYNEXTDOOR, Majid Jordan, Roy Woods and Popcaan.
In January 2024, Sony Music announced that Santa Anna Label Group had invested in and partnered with OVO Sound. Santa Anna was to provide services including A&R, production, finance and accounting, marketing, and artist and label services. Sony said OVO Sound would remain a stand-alone label distributed and marketed through Santa Anna. Sony Music’s announcement, January 23, 2024; OVO Sound’s official site.
Rank #2
3. 100 Thieves: investment and co-ownership in esports
100 Thieves combines esports and gaming-related activity with lifestyle apparel. In an October 2018 announcement, the company said Drake and Scooter Braun co-led its Series A funding round and that Drake would join as a co-owner and strategic advisor. The announcement reported that 100 Thieves had raised more than $25 million in funding to date; that is a company-reported cumulative funding figure from 2018, not Drake’s individual investment amount.
The company’s current About page continues to list Drake among its owners. Neither source gives his ownership percentage, so the size of his stake cannot be stated from these disclosures. 100 Thieves’ October 23, 2018 announcement, distributed by PR Newswire; 100 Thieves About page.
Rank #3
4. DreamCrew: production and entertainment
DreamCrew appears on Drake’s official Drake Related website, connecting it to his business activities. A 2025 court-filing search result described DreamCrew as a multidisciplinary media production company with management, production-house and content-studio activities. That description should not be taken as proof of the company’s current operating status: the available official-source detail does not establish its exact ownership, present project slate or current operations. Drake Related.
5. Virginia Black: a past whiskey venture
Virginia Black is a whiskey venture associated with Drake. The available evidence does not establish its current ownership, business terms or whether it is presently available, so it is more accurate to describe it as a past venture than to claim it remains an active Drake-owned business. No reliable, primary-source earnings or sales figure is established here.
Rank #4
What the ventures show—and what they do not
These businesses use different models: OVO sells apparel and accessories; OVO Sound develops and releases music; 100 Thieves operates across esports, gaming and apparel; DreamCrew is associated with media production; and Virginia Black was a whiskey venture. The documented roles range from co-founder to investor and co-owner, while the evidence for current operations is uneven.
There are no reliable, comparable revenue or valuation figures established for these ventures, and the information above does not amount to a complete inventory of Drake’s business interests. In particular, it does not support a calculation of how much he personally earns from them.
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