Damon Dash stands on New York City’s Lower East Side and shivers. It’s the first wintry night in November, and the 42-year-old former hip-hop mogul, with gray chin stubble and a low-riding cap—the man who cofounded Roc-A-Fella Records with then-best friend Jay-Z—jams a fist into his pocket and braces against the wind.
“This is reality-show drama,” says Dash, kicking the gummy sidewalk as he checks his iPhone. He’s come from the basement of the Mercury Lounge, where Jim Jones, the rapper he is promoting later tonight, is holed up between the boiler and some empty beer crates. Surrounded by a dozen or so hangers-on and wreathed in a cloud of pot smoke, Jones is trying hard to learn the lyrics of his own songs. The drummer Dash hired has no cymbals and is racing around the city to find a set. Dash’s showcase is starting to look like amateur hour. “Shit is wack,” he says.
But shit wasn’t always this wack. At the height of his power, Dash presided over a cultural empire without peer. He jump-started Jay-Z’s career from the trunk of his car, selling the rapper’s discs when no one would sign him. Together with a third partner, Kareem “Biggs” Burke, they launched Roc-A-Fella in 1995, released Jay’s seminal first album, Reasonable Doubt, in 1996, and produced nine No. 1 albums together. Dash also discovered Kanye West, Cam’ron, and Beanie Sigel. And he built his brainchild Rocawear into a fashion brand that brought in a reported $400 million a year in revenue.
Yet to many, Damon Dash will always be the man left behind, the Steve Wozniak to Jay-Z’s Steve Jobs. When Dash and Jay split in 2004—after two years of clashing egos—Hova moved up the corporate ladder to be president of Def Jam and took Roc-A-Fella Records with him. A year later he bought Dash’s share of Rocawear.
Dash didn’t seem to care. With the multi-million-dollar checks from those buyouts—$3 million–plus for Roc-A-Fella, $7 million for Rocawear—he had money to burn, and burn it he did: on private chefs and jets, butlers and bodyguards; two lofts in Tribeca, a mansion in Beverly Hills, a $35,000-a-month London apartment, and a $400,000 Maybach. But then shit really did get wack. And amid a series of high-profile repossessions, foreclosures, liens, and press hits that have painted him as a pauper, Dash has tried to rebrand himself as a downtown hipster—a Warhol in baggy jeans running a Lower East Side art collective. Although Dash has shown flashes of his old touch—showcasing indie bands like Sleigh Bells and connecting pals like Mos Def with alt-rock darlings the Black Keys—he has presided over a series of record labels, clothing lines, Internet start-ups, vodkas, movies, sneaker brands, watches, and, inexplicably, motor oils, most of which have failed to take flight.
“We’ve been in a recession,” Dash says by way of explanation. “These things don’t crack overnight.” Even as some of his businesses have limped along, he seems content to keep pumping funds into them until something—or many things—works. “I don’t respect anyone who does not give up their own money,” he says. “I don’t give a fuck how much money someone else gave you to watch. That’s not the game I play.”
Dash isn’t down-and-out, but he’s not exactly living it up. He’s made the commute to tonight’s show from Greenpoint, Brooklyn, where he’s been crashing with a friend (a few weeks later, Dash was reportedly staying in a rental building on the Lower East Side). He’s here to shoot a “video look book” for Vampire Life, the clothing line he co-owns with Jones. The idea is to get Jones to change into different outfits between songs during his set and to post video to the line’s website, while presenting fans, who will be given merch to wear for the shoot, a live performance.
Coming in from the cold, Dash enters the bar and seeks out Justin Korkidis, his marketing director, part of a six-person staff that Dash relies on to design clothes, bring in street artists, film his every move, and generally hang out with him. Mostly twentysomethings, they are part of his Poppington collective, his multimedia art, fashion, and branding machine. Korkidis, sporting a knit cap, looks beleaguered.
“So what’d they say about our drink tickets?” Dash asks.
“That it has to be worked out,” Korkidis says. “But it’s half-price. I don’t know if you want half-price?”
“Damn, that’s crazy,” Dash says. “We don’t get no drink tickets?!”
Korkidis walks away, sulking.
“The people here are bullshit,” Dash calls after him, raising his voice so the bartender can hear. “You ask or you don’t get it. Tell them to get us some drink tickets. Get us some beers. Get it flowing!”
Like so many of Dash’s genius strokes, the video was pure hustle, a fake-it-till-you-make-it fantasy—because neither he nor Jay had those things, not yet. Dash made the video for $16,000, borrowing a friend’s boat and creating an ersatz playa’s paradise of sun, Cristal, and G-string-clad babes on the island of St. Thomas. But it wasn’t surprising coming from Dash, who had grown up moving between the make-your-own-way world of the inner city and the halls of privilege.
