In July 2009, Forbes published their third annual list of “Cash Kings.” After abdicating the throne to allow for Curtis “50 Cent” Jackson's rise in 2008, Jay-Z re-emerged to take his rightful place atop hip hop’s financial index. Propelled to his victory courtesy of Cola Cola’s procurement of Vitamin Water, 50 would notoriously file for bankruptcy within seven years of receiving the prestigious honor. Conversely, the Marcy Projects resident that used to “sell snowflakes by the OZ” hasn’t only retained his pre-existing wealth, but has expanded it to unprecedented levels. Whilst hip-hop and entrepreneurship are far from distant cousins, Shawn Corey Carter’s sustained level of success in both avenues is improbable at best and, at worst, nonreplicable.

By and large, rappers will secede from the frontlines of artistry when it comes time to attain mogul status. Instead, Jay saw that diversifying beyond one of the most erratic industries in the world didn’t mean closing that revenue stream for good. Three years on from bidding a fond farewell to the rap game with The Black Album, Jay-Z was back and more acutely aware of his value than ever. Where other rappers would’ve embarked on the conventional press junket, Hova signposted the forthcoming release of 2006’s Kingdom Come with a Budweiser ad campaign that he’d soon parlay into a co-brand director position for their Select Range. In March of that same year, the then-Def Jam president pulled off an impressive coup as he sold his Rocawear clothing line to fashion magnates Iconix for a whopping $204 million, setting the tone for a career renaissance that would see his musical exploits and business endeavors coexist in a harmonious fashion.

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“That was the greatest trick in music that people ever pulled off, to convince artists that you can't be an artist and make money. I think the people that were making the millions said that. It was almost shameful, especially in rock 'n' roll. Here you got these millionaire guys who had to pretend as if they weren't successful at all or it would be like a detriment to their career.”

- Jay-Z to Forbes in 2010 

With a well-documented history of balking at the conventional, this reluctance to adhere to the industry playbook has been the impetus behind some of his most inspired money moves. After all, this is a man that infamously turned down Def Jam’s first attempt to sign him on the grounds that “I own the company I rap for.” An audacious move even by his standards, it explains why he would resign from his post as president of that same label on the grounds that “I felt like I would be a waste there.” Less than a year later, he’d unveil his new label Roc Nation, doing so alongside a lucrative deal with Live Nation valued at $150 million. Marked by Jay’s assertive claims that “I’ve turned into The Rolling Stones of hip-hop,” Live Nation renewed it for $200 million 10 years later. “Jay Z is one of the world’s preeminent touring artists,” said the company’s CEO Michael Rapino upon its announcement. “This strengthens the creative and business partnership of someone that continues to expand his touring base and reach.”

Anything but an isolated incident, this vast increase in price tag mirrors the shrewd business move that saw him sell his stake in the team he’d help rechristen as the Brooklyn Nets. Although he maintains that he’ll a fan of the team “forever,” he turned his investment into a reported profit of 135% - and that’s before he’d offloaded his share of the Barclays Center or set up his new management agency Roc Nation Sports. Impressive achievements in their own right, what makes the increasing price tag on his Live Nation Deal or his ability to turn positive equity into profit all the more noteworthy is how it neatly mirrors the art-collecting analogy he details on 4:44’s“The Story Of OJ”: 

“I bought some artwork for one million
Two years later, that shit worth two million
Few years later, that shit worth eight million
I can't wait to give this shit to my children”

As alluded to in his 2010 memoir Decoded, Jay’s rapacious need to keep the money flowing in was partly inspired by watching MC Hammer go from being “in Forbes Magazine with eight figures to his name, big pants and all” to “filing for bankruptcy” a couple of years later. Therefore, it’s unsurprising that Jay wants to safeguard his family’s financial freedom for generations to come. To a kid that grew up in the treacherous Marcy Projects, money is empowerment. An escape route from systemic injustices that countless can never outrun. As a result of the prevalence of this reality, Jay and Beyonce’s decision to give their daughter Blue Ivy credits on a number of tracks exemplify how he’s looking to secure her future. Detailed on 4:44’s “Legacy”, the track that doubled as an ad-hoc living will, Hov is simply following the example that his mother once set for him:

“My parents ain't have shit, so that shift started with me. My mom took her money, she bought me bonds. That was the sweetest thing of all time.”

Self-reliant to the hilt, Jay is one of the few men on earth that could conjure up bars such as “put me anywhere on God’s green earth, I’ll triple my worth” from “U Don’t Know” without coming across as misguidedly arrogant. But for every unequivocal victory that he’s notched, he’s as susceptible to false starts or miscalculations as the rest of us. Compiled in an article by Gizmodo, the news that he intended to launch a new venture capital fund for start-ups led them to reappraise his history of investments, uncovering some blemishes in the process. Whilst the oft-debated profitability of Tidal has been a hot topic of conversation for years, high-reward investments that he’d made with sock brand Stance and Uber were offset by ill-fated backing of social media platform “Viddy” and private plane-renting app Blackjet. 

Undeterred by these small mishaps, Jay has plowed money into Californian cannabis company Caliva, meat-free alternative Impossible Foods, and even threw his hat into the private jet ring once more with JetSmarter. His refusal to second guess himself after failure recalls a line from Kingdom Come’s reflective number “Beach Chair:” “Some said: ‘Hov', how you get so fly? I said ‘From not being afraid to fall out the sky.’” Where others might have faltered and mimicked the demise of the proverbial Icarus, Hov simply brushed the dirt off his shoulder and moved on to the next one. A man that has crafted far more than the 3 Blueprints that he's committed to record, if any further evidence of Hov’s unequaled tenacity is needed then look no further than this character-defining anecdote from none other than The Roots’ own Questlove:  

“Lawyers were holding up the record because of the “You and Whose Army” sample. Jay-Z was still president of the label then. I was like, “Can you get me on the phone with those guys in five minutes?” He was like, “Yeah.” I said, “Do you know those guys?” He said, “No.” I was confused. So I asked, “Well, how are you going to get through to those guys?” He said, "Watch.” Sure enough, in five minutes I was jogging on the treadmill talking to the Radiohead guys. Lawyers can’t make it work, but Jay-Z can.”