Rush Hour

The middle son of three boys in a middle-class family, Simmons decided early on that the straight path of his dad, a teacher, and his mom, a recreation director, was not for him. School bored him, and he wanted nice clothes, so he turned to the street, selling ganja for extra money. He joined an infamous gang, the Seven Immortals, watched his older brother Danny--now a successful artist--go to jail for using drugs, got a job at the Orange Julius store in Greenwich Village, and eventually graduated to selling fake cocaine. Bogus coke wasn't illegal and the margins were better, Simmons says, plus he reasoned the only people you had to worry about were ripped-off clients.

Everything changed one day in 1977, when Simmons saw a man named Eddie Cheeba whip a club crowd into a frenzy by shouting out rhymes. Simmons had an epiphany. "Just like that, I saw how I could turn my life in another, better way," he writes in his autobiography, Life and Def: Sex, Drugs, Money + God (Crown Publishing, 2002). "All the street entrepreneurship I'd learned selling herb, hawking fake cocaine, and staying out of jail, I decided to put into promoting music." Simmons quit dealing and became a concert promoter for New York-area shows and then eventually a manager, helping to get some of the first rap singles on the radio. He got his biggest break when he coproduced Run-DMC, the rap group featuring his kid brother. The group became the first rappers to appear on MTV and the first to score crossover hits with white listeners, particularly because of its rap-rock collaboration "Walk This Way," with heavy-metal band Aerosmith. Today, the marriage of hard rock and rap seems natural, two strands of the same teenage angst and anger. But in the mid-1980s, the idea that black street kids and white suburbanites could like the same music was shocking.

Simmons learned a huge lesson from Run-DMC's success. The group made it precisely because it wasn't trying to cross over at all. Unlike other aspiring rappers, the members of Run-DMC didn't wear fancy superstar clothes but rather leather suits, hats, and Adidas sneakers--exactly what was being worn in the 'hood at the time. By appealing to a smaller audience with their own authentic style, they became mainstream stars. Simmons says this insight has been a constant in every business he's owned. "You have to tell the truth," he says. "It endears you to the community. The [people] can smell the truth, and they're a lot smarter than the people who put the records out."

In 1985, Simmons and his partner Rick Rubin cofounded Def Jam Records, the label that featured such huge rap stars as Public Enemy, the Beastie Boys, and LL Cool J. Then, as now, he surrounded himself with a small cadre of smart, loyal partners and employees who flourished in a disorganized, entrepreneurial free-for-all. The lifestyle was wild--Simmons says having sex and snorting cocaine in the office was part of a normal business day--but it was a rush to be on the edge of a rapidly changing culture. Island/Def Jam's Cohen has worked with Simmons for 20 years and remembers those days fondly. "I lived in a welfare hotel and slept on the floor, and it was an incredibly fun period of time," he says. "We had the tremendous amount of arrogance that's necessary to swim against the tide."

Def Jam teamed up with Sony before selling a 60% share to Polygram, and in 1999, Simmons sold the remaining 40% for $120 million. Today, he has little operational involvement at Island/Def Jam but serves as a father figure to rappers such as Ludacris and Jay-Z, helping to solve legal and personal problems and teaching them the business of entertainment. "We talk every now and then about the industry, music, etc.," says Ludacris. "I look up to him. I want to follow in his footsteps in terms of the business ventures."

Those ventures extend far beyond music. In 1990, Simmons started Rush Communications, an umbrella company for a variety of ventures aimed at American youth. Today, the company is a percolating mix of businesses, led by Phat Fashions clothing, which was founded in 1992. Phat Farm's advertising and brand is quintessentially Simmons: The men's and boys' clothing lines have the classic styling of a Tommy Hilfiger or Ralph Lauren but with a slightly edgy twist. There are sweat suits, jeans, and preppy pink argyle sweaters, all made well enough (and priced high enough, says Simmons) to satisfy the aspirations of the poor yet also appeal to the rich. The multi-ethnic ads show more attitude than you might see in a Ralph Lauren spread, and they frequently carry a social or political message. Often, you'll see Simmons's cross-marketing skills at work; he loves to use Def Jam rappers as models, or feature the platinum-colored Motorola flip phone he designed, complete with the Phat Farm logo and Simmons's signature (it retails for $549). Today, Phat Farm has become the most broadly distributed urban brand, although primarily through smaller chain stores. In order to go head to head against such retail giants as Tommy Hilfiger and Ralph Lauren, Simmons's stated goal, Phat Farm must break into department stores. Federated Department Stores Inc., the owner of Macy's and Bloomingdale's, has carried Phat Farm for several years, but others haven't, believing the crossover appeal is limited.