“The difference between him and a lot of other people is you really couldn’t tell that he was this guy that had a whole bunch of money from being in the streets because he wasn’t out there buying Benzes,” says Kent. “He was doing little things, like, you know, a little Lexus here, but he was buying a Lexus when all these guys in the street were buying Benzes and BMWs. To be smart enough to play yourself down to just keep the paper means you’re doing business properly. And Jay-Z was always about keeping the paper.”
These days, some question Jay-Z’s drug-dealing résumé and challenge his street cred. DeHaven, who hasn’t spoken with Jay-Z since their falling-out in the late 1990s, doesn’t deny the rapper’s involvement in the drug scene. However, he suggests that many of Jay-Z’s lyrical depictions of hustling were really stories borrowed from his own life—and that Jay-Z distanced himself because he didn’t want people to know. “I’ve been around one of the greatest sellers in the world, whether the story was real or not,” says DeHaven with a smile that betrays a hint of nostalgia. “An O.G. [original gangster] explained it to me on that level. He said, ‘If Jay was ever jealous or he ever wanted to be you, what purpose is there to have you around? ’Cause then people could see who’s who.’ Like, ‘The person you rap about seems to be [DeHaven].’ ” Still, one person who spent time with both Jay-Z and DeHaven during the early 1990s estimates that Jay-Z was moving a kilogram of cocaine (a $12,000 value27 before the fourfold street markup) per week. “He was definitely involved in the narcotics game,” says the source, who asked to remain anonymous. “There’s no denying that.”
In 1992, Jay-Z’s musical prospects got a boost when Atlantic Records hired Clark Kent. As part of the artists and repertoire (A&R) department, Kent was charged with scouting new talent. His mind immediately flashed back to the youngster he’d met in the Marcy projects years earlier. But now that Jay-Z was a successful drug dealer, he was hard to track down. Kent was eventually able to get Jay-Z’s number from a friend. “The conversation was, ‘Yo, I’m over here at Atlantic Records, we gotta do this.’ He’s like, ‘Nah, I’m good,’ ” Kent remembers. “And then daily, for two months or so, I’m like, ‘Yo, I’m over at Atlantic Records, we gotta do this.’ It was still a lot of, ‘Yeah, aight, whatever.’ ”
Jay-Z remained hesitant to devote time to music that could be spent making more money hustling. But after continuous prodding, Kent finally convinced him to appear on a remix, then on a song called “Can I Get Open” with a group called Original Flavor in 1993. “I convinced him, unwillingly,” says Kent. “He was like, ‘I’m not spending money to do this. If it happens, it happens, but I’m going to be doing what I gotta do, so it’s only going to happen when I come up from down south.’ ”
Jay-Z’s reluctance to splurge on music was understandable, as there are a lot of people to pay when recording a hip-hop song. There’s the producer, who uses an array of gizmos including drum machines, synthesizers, and a technique called “sampling” to create the basic repeating element, or “hook,” of the song. Samples are elements of previously recorded songs—perhaps the horns from a soul record or the snare drum from an old jazz standard, or occasionally the entire song minus the original vocals—and are often used to help create a song’s musical backbone, known as the “beat” or the “track.” In the mid-1990s, a producer might charge $5,000 per song plus a 50 percent share in the rights to the song, which translates to a 3 to 4 percent royalty on a whole album (on top of that, the use of a single sample might cost $5,000 to $15,000, plus an additional royalty cut28). The rapper, also known as the MC or emcee, records vocals over the beat. Once the lyrics are added, sound engineers adjust volume levels and add effects to complete the process. Postproduction and promotion add to the tab, as does studio time—as much as $2,500 per hour for a minimum of four hours during the period in which Jay-Z first started recording.29
Kent, a veteran producer, hoped that with enough songs under his belt, Jay-Z would be able to impress Atlantic or another label enough to get a record deal to fund future recordings. To that end, he persuaded Jay-Z to record a song with a rapper named Sauce Money. At the time, Kent and Sauce were working with a production company called 3-D Enterprises owned by former NBA star Dennis Scott. Patrick Lawrence, a 3-D employee and producer known professionally as A Kid Called Roots, was in charge of booking studio time for Kent, Sauce, and Jay-Z. Though the song never made it onto anybody’s album in the end, Lawrence remembers the impression Jay-Z left on him during the session. “Jay-Z was a street dude who didn’t realize how talented he was,” recalls Lawrence between bites of garlic naan at a Manhattan eatery. “He thought it was like, ‘If it was really that complicated, it wouldn’t be that easy for me.’ So he didn’t take it serious. It was Clark Kent who said, ‘You need to go hard with this,’ and convinced him to fall back on the street thing and go full steam with the music.”
