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Where is Drake placed on the list of the wealthiest rappers of the world? Consider, he’s the most streamed artist of the last decade, selling out every arena and stadium he plays multiple nights over. His endorsements with Apple, Sprite, & Nike proved lucrative for all parties and his money is diversified in both blue chip and startup stock with several brands taken under his OvO product line. Drake’s Virginia Black whiskey broke records and continues to pull in revenue through an evolving international distribution strategy. Currently, Drake is the second most popular artist in the world behind Taylor Swift according to the Billboard Artist 100 where he often sits at the top, ahead of Meek Mill and YoungBoy Never Broke Again who hold the next rankings for hip hop artists. Drake’s catalogue spans genre and remains the highest performing of his peers with a staggering 258 songs charting on the Billboard 200, 54 reaching the Top 10, and nine reaching the top spot.
Which is why it surprised me to see where he ranks on the Top Ten Wealthiest Rappers of 2021 …He’s eighth on the list; actually. Eighth, the bottom of the Ten. Drake is seated behind Pharrell, Eminem, and even Master P, ahead of only Usher and Ice Cube in the top ten richest urban artists turned entrepreneurs. How does that work? The news cycle routinely churns out stories of his investments, four major contributions to rounds of funding for startups in 2021 alone and various personal projects have taken advantage of his enormous cache. For one, Drake only 34, has had significantly less skin in the game than Jay-Z, Dr. Dre, or dare I say his industry counterpart Kanye West, all of whom have spent the better part of the past decade placing their finances in rapidly growing industries from tech to retail fashion to cannabis (all of which are places Drake has put his money).
Drake’s portfolio, while young, is nothing short of impressive. DreamCrew, his production company run with Adel “Future” Nur produces Top Boy and the immensely popular Euphoria, which is currently in production. The rap superstar continues to hold money in Players’ Lounge, an e-sports betting book along with Marissa Mayer and recent actions signal that Aubrey’s money is probably about to be the hare in the rap billionaire tortoise race.
If not for Drake’s promising investments in everything from quick service restaurants to fintech this year, it may be fair to assume a lack of business skill and acumen based purely off his failures. Drake’s dove into the restaurant business twice, both times resulting in closure following various scandals with both gang violence and workplace rights. His partnership with cannabis branding giant Canopy Growth was moved down their IP docket before eventual abandonment. Most recently comes the characteristic delay of The 6ix God’s newest passion project…History, a mid-scale live music venue originally set to make its splashy debut on the East Side of Toronto this October with a month’s slate of respectable bookings until Thanksgiving Monday when it was announced the venue would be cancelling its first concerts. A press release points the finger to COVID-19 regulations as the city announces its return to 100% capacity live events, though many speculate a lack of organization and preparation as the actual reason.
In anticipation of History’s eventual opening, we broke down Drizzy’s business ventures and where all his money is going; some places successful, others not; some businesses are still operational, others have been long shuttered; all are examined to provide context as Drake navigates the market for wealthy rap investors and presumably climbs the billionaire mountain.
Drake’s lifestyle brand founded with tour manager Oliver El-Khatib started as an entourage-run blog with the intentions of tracking the meteoric rise of the pop superstar. It has since evolved into a record label, music festival, and product line spawning several fragrances and an in-demand clothing line. Known as OvO (get it? Like the face of an owl?), Drake's fashion retail brand is more leveraged on the cache of its face, opposed to any ultra-superior design, a product strategy perhaps more in line with the exploits of his mortal enemy than the one he chooses to employ. Still, OvO pulls in serious coin boasting respectable collaborations including the Canada Goose Chilliwack, the Bape 1st Camo snowboard jacket, the “Anaconda” Air Jordan 3, and a line of varsities with inherently national brand Roots.
Drake’s adjoining to Brent Hocking’s empire of luxury brands created big returns and name brand value. Their Virginia Black Whiskey, founded together in 2016 smashed records debuting with 1,779 bottles sold on opening day through the LCBO, 4650 in its first week, and 30,000 cases in its first year, incurring serious margins. Now offered in the Dubai International Airport and throughout Australia, it’s reviewed well as an introductory brand aiming for universal appeal with gateway nodes like vanilla and caramel showing up in every flavour profile review. Other than that, there doesn’t seem to be much growth; Virginia Black’s Instagram has posted all but twice in the last two years and a $30 million round of funding in 2018 run by Cambria Capital delayed sale of shares to this year.
