This paper examines the case of Boston’s Long Wharf, a joint-stock company locally chartered in 1710, in order to gain insight into the significant internal and external challenges early American investors faced when their investment was in a physical structure. These challenges that were addressed by the shareholders, who were referred to as the proprietors, are examined over a period of 115 years from the points of the wharf’s construction to its diminution. An analysis of the company’s various records shows that the more serious challenges for the proprietors were seen in building the wharf itself, trying to prevent avoidable damage, addressing maintenance need, surviving the economic consequences of the American Revolution and the War of 1812, and adjusting to Boston’s physical and commercial growth. It is concluded that the proprietors did an admirable job in addressing the major challenges of their time and produced results that kept the wharf active economically for the long term.