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."
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