For the rest of the interview, Diddy blustered brilliantly. “I’m gonna be bigger than [billionaire] David Geffen,” he told LaFranco. “The torch has to be passed to somebody. That’s the only reason I’m in the game.”22
LaFranco couldn’t help but be amazed at the young entrepreneur’s ambition. Perhaps even more impressive was his frenetic pace, not to mention his ability to constantly function without sleep—a trait LaFranco also noticed while interviewing billionaires like Rupert Murdoch.
“[Diddy] was constantly on the phone, he was recording, he was singing, he was fucking, he was drinking, he was getting high, he was marketing,” says LaFranco of his time with Diddy. “And he never slept. He was in the studio till two, three in the morning, then they’d go out to the club. The latest they ever got in was eleven in the morning. When was he sleeping?”
After completing the interview in Atlanta, Diddy returned to New York to do a cover shoot alongside Jerry Seinfeld, the subject of a profile in the same issue. Diddy demanded organic juices and smoothies, fruits, and a full soul food meal catered for twenty on-site, along with five racks of fur coats and Hugo Boss suits to choose from; naturally, he showed up in a Rolls-Royce. Seinfeld, by contrast, asked only for granola and strawberry yogurt and arrived in a cab with one suit thrown over his shoulder.
Despite their radically different approaches to the shoot, Diddy and Seinfeld hit it off and began to discuss the idea of collaborating on an album—Seinfeld would do comedy routines, while Diddy would produce music to fill in the background (the idea never came to fruition). In the end, for the photo that ended up on the cover of Forbes, Diddy wore dark pants and a white shirt bearing a Sean John Denim logo, turning the cover shot into a free advertisement for his new clothing line. The entire episode served to amplify Diddy’s desired image: bigger, badder, and bolder than anyone in show business.
“Why he needed all the other clothing to set that up, I don’t know,” says LaFranco. “It’s all about the show, right? That’s the brilliance of Puffy.”23
While Diddy swaggered his way to the top of the entertainment universe, Jay-Z faced a conundrum. The massive critical success—and relatively modest commercial performance—of Reasonable Doubt made it clear that he could have a tolerably remunerative career as a rapper and leave the streets behind. But to reach the topmost layers of monetary success, he needed to capture the attention of the mainstream.
“I can’t be too deep. I have to spoon-feed ’em,” he said one day while driving through Brooklyn, according to his cousin Briant “B-High” Biggs. “Once I spoon-feed ’em lightly, feed ’em sugar… then give them something more, some knowledge on top of that, then they’ll take that and start growing.”24
To provide some of that sugar, Jay-Z turned to Diddy. The Bad Boy chief and his stable of producers provided the bulk of the sonic work behind In My Lifetime, Vol. 1, and the gritty beats of Jay-Z’s debut album gave way to glossier production. The record, which debuted in November 1997, is regarded as one of Jay-Z’s worst, a clumsy attempt to court pop audiences. Though it sold 138,000 units its opening week, triple the opening week of Reasonable Doubt, top albums routinely debuted with sales north of 500,000 in the late 1990s heyday of the music business.
As much as he chased Diddy’s sound at the time, Jay-Z also tracked his lifestyle. Jonathan Mannion, who continued to shoot Jay-Z’s album covers, remembers the rapper picking him up one day in a Bentley convertible—the same model Diddy had.
“You own this, man?” asked Mannion.25
“Nah, I’m thinking about buying it. Puff has one, so I figure…” Jay-Z replied, trailing off. To Mannion, the move was a quiet sign of respect.
“It wasn’t like, ‘Fuck that guy, I’m going to have more than him.’ It was like… ‘He’s moving at the highest level, and if he has one, I should at least consider that one.’ It was never from a position of, ‘I’m beneath, he’s above.’… Diddy and Jay, they’re cool with each other, but they’re definitely competitive.”
