Great question and somewhat tricky. I collect unemployment and I am a sole proprietor. But the only reason I can collect unemployment is because my business has not brought in any money, nor do I pay myself. Each state sets their own "dollar limits" as to how much you can make while on unemployment. Florida is set at anything under 52.00 gross a week will not effect your unemployment wages. Anything over 52.00 gets deducted from your unemployment wages but you don't use up your "points" so-to-speak. You can always file to see if you get approved or not. Just be honest and see what happens.