It pays to be the manager of Jessica Simpson. Not so much Ashlee Simpson though. According to Radar, Joe Simpson recently went to Cabo where he dropped $300K on a little vacation that he took with a mystery guest. This of course comes on the heels of his Hawaii vacation that he took with his daughter Jessica after Tina and Ashlee went back home. Radar also says that Tina is ticked off because the money came from their joint bank accounts and that the couple are fighting over their $300M fortune which means if they have $300M, then Jessica pretty much has more money than anyone. Ashlee must be depressed about that everyday. Maybe she can become a backup singer on Fall Out Boy's new tour. Oh wait. I forgot. To be a backup singer you really do need to sing. I guess she will just have to be happy with the paycheck Jessica sends her every two weeks for doing nothing.