1. Harry Truman
After serving in World War I, Turman opened a men’s clothing store with friend Eddie Johnson upon returning home to Kansas City. It is said that the saying “clothes make the man” could have been coined by Truman. The store was open from 1919 to 1922 but eventually fell victim to the post-war recession. Truman found himself just barely escaping bankruptcy, however, he managed to eventually pay off all his debts.