Damon Dash: The man who would be Bling

Damon Dash has a butler, a chef, a glass-roofed limo... and a lot of time on his hands. Eric Konigsberg glimpses the existential angst of the hip-hop mogul who sold up after his every diamond-encrusted dream had come true

In the business of hip hop, diversification is the name of the game, and Damon Dash owns a record label, five clothing and shoe companies, a Swiss watch company, a vodka company, a television-production company, and a film-production company. What he doesn't have a lot of these days is pressing engagements.

Today, at the crack of noon, he finds himself looking around for something to do. "Monday," he murmurs. "Monday. Monday. Monday. Mondays are a motherfucker."

He's contemplating breakfast. Then, maybe, he'll hit the gym. If he can get to the editing bay, there's the possibility of checking in with the producers of his US reality-TV show, Ultimate Hustler, and helping them trim a few seconds off the last two episodes. Of course, that involves sitting still for a couple of hours, which is never easy. He says he might fly to Los Angeles later in the week to produce a song with Carmen Electra, on a lark, and is hoping to find something else to do while he's out there - "movie meetings, maybe, music meetings, whatever I can drum up." In a few weeks, he's been invited to Milan to introduce a performance at La Scala. ("Some opera or something, I don't know.")

Lassitude, however, doesn't mean solitude, and Dash still has many people waiting on him. In his loft in New York's Tribeca district, on this particular Monday, there's a Danish architect in oval glasses and striped trousers who has big plans for the place; Dash's personal assistant, not to be confused with his executive assistant up on Seventh Avenue, who is preparing for the day ahead by charging a half-dozen batteries - for Dash's A mobile phone, his B mobile phone and his BlackBerry - and then back-up batteries for each; a chef; a bodyguard; and a man auditioning for a job as his butler.

"Not many people understand how important having a butler is, but it is," Dash says. "I need somebody to help me get everything I'm going to wear for the day all set up, know what I'm saying?" A day with Damon Dash is like a Britney Spears concert, with a change of outfits for every phase (he's currently wearing below-the-knees shorts, a long-sleeved T-shirt, and spotless leather high-tops, all in red). "You'd think it's easy, but I've got a lot to put together, accessory-wise, especially at night. Cuff links are a motherfucker."

Dash is no longer renting the £19,000-a-month house in Chelsea, west London that his friend Victoria Beckham found for him, but he does own a house in Beverly Hills as well as the Tribeca loft. Here, there are 25ft ceilings in the great room, elaborate crown mouldings, a large Peter Beard giraffe photo, plain floors, no windows at eye level, and, though he and his family - his wife, Rachel Roy, and his three children, by three different mothers - have been there for nearly a year, dozens of unpacked boxes.

Just a couple of years ago, Dash could rightly call himself one of the most important men in the music business. Along with the rapper Jay-Z and a third, silent partner, Kareem "Biggs" Burke, he launched Roc-A-Fella Records in 1996 by releasing Jay-Z's debut album, Reasonable Doubt, and the state of hip hop has never been the same since.

Under Dash's supervision as his manager and business partner, Jay-Z recorded nine number-one albums in the US and won four Grammys. Another rapper from the Roc-A-Fella stable, Kanye West - Dash's discovery and Jay-Z's protégé - sold 3m copies of his first album, The College Dropout. (omega)

But even happy couples aren't immune to divorce, and with two swift strokes of Jay-Z's pen, the rapper broke up his union with Dash. The first came in 2004, when Def Jam Recordings, which, since 1997, had owned a 50 per cent stake in Roc-A-Fella, purchased the label outright and Jay-Z agreed to take a position as Def Jam's president. Then in the autumn of 2005, Jay-Z divested Dash of his last ties with the Roc when he bought him out of Rocawear, the urban hip-hop clothing line that they had started in 1995.

Def Jam has, since its inception in 1984, been rap music's pre-eminent label, and it is owned by Vivendi Universal, the world's largest record company. Jay-Z was going corporate, accepting a corner-office job that, if you'd followed the Roc-A-Fella group's history, you might have expected to go to Dash. Instead, Dash got the intellectual-property equivalent of a lump of coal, as the bulk of Roc-A-Fella's artists followed Jay-Z to remain on the label.

