Damon Dash doesn't look like a CEO this morning. He's sparring with his trainer in the courtyard of his Spanish-style Beverly Hills home, high above Hollywood's canyons , and trash talking all the while. "I ain't goin' down--I can hang as long you can," he pants. "Don't let my heavy breathin' fool ya." You may not recognize Damon Dash's name, but you've probably seen him in his business partner Jay-Z's rap videos--he's the one in the background, dancing with a bottle of vodka in his hand. Don't let that, or the baggy shorts, or all those tattoos (including the one of his mother) fool you either.

Over the past 10 years, Jay-Z's music and Dash's business savvy have built their Roc-A-Fella Records into a half-billion-dollar empire. (Despite rumors of a rift, they're still partners.) Dash, 34, now has multimillion-dollar homes on Fifth Avenue and in the Hamptons; last Christmas, when he vacationed in Antigua, he quickly made friends with his next-door neighbor, Robert DeNiro. He represents a new type of businessman--bred in the world of hip-hop, and with a strong sense of entitlement. "I'm tired of people looking at us as thugs and crooks," he says. "Most of us have big plans for our futures, and big plans on how we plan to have those big futures."

Dash has a gift for turning grievances into opportunities. After watching rappers on his label giving free endorsements to liquor brands in their videos, he bought Armadale vodka "to keep the money in the family"; last year, Armadale grossed more than $2 million. When he felt dissed by such major fashion labels as Iceberg, he started his own Rocawear line of street gear; in its first year and a half, it took in more than $80 million. Noting no magazine captured his sense of a multicultural America, he decided to publish his own: an $8 glossy called America, which tackles everything from fashion to politics; it debuts this month with Alicia Keys on the cover. As rap impresario Russell Simmons says, "Damon sees no boundaries."

Dash got his mixture of street smarts and Wall Street smarts in both East Harlem and Connecticut. His mother worked as a secretary and made clothes to send him to private school; when she died--he was 15--he used the money she'd left to attend boarding school in South Kent. "I was around rich kids, saw the lives they led and never thought it wasn't possible for me to have the same life one day. That's how I want kids to think coming up behind me."

For someone as driven as Dash and with as strong a sense of where the culture needs to go, it's natural he'd end up in Hollywood. "But I knew I had to have the cash to do my own thing because Hollywood wasn't going to give money to a ghetto kid like me." He's been using his own money to direct, produce and distribute such films as the hard-edge 2002 "Paid in Full." This year he'll be the executive producer of "The Woodsman," starring Kevin Bacon and Benjamin Bratt.

Dash knows how he looks to mainstream Hollywood with his tattoos, his shorts, his attitude. But he sees that as their problem. "My culture is the one that's selling," he says, "so why do I need to change? I represent what they're looking for, and they need me whether they know it or not. And that means accepting me and everything that I bring to the table--however I bring it there." Given Dash's track record, they can probably work this out.