For Jay-Z’s next album, Vol. 2… Hard Knock Life, the cover features him standing in front of the car, a possessive hand on its hood and a scowl on his face. The record was lighter on Bad Boy guest appearances and instead prominently featured producers now known as Jay-Z’s go-to beatmakers: Timbaland, DJ Premier, and Swizz Beatz, all of whom helped craft a critically acclaimed record that still had the pop prize very much in its sights, particularly with the title track. With its infectious sample from “It’s the Hard Knock Life,” from the musical Annie, the title song captured the mainstream imagination and, per SoundScan, helped Jay-Z once again triple the opening week sales of his prior album.
His friends at Def Jam had millions of reasons to urge him to crank out Vol. 2, the best-selling album of his career, less than a year after its predecessor. In 1998, Russell Simmons was in negotiations to sell the rest of his label to PolyGram; the year before, the Dutch company had offered $50 million, and then reduced the number to $34 million. Def Jam’s executives realized that the size of the offer centered on a multiple of the label’s revenues, not its earnings; in other words, to up the price, all they needed was to sell more records.26
So Simmons and Lyor Cohen leaned on their two biggest artists: Jay-Z and volatile Yonkers rapper Earl “DMX” Simmons. (“I thought DMX was greater than Jay-Z,” recalls the Def Jam cofounder. “That’s the difference between honing your talent and destroying it.”) The latter’s album went quintuple platinum. The former launched his quadruple-platinum debut in May 1998—and followed it in December 1998 with a triple-platinum record, an unheard-of turnaround time in the record business, even back then. Releases generally followed a structure: put out an album’s lead single, then the album itself, then the next single, and then the next, waiting for months in between each step as each song racked up radio spins, and then died down. At least that was the custom for much of the 1990s.27
“Jay-Z and DMX were amongst the first, I think, to ignore that goal; everybody followed suit,” says Simmons. “You can’t get out the seat for a year now… In hip-hop, if you get off your seat, somebody’s sitting there.”
That year, Def Jam did a record $175 million in billing—and in 1999, PolyGram bought the remainder of Simmons’s company for $135 million. Cohen signed a five-year deal to stay on board as CEO, while Simmons kept the title of chairman. The pair added double-digit millions to their net worth, thanks in no small part to the efforts of Jay-Z and DMX.28
Says Simmons: “We sold it definitely because of those guys.”29
Not to be outdone by his Def Jam rivals, Diddy departed from the music industry norm of shutting down his company over the holidays. Instead, he made his team truly earn their year-end bonuses. At one particular meeting two days before Christmas in the late 1990s, Diddy emerged from an elevator with his bodyguards wearing a mink coat, gaudy jewelry, and sunglasses. Then he went to get some apple juice, forcing his colleagues to wait for five minutes before his return.
“Y’all are mad as fuck, ain’t you?” said Diddy, according to employee Jayson Jackson. “You see me sitting here with my fur and all of that and you[’re] like, ‘Fuck Puff.’ But you know what? I dare one of y’all to come get it. I dare one of you to work harder than me… I come in here and work harder than you in the day, then go to the club and work. You think I’m in the club getting drunk? I’m looking at who’s dancing to what, figuring out which song is working in what way, which DJ is making it hot. Tell me who’s doing that more than me.”
Holy shit, Jackson thought. He sleeps no more than four hours a night. And every waking hour, he’s figuring out how to make more money.30
But the new year took Diddy’s career trajectory in the wrong direction for the first time in quite a while. In March, he was charged with assault after allegedly bashing record executive Steve Stoute over the head with a champagne bottle. Diddy is said to have enacted this heavy-handed metaphor for rap’s late-1990s excesses after Stoute refused to pull the plug on a video in whic
h Diddy and Nas were shown being crucified. (Both rappers had willingly participated in the shoot, but the former apparently had second thoughts.) After Diddy publicly apologized, Stoute asked the Manhattan district attorney not to press charges; the Bad Boy chief’s only punishment was a day at anger management class.31
In a bigger blow, at least to Diddy’s ego, his album Forever climbed to number two on the charts but earned only a single-platinum certification, a far cry from No Way Out’s seven.32 Complex named Forever number six on its list of the fifty all-time worst rap album fails, and Chris Rock cracked a joke about the record during his monologue at the 1999 MTV Video Music Awards: “Puffy got a new album called Forever. Forever? What you trying to say, Puff? Forever? You know if the album don’t sell, the next one gonna be called, How About Three More Months?!”33
Later that year, Diddy found himself in an even worse situation. When gunfire erupted during a dispute at a nightclub he was attending with then girlfriend Jennifer Lopez, the two fled the scene with Diddy’s bodyguard and driver. Police pulled over their vehicle after it ran a red light and discovered a pistol.34 Diddy got charged with bribery and possession of an illegal weapon. In the year of legal wrangling and trial that followed, he denied carrying a weapon and offering his driver a $50,000 bribe to take the gun rap for him. He was eventually cleared of all charges, as were his bodyguard and driver. But his latest protégé, Jamal “Shyne” Barrow, also on the scene at the time, caught an assault conviction and spent nine years in jail.35 (Barrow and his team did not respond to a request for comment.)
