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.

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.

A HARD KNOCK LIFE

Shawn and his three siblings were being raised by their mom after their alcoholic dad had walked out. The previous year, Shawn had shot his heroin-addicted older brother in the shoulder for stealing his jewelry. Soon he was trading vast amounts of cocaine and being sucked into a deadly underbelly of street crime and turf warfare. To quote the title of his biggest-selling album, it was, to put it mildly, a Hard Knock Life.

He was shot three times before he was 18, and, by rights, his story should have ended in either a prison cell or pool of blood. But the same entrepreneurial flair that made him hip-hop’s first billionaire was evident right from the start.

“I know about budgets,” 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 … At some point, you have to have an exit strategy, because your window is very small.”

His exit strategy was music, but rap was every bit as cutthroat as the drugs scene and his first few singles failed to stand out from the crowd, leaving record companies unimpressed. But even then, he had the confidence and drive to know exactly what to do. He and two friends started their own label, Roc-A-Fella Records, and Jay-Z drew up plans for a campaign to get him noticed.

ESCAPING THE STREETS

The biggest rapper at the time was LL Cool J, so Jay-Z found out exactly where he’d be each night and challenged him to a series of rap battles, winning them all. Now the major labels were impressed with this cocky upstart and lucrative offers flooded in, but they were too late. His music career was about to skyrocket on his terms and, with it, his commercial empire.

“I was forced to be an artist and a CEO from the beginning,” he once commented. “So I was forced to be like a businessman because when I was trying to get a record deal, it was so hard to get a record deal on my own that it was either give up or create my own company.”

Jay-Z and wife Beyoncé are the undisputed king and queen of the music world.

Over the following two decades, Eminem sold nearly twice as many albums and many more concert tickets, but Jay-Z’s net worth is some six times higher. You won’t find Jay-Z on lists of highest-grossing concert tours, yet he’s worth considerably more than those artists who do appear.

“I’m not a businessman, I’m a business, man,” he rapped on the 2005 remix of the Kanye West track ‘Diamonds from Sierra Leone’. And while he busied himself shifting 50 million albums, 75 million singles and amassing 23 Grammy Awards, his Midas touch for seizing opportunities never deserted him.

Jay-Z founded urban clothing brand Rocawear in 1999, selling it for US$204 million eight years later, and he bought a chain of nightclubs, a sports management company and vodka and cognac brands.

HIP-HOP CHAMPAGNE WARS

One of his most successful deals came about after an unseemly squabble with Cristal Champagne in 2006. The brand had become a favorite with hip-hop stars and many, including Jay-Z, had referenced it in songs.

But in an interview with The Economist, the brand’s Managing Director Frédéric Rouzard had appeared to peer down his nose at the idea of rappers associating with his premium cuvee. Asked if he thought his brand was being damaged, he replied haughtily, “That’s a good question, but what can we do? We can’t forbid people from buying it. I’m sure Dom Pérignon or Krug would be delighted to have their business.”

An incensed Jay-Z branded the comment “racist” and promptly banned Cristal from his chain of 40/40 Club lounges and then, in an act of vengeance, bought his own Champagne brand, Armand de Brignac. Revenge was served lightly chilled in a crystal flute.

It was about as far removed from hustling crack on the streets of Brooklyn as it was possible to get, but every bit as vicious. In his ‘Show Me What You Got’ video, he’s offered a bottle of Cristal and pointedly sends it back before the waiter returns with one of Armand’s distinctive US$285 gold bottles.

When Jay-Z offloaded half his share of the brand earlier this year for an undisclosed sum, he’d built the business up to selling 500,000 bottles a year. In one rap, he implied the company was worth US$500 million, but in reality, it was more.

MUSIC’S BIGGEST POWER COUPLE

Amid the touring, recording and deal-making, in 2008, Jay-Z married Beyoncé Knowles, then the world’s highest-earning musician. She’s now worth more than US$500 million in her own right and tops her husband’s Grammy’s total by five.

That same year, he inked one of the biggest music contracts of all time when he signed a US$150 million deal with Live Nation that included three albums and a tour, dwarfing the company’s arrangements with Madonna and U2.

Business Insider sneered at the time that the US$30 million component for his next three albums “will be tough to earn back, given that Jay’s last effort underwhelmed and hip-hop fans tend to favor youngsters, not dudes who can remember the Ford presidency”. All three topped the US Billboard charts with more than 3.5 million sales.

Then there’s the Uber stock. The US$2 million he invested in 2013 is now valued at more than US$70 million. No wonder Warren Buffett once remarked that, when it comes to business, “He’s the guy to learn from.”

And worrying about his children continuing his legacy isn’t one of his 99 problems. His eldest daughter Blue Ivy has clearly inherited her parents’ work ethic, launching a beauty line at five, buying fine art at six and, this year, winning a Grammy aged just nine. Unlike her dad, she isn’t having a hard knock start to life.

The rapper launched his own music streaming service Tidal in 2015, with the support of other music stars.