Hence Dash's existential funk. Julian, his chef, sets several plates on the counter for him to choose from: eggs, pancakes (one per plate), fresh fruit. Affixed to the edge of each is a Post-it note listing the carbohydrate count. Standing between two stools, Dash devours one serving of eggs ("OMELETTE, 4 CARBS"), then starts on another.

"Julian is no joke, let me tell you," Dash says. "I was looking for a chef for a year." Julian asks Dash what he wants to drink.

"Anything diet," Dash says. He's been on a campaign to lose 15lb and has even gone vegetarian the past month, with some lapses. "What was that chicken you made the other day? It was like Indian chicken fingers. I had to eat that shit. I just came from Miami, and I was hungry, for real."

Dash was in Miami to look at a house. It's nice, but he won't commit. "The issues that I have with it is, I have apprehension about spending that kind of money," he says. "Eight million dollars is a lot for Miami, plus, since my looking at it ended up in [US celebrity gossip magazine] Page Six, I figure the real-estate people have to take at least $100,000 off for leaking it."

He lifts a plate. "Whose pancake is this? I gotta have one."

"All yours," Julian says.

"My man, right there!" Dash says, pointing to Julian.

"That's only four carbs," Julian says. "As long as it's no syrup."

Dash eats it dry. His mobile rings. He's supposed be checking out an office. "I'm in the car, on my way," he says and sets down the phone. He puts syrup on another pancake.

Upstairs is for Dash's clothes collection. It's a sort of three-bedroom closet, where the dressing room and the trainer room each have their own bathrooms. One wall of shelves is for T-shirts and socks; he wears a new set every day, and, every month, he donates 30 once-worn shirts and pairs of socks to charity. "That way, somebody gets to own basically new stuff and I get to be fly," he says.

Same goes for his trainers, which are shelved row upon row upon row, floor to ceiling across a wall three times as long (he has 300 at home and an additional thousand in storage). "I get pretty much every cool sneaker that comes out," he says. "I used to prefer Nikes, but then, in 2004, I bought Pro-Keds." He means he bought Pro-Keds, the entire trainer company, and repositioned it as a hip-hop brand.

Dash gets around town in the back of a 2005 Côte d'Azur- blue Mercedes Maybach 62 with a cream-on-cream perforated-leather interior. It retails for £220,000 and features a panoramic glass roof with burled-walnut coffering, a 543-horsepower engine, and, thanks to its extra-long wheelbase, fully reclining passenger seats.

Dash is 35, which is old for the hip-hop business, and even in shorts and an XXXL T-shirt, he has the aspect of a paterfamilias about him, with heavy-lidded eyes and a thickening waist and, quite often, a round, four-carat lemon-yellow diamond on one earlobe. His life still has all the bling it ever did, but, for the time being at least, it's running a deficit of excitement, of heft... of meaning. It's the problem any mogul faces when he reaches a crossroads, although to break down Dash's particular status more clinically, through the prism of the debate recently taken up among leading black thinkers in the US, is to see him as Dionysus in exile.

The theory of "the Dionysian trap for young black men" was posited in March in the New York Times by Orlando Patterson, the Harvard sociologist, to explain the findings in several recent economic studies diagnosing "the tragic disconnection of millions of black youths from the American mainstream." Patterson decried the pervasiveness and bankruptcy of "the 'cool-pose' culture of young black men" - "hanging out on the street after school, shopping and dressing sharply, sexual conquests, party drugs, hip-hop music and culture" - the power of which, he said, is "almost like a drug."

Under this theory, then, Dash looks more and more like the dupe of a corrupt value system, an object lesson of empty consumerism. Dash has never been very interested in hip hop as an artistic movement. "It's all about finding ways to make money off an upscale urban product," he says. "That's what I do. I'm a businessman. Period." In his view, if there's more to life than money and taste, it's all the great stuff you can get if you have money and taste.

Dash may be no more or less a guilty party in the commercial exploitation of hip hop than some of his peers - Sean "Diddy" Combs comes to mind - not to mention the (mostly white) record-company executives who got in on the action. But Dash is the one whose cash cow left him, and he still doesn't seem to know what hit him. Currently, his payroll includes a photographer, Monique, who is at his side to capture his every move - the benefits he attends and the occasional audition he gives aspiring rappers.

"Damon says this is the most important year of his life, and he doesn't want the world to miss out on it," Monique says. She is at Damon's office to shoot the scene when his barber arrives and sets about shaving his head. This happens every other day.

