Being broke is no fun — especially if the circumstances were totally under your control. We’ve all been there at some point in our lives. Spending too much money on a new outfit to wear out and consequently blowing the grocery budget for the month, or eating and drinking out five days a week and having to forgo cell phone access for three weeks. In those subsequent days of eating Ramen and downing tap water, there’s ample time to reflect on poorly made financial decisions.

We suspect that’s what some celebrities are rehashing now, thanks to good old fashioned financial negligence. And since everyone loves a good Riches to Rags story, we’re going to use these celebrities as an example of how NOT to spend your cash.

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.