Harry Truman
Truman now ranks as one of the most well-regarded presidents in American history but public opinion was less kind during his time in office. When Franklin D. Roosevelt picked him as his vice President in 1945, Truman was a political nobody. Truman only served a few short months before FDR died. His political fortunes as president would be up and down (e.g., the famous “Dewey Defeats Truman” headline says it all: the result was actually, and surprisingly, the opposite) but you may not have been aware of Truman’s background as an entrepreneur. He worked for a time in construction and as a bank clerk before serving in World War I. When he returned, Truman opened a haberdashery (a men’s clothing shop) with a friend but it would fail in short order thanks in part to a broader economic downturn.