They were making money....
Some of these guys just don't know how to keep the money they make. One of the billionaires said, "It's not how much you make, it's how much you keep." The amount that you keep depends on your money management skills. A lot of these rappers are living strictly off of rap money and blowing it on nonsense. They have no outside investments, they're not being responsible with their money, etc. That's why people like Master P, Jay-Z, 50 Cent, etc. are worth hundreds of millions of dollars.
The bolded brings to mind a quote from 50 a while back: "...The only thing that don't come with instructions is money!"
Maybe he should've told Buck that back in '03, and he wouldn't be in this predicament now. Didn't the IRS raid Buck's house a few months ago? On another note, Wayne, B.G., and some other rappers have been tryna work w/Buck for a while now, but 50 won't let him. This is despite 50 saying that he wanted to sit and talk with Buck last summer. It goes without saying that the whole situation is f**ked up...