For nearly half a century, Stephen Smith worked as a cabinetmaker in Boston, beginning as a relatively small artisan and building his trade into a substantial firm with three partners. He is first listed in the city directory in 1829, and by the following year was recorded as a cabinetmaker with a shop in Wilson Lane and home at 3 Purchase Place. Smith remained at this address through most of the decade, but by 1839, he had moved his shop to 44 Cornhill, and in the late 1840s he relocated once again to 49 Cornhill. A major part of Smith's business during these years was the retail of stoves manufactured by his brothers-in-law, Thomas and John L. Lothrop, of Provincetown, Mass., but he also carried on a brisk trade in the manufacture of office and church furniture, cabinetry, and clocks, some of which he contracted out. At one level, business seems to have dominated Smith's life. Not only was he married to the sister of an important supplier of his, but his own sister, Sarah, was tied into his expanding business interests through her marriage to an associate, Daniel Scudder. Thomas Lothrop, too, was an avid businessman; so much so that he wrote of the death of his daughter in 1841 only to explain why he had not been able to transact his business affairs sooner.
George L. Smith, Stephen's brother, attempted to take a different path to financial success. Having heard of the discovery of gold in California in May, 1849, George wasted little time in deciding to try his hand at mining, and between September, 1849, and September, 1850, he worked claims along the Yuba River and in the vicinity of Sacramento. Unlike many miners who found as much disappointment as gold, George fared moderately well, and was able to send home several hundred dollars for his year's labor.
Eventually, as his trade expanded, Stephen Smith came to specialize in "bank and counting room furniture," and the 1865 business directory lists him as a furniture dealer, rather than manufacturer. In that year, his firm, Stephen Smith & Company, included George H. Crocker, James Norris, and George L. Smith as partners. The firm remained in business until at least 1877.