Born in Hornsea, near Hull, Yorkshire, England, his father died when he was only six weeks old, leaving four young children to be raised by his mother.

He made his way by Durham boat to Prescott, Upper Canada where he boarded the steamboat "William the Fourth" for York, arriving in Toronto in 1833.

[2] He built the William Cawthra house (a mansion at the corner of King & Bay, Toronto) which was demolished in 1946.

When he was Foreman of Public Works, he refused to build the gallows to hang two leaders of the Upper Canada Rebellion, Samuel Lount and Peter Matthews.

His son, Dr. Charles Sheard, became the city's Chief Medical Officer and also served as a Member of Parliament.