JJ Da Boss worked as a roofer for 20 years. Then with the earning he made, JJ used to recondition cars and sell them. However, back in past, JJ made some bad choices and went to Federal Prison. He spent eight years and a month behind the bar. So far, the reason behind his conviction is still unknown. But he took the dark part of his life as a learning process and later started own business of buying, fixing and selling old cars.