Dashing Diversification

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Since his childhood in Harlem, Dash has brandished the idea that he would come out ahead of the game. He would sweep barbershop floors and hawk newspapers to get money so he would have the very latest Fila sneakers. And there's that action-hero name. His mother Carol Young Dash raised Damon alone and worked a couple of jobs to provide a middle-class life for her son. Her labor, and scholarship money, enabled Dash to attend Dwight, a prestigious Manhattan prep school, and later a Connecticut boarding school. "I was around kids that had country houses and cooks and maids and stuff like that," he says, "and I didn't think anyone was that much better than me. I was like, Why shouldn't I have that stuff?"

His mother never saw him get it. An asthma attack killed her when Damon was 15. Her portrait covers his left biceps. Two years ago, tragedy struck again when his fiance, the singer Aaliyah, died in a Bahamas plane crash. Dash shocked co-workers when he strutted through the office only a week after Aaliyah's death. "Once I realized how many people depend on me at Roc-A-Fella, I knew I had to recover," he says.

Roc-A-Fella first bounced into Dash's mind when, at age 19, he went to a birthday party for rapper Heavy D at a cousin's Manhattan nightclub. The money and beautiful women hooked him. Two years later, a local DJ introduced Dash to Brooklyn rapper Shawn (Jay-Z) Carter. They teamed up, and Dash took Jay-Z on the road, but record labels weren't interested. Frustrated, Dash kept hustling Jay-Z at clubs in order to raise the money to start his own label, named in homage to the oil barons. He eventually persuaded Priority Records to distribute Jay-Z's debut, Reasonable Doubt, and it quickly sold a million copies. In 1997 Def Jam bought a 50% stake in Roc-A-Fella for about $1.5 million. Dash still laments the price but learned a business lesson. "We should have held out for more," he says. "Those f______ got us so damn cheap." Roc-A-Fella has averaged some $50 million in annual revenue over the past seven years.

Dash started Rocawear apparel in 1999. Sales of its jackets, sweatbands and tank tops now total about $300 million a year, making the company one of the major urban-gear brands, alongside Phat Fashions and Sean John. "I like the nylon windbreakers, the logo — Rocawear's stuff is just rugged," says Simmons. "People shouldn't be asking me about what I've taught Damon Dash. They should be asking me about what I've learned from him."

Almost every big rap star has a line of clothes, but only Roc-A-Fella lifts its own drink. Tired of seeing liquors like Allied Domecq's Courvoisier profit from mentions in songs, Roc-A-Fella partnered with William Grant & Sons, a Scottish distiller, to release Armadale, a premium vodka, last January. Armadale has already produced a $700,000 profit as well as criticism of Dash for pushing liquor to kids. Dash sees a double standard. "We're not saying kids should drink it," he says. "We're saying, 'Hey, kids, you can start a business.' Is it a negative thing when someone else starts a vodka company? As soon as hip-hop does it, there's criticism. It's really funny to me."

These days Dash spends most of his hours building up his less controversial film business. Death of a Dynasty, a hip-hop-industry spoof that Dash financed, produced and directed, will be released soon. Dash Films will shoot State Property 2, a revenge drama, in February. The pressure sometimes is evident. When Artie (Choke) Alston, a cameraman, shows Dash some backstage scenes on a laptop one recent afternoon, Dash doesn't hide his displeasure. "Everything gets done half-ass with you," he says. Choke then sits on a windowsill, staring at his feet. Dash is hard not only on the movie crew. "Sometimes you just want him to shut up," says Samantha Ronson, whose debut rock album, Red, is scheduled for release in March. "But then you remember he came from nothing and built all this, and you respect what he's saying." Ronson, 26, should cherish such attention — Dash has been hawking her single, Pull My Hair Out, in clubs and on the street. (He says CEOS should not avoid dirty work once they reach the top.) Red is Dash's first diversion from hip-hop, and some wonder why he's starting an unproven ex-club DJ on opening day. "He's putting his reputation on the line with me," Ronson says.