John was his father’s oldest son. In 1785 his father sent him to St. Eustatia in the Dutch West Indies to manage the Caribbean end of the family shipping business. While there he made an unfortunate marriage with a woman known as the Widow Stevens and failed to realize his father’s hopes for increasing the trade in tea and sugar. In 1790 John returned home in disgrace, and with his father’s support and urging divorced his wife.