Born Giovanni Montana in Montedoro, Sicily, Montana came to Buffalo at the age of 13 in 1907 and quickly began to show his entrepreneurial business talents. In grade school, Montana made his first dollars as a messenger for a West Side candy shop running errands and messages. With his brothers Salvatore, Angelo, Peter and Joseph, the 17-year-old John Charles Montana first pushed a popcorn cart through Buffalo’s Little Italy at a time when Italians lived in a high density area on the Lower West Side and downtown. Because the demand was so great, the Montana brothers had to fold their first business as they couldn't supply the many people who wanted their goods.