"I know Damon will figure something out, because he's Damon Dash," says Russell Simmons, Def Jam's founder (he no longer owns the company). "The thing you have to understand about this guy is, he thought the whole thing up. Jay-Z just came from Damon's imagination. The man is a visionary."

At the moment, Dash says, he is focusing on his clothing lines - there's the Damon Dash Collection, which consists of expensive handmade suits and dress clothes; CEO, for hip-hop clothes; State Property (which Dash created for the rapper Beanie Sigel when he went to prison), for canvas "work clothes - don't call them 'prison clothes'", Dash says; and his wife's Rachel Roy ready-to-wear line. And Pro-Keds, it's worth noting, if only because of the weirdness factor, is introducing a line of sneakers with fruit-scented polyurethane soles. ("They smell like Italian ices - yellow is lemon and the green and red kicks are watermelon," Dash says one day, pressing a tennis shoe against his face. "Man, my sneaker game's ridiculous.")

Dash, who currently estimates his net worth to be around £14.7m (he made nearly £6m from Jay-Z's buy-out), grew up in Harlem, on 109th and First Avenue - "in the best building in a bad neighbourhood," he says, noting the first of many subtle contradictions in his background that fostered his awareness of class and notions of authenticity.

His father - divorced from his mother - ran a methadone clinic on 116th Street. His mother, he says, "was a hustler. She (omega) was a secretary, she sold clothes out of our apartment. She got stuff before it was in stores."

"As a kid, I always knew he'd do pretty much something," says Damon's older brother, Bobby Dash, a longtime employee of Dash's enterprises. "When we saw Superman, the little nigga was asking questions every two minutes. When he was like 16, 17, and I got into trouble with a crack game, I always called on him to get me out of the jam."

Dash was in and out of a number of public and private schools (via scholarships) finally ending up at Westside High. "Westside was for everybody that got kicked out of the place you went when you got kicked out of someplace else," he says. He even managed to get expelled from Westside, for driving his car to school and parking in the headmaster's spot.

He was always ambitious, even about having fun. "It was Damon's idea to start throwing parties, and we rented out a club and started charging money," says Steve Mack, a childhood friend who works for Dash's record label. Word spread about the parties - Dash credits their success largely to a standing offer to give a free bottle of Moët & Chandon to the first 100 ladies in the door each week. Rappers began showing up, as well as pro athletes visiting New York, and Mike Tyson.

"It was going so well, I said, 'We should do a record company and a clothing line,' " Dash says. The only problem was that he didn't make any music - didn't rap, didn't write rhymes, didn't know how to produce a record. He didn't even have a particular musical sensibility or, at that point, a very good ear. He did, however, believe that he understood how to put his Harlem experience in the appropriate consumer context.

The Dash cousins began to manage an act, the Future Sound, and got the group a record deal with Atlantic. The executive who signed them was Clark Kent - real name Rodolfo Franklin - who moonlighted as a DJ and had his ear to the ground. In 1994, Kent told Dash he had to meet an ex-drug dealer from Brooklyn who was trying to get a rap career off the ground.

"I'd never heard anybody rap so fast," Dash recalls of the rapper, whose name was Shawn Carter and who came to be known to the world as Jay-Z. In addition, his songs were full of clever, metaphor-heavy rhymes ("I've got extensive hos with expensive clothes/I sip fine wine and spit vintage flows"). Dash put up money for him to record a bunch of songs and, when a record deal was not forthcoming, began pressing the discs himself and selling them out of his car, and Roc-A-Fella Records was born.

Although Jay-Z had already spent years searching in vain for a record deal, Dash says he was drawn to him from the outset. "Everybody thought he was too old; they didn't like the way he dressed: like a Harlem dude. He wore Nike Airs, which everybody called uptowns." The class distinctions were lost on nobody. "The Brooklyn cats who were more dominant were known for doing things like gold teeth, much more ghetto," and they viewed Harlem's aesthetic as soft. But Dash saw in Jay-Z an uptown swagger. "I was shocked. Here was a guy with the aspirations I had. We wanted to be known for making money. All we talked about was making money and how to spend it, what the best of everything was and how bad we wanted it."

The two of them knew, also, that the making of records alone was not going to pay the kind of bills they hoped to be incurring. "The music business isn't so profitable, especially not hip hop," he says, attributing this to the copyright fees of sampling other songs. "I couldn't buy what I wanted to buy. I'm talking cooks and drivers. I got into clothes to make more money." The Rocawear clothing label was a success of cross-promotion. Anything Jay-Z wore in his videos sold out within days.