“I came from the streets, and you got to hustle in the streets,” says Dash, who grew up in East Harlem. “That’s why I always have a chip on my shoulder. No one ever gave me anything.” His mother, a secretary who sold clothes as a sideline out of their apartment, died of an asthma attack when Dash was 15. His father (his parents divorced when he was 3) ran a methadone clinic. Hyperverbal, quick-witted, and sometimes a handful, Dash bounced between public and private schools. At one point, he earned himself a ticket to the South Kent boarding school in Connecticut, known as a fix-it destination for boys with behavioral issues and for attracting wealthy foreign kids. “I’m one of those guys who has two very concrete experiences,” he says. “One was the authentic experience in the street, and the other was boarding school and people from different cultures. So just like Jay, I’m able to articulate my experiences.”
When Dash was 18, he and his crew, calling themselves the Best Out, began throwing huge parties each month at the Cotton Club in Harlem. They hired the DJ-rapper Kid Capri and attracted thousands of people, including rappers and pro athletes. His big business idea: giving away free bottles of Moët & Chandon to the first 100 women through the door and creating limited-edition T-shirts commemorating each event. “People wanted to buy those shirts for $300 to $500,” Dash says. “I was learning about how to make a brand.” In 1990, his cousin Darien Dash, whose stepfather worked in A&R, got them into a party for Heavy D. The crowd was older and, to the street-savvy Dash, beyond its prime. “All these guys were making all this money and they looked weak,” he says. “They looked like prey to me. I felt like I could get into this industry and take it.”
Together with his cousin, Dash started managing two groups called Future Sound and Original Flavor. Dash’s uncle introduced them to Rodolfo Franklin, a.k.a. DJ Clark Kent, at Atlantic Records, who signed the groups. But according to Dash, the label failed to support them, so he started touring his acts on the East Coast with another artist Kent had introduced him to: a 24-year-old former Brooklyn drug dealer named Shawn Carter, who took the stage name Jay-Z. “He could rap fast, and his raps were witty and fresh,” says Dash, still visibly impressed. “And everything he said was authentic. That made him better than . . . everyone.”
But despite his wit and talent, no label would sign Jay-Z. At the time, West Coast gangster rap was ascendant, with its street rhymes about gunplay, murder, and crack. Jay-Z was playful and cocky, rapping about the hustler’s good life and making bank: “You can’t change a player’s game in the ninth inning/ The chrome rim spinning keeps ’em grinning/ So I run way the fuck up in ’em/ And wrinkle they face like linen.”
Dash paid out of his pocket to get Jay-Z in the studio. When they still couldn’t get a record deal, they launched Roc-A-Fella Records with Burke, another street hustler, who was later convicted of drug trafficking. The combination of Dash’s entrepreneurial bravura and Jay-Z’s talent paid off. In 1996, they released Reasonable Doubt, which many critics still consider Jay-Z’s finest work. Dash—bellicose and shrewd—struck uncompromising deals for himself and his partners. When they signed a distribution deal with Def Jam the following year, Dash insisted he, Jay, and Burke retain half-ownership of Roc-A-Fella and full title to Jay-Z’s master recordings. “Damon was a leader and a visionary,” says Def Jam’s founder, Russell Simmons. “Without Damon, there would have been no Jay-Z or Kanye or Cam’ron and no Roc-A-Fella. What he did for Jay and everyone, he was selfless. He took the bullets.”
But Dash wasn’t satisfied with music’s small profit margins. He wanted a lifestyle brand, “like Ralph Lauren,” he says. His timing was perfect. Hip-hop artists had started to ask why they were shilling for these brands in their music videos—brands that were then bought by millions of fans—when they could be making their own clothes, vodkas, champagnes, and sneakers. So Dash started Rocawear, and each time Jay-Z wore a bomber coat, a warm-up jacket, or a snapback in a video, sales boomed. By 2003, Dash had landed Victoria Beckham as a model, putting her in satin jackets and high-riding booty shorts.
But Dash and Jay-Z’s relationship soon began to fray. Word of his partner’s volatile temper started reaching Jay. In an infamous YouTube video, Dash lashes out at a boardroom full of Def Jam brass for allegedly holding a meeting about Jay without inviting Dash. “Y’all should have called Damon Dash,” he rants. “Y’all don’t know shit about my culture.”
“Damon was all creative aggravation, and he had to be when making Roc-A-Fella great,” Simmons says. “It was a commitment not to compromise.” It worked on the streets and in building a company, but not in a corporate workplace. “Damon was a bull in a china shop,” Simmons says.
Dash says he was never cut out for that world—he wants to be a Richard Branson–type entrepreneur-cum-magnate, creating companies and getting other people to run them. He also heaps scorn on the Def Jam team that would later become Jay-Z’s inner circle. “Those people are corny. You think I’m rolling to a club with Lyor Cohen or John Meneilly?” he says, referring to the former head of Island Def Jam and Jay’s manager. “No disrespect to Jay—but every single person I see hanging around him is making money off him. They all conform so they can eat off of him.”