When Jay-Z arrived to record his verse, he hadn’t yet heard the beat. Instead of asking to hear it or practicing his verse, he started joking around with Sauce, much to Lawrence’s chagrin. Though Lawrence had heard rumors that Jay-Z memorized all his verses in lieu of writing them down, nothing was getting done and he was getting antsy. “I’m thinking to myself, ‘This guy hasn’t written his song, nobody’s heard his verse or anything like that,’ ” recounts Lawrence. “We’ve been here for three hours, and they’ve just been laughing and talking about stuff and haven’t been talking about music. So I finally was like, ‘Jay, come on, man, you gotta fucking lay your vocals, man. This is on my ass, I’m wasting studio time, I’m almost over budget!’ Everybody’s like, ‘Oh, this guy’s getting feisty.’ So [Jay says], ‘Okay, let me hear the song.’ ”30
Lawrence played the track. Jay-Z began mumbling along to it, then picked up a pen and a notebook and seemed to start scribbling notes. He placed the pad on the sofa and started pacing back and forth, muttering more half-formed words. After five minutes, he glanced once more at the pad and told Lawrence he was ready. While Jay-Z was in the sound booth recording his verse, Lawrence went over to see what he’d written in the notebook, which was still sitting on the couch. “I walk to the pad, and there’s fucking nothing on it,” Lawrence recalls. “He was doing it as a fucking joke, like just to show people. That was when I was like, ‘This guy is the best rapper.’ ”
Brilliant rapper though he was, Jay-Z continued to hustle. The decision was part of a business philosophy that can be boiled down to a very simple rule: focus on whatever venture offers the most realistic opportunity to make the most money. Early on, that meant selling drugs; Jay-Z saw music as a fun side project, or perhaps a way to diversify his revenue streams. “His first album was supposed to be his only album. . . at least that’s what he said,” notes Touré, who authored Rolling Stone’s 2005 cover story on the rapper. “I think that was real in his mind. He was like, ‘This is a pay cut.’ ”31
It would take more than a nudge to make Jay-Z change his attitude. According to DeHaven, that came suddenly and violently sometime in 1994. “He saw death,” DeHaven explains. “He saw the bad side of the game. He almost had his life taken. And that’s what did it. He messed with the wrong people.” Jaz-O recalls the same incident: “When he saw the individual [preparing to shoot], he ran for his life, which he should have. A couple of shots fired, but the gun jammed and that’s what saved his life.”
Both DeHaven and Jaz-O take credit for the fact that Jay-Z’s assailant never came after their friend again. Jaz-O claims he used street diplomacy to snuff out the dispute, which he says was sparked by “dirty dealings” (he wouldn’t elaborate). DeHaven implies something a bit more direct. “How did he ever think them people stopped looking for him?” he says, grinning ominously. “That was me all along.” Though Jay-Z himself has never confirmed or denied that either Jaz-O or DeHaven served as a guardian angel, he has said that he stopped dealing in the mid-1990s after being ambushed by rival drug dealers: “I had near brushes, not to mention three shots, close range, never to
uched me, divine intervention.”32
Clark Kent doesn’t believe those experiences were what caused Jay-Z to stop hustling. “That shit don’t mean nothing,” he says. “Getting shot at is something that you expect when you’re in the street hustling. . . Shit, I got shot at, you know what I’m saying? You’re going to get shot. You’re going to get shot at. And if you live, it’s all good. That just meant he lived to hustle another day. It wasn’t that. What I think changed him and made him say he was going to commit [to music] was the success of that first record.”
