Born in Virginia to one of the British colony's most influential families, it has been contended that he was educated at the College of William and Mary, although no evidence exists to support that fact.
What is known is that at some point after his father's death in 1768, he moved to New York, likely to his cousin Beverley's household and was there at the beginning of the American Revolution.
On June 26, 1781, he was commissioned an Ensign in the Queen's Rangers under John Graves Simcoe and served through the surrender of the British Army at Yorktown, until 1783.
In 1792, Simcoe, now Lieutenant Governor of Upper Canada, offered him a post as a minor surveyor general and he moved to Kingston.
In 1794, he received his license to practice law and, in 1796, he was elected to the 2nd Parliament of Upper Canada representing Ontario & Addington.