The investment: While Jay Z's business investments have hardly caused the hip-hop mogul 99 problems -- he is unquestionably one of the most successful businessmen in music -- they have caused a few.
With huge financial success in touring, apparel and more, Jay Z's efforts in the hotel business were not met with as much good fortune. His proposed luxury hotel endeavor in New York City, J Hotels, failed to get off the ground.
The dive: Jay Z's company purchased a property in the Chelsea neighborhood in 2007 -- reportedly for a 150,000-square-foot luxury hotel -- but construction was halted in 2008 due to lack of funds caused by the recession. When the company defaulted on the $52 million loan used to purchase the property, the hotel partners eventually handed the property back to the lenders. The parties were also enmeshed in a legal battle over additional costs until settling out of court for undisclosed terms in December 2010.
Things have turned around for Jay Z, at least financially. He and his wife, fellow musician Beyonce, topped the Forbes list of richest celebrity couples by earning an estimated $95 million from June 2012 to June 2013. Aside from the millions he earns on tour, Jay Z has started a sports agency called Roc Nation Sports.