Lopez soon parted ways with Diddy, a move that left him humiliated. He reportedly tried to date model Naomi Campbell, and after she rejected him—she was engaged at the time—he begged her to appear in public with him so that the tabloids would think they were together. “Sean told Naomi that he desperately needed ‘prestige’ on his arm to recover his ladies’ man reputation,” a source told Vogue.36 “In his mind, he’s a pimp, lover, Casanova,” says Chenise Wilson. “He’s one of those who gets his feelings hurt really quickly, so he becomes the pimp persona in order to guard his feelings.”37
Both his personal life and his financial empire seemed to be spinning out of control; though he avoided jail time, Diddy had to field civil lawsuits worth a combined $1.4 billion. His lawyers would eventually deflect most of them, but even after recovering from the violent associations of the mid-1990s, Diddy’s reputation had taken another hit, jeopardizing his appeal to mainstream companies he was courting for new mass-market ventures (the line of packaged food he’d been contemplating, for instance).38
In order to reach the David Geffen–esque heights he was shooting for, Diddy would have to reinvent himself yet again. “If you’re a dreamer, you’re a visionary,” he later explained to me. “People may know about five or six of the things you’re pursuing, but you may have a thousand dreams in your head.”39
Over the past hour or so in front of the packed room in Austin, Diddy has hooked the crowd with his usual unfiltered banter. But his words have taken on an increasingly instructive tone—this grown version of Diddy draws on the lessons and the swagger of his youth, mixing in the trappings of a life coach and a motivational speaker—and the crowd is eating up his advice, even when his outlook is less than optimistic.
“If you were one of those kids who are just graduating from high school or college,” I ask, “how would you do it if you were starting from scratch?”
An audience member rushes the stage and hands Diddy a CD, presumably a recording of her music, which he accepts before replying to my question.
“I want to give you an honest answer—I don’t want to give you the schoolteacher answer. I would be scared to death,” he says. “I would probably be doing the same thing that y’all are doing right now… Never letting go of your dream is the only thing I can say, but I can’t sugarcoat it and say it’s gonna be easy.”40
We begin taking questions directly from the audience.
“If I go up to Revolt TV,” asks one young man, “am I gonna get somebody to look at my videos and listen to my music? ’Cause I ain’t gonna spend that train fare if I ain’t gotta.”
“What I’m gonna do is I’m gonna save you your train fare,” says Diddy. “I’mma have somebody watch it and listen to it in the next fifteen minutes… [If] you put something up that’s dope—it’s just dope, man—it’s gonna spread like the bird flu.”
Next, a towering man who looks to be in his late thirties raises his hand and explains that he’s an aspiring DJ with two ex-wives, four kids, and another on the way. His question: “What do I do now?”
“I’mma be Dr. Phil for you. Want to come up closer so you can get it?” asks Diddy. His “patient,” who is nearly seven feet tall, walks up and sits on the mogul’s lap. “Keep taking care of your kids, keep paying that child support so you ain’t in trouble… You gotta be able to raise the kids and also put your all into it and know that you have a harder road than somebody that’s seventeen, eighteen, nineteen trying to get into the game. And that’s just real talk.”
The DJ ambles off the stage, and a young woman asks the next question. “Back in the day I used to go by She-Diddy because I modeled my career after you,” she says. “I want to be the next Diddy. Do you have any advice for kind of getting over that hump?”