Drake’s foray into the adventures of restauranteering seemed like a curse in the eyes of an industry vet, until you read into the malpractices of his good friend and noted Toronto food scene staple Chef Susur Lee & his colourfully influential sons Kai & Levi. Their Fring's, owned alongside Drizzy & an amalgamation of Western and Lee’s signature Asian fusion on King Street West, opened in Summer 2015 to large reception and swanky appearances from Jayden Smith, Serena Williams, and Drake himself who manned the DJ tables from opening onward.
It closed in 2018 after a Lee restaurant tipping scandal affected business. Allegations that upper management was withholding front of house tips to pay for spilled drinks, server errors, and dine & dashes was proven true two years after opening, violating Canadian workplace law, and creating a public crisis for the Lee brand with Fring's employees testifying to being shaken down. The restaurant also had their liquor license revoked in April that year after some reported overcapacity and a lack of due diligence on behalf of the bar staff who were serving guests to the point of “immoderate consumption.” The restaurant’s social media instead blamed renovations for the one-week closure. The restaurant served its last customer four months later.
Pick 6ix, Drake’s other restaurant concept on Yonge and Wellington, locked its doors in February 2020. After opening in partnership with Montreal sushi chef Antonio Park to mixed reviews, it was rebranded to a sports bar in 2019 after numerous incidents. On May 20, 2018, three suspects chased a Pick 6ix patron down a parkade, shot him 20 times, and took off in a Honda Civic just hours after Drake made an appearance at the restaurant. Then in August after rainstorm flooding, the restaurant closed for nearly seven months before the final nail was hammered in the coffin due to $70,000 in unpaid rent.
Drake’s first entry into canna-commerce came to a final close last June when market giant Canopy Growth Corp. ended their partnership. Canopy had invested a 40 per cent ownership stake in Drake’s More Life Growth Co. in late 2019, with the companies planning to share a two-floor building in Scarborough that planned to grow about 4 tons of pharmaceutical-grade cannabis annually. Canopy at the time already boasted an illustrious line of usable IP as the distributor of Seth Rogen’s Houseplant and Martha Stewart-branded CBD isolate gummies on referral from storied Canopy investor Snoop Dogg. The company admitted Drake was low on their list of cross-promotions to Bloomberg in August 2020 along with news that the collaboration had "not been progressing as originally intended."
Strict Canadian Endorsement Regulations in The Cannabis Act preventing celebrities or fictional figures from commercially promoting cannabis retail brands has caused companies to restructure their promotional plans: "Leafs by Snoop" brand was renamed "LBS" for Canadian sales while Rogen never publicly commented on Houseplant, a partnership which ended this July. Drake’s inability to use his name to promote his cannabis venture potentially contributed to its end, but the company claims More Life’s main strategy of investing in physical locations amid a rapidly changing post-COVID retail landscape was a major red flag.
"I would say that [More Life] has not been progressing as originally intended and we're still working on details to determine where it goes," CEO David Klein told BNN in a phone interview, "it may be something that can't get to where we all want it to go. In many regards, at its essence, it's almost a real estate play where More Life is going to do a lot of activity on cannabis destinations. I don't know if that still fits anybody's way of thinking, at least in the COVID world." Canopy has since converted the Scarborough facility to an R&D wing.
And here we are, with Drake’s camp once again shadily blaming external factors over unpreparedness or control of scope. Just two days ago (10/11), History recently cancelled their first few shows of 200 that they intended to host annually. The 2500-person venue declared its intention of giving major artists a more intimate experience while providing a configurable space for galas and community programs with the announcement of Drake’s addition, occurring last June despite its development ongoing for three years.
History already promises a slate of impressively ranged booking which reads like the best festival yet to exist this side of the border: Thundercat, Jack Harlow, Teyana Taylor, Flaming Lips, Ashnikko, Zeds Dead, and CHVRCHES are all booked for November with Kaytranada, Beaches, Clairo & Arlo Parks, Chet Faker, July Talk, U.S.S., Duke Dumont, Glass Animals, and King Gizzard & The Lizard Wizard sure to bring large audiences into 2022… if it opens as promised. The venue is located at 1663 Queen Street East, just before Kingston Road in the Beaches, taking over the defunct Champions Greenwood off track betting outlet. The venue plans to host its first show on November 1 with English singer songwriter Passenger.
