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."

• • •

In early August, three months before the Jim Jones show, Dash posted an Instagram photo of himself with his arm around Jay-Z's shoulder, both men smiling at a friend's birthday party in Williamsburg. The image lit up the Internet. The two hadn't spoken much in 10 years, except to exchange polite fist bumps when crossing paths at industry events. It was a welcome distraction for Dash, who had lived under a barrage of tabloid reports all summer and fall, airing his personal money woes. Damon Dash left jewelry, art behind when he "abandoned" mansion, read the headline in the New York Post when Dash's possessions—including drug paraphernalia, according to a court filing—were carted off from an upstate home, where the landlord claimed he owed $162,000 in back rent (Dash says it was a misunderstanding). Other reports cited his court battle with a former clothing partner, whom he owes $237,000 for an old loan (Dash says it's now paid off), and the IRS's hitting him with a $2.8 million lien for back taxes.