Jay-Z has admitted that a number of factors led to his decision to stop hustling. “It wasn’t specifically one thing,” he told the Washington Post in 2000. “It was more so out of fear. You can’t run the streets forever. What are you going to be doing when you’re thirty years old, or thirty-five or forty? I had a fear of being nothing—that pretty much drove me.”33 For the burgeoning businessman, the decision to stop dealing sometime around 1995 could also be explained as a simple recalibration of risks and benefits. “When he saw the money that he could make in the music business,” Touré muses, “and be legal with it, and not have to worry about the police, and getting shot by other drug dealers, and all the other predators who’d been coming at him, it made a lot of sense.”34
Jay-Z explains his thought process in verse: “I sold kilos of coke, I’m guessing I could sell CDs.”35 As usual, he proved to be a quick study. He would find his primary instructor in that field when Kent introduced him to a young Harlem entrepreneur named Damon Dash.
“If they were still together,” says Kent, “they’d be billionaires.”
2
The Roc-A-Fella Dynasty
Just as Bill Gates dropped out of Harvard to start Microsoft, one could say that Jay-Z left the Damon Dash school of business to start his own ventures—but not before building an unparalleled commercial hip-hop empire encompassing music, film, liquor, and a clothing company that grew from a few sewing machines into a giant that produced $700 million in annual revenues.1
During that time, Jay-Z’s erstwhile business partner lived like a modern Louis XIV and sported an attitude to match. “I am trying to take over the whole world,” Dash declared in 2003. “I want a billion dollars after tax.”2 The stocky, baldheaded dynamo once boasted a butler, a personal chef, and a glass-roofed limo. He purchased pricey dwellings around the world and stocked them with hundreds of pairs of shoes he’d never wear. Shortly after he and Jay-Z parted ways in 2004, the cash evaporated, and so did the lifestyle.
These days, you usually don’t find Damon Dash unless he wants you to. So when, after trying no fewer than ten different numbers for him, I heard his voice on the other end of the line, he seemed just as startled as I was.
“How did you get this number?”
“Spent two months asking everybody I know.”
“I must be getting sloppy.”
Perhaps because he was impressed, perhaps because he was startled, perhaps because he had an ax to grind, he started telling me the tale of how it all began.
“Me, Jay . . . we all did illegal things,” he began. “And we found a way to make it in the industry.”3
In 1994, Dash was managing a group called Future Sound and making money as a party promoter. He generated hype for his events by handing out free bottles of champagne to the first one hundred women to enter; everyone else had to pay a cover charge. Clark Kent noticed that flair for marketing and decided that all Dash needed was a top-line talent to promote. He suggested a meeting with Jay-Z, but the Harlem-based Dash was skeptical at first.
“He couldn’t believe there was this Brooklyn guy who was this good,” recalls Kent. “He was, like, scared to go to Brooklyn,’cause all he thinks is stickup artists and killing. And when I introduced him [to Jay], the first thing he did was see he was wearing [Nike] Air Force 1s and was like, ‘Hold up, this guy is cool.’ So he got it immediately, and they were cool, and then he heard Jay rhyming.”
Just as Jaz-O and Clark Kent had been wowed by Jay-Z’s lyrical prowess, so, too, was Damon Dash. With Dash on board as Jay-Z’s business partner, the rapper released the single “I Can’t Get with That” in 1994, complete with shout-outs to Dash and Kent. By the end of 1995, Jay-Z had recorded the bulk of what would eventually become his first album, Reasonable Doubt. Thanks to his well-connected friends, Jay-Z was able to land tracks from some of the most highly esteemed producers in hip-hop: Clark Kent, DJ Ski, and—perhaps most impressive of all—DJ Premier, also known as Primo.