By 2003, as Jay-Z talked about retiring after the release of The Black Album, Dash began turning his attention away from his star talent and best friend and toward his newer finds—Kanye, Cam’ron, Jim Jones, and Beanie Sigel. While Jay-Z was on vacation, Dash made Cam’ron and Sigel vice presidents of Roc-A-Fella. Dash was also using his own money (up to $6 million) as well as Rocawear’s to launch a new fashion line, Rachel Roy. He had started dating Roy when she was a Rocawear intern and later married her, in 2005 (they divorced four years later, and they still control half of the brand).
Dash’s overreaching ambitions and hot temper became too much for Jay-Z. In December 2004, he invited Dash to a sit-down at the restaurant Da Silvano in New York’s Greenwich Village. They had already agreed to sell their remaining half of Roc-A-Fella and its roster of contracts, including Kanye’s, to Def Jam for $10 million. But in a twist, Jay-Z announced he would become president of Def Jam, taking on a role that would seem, by right and reason, destined for the business-minded Dash, a role Jay-Z could not perform if Dash were in the picture. Jay-Z had one carrot to dangle in front of his old friend. He offered Dash the Roc-A-Fella name in exchange for turning over the rights to Reasonable Doubt, which Jay called “my baby.” Dash refused. “Honestly, I didn’t give a fuck,” Dash says. “The whole thing was based on our friendship. He made it clear he didn’t want me to be a part of Roc-A-Fella. I was like, ‘A’ight.’ Everything else was like, ‘Go be you. You want to do this, do it.’ He told me it was just business. He said that it was business. ‘I want to look like a businessman, and I can’t be a businessman around you.'”
Before you even see the large Poppington neon sign above the door, you can smell pot smoke wafting down the block. One day in late November, a week or so after the Mercury Lounge show, the bottom floor of the 6,000-square-foot duplex is deserted. A few pieces of geometric acrylic artwork line the walls. An open loft overlooks the gallery, and a set of back stairs leads to it. Up here, Dash’s crew is working or hanging out while the boss is getting his twice-weekly haircut. They sit amid a clutter of flat-screen TVs, watercoolers, bottles of Dash’s Dusko whiskey, red Vampire Life vodka, and whiteboards with sketches of puffer vests.
A designer named Klindy Lindenbaum, whose fashion ethos is polka-dot “clown chic,” is working on wine labels and the new Lady Vamp clothing line. Korkidis is deep in an egg chair, tapping on a laptop. A rapper named Smoke consults with a director on the script for his new music video. It’s like a coffee shop of freelancers—until Dash shows up.
He’s got a joint in one hand, a diamond watch on his wrist, and a diamond angel pendant draped over a black tee. “The people in here—honestly?—are, like, the snobbiest people in New York,” says Dash, talking to the room. They don’t nod so much as wait for the rest, writing e-mails or rolling blunts of their own. “Their taste level? They work hard. We don’t need to deal with corporate. This is a collective that supports itself.”
The place is cluttered with racks of graphic tees, a discarded silk-screen frame, a box of empty spray-paint cans. The rest of the world, people who work in corporations, especially at big music outfits like Def Jam, are “corny” or “squares,” slaves who have “put their balls on a silver platter” for the security of “three meals a day, a warm bed.” “I’m not looking for a boss or a master,” Dash says, laughing. “I’m not hire-able.”
He likes to see his role here as a connoisseur of cool. He relies heavily on the cultural antennae of the millennial kids of the Poppington collective. “We don’t have contracts here or anything like that,” says David Chang, a graphic and clothing designer Dash hired as an intern four years ago who helped create Poppington. Another intern turned designer, Raquel Horn, turned Dash on to the Black Keys in 2009. Dash liked their music and connected them with a lineup of his rapper friends—Mos Def, Ludacris, Q-Tip, and even, via unused vocal tracks, the late Ol’ Dirty Bastard—to record Blakroc. The album was a critical success, an example of the kind of creativity that impressed even his old foils. The next year L.A. Reid, then-CEO of Island Def Jam Music Group, agreed to distribute a pair of albums by Curren$y that Dash produced, out of his regard for Dash’s acumen. “I respect anyone who is clear about what they do and don’t want, and though it may occasionally offend some people, it’s what winners are made of,” Reid says. “Any man with the amount of vision that Damon has shown throughout the years is, by design, an entrepreneur.”
