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O.C. Barber's journey began in Middlebury, Ohio, where he was born into a working-class family. His father was a matchmaker, and from a young age, Barber was involved in the family trade. Leaving school as a teenager, he took to the streets selling matchboxes with a horse-drawn wagon. His determination and natural charisma led him to become a partner in his family business by the age of 21.