Despite a discrepancy between Drake’s placement as a rap businessman vs his usual position as the most streamed artist on earth, 2021 saw Drake aggressively put his money in a line of solid, diversified investments, signaling big money coming for the superstar.
Sports Media Company
Round of Funding: $80 million
Assessment: Drake joins Jeff Bezos, Reddit founder Alexis Ohanian, and several NBA players to invest in Overtime, a company that distributes original sports content using social media like Snapchat, YouTube and Facebook’s platforms. The firm just started a basketball league for 16- to 18-year-olds offering them six figure contracts and additional scholarships should they choose not to pursue NBA careers.
Plant-based food company
Round of Funding: $40 million
Assessment: The rise of chicken as the most popular meat in the US makes its faux counterpart a clear target for growth in the near future. Daring Foods (practically in its infancy hitting shelves in 2020 and select US Costcos in March) is making waves in the industry for its convincing recipe which metabolizes its product from soy protein as much of the population are embracing plant-based diets. The global plant-based chicken category is expected to reach $8 billion by the end of this decade.
Online Investment Management Service
Round of Funding: $750 million
Assessment: Wealthsimple’s $5 billion valuation made serious waves earlier this year before the GameStop mess, pulling in a huge round of funding from five venture capital investment firms including Meritech, Greylock, Dragoneer, & iNovia and Canadian celebrities Ryan Reynolds, Michael J. Fox, and yours truly. Wealthsimple provides services to 2 million users nationally including Wealthsimple Trade, a commission-free stock trading platform; Wealthsimple Crypto, which allows users to buy, sell & hold cryptocurrency assets; and Wealthsimple Cash, a peer-to-peer money transfers app.
Quick Service Restaurant
Round of Funding: unknown
Assessment: Launched in 2017, Dave’s Hot Chicken entered Toronto’s saturated food service industry in February to long lines and some backlash after not enforcing proper social distancing. Since then, they’ve opened two more locations in Leslieville and Mid-town as part of an aggressive growth plan featuring three openings in one week in Houston, Santa Ana and Santa Rosa just last month. Dave’s plans to double their locations by the end of year with other key investors like Red Sox Chairman Tom Werner and Samuel L. Jackson making up under 50% equity.
Check out our article on Drake's romantic life here.
Where is Drake placed on the list of the wealthiest rappers of the world? Consider, he’s the most streamed artist of the last decade, selling out every arena and stadium he plays multiple nights over. His endorsements with Apple, Sprite, & Nike proved lucrative for all parties and his money is diversified in both blue chip and startup stock with several brands taken under his OvO product line. Drake’s Virginia Black whiskey broke records and continues to pull in revenue through an evolving international distribution strategy. Currently, Drake is the second most popular artist in the world behind Taylor Swift according to the Billboard Artist 100 where he often sits at the top, ahead of Meek Mill and YoungBoy Never Broke Again who hold the next rankings for hip hop artists. Drake’s catalogue spans genre and remains the highest performing of his peers with a staggering 258 songs charting on the Billboard 200, 54 reaching the Top 10, and nine reaching the top spot.
Which is why it surprised me to see where he ranks on the Top Ten Wealthiest Rappers of 2021 …He’s eighth on the list; actually. Eighth, the bottom of the Ten. Drake is seated behind Pharrell, Eminem, and even Master P, ahead of only Usher and Ice Cube in the top ten richest urban artists turned entrepreneurs. How does that work? The news cycle routinely churns out stories of his investments, four major contributions to rounds of funding for startups in 2021 alone and various personal projects have taken advantage of his enormous cache. For one, Drake only 34, has had significantly less skin in the game than Jay-Z, Dr. Dre, or dare I say his industry counterpart Kanye West, all of whom have spent the better part of the past decade placing their finances in rapidly growing industries from tech to retail fashion to cannabis (all of which are places Drake has put his money).
Drake’s portfolio, while young, is nothing short of impressive. DreamCrew, his production company run with Adel “Future” Nur produces Top Boy and the immensely popular Euphoria, which is currently in production. The rap superstar continues to hold money in Players’ Lounge, an e-sports betting book along with Marissa Mayer and recent actions signal that Aubrey’s money is probably about to be the hare in the rap billionaire tortoise race.