If Dash has regrets—about giving up the power and the money and the influence he once possessed at Roc-A-Fella—he won’t show it. As for Jay-Z’s vast empire—estimated to be worth $475 million—and cultural currency, Dash makes no claim on them. “I’m not counting that man’s money,” he says. “No one’s taken anything from me. It’s like saying, ‘I used to mess with a girl, and before I used to mess with her, she was mediocre. But because she started messing with me, I taught her things. I dressed her, and then I taught her how to have a career.’ Does that mean after we break up I’m still supposed to be able to get some ass?” He laughs at his crass analogy. “Like, I don’t feel entitled to that pussy. You understand what I’m saying? I don’t feel entitled to nothing he got.”
Yet it’s easy to see Dash’s art collective as a reaction to what went wrong at Roc-A-Fella. If one of his staff comes up with an idea, and if Dash wants to back it, they agree to split proceeds 50/50. “Dame always says anything you played a major part in creating, you’re gonna get a check,” Chang says. The important thing, Dash says, is that they don’t go corporate. “Roc-A-Fella was never about the money or the volume,” he says. “It was always the spirit of it, the fuck-you-to-everybody-else of it.”
Dash is investing a lot of his time in the Vampire Life line, which he says generates $2 million a year in cash flow and subsidizes the other projects he and his staff dream up. Among them: Dusko whiskey, the art gallery, and even his motor-oil company, Dash Motors. They’ve traveled to China and Thailand to stage art exhibitions—and from the looks of photos, to party—and sponsor visiting Chinese artists.
Dash breaks from one of his rants about corporate America, noticing that a video editor is piecing together footage from the Jim Jones “look book” shoot. “Nah, it looks like a commercial,” Dash says. “It’s got to look like a show. And make sure we’re seeing Vampire Life on him.”
Dash has been flogging Jones for years now. In 2008, he produced the short-lived Off Broadway play Hip-Hop Monologues: Inside the Life & Mind of Jim Jones. His Poppington crew designs the Vampire Life line, which piggybacks on the popularity of Jones’ VH1 reality show, Chrissy & Mr. Jones, costarring his girlfriend, Chrissy Lampkin. There are vodka and wine tie-ins and a plotline in which Chrissy designs a Lady Vamp line.
But Vampire Life, whose baseball tees sell online for $42, is easily overshadowed. A few days earlier, Jay-Z launched his line at Barneys, with $1,000 cedar-lined humidors, $2,590 leather boxing shorts, and $875 python-brimmed ball caps. The comparison rankles Dash.
He gamely counters that Jones’ show and its 1.7 million viewers a week will catapult Vampire Life to new heights. “It will be bigger than Rocawear,” he promises. “You can’t compare me to Jay-Z. At all,” he continues. “I am not the greatest rapper of all time. I’m a businessman. I guess I’m famous like a rapper, I got swag like a rapper—I don’t know. But I’m not a rapper. And every time, they expect me to be a rapper. I can’t make money performing records that I made 10 years ago. I can’t sell my rights to my show. I got to keep creating businesses. I don’t sell celebrity. I sell product. I’m an animal. I got to eat the food I kill.”
A radio interviewer on Hot 97 asked Jay what he thought of Dash and his money troubles. He said, “I can only have love for Damon,” because of what they created as young men. “I have ultimate confidence in him that he’ll find his way, because he’s an amazing and really smart guy.” Representatives for Jay-Z declined to comment for this story.
At the Jones show, Dash does not seem like a man with 99 problems, or any. “The news has been talking about the same tax shit for five fucking years,” he says, weaving toward the stage, where Jones is finally rehearsing. “Oh, he’s fucked-up. I ain’t going bankrupt. Everybody’s waiting for it. Every single year, everyone’s focus is my pockets. And they ain’t even worried about what I’m doing—only what I’m holding?”
A few minutes later, as I watch Dash in the smoky basement that serves as the Mercury Lounge’s green room, it’s hard not to think about his and Jay-Z’s divergent paths. Jay is on the cover of Vanity Fair, in a concert documentary shot by Ron Howard, trading texts with Obama, and negotiating a $240 million contract with the Seattle Mariners for Robinson Cano (oh, Jay-Z is a sports agent now, too), while Dash leads a crew of strivers who skitter about as Jim Jones learns his lyrics.
But there’s no envy. No humility. Dash is as brash and as boastful as the guy speeding around on a (borrowed) boat full of babes. “When I see Jay on a magazine cover? That’s me,” he says. “I’m proud. I don’t see why that means me against him. It makes me look big. I don’t understand. How does that not make me look big?”
He turns his attention to Jones, who sits with his head hanging low. Dash tells him to think like a rock star. “Like Jim Morrison, man,” he says, ducking under a graphic tee hanging from a heating pipe. “Shit is hot up in here!” Dash yells. “This is the real shit!” He stands over Jones like a boxing trainer exhorting his fighter between rounds. “Somebody get this nigga high!” Dash says. He is met by a dozen glazed stares. “Nobody got weed? Y’all smoked it all? Before the show?!”