After leaving Eastman's College, Woodruff went to
New York City where he was hired as a clerk for a wholesale salt supplier. Within a year Woodruff was made a partner in the firm. Woodruff also became involved in warehousing on the
Brooklyn waterfront, gaining a controlling interest in several commercial frontages and two grain elevators. This warehousing operation was consolidated in January 1888 as the Empire Warehouse Company, which in turn became the Brooklyn Grain Warehouse Company in May 1889. Woodruff maintained other commercial interests as well, serving as president and principal proprietor of the Maltine Manufacturing Company, as president of the
Smith Premier Typewriter Company, and as a director of the
Merchants' Exchange National Bank. As a prosperous businessman and avid fisherman Woodruff found himself with the means to purchase land and a summer cabin on Sumner Lake in the
Adirondacks near the
Hamilton County town of
Long Lake. Woodruff later purchased additional land in the Adirondacks, where he developed a popular commercial camp called Kamp Kill Kare. ==Political career==