Dash looks down on other music-industry executives for having what he sees as an ambition deficit. "The people in this business all think they've made it because they're in charge of their little record labels," he says. "I'm like, this isn't even my main source of income. I already did this business. And I made movies" - he got an executive producer credit on the film The Woodsman, in 2004, and has also produced the forthcoming Shadowboxer starring Cuba Gooding Jr and Helen Mirren - "and I designed clothes and I got my own vodka and my own Swiss watchmaker" (Armadale and Tiret, respectively, newer additions to Dash's horizontal empire). "I like to be the brokest guy in the room. That inspires me. I don't get why people are proud to say they're old money," he continues. "That just means they had it given to them. I rubbed two sticks together and made money."

In 2002, there were rumours in the hip-hop press about a rift between Dash and Jay-Z. One factor was Dash's giving the rapper Cam'ron, a childhood friend and somebody Jay-Z had never been fond of, his own imprint at their record label, behind Jay-Z's back. Subsequent tension allegedly involved the conflicts of interest posed by each man's side projects. Dash made a small, satirical film, Death of a Dynasty, about the rumours, and it turned out to be prophetic. In December 2004, Jay-Z invited Dash to dinner to discuss the offer from Def Jam. In playing the bottom-line card and brashly chalking up the decision to leave as "just business," Jay-Z - pensive and sphinxlike - was beating Dash at his own game. It upsets Dash to not be able to view the matter as coolly as the person he'd always let on he was would. "Despite what he says, Damon takes everything personally, way too personally," says Al Branch, a former Dash employee who now works for Kanye West. "He thinks everyone's out to get him."

Dash says that when he runs into Jay-Z at an event - as he did a few months back - there's no hostility and no love. "I just give him a pound and move on. I'd still like to know what happened. But I don't think Jay would ever explain what he was thinking. He's not explicit like that."

"It's been hard on both of them," says Clark Kent, who is still working with Dash and has remained close friends with both men. "Now each one of them is struggling to do what they used to do, but each man on his own. The Roc hasn't had any great successes with their new acts with Damon gone. They'll never be able to replace each other."

"I like making everybody around me famous," Dash says one night. He is holding court at Soundtrack Studios in New York, trying to give his core group of music employees a pep talk. A half-dozen black men in baggy jeans and new high-tops sit before him in an irregular circle, including Biggs, Clark Kent, Steve Mack, and Little Shawn.

"Now, it would be hard for me to hit the street looking for talent," Dash goes on. "I'm 35. I go to operas and shit in Milan. I want everything different now."

"Different how?" Mack says.

"Beautiful music, man," Dash says, adding that he's just not going to be the one looking for it and pushing it.

"Word," Biggs says without looking up from a copy of the Essential Kitchen, Bathroom, Bedroom magazine.

There is, for the first time in a long time, a record to work on tonight. Dash has a cache of 20 new songs - by Nicole Wray, Rell, Sizzla, among others - that he needs to whittle down to 10. He pops in a song by the late rapper Ol' Dirty Bastard that he's had remixed for a more up-to-date sound, and all the people in the room start rolling their shoulders, nodding to the beat and mouthing the lyrics. Then comes the Carmen Electra number (with Sizzla rapping), then Busta Rhymes. Dash, still in his executive swivel chair, is throwing shapes to the music, freezing positions, grabbing his crotch, the whole routine.

At around 11pm, there's a knock at the door, and a skinny man in a baby-blue leather jacket and matching Timberlands enters. It's Chef Chardon, a leading caterer in the hip-hop world, as well as a rapper. Dash had an assistant call him, and he's driven in from New Jersey with a feast. "What's up?" he says.

"Chef Chardon!" Dash says. "I'm starving is what's up."

The chef begins opening a stack of foil trays. The music comes back on, and everybody digs in. "Right here, I've got my barbecued urban-suburban ribs," Chef Chardon offers. "Urban-suburban, that's my cuisine. I got my backyard barbecue chicken. And my urban-suburban Cajun rice. And then shrimp - sautéed in my own garlic-butter sauce. I don't even have a name for it."

"We'll come up with something," Dash says, bouncing with delight. "It's all good. We got food, we got drink. We have a long night ahead."