How Jay-Z went from teen drug dealer to the world’s richest musician

The irony can’t have been lost on Jay-Z when he announced his latest business venture in late 2020. In addition to owning clothing lines, a record label, sports agency, streaming service, top-shelf liquor brands and around one per cent of Uber, he would now be a purveyor of cannabis through his startup Monogram.

However, this wasn’t shrink-wrapped crumbling lumps of hash from under the counter of the corner store. Instead, he announced solemnly, it “marks a new chapter in cannabis, defined by dignity, care and consistency … it is still an industry whose legacy of skilled craftsmanship is often overlooked”.

The pre-rolled cigars and tins of dried flowers are packaged in sophisticated black boxes and retail for up to US$70. The veteran rapper is the firm’s Chief Visionary Officer, a far cry from the last time he worked in the narcotics industry some 38 years earlier.

“To be in a drug deal, you need to know what you can spend, what you need to re-up … At some point, you have to have an exit strategy, because your window is very small.” – Jay-Z

Back then, there wasn’t much craftsmanship involved in cooking up the crack cocaine that a 13-year-old Shawn Corey Carter was selling in back alleys around the notorious Marcy housing projects in the deprived Bedford-Stuyvesant district of Brooklyn where he’d grown up. Nor was there much dignity in the almost daily murders and stabbings as rival gangs defended their territories.

Drug dealer

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The Jigga man has been very open about his past as an illegal pharmaceutical entrepreneur, both rapping about it and discussing it in interviews.

“I know about budgets. I was a drug dealer,” he told Vanity Fair in 2013. “To be in a drug deal, you need to know what you can spend, what you need to re-up. Or if you want to start some sort of barbershop or car wash—those were the businesses back then. Things you can get in easily to get out of [that] life.”

It helped prepare him for the cutthroat music industry, he has said. Though if you think it’s tough out here on the charts, it’s nothing compared to what Jay saw on the streets.

“At some point, you have to have an exit strategy, because your window is very small,” he said about drug dealing. “You’re going to get locked up or you’re going to die.”



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Start a debate about the best rap artists in history and three names will always appear on the list: Tupac Shakurthe Notorious B.I.G. and Jay Z. (Sorry, Nas.)

Jay has sold millions upon millions of records and was one of the pioneers who helped to define urban music in the late 1990s and early 2000s.

He’s won multiple awards including 21 Grammys and a Sports Emmy for outstanding music composition/direction/lyrics in recognition of his Super Bowl XLIV opener of his song “Run This Town” featuring singer Rihanna.

In 2013 he broke a Spotify record whern his “Magna Carta Holy Grail” album was streamed 14 million times.

This from a man who once famously “retired” from rap.


Music executive

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Every successful dealer knows the key is controlling your product.

In 1996 Jay Z formed Roc-A-Fella Records with friends Damon “Dame” Dash and Kareem “Biggs” Burke specifically to market the rappers music.

Over the years their artist roster grew to include such names as Kanye West, Memphis Bleek and Beanie Sigel.

Jay Z and his partners sold Roc-A-Fella to Island Def Jam and he was appointed to a new role as president and CEO of Def Jam Recordings in 2004.

In 2008 the rapper founded an entertainment company, Roc Nation, which includes a record label that is home to artists like Drake, and Rihanna.

A strong crew is everything in the game.




Before there was ever any talk of a potential deal between Apple and Tidal, Jay was all about streaming music.

In 2013 he strategically partnered with Samsung to make his “Magna Carta Holy Grail” album available first via download on specific Samsung phones over the July 4th weekend.

It was consistent with other high profile partnerships he’s made throughout his career: His Roc Nation label came about in part thanks to a $150 million profit sharing deal with entertainment giant Live Nation.

In 2015 Roc Nation announced it would be teaming with Philymack, the management firm that oversees pop stars Nick Jonas and Demi Lovato.

“We sat down and dreamt about what the future could hold if we partnered,” the rapper said at the time. “Our views aligned on nurturing, growth and allowing creatives to stay true to their voice. That dream we are living today and it’s been amazing for all parties. We look forward to what tomorrow brings.”



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Who could ever forget that the rapper once owned a small part of the New Jersey Netsand helped make them the Brooklyn Nets?

He is credited with — or blamed for  the creation of last year’s “Jay Z rule” which said teams can only have 25 or fewer individual owners with each owning at least a one percent stake. According to Grantland, Jay Z only owned 0.15 percent of the team before he sold his stake to Jason Kidd and an unidentified investor in 2013.

That same year Jay Z formed Roc Nation Sports, which manages professional athletes.

He’s also been savvy enough to get pieces of various businesses over the years including the 40/40 Club sports-bar chain. And he’s an investor in several other restaurants, starting with New York hotspot The Spotted Pig.




“I made the Yankee hat more famous than a Yankee can” he rapped in his 2009 hit “Empire State of Mind”  and he’s not wrong.

His early understanding that the street style of hip hop was one fans wanted to emulate led him and Dash to establish the urban apparel line Rocawear early on. He cashed in on it when he reportedly sold the rights to Iconix Brand Group in 2007 for $204 million.




What is success if you don’t have anyone to share it with?

Jay Z blessed us all with his lessons learned and reflections in his 2010 memoir “Decoded.”

Of course, since it’s Jay, the biography debuted in the top five of the New York Times bestseller list.

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