In 1932, Roy started his trucking business, at age 20. By 1958 his fleet had grown to ten trucks. For 36 years, Roy primarily hauled livestock to St. Paul and back-hauled freight to the Brandon area. Truck drivers for Roy were: Cliff Augdahl, Tony Skrove, Ray Stich, Dorland Ranstead, Kenneth Schjei, Dayton and Les Hermanson, Vernon and Cliff Strom, Ralph Angen, Dean Christopherson, Ervin Grubb and Jerry Klein. In 1968 Roy sold his business to Kenneth Schjei.