“This is a great time in the world of business and in the world of media, and I think this is just a great time for women,” he says. “There has been a turn in the hiring process where women… Y’all will run the world.”
As we wind down our talk, I decide to find out whose advice Diddy might want: “If you could have lunch with anyone in the world you’ve never met, who would it be?”
“Number one would probably be Steve Jobs, but we know he’s not here,” he says. “But I’m pretty sure he’s figured out a way for me to have lunch with him one day. And I’m the worst with names, but I asked my staff this before I came: the brilliant woman who runs Facebook—”
“Sheryl Sandberg?”
“I would love to have lunch with her, because I feel like what she’s trying to do to empower women and shake things up is the same thing I’m trying to do with youth culture,” he says. “I think that that’s somebody that I could learn from and that I can get inspired from. So if any of y’all know her, let her know Diddy wants to take her out to lunch.”
CHAPTER 6
Fashion Fortunes
Russell Simmons stands out from his peers in the world of hip-hop—and the broader entertainment industry—in numerous ways, from his business savvy to his more recent embrace of yoga and veganism. (He’s also set apart by the allegations of sexual assault leveled at him as this book was going to press; he has denied the accusations.) But the first thing you notice in person is that, unlike most big names in showbiz, the Queens-born tycoon shows up to appointments on time, or even early.
I roll into the lobby café at the Mercer Hotel in SoHo at 10 a.m. on the dot, only to find him already slurping up a bowl of sweet pea soup and a beverage that later shows up on my receipt simply as “Green Juice.” Simmons is decked out in his trademark navy-blue New York Yankees cap, tilted jauntily to the side, and a pair of the still-chic Adidas shell-toed sneakers that Run-D.M.C. rapped about so many years ago. The centerpiece of his outfit is a patterned dress shirt by Argyleculture, his new fashion line. All in all, it’s a representative sampling of his eclectic style, which for decades has combined his favorite aspects of street wear and yacht club attire.
The Mercer is an appropriate meeting spot. In March 1993, Simmons opened the flagship store for his first clothing line just a few blocks away. “When I started Phat Farm,” he says, “there was no such thing as a black designer even doing fashion.”1
Under Simmons’s watch, Phat Farm made what he calls “classic, simple stuff that kids could wear the way they wanted.” And unlike most other clothing chiefs at the time, he knew not only what kids wanted to wear but how to create new trends—argyle sweater-v
ests outside the golf course, for instance—and capitalize on them. At its late-1990s peak, Phat Farm raked in nearly $1 billion per year in retail sales.
Soon some of hip-hop’s savviest operators went into the apparel business. Diddy launched his Sean John clothing line in 1998, and Jay-Z followed with Rocawear a year later. Both released sneaker lines as well. Dr. Dre nearly did, too, but found focusing on headphones to be much more lucrative. It was Simmons who laid the groundwork for the rise in hip-hop’s fashion fortunes.
When Simmons first started selling clothing, Dr. Dre had barely released one album, Diddy had just graduated from his Uptown internship, and Jay-Z hadn’t left the drug business. The day Simmons’s boutique in SoHo opened, Phat Farm was a drop in the proverbial bucket for a man whose businesses were grossing $40 million annually by the early 1990s.
“It’s fun and I can afford to do it,” Simmons told the New York Times at the time, after casually explaining that he started a clothing line because he often dated models. “So if I lose a lot of money on it, I had fun. If I make money, I’ll have even more fun.”2
At the outset, Phat Farm’s fifty-item catalog seemed to borrow heavily from established brands like Tommy Hilfiger, Ralph Lauren, and the Gap. The pieces, which ranged from $50 khakis to $650 leather jackets and were designed by a pair of untrained twenty-two-year-old graffiti artists, “could be worn by a sixty-year-old Jewish guy,” Simmons liked to say.
But the SoHo shop (burnished by $175,000 in renovations) and the rural-meets-urban theme (complete with a bull mascot called Money Moo) combined with the European sensibilities of Simmons’s partner—a Frenchman named Marc Bagutta—to create a brand that resonated with a new generation of upwardly mobile hip-hop enthusiasts. Attending fashion shows before founding Phat Farm sparked Simmons’s thinking.
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