“Getting on a Primo beat at the time Jay-Z got on a Primo beat for the first time was the equivalent of driving a Ferrari or something like that,” says Elizabeth Mendez Berry, who has interviewed Jay-Z extensively and is now an adjunct professor at New York University’s Clive Davis Department of Recorded Music. “It was a moment of arriving.” 4
With Jay-Z’s debut album nearly complete, he and Dash shopped it to all the major record labels, but there were no takers. They couldn’t even get a deal at Atlantic Records, where Clark Kent had the ear of key decision makers. “They just didn’t get it,” says Kent. “The reality of what he was talking about was a little too much for the people in the company. There were people who were doing reality rap, but they weren’t doing his reality rap. A lot of what [Jay] said went over a lot of people’s heads. When you hear NWA, you hear gun killin’, drug sellin’, but you hear it in such a very plain English that when you get this guy who’s extremely crafty with words, he’s probably going all the way over your head. And he’s saying it in a way that you have to practically be a drug dealer to understand it.” Entertainment lawyer Donald David believes the major labels turned Jay-Z down for a different reason. “They were scared of the violence,” he says. “There was still the East-West rivalry concept, and people were a little bit concerned about the content and lyrics of his music. The stuff was pretty rough stuff.”5
So Jay-Z and Dash pooled their resources with a silent partner, Kareem “Biggs” Burke, to start their own record label, Roc-A-Fella Records. They picked the name to signify wealth on the level of John D. Rockefeller, the world’s first billionaire, and to evoke images of the Rockefeller family’s enduring dynasty. In typically ironic fashion (“Jay-Z is the king of the double entendre,” says Kent), the name of the record label founded in part with Jay-Z’s cocaine-dealing profits was also a clever jab at New York’s draconian Rockefeller drug laws.
“These guys started up the pressing of their own records, their CDs, their T-shirts, their stickers, their flyers, with their own money,” recalls producer Patrick “A Kid Called Roots” Lawrence. “Where that money came from? I knew it didn’t come from a label. It came out of their own pockets. And we know that they didn’t work at Target.”6
They began peddling music from the backs of their cars, Jay-Z from his trademark white Lexus, Dash from his Nissan Pathfinder. They traversed the five boroughs of New York, distributing Jay-Z’s tracks in clubs and on street corners, using the same hustling skills Jay-Z learned as a drug dealer. To say they sold music in a few unorthodox locations is an understatement.
“We were going to barbershops! You name it, we was there,” recalls Dash. “The energy was definitely there, you know? Like I said, I could see myself working with him in the future. We made a pact to do what we had to do.” To that end, Jay-Z kept releasing more singles in an effort to build on his burgeoning popularity. In early 1996, he put out a song called “Ain’t No Nigga”; a seventeen-year-old Foxy Brown sang the catchy hook. “Within three months,” recalls rapperturned-businessman Michael “Serch” Berrin, “that record was the hottest record in New York.”7
Jay-Z helped fuel his growing legend—that of the slick kingpin-turned-rapper—at open microphone nights such as Mad Wednesdays, a weekly unsigned artist showcase in Manhattan. He wowed crowds by deftly delivering lyrics like “I got extensive hoes with expensive clothes / And I sip fine wines and spit vintage flows”8 and by crafting clever songs like “Twenty-Two Twos,” in which he
repeats the words two, to, and too a total of twenty-two times in the first verse. “Jay before he got [big] was a totally different person than he is now. He was hungry,” Dash remembers. “He was willing to quit hustling, he was willing to do whatever it took.”
At the time, Jay-Z claimed he was only in for one album, and that he would go back to the more lucrative occupation of hustler after he finished. Those who spent time with him in the mid-1990s say it was all part of his marketing plan. With the hype growing around Jay-Z and Roc-A-Fella Records, Jay-Z was able to land a distribution deal with Will Socolov’s Freeze Records in partnership with California-based Priority Records. Under the terms of the deal, Roc-A-Fella would handle the production and promotion, and Freeze and Priority would handle the manufacturing and sales of the finished product; they also gained control of the masters. Profits would be split down the middle. “Back then, the standard royalty was 20 percent, or two dollars per album,” says David. “To have a deal where you’re splitting the profits fifty-fifty is far more beneficial for the artist. Jay-Z was very smart to do what he did.”
By the time Jay-Z and Dash landed their first deal, they’d built up so much underground buzz about Jay-Z’s music that the gritty Reasonable Doubt sold 420,000 copies in its first year.9 Counting copies sold informally on the street, Serch estimates that the real number was closer to 800,000. But when Jay-Z went to collect his paycheck, he got his first taste of corporate bureaucracy.
“Will Socolov gave him the whole corporate label bullshit: ‘I don’t have the money, you’ve got to wait,’ this and that,” Serch recounts. “At that time, now everybody was barking up Jay’s door. He’s got all these records sold, and he’s owed all this money, and he’s not getting his money from Freeze. So he says, ‘All right, I’ve got to get off this label.’ And negotiated his release, but negotiated it with his masters. So he got to keep his masters, which was unheard of. For an independent artist to leave a label? He always seemed to be unique and special.”10
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