After speaking to various older coworkers and family members, I’ve come to the realization that it’s not only the younger generations that need a crash course in personal finance — many of the ones closing in on retirement need a refresher course too.

On Friday, the New York Daily News ran a story about Damon Dash, the co-founder of Roc-A-Fella Records(most famous for a little rapper you may have heard of named Jay-Z) and the accompanying Rocawear clothing line. Dash, who just a few years ago looked to be the second coming of Russell Simmons, is now in the poor house.