In 1883 his industrious nature led him and his brothers Charles and Albert to form Stickley Brothers & Company, the same year in which he married Eda Ann Simmons. Within five years, the company was dissolved and Stickley’s ambitions led him to partner with Elgin Simonds, a salesman in the furniture trade, to form the firm of Stickley & Simonds in Binghamton, New York. During the 1890s, Stickley divided his efforts between his new enterprise and, with his brother Leopold, served as a foreman of furniture operations at the Auburn State Prison.