If not for Drake’s promising investments in everything from quick service restaurants to fintech this year, it may be fair to assume a lack of business skill and acumen based purely off his failures. Drake’s dove into the restaurant business twice, both times resulting in closure following various scandals with both gang violence and workplace rights. His partnership with cannabis branding giant Canopy Growth was moved down their IP docket before eventual abandonment. Most recently comes the characteristic delay of The 6ix God’s newest passion project…History, a mid-scale live music venue originally set to make its splashy debut on the East Side of Toronto this October with a month’s slate of respectable bookings until Thanksgiving Monday when it was announced the venue would be cancelling its first concerts. A press release points the finger to COVID-19 regulations as the city announces its return to 100% capacity live events, though many speculate a lack of organization and preparation as the actual reason.
In anticipation of History’s eventual opening, we broke down Drizzy’s business ventures and where all his money is going; some places successful, others not; some businesses are still operational, others have been long shuttered; all are examined to provide context as Drake navigates the market for wealthy rap investors and presumably climbs the billionaire mountain.
Drake’s lifestyle brand founded with tour manager Oliver El-Khatib started as an entourage-run blog with the intentions of tracking the meteoric rise of the pop superstar. It has since evolved into a record label, music festival, and product line spawning several fragrances and an in-demand clothing line. Known as OvO (get it? Like the face of an owl?), Drake's fashion retail brand is more leveraged on the cache of its face, opposed to any ultra-superior design, a product strategy perhaps more in line with the exploits of his mortal enemy than the one he chooses to employ. Still, OvO pulls in serious coin boasting respectable collaborations including the Canada Goose Chilliwack, the Bape 1st Camo snowboard jacket, the “Anaconda” Air Jordan 3, and a line of varsities with inherently national brand Roots.
Drake’s adjoining to Brent Hocking’s empire of luxury brands created big returns and name brand value. Their Virginia Black Whiskey, founded together in 2016 smashed records debuting with 1,779 bottles sold on opening day through the LCBO, 4650 in its first week, and 30,000 cases in its first year, incurring serious margins. Now offered in the Dubai International Airport and throughout Australia, it’s reviewed well as an introductory brand aiming for universal appeal with gateway nodes like vanilla and caramel showing up in every flavour profile review. Other than that, there doesn’t seem to be much growth; Virginia Black’s Instagram has posted all but twice in the last two years and a $30 million round of funding in 2018 run by Cambria Capital delayed sale of shares to this year.
Drake’s foray into the adventures of restauranteering seemed like a curse in the eyes of an industry vet, until you read into the malpractices of his good friend and noted Toronto food scene staple Chef Susur Lee & his colourfully influential sons Kai & Levi. Their Fring's, owned alongside Drizzy & an amalgamation of Western and Lee’s signature Asian fusion on King Street West, opened in Summer 2015 to large reception and swanky appearances from Jayden Smith, Serena Williams, and Drake himself who manned the DJ tables from opening onward.
It closed in 2018 after a Lee restaurant tipping scandal affected business. Allegations that upper management was withholding front of house tips to pay for spilled drinks, server errors, and dine & dashes was proven true two years after opening, violating Canadian workplace law, and creating a public crisis for the Lee brand with Fring's employees testifying to being shaken down. The restaurant also had their liquor license revoked in April that year after some reported overcapacity and a lack of due diligence on behalf of the bar staff who were serving guests to the point of “immoderate consumption.” The restaurant’s social media instead blamed renovations for the one-week closure. The restaurant served its last customer four months later.
Pick 6ix, Drake’s other restaurant concept on Yonge and Wellington, locked its doors in February 2020. After opening in partnership with Montreal sushi chef Antonio Park to mixed reviews, it was rebranded to a sports bar in 2019 after numerous incidents. On May 20, 2018, three suspects chased a Pick 6ix patron down a parkade, shot him 20 times, and took off in a Honda Civic just hours after Drake made an appearance at the restaurant. Then in August after rainstorm flooding, the restaurant closed for nearly seven months before the final nail was hammered in the coffin due to $70,000 in unpaid rent.
Drake’s first entry into canna-commerce came to a final close last June when market giant Canopy Growth Corp. ended their partnership. Canopy had invested a 40 per cent ownership stake in Drake’s More Life Growth Co. in late 2019, with the companies planning to share a two-floor building in Scarborough that planned to grow about 4 tons of pharmaceutical-grade cannabis annually. Canopy at the time already boasted an illustrious line of usable IP as the distributor of Seth Rogen’s Houseplant and Martha Stewart-branded CBD isolate gummies on referral from storied Canopy investor Snoop Dogg. The company admitted Drake was low on their list of cross-promotions to Bloomberg in August 2020 along with news that the collaboration had "not been progressing as originally intended."
