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He bagan to build his own vessels essentially selling them to himself at a considerable profit. He built a commercial empire by also selling or renting ships to merchants and this was initially solidified during the American Revolution during which he was given military command of most of the Great Lakes.

However, in the course of the revolution Grant lost much of his income with the loss of 12,000 acres (49 km²) of land he owned in New York and the end of his participation in private shipping.

Grant recovered, however, and rose to a position of prominence in civil society being appointed a justice of the peace in 1786 and to a succession of governmental and poltiical positions in both Upper Canada and Lower Canada. He joined the Executive Council of Upper Canada under governor John Graves Simcoe as well as the Legislative CouncilA Legislative Council in British constitutional thought is the second-to-top tier of a government led by a Governor-General, Governor or a Lieutenant-Governor, inferior to an Executive Council and equal to or superior to a Legislative Assembly. Though the. He also, in 1799, became a deputy superintendent of Indian Affairs.

In August 1805, Grant became administrator of Upper Canada on the death of Lieutenant-Governor Peter HunterPeter Hunter (1746-1805) was a British Army officer and colonial administrator. Hunter was born to a landed gentry family in Perthshire, Scotland. In 1767 he entered the British Army by purchasing an Ensign's commission. He rose to Lieutenant in 1770 and and continued Hunter's policies until a new lieutenant governor, Francis GoreFrancis Gore ( 1769- 1852) was a British colonial administrator. After serving in the British Army and achieving the rank of major. Lieutenant-Governor of Upper Canada from 1806 to 1811. Gore's administration built roads, reorganised the militia and found, arrived from Britain in August 1806.