The mogul who launched the careers of Jay Z, Kanye West, Cam'ron and many more, Damon Dash became one of the wealthiest men in hip hop — he claimed to be worth "about $50m" in 2006 — but ended up losing his fortune. A visionary businessman and flamboyant extrovert with a thirst for the private-jet lifestyle that was both the making of him and his Achilles heel, he co-founded Roc-A-Fella records and Rocawear clothing with Jay Z, but they parted company in 2005 after falling out. Dash's career has floundered since, as the bills have piled up — though in 2016 he made a comeback with a lifestyle TV network, Dame Dash TV.
Growing Up in the Ghetto
Born on May 3, 1971, Dash grew up in Harlem "in the best building in a bad neighborhood," as he once described it to New York magazine. His father — divorced from his mother — ran a local methadone clinic; his mother was a secretary and a "hustler," who sold clothes out of their apartment. She died from an asthma attack when Dash was 15. Dash was a bright kid who won scholarships to a succession of private schools ("I used to play lacrosse — that bugs people out," he told CNN in 2006), but was repeatedly kicked out for bad behavior. From a young age he was both streetwise and able to roll with an uptown crowd, a social fluidity that would serve him well.
Signing Jay Z
Dash began hiring Harlem's Cotton Club to throw parties and as their popularity grew so did his entrepreneurial ambition. He had a vision for a record label and a clothing line, and after attending a party thrown by the rapper Heavy D in 1990, Dash became convinced that hip hop was the way to get rich. He and his cousin Darien began to manage an act called Future Sound, landing them a deal with Atlantic Records. In 1994 a contact Dash had made at Atlantic introduced him to an unsigned rapper from Brooklyn who had great potential — he was both lyrically gifted and super-fluid on the mic. That rapper was Shawn Carter — the young Jay Z.
Jay Z's debut album in 1996, Reasonable Doubt, was released on a new independent label that Dash co-founded with the rapper and a third, silent, partner, Kareem "Biggs" Burke. The label was called Roc-A-Fella, and it became the focus for a new wave of East Coast rap — in 1998 Jay Z's album Vol 2... Hard Knock Life sold over 5 million copies in the U.S. alone, followed by gold-selling debut albums by Memphis Bleek (Coming of Age, 1999) and Beanie Sigel (The Truth, 2000).
The dollars were rolling in — and nobody was better than Dash at spotting further opportunities and capitalizing on them to the max. In 1999 he organized the 54-city Hard Knock Life arena tour, featuring Jay Z, DMX, Ja Rule, Redman, Method Man and Eve, which netted a $19-million profit. That same year, he and Jay Z launched the hip-hop clothing label Rocawear — sales spiked every time the rapper wore new pieces in his videos.
With Dash as his manager, Jay Z had nine No. 1 albums; in 2004 Roc-A-Fella released the debut album by another Dash discovery, Kanye West — Late Registration went on to sell over 3 million copies.
By now Dash was a celebrity himself, rivaling Diddy as hip hop's most prolific and ostentatious CEO, who "reveled in his reputation as a pugnacious asshole in the boardroom" according to the Village Voice. But despite his champagne lifestyle he did not publicly flaunt his relationship with the R&B star Aaliyah, who died in a plane crash in the Bahamas in 2001. After her death, the grief-stricken Dash told MTV that they had planned to marry. "She was the one — she was definitely the one for me," he said. Three years later he married the fashion designer Rachel Roy, and they had two daughters together, Ava and Tallulah. Dash also has a son, Damon Dash II, from a previous relationship.
Fallout with Jay Z
Rumors of a rift between Dash and Jay Z began circulating in 2002. There were various theories why. One was that Jay Z disapproved of his business partner's growing flirtation with Hollywood — Dash produced the movie The Woodsman starring Kevin Bacon in 2004, and was involved in Shadowboxer, starring Cuba Gooding Jr. and Helen Mirren, the following year. Another theory is that Dash caused friction by giving his friend, the rapper Cam'ron, whom Jay Z did not get on with, his own imprint at Roc-A-Fella.
Things reached a head in late 2004, when Def Jam Recordings made an offer to buy Roc-A-Fella outright — it had owned a 50% stake since 1997. Def Jam also offered to make Jay Z its president, but Dash was opposed to the move (he also refused to relinquish the rights to Jay Z's debut, Reasonable Doubt). In the end the partners split — Jay Z went to Def Jam, while Dash retained Roc-A-Fella. But most of Roc-A-Fella's acts chose to follow Jay Z to Def Jam rather than remain with Dash, which the latter saw as a betrayal by artists who owed him their careers.
Years later Kanye West spoke of his regret at leaving Dash. "It made more sense for me, career-wise, to roll with Jay," he told VH1 News. "I came to Roc-A-Fella because Jay Z was my idol, and it would've been very hard for me to separate from my idol." Although any guilt he may have felt at the time did not prevent him including a guest verse from Jay Z in his 2005 single "Diamonds from Sierra Leone," which appeared to take aim at Dash. "I'm not a businessman, I'm a business, man," Jay Z rapped. "Let me handle my business, damn!"
The separation was complete by the fall of 2005, when Jay Z bought Dash out of his share in Rocawear for a reported $22 million. With hindsight this would seem a bad deal for Dash when, two years later, Jay Z sold the rights to Roc-A-Wear to the Iconix Brand Group for $204 million in cash. According to the New York Times, Jay Z also retained his stake in the Rocawear operating company, which manufactures its menswear clothing, as well as remaining in charge of product development, marketing and licensing.
Excessive Lifestyle, Financial Issues
In the years that followed, Dash tried his hand at a number of ventures in music, fashion, beverages, boxing promotion, publishing and reality TV. None worked out, bar his wife Rachel Roy's eponymous fashion label, which Dash backed financially; it became a favorite of Michelle Obama and Kate Hudson. But although he was unable to repeat his former stratospheric success, he continued to live a high-net-worth lifestyle. In 2006 Eric Konigsberg reported in New York magazine that Dash owned a mansion in Beverly Hills and a loft in New York's Tribeca (where he also later had an art gallery and recording studio). He flew to meetings by private jet and had a butler, a chef and a glass-roofed limousine. He boasted of owning 1,300 pairs of trainers, and of donating his shirts and socks to charity after wearing them just once. He was living like "Dionysius in exile," Konigsberg wrote.
The debts piled up. By 2008 Dash owed $2 million in unpaid taxes and faced lawsuits from creditors and landlords. He and Rachel Roy divorced in 2009 — during proceedings Dash revealed that his car had been repossessed and that he had been forced to vacate his $9 million Tribeca home, which was eventually sold into foreclosure for $5.5 million. In 2015 Page Six revealed that Dash owed $4.14 million in back taxes to the State of New York.
Back in the Game with Dame Dash TV
In August 2016 Dash announced the launch of a new lifestyle TV network for millennials, Dame Dash TV, in partnership with the streaming service FilmOn, which claims a global monthly audience of 75 million; an accompanying shopping app allows viewers to purchase clothes they see on the shows, including pieces by his own label, Poppington.
According to Billboard magazine, programs include The Secret to Ballin,' in which artists like Snoop Dogg, Chris Brown and Redman share tips on how to get rich and successful; International Grizzly, in which Dash "loads up a private jet" with guests and hits the world's music and fashion capitals; and — most intriguingly — a "brutally honest" television series in the pipeline that promises to tell the story of Roc-A-Fella Records, as well as Dash's relationships with Aaliyah and Rachel Roy. Lawyers will no doubt be watching with keen interest.
(Profile photo of Damon Dash by Mark Mainz/Getty Images)
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