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The Life And Times Of Jay-Z: From Rapper To Music Mogul
"I'm not a businessman. I'm a business, man." — Jay-Z
That lyric predated Jay-Z's forming his entertainment company, Roc Nation, in 2008 — before buying and selling his stake in the Brooklyn Nets in 2013 (only after bringing them from New Jersey to Brooklyn), prior to acquiring Ace of Spades champagne in 2014, before becoming stakeholder of Tidal in 2015, and before reportedly reflecting a net worth of $810 million in 2017.
Raised in the gritty Marcy Houses housing project in the backwaters of the Bedford-Stuyvesant section of Brooklyn, N.Y., Shawn Corey Carter didn't have the most idyllic upbringing. His early life of drug dealing in the '80s included tinkering with rap before it ultimately became his bread and butter in the mid-'90s. In 1995 Roc-A-Fella Records was born from the hive mind of Jay, Damon Dash, and Kareem "Biggs" Burke.
In 1996 Jay-Z released his debut album, Reasonable Doubt. The project became a pillar of New York City rap, as artists like Jay, Nas, Mobb Deep, the Notorious B.I.G, and Dipset were curating a new, authentic sound for hip-hop.
"[Jay-Z] was one of us. He was one of the n***as I used to go out and do business with, one of the n***as I used to hang out with," says Jim Jones, a founding member of Dipset (alongside Cam'Ron) and now a Roc Nation artist. "His music reflected the things we all did: throw parties, take a risk and sell drugs, the shootouts, the violence, pull all the pretty ladies."
By 1998, Jay-Z earned his crowning musical achievement of the '90s with his third studio album, Vol. 2... Hard Knock Life. The project propelled him to the mainstream, netting him his first GRAMMY for Best Rap Album at the 41st GRAMMY Awards and selling more than 5 million copies. The following year he launched Rocawear, his first lucrative pivot from music, capitalizing on the gems of business tutelage he received early on in his dealings on the streets and behind closed doors.
"I think there are a couple of guiding philosophies [for Jay-Z] and one of them is 'Don’t give away your advertising,'" says Forbes editor Zack O'Malley Greenburg, who is also the author of the upcoming book 3 Kings: Diddy, Dr. Dre, Jay-Z and Hip-Hop's Multibillion-Dollar Rise. "If you're gonna rap about a clothing line or liquor, either start your own or pay somebody to do it because he learned early in his career he was building up all these companies like [fashion line] Iceberg and a couple of others — boosting their sales — but when he tried to get endorsement deals they laughed him out of the room. That's why he started Rocawear."
As he entered into the early aughts, Jay-Z's music flipped from guarded mystique to more overt and direct, especially on the Nas diss track "Takeover" in 2001. His music was evolutionary, as each project introduced a new iteration of Jay-Z, yet remained consistent to his credo of authenticity.
"We adopted this mantra with him: 'If somebody else did it, we're not doing the same thing somebody else did,'" says Kevin Liles, former Def Jam President and co-founder of 300 Entertainment. "We're gonna do it the Jay-Z way."
Jay-Z purchased his first 40/40 Club in 2003, but would seriously change the face of hip-hop the following year by becoming the first rap artist to turn executive as president of Def Jam.
"A lot of people have to realize that Jay has always been a businessman and because I left [Def Jam] in 2004, they consulted me on decisions of who should run," Liles explains. "At the end of the day you're talking about an iconic figure, a guy who never wanted to sign to a label — who wanted to be his own label — and now has an opportunity to be the fifth president of the most iconic label in hip-hop. The stars were aligned.”
After releasing The Black Album in 2003 — and announcing a retirement that would last only three years — Jay-Z spent the next decade and a half focusing on building his brand. The music would be an accompaniment, though as he evolved into a leader, his life traveled further and further from transparency. After marrying Beyoncé in 2008, his private life became even more distant from the public eye, only enhancing his "larger than life" status. That same year, he formed Roc Nation, a boulder that was derived from Roc-A-Fella Records pebble. Roc Nation Sports soon followed, and it wasn't long before he was dictating moves beyond hip-hop and in the mainstream sphere.
Jay-Z with Roc Nation Sports client Kevin Durant
Photo: Shareif Ziyadat/FilmMagic/Getty Images
"It was not saying 'yes' to everything that came across the table," says Lenny Santiago, senior vice president, A&R, artist management for Roc Nation. "It was more so thinking of what exactly he wanted, and how he wanted to revolutionize this industry and change the game, and make music to last forever, and business deals that would change the culture."
Jay-Z was now a minted mogul, known for only solid wins and shielded losses.
"I think Jay-Z is someone who really takes inventory of his wins and losses, because very rarely do I see him, at least publicly, lose in the same manner twice," says Tracy G, on-air personality on "Sway In The Morning" and host of "She’s Beauty And The Beast" podcast. "It just doesn’t seem to happen."
O’Malley Greenburg footnotes that sentiment with an anecdote from his first book, Empire State Of Mind: How Jay Z Went From Street Corner To Corner Office — where he details Jay-Z arranging a Rucker Park Tournament with the likes of basketball players LeBron James and Lamar Odom — but canceling the documentation of the event when his team forfeited.
"In the beginning, there was this sort of 'I will not lose ever' mentality as indicated in his lyrics," O’Malley Greenburg explains. "And you can see by some of his ventures and what he chooses to publicize and not publicize that if the result of whatever it was didn't end up as a complete victory, he didn't want anybody to hear about it. The new JAY-Z of 4:44 is different. He says, 'A loss ain't a loss, it's a lesson’ [on 'Smile']."
Released in 2017, the Album Of The Year-nominated 4:44 arguably serves as the culmination of everything Jay-Z has come to be. As rumors of a stormy marriage and shaky investment in Tidal loomed overhead, he chose to be his most maturely intimate on his latest LP, even admitting to missteps in both his personal and professional life.
"He's now reached this status where he's comfortable revealing some of his failures in addition to his many successes," O’Malley Greenburg notes. "I think this was his way of making 'lemonade,' if you will."
At the heart of his remarkable history and his growth, Jay-Z has scaled the heights by keeping one notion in mind: to keep his circle small.
"He's true to himself, true to his friends. He's a good dude,” says former Roc-A-Fella and current Roc Nation artist Freeway. "Being around him, you wouldn't know he accomplished all of the things he accomplished. He's just … cool."
Some might say Jay-Z used The Secret and manifested his wins into existence; others would credit his work ethic and faith in his abilities and that of his winning team. The reality is that Jay-Z — like he claimed 13 years ago — in and of himself is the business. His music has withstood the test of time — as the 48-year-old reigning champ of rap has proven false the tagline that hip-hop is a "young man's game." His business acumen has been benchmarked by peers, where even predecessors like Diddy learned from Jay's business model. Jay-Z doesn't win for winning's sake. He wins to change the industry he entered and leave it better than he received it.
"The best piece of advice Jay-Z ever gave me was, 'Let's bet on ourselves,'" Liles reflects. "It's why he started Roc-A-Fella, it's why he took on the position as president at Def Jam, it's why he was one of the first artists to do a Live Nation deal, and one of the first artists to perform a concert in front of a Mike Tyson fight. He constantly bets on himself."
(Kathy Iandoli has penned pieces for Pitchfork, VICE, Maxim, O, Cosmopolitan, The Village Voice, Rolling Stone, Billboard, and more. She co-authored the book Commissary Kitchen with Mobb Deep's late Albert "Prodigy" Johnson, and is a professor of music business at select universities throughout New York and New Jersey.)