Crump worked as a salesman at Streight's Indianapolis lumberyards for nearly a year, until poor health forced him to return to New York to recuperate.

Crump resigned his position in 1868 and married Phebe A. Tucker of Craigsville, New York, and then went to Winona, Minnesota, to work with the Laird, Norton & Co., planing mill and lumberyard.

Crump next formed a business partnership with his uncle, James Cutting, in Simcoe, Ontario, where they operated a general lumber, stave, sash, shingle, and door factory.

In the summer of 1881, Crump and his wife made a tour of the Great Lakes, visiting Northern Michigan, including the Bay City area.

The company dropped the retail lumber, sash, door, and blind business and became one of the largest box and package manufacturing plants in the country at that time, employing over 100 persons.

Crump was a member of the Episcopal Church and was active in Masonic fraternities, including the Royal Arcanum, Foresters, Pythians, Knights Templar, Michigan Sovereign Consistory of Detroit and Moslem Temple, and the Ancient Order of United Workmen.