Matthew Ashby was born in York County, Virginia, in 1727. He is a notable and rare example of the successful escape from slavery and indentured servitude. The son of a black slave and a white indentured servant, he was born free under Virginia law, which at the time gave children the legal status of their mothers. Ashby worked around the Williamsburg area as a carter and carpenter. He was also known to deliver messages for the state, working for Governor Botetourt. Although he himself was indentured until the age of 31, by law, he managed to acquire many things that were well out of the realm of the average slave or servant, including a silver watch, candle making supplies, tea boards, and books.