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10 Terrible Financial Choices in Music History

Stocks in this article: SNE TWX VIA.B ERTS

8. Damon Dashes from Jay-Z
In 2006, Roc-a-Fella Records co-founder and Jay-Z partner Damon Dash did an interview with New York Magazine in which he went into detail about his $50 million personal worth, opulent Manhattan home (with a whole level dedicated to his wardrobe), staff of butlers and personal assistants, $400,000 Maybach, more than 1,200 pairs of shoes and stylist wife Rachel Roy.

Just about all of that is gone now, as Dash's split with Jay-Z and ensuing business decisions left him owing New York State $2 million in taxes, putting two of his condos into foreclosure (including a 5,200-square-foot Tribeca duplex loft that went up for auction last year after Dash stopped paying the $78,000-a-month mortgage with $9 million left in the balance) and watching his Chevrolet Tahoe get repossessed after he failed to make the $714 payments. Roy, meanwhile, filed for divorce two years ago as the creditors moved in and lawsuits began piling up.

So where did Dash go wrong? Let's start in 2004, when he sold his stake in Roc-a-Fella to Island Def-Jam Records for $10 million after a reported dispute with Jay-Z about the direction the company would take. When Jay-Z became head of Def Jam that same year, he basically took sole ownership of the company he, Dash and partner Kareem Biggs had started and took artists such as a then up-and-coming Kanye West with him. Apparently trying to cut more ties with Jay-Z, Dash sold him the remainder of their Rocawear brand for $22 million in 2005.

It's a shame Dash washed his hands of Mr. Shawn Carter, as Jay-Z could have taught him a few things: like how to turn a dying $22 million clothing label called Rocawear into a $204 million windfall by flipping it to a company such as Iconix Group. Or how to turn experience with Roc-a-Fella's overpriced Armadale vodka house label into a gig as Anheuser-Busch InBev's (BUD) co-brand director for Budweiser Select. Or how to invest money into money-making enterprises including the 40/40 sports clubs or foundering-but-moving NBA franchises such as the New Jersey Nets instead of buying cars and bottles of Crystal.

Last year, Jay-Z made $63 million and topped Forbes' list of hip-hop's cash kings -- a list from which Dash was noticeably absent.

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