[1] In 1796, he joined the counting house of his uncle Russell Sturgis (1750–1826), and less than two years later became connected with James and Thomas Handasyd Perkins' maritime fur trade between the Pacific Northwest coast and China.

Upon his father's death in 1797, he went to sea to support the family as assistant trader on the Eliza, then as chief mate of Ulysses.

[2] In 1804 Caroline sailed from the Columbia River to Kaigani, just south of Prince of Wales Island, Alaska, acquiring some 2,500 sea otter skins that netted $73,034.

In 1809, his ship Atahualpa, owned by Theodore Lyman, was attacked by Chinese pirates while moored at Macau Roads.

Using these, they managed to fight long enough to sail within range of the protective guns of the harbor, and the pirates were captured, their commander Apootsae later being tortured to death by the Mandarin authorities.

It was with advice from Sturgis that John Murray and Robert Bennet Forbes started their investment in the railroad business in 1843.