The "Hollywood Madam" once ran a highly-successful prostitution ring, but then the pesky law got in the way. Fleiss was convicted in 1995 and served 20 months in a California prison for running the prostitution ring.
Since then, Fleiss' business skills haven't improved. Her failed businesses include a stud farm in Nevada where sexy men were sold to women for $250 an hour. One little problem, however, in Nevada convicted felons can't work in the sex trade. Fleiss also struck out with a sex toy shop, Laundromat, and a pet grooming shop. Her latest venture is a pet spa in Las Vegas. Yeah, that should work well in a recession. (Photo: AP)