Attempting to overcome the failure of his first contracting business following World War I, Dutton operated a second using the money he earned with the Tigers and Maroons. It too failed in 1933 as a result of the Great Depression. In 1938, he tried again, joining with Reg Jennings and his brother Jack to form the Standard Gravel and Surfacing Company in Calgary. The company proved immensely successful during World War II, building numerous airports within Canada as part of the British Commonwealth Air Training Plan as well as completing highways in northern Alberta and the Northwest Territories. After serving a year as vice-chairman, Dutton was named the chairman of the prairie roadbuilders section of the Canadian Construction Association in 1950. By 1960, the company had become Standard Holdings Ltd., operating 20 different companies that had $70 million in contracts for that year alone, and Dutton had personally become a millionaire.