Strict Canadian Endorsement Regulations in The Cannabis Act preventing celebrities or fictional figures from commercially promoting cannabis retail brands has caused companies to restructure their promotional plans: "Leafs by Snoop" brand was renamed "LBS" for Canadian sales while Rogen never publicly commented on Houseplant, a partnership which ended this July. Drake’s inability to use his name to promote his cannabis venture potentially contributed to its end, but the company claims More Life’s main strategy of investing in physical locations amid a rapidly changing post-COVID retail landscape was a major red flag.
"I would say that [More Life] has not been progressing as originally intended and we're still working on details to determine where it goes," CEO David Klein told BNN in a phone interview, "it may be something that can't get to where we all want it to go. In many regards, at its essence, it's almost a real estate play where More Life is going to do a lot of activity on cannabis destinations. I don't know if that still fits anybody's way of thinking, at least in the COVID world." Canopy has since converted the Scarborough facility to an R&D wing.
And here we are, with Drake’s camp once again shadily blaming external factors over unpreparedness or control of scope. Just two days ago (10/11), History recently cancelled their first few shows of 200 that they intended to host annually. The 2500-person venue declared its intention of giving major artists a more intimate experience while providing a configurable space for galas and community programs with the announcement of Drake’s addition, occurring last June despite its development ongoing for three years.
History already promises a slate of impressively ranged booking which reads like the best festival yet to exist this side of the border: Thundercat, Jack Harlow, Teyana Taylor, Flaming Lips, Ashnikko, Zeds Dead, and CHVRCHES are all booked for November with Kaytranada, Beaches, Clairo & Arlo Parks, Chet Faker, July Talk, U.S.S., Duke Dumont, Glass Animals, and King Gizzard & The Lizard Wizard sure to bring large audiences into 2022… if it opens as promised. The venue is located at 1663 Queen Street East, just before Kingston Road in the Beaches, taking over the defunct Champions Greenwood off track betting outlet. The venue plans to host its first show on November 1 with English singer songwriter Passenger.
Despite a discrepancy between Drake’s placement as a rap businessman vs his usual position as the most streamed artist on earth, 2021 saw Drake aggressively put his money in a line of solid, diversified investments, signaling big money coming for the superstar.
Sports Media Company
Round of Funding: $80 million
Assessment: Drake joins Jeff Bezos, Reddit founder Alexis Ohanian, and several NBA players to invest in Overtime, a company that distributes original sports content using social media like Snapchat, YouTube and Facebook’s platforms. The firm just started a basketball league for 16- to 18-year-olds offering them six figure contracts and additional scholarships should they choose not to pursue NBA careers.
Plant-based food company
Round of Funding: $40 million
Assessment: The rise of chicken as the most popular meat in the US makes its faux counterpart a clear target for growth in the near future. Daring Foods (practically in its infancy hitting shelves in 2020 and select US Costcos in March) is making waves in the industry for its convincing recipe which metabolizes its product from soy protein as much of the population are embracing plant-based diets. The global plant-based chicken category is expected to reach $8 billion by the end of this decade.
Online Investment Management Service
Round of Funding: $750 million
Assessment: Wealthsimple’s $5 billion valuation made serious waves earlier this year before the GameStop mess, pulling in a huge round of funding from five venture capital investment firms including Meritech, Greylock, Dragoneer, & iNovia and Canadian celebrities Ryan Reynolds, Michael J. Fox, and yours truly. Wealthsimple provides services to 2 million users nationally including Wealthsimple Trade, a commission-free stock trading platform; Wealthsimple Crypto, which allows users to buy, sell & hold cryptocurrency assets; and Wealthsimple Cash, a peer-to-peer money transfers app.
Quick Service Restaurant
Round of Funding: unknown
Assessment: Launched in 2017, Dave’s Hot Chicken entered Toronto’s saturated food service industry in February to long lines and some backlash after not enforcing proper social distancing. Since then, they’ve opened two more locations in Leslieville and Mid-town as part of an aggressive growth plan featuring three openings in one week in Houston, Santa Ana and Santa Rosa just last month. Dave’s plans to double their locations by the end of year with other key investors like Red Sox Chairman Tom Werner and Samuel L. Jackson making up under 50% equity.
Check out our article on Drake's romantic life here.
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