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The Drake Business Portfolio: OVO, AC Milan, and More

Last Updated: October 11, 2023
Drake is preparing to drop his tenth studio album, but he stays busy outside of the studio. Boardroom takes a closer look at the biggest investments on the Toronto rapper’s roster.

I like it when money makes a difference but don’t make you different.”

Aubrey Graham is no stranger to a bag. The Toronto rapper better known as Drake stepped onto the stage at 15 with a central role on the hit Canadian show Degrassi: The Next Generation. But even as he played Jimmy, his heart belonged to music, recording late at night to accommodate his shooting schedule and ultimately catching the attention of Lil Wayne.

His first mixtape notched $304, but now he stays on top as one of the world’s most popular rappers. With each album turning certified Platinum and with 131 Platinum tracks overall, Drake knows success.

Once his music career took off, Drake quickly got into the entrepreneurship and investment game, developing a diverse portfolio that fuels his bars. From restaurants to sports teams, clothing collabs to betting on himself, he’s crafted a personal brand that mimics the range reflected in his catalog. And he’s just getting started.

The OVO founder has expressed a desire to get into basketball with the WNBA and his beloved Toronto Raptors. In the meantime, he’s testing the waters of team ownership with the likes of the Brooklyn Aces and AC Milan.

Let’s take a closer look at the Drake business portfolio.

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Drake Business & Investments Overview

NOTE: This list is Boardroom’s curation of the most important Drake businesses and ventures and is not to be considered exhaustive.

OVO Clothing 

  • Type: Clothing Brand
  • Role: Co-founder
  • Founded: 2011
  • Fun fact: Between collabs with the NFL, MLS, and its own bespoke drops, OVO Clothing brings in more than $50 million in sales each year.

OVO Sound

  • Type: Record Label
  • Role: Co-founder
  • Founded: 2012
  • Fun Fact: In January 2023, OVO Sound signed its first female artist, Naomi Sharon.
@boardroom Drake’s level of braggadocious reaches new heights on his ‘For All The Dogs’ album. We take a look the record’s most lofty lyrics in the first installment of “Boardroom Bars.” #drake #forallthedogs #hiphop #rapper ♬ original sound – Boardroom

DreamCrew Entertainment

  • Type: Production Company
  • Role: Co-founder
  • Founded: 2017
  • Fun fact: Drake became a fan of crime drama series Top Boy after its cancelation in 2013. He mobilized a team to re-pitch the show to Netflix, where it found a second life six years later. Its fifth and final season will premiere in Fall 2023.

Brooklyn Aces

  • Type: Major League Pickleball Team
  • Role: Investor
  • Invested: 2023
  • Fun fact: Drake joined the investment group of the Kevin Durant- and Rich Kleiman-founded pickleball club alongside fellow investors Michael B. Jordan and Steve Stoute.

AC Milan

  • Type: Serie A Soccer Club
  • Role: Investor
  • Invested: 2022
  • Fun fact: Since kicking off his investment alongside LeBron James, AC Milan has upped its signature style, dropping collabs with Off-White.

Toronto Raptors

  • Type: NBA Team
  • Role: Global Ambassador
  • Invested: 2013
  • Fun fact: In the 2019 playoffs, the NBA issued a warning to the Raptors after Drake aggressively heckled the Milwaukee Bucks and even gave head coach Nick Nurse a shoulder massage during a timeout.

Stake.com

  • Type: Gambling Website
  • Role: Ambassador
  • Joined: 2022
  • Fun fact: Throughout the course of their partnership, Drake has wagered over $1 billion on the crypto gambling site.

NOCTA // Nike

  • Type: Nike Sub-label
  • Role: Founder
  • Established: 2020
  • Fun Fact: Drake first signed with Nike in 2013. After unveiling a number of exclusive shoes through the years, the rapper launched his sub-label with the Swoosh in 2020. The name takes inspiration from “the nocturnal nature of the rapper’s creative process.”

Dave’s Hot Chicken

  • Type: Restaurant Chain
  • Role: Investor
  • Invested: 2021
  • Fun fact: Dave’s Hot Chicken was deemed “the fastest-growing chain of the year” in 2022, having grown from two locations to 118 in just three years. It also saw its sales surge 156% year-over-year.

Wealthsimple

  • Type: Financial Technology Company
  • Role: Investor
  • Invested: 2021
  • Fun fact: Drake joined the company’s Series C alongside several other prominent Canadians in the $750 million round, including Ryan Reynolds and NBA player Kelly Olynyk.

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Bernadette Doykos

Bernadette Doykos is the Senior Director of Editorial Strategy at Boardroom. Before joining the team, her work appeared in ELLE. She previously served as the head of evaluation for a nonprofit where she became obsessed with systems and strategy and served as the curator of vibes and extinguisher of fires for the design thinking firm Stoked. She is constantly plotting a perfect tunnel ‘fit and a playlist for all occasions.