In 1959, he bought Sheardown Transport from his father. He sold this business in 1970 to create Sheardown Tire, which still operates in suburban Toronto. In the mid-1970’s, he began acquiring trucking and transportation companies, operating 300 trucks and trailers. In 1976, he owned and operated Atlantic Bus Lines, a 200-school bus operation in Markham, ON. He was the private subcontractor for the first incarnation of Wheeltrans, the elderly/disabled service for the Toronto Transit Commission. Mr. Sheardown bought Ontario Bus Industries in 1979. He grew this company from 80 employees with $2 million in annual revenues to a staff of 1,300 with $150 million annual revenues. He entered the U.S. bus market by establishing a manufacturing facility in Utica, NY. His firm designed and built the ORION II in 1983, thus providing the first low floor bus designed to enhance access and mobility for people with disabilities. He began exporting the ORION II to Sweden in 1988. The CNG ORION was developed in 1987, the first hybrid ORION was developed in 1988 and the ORION V was developed in 1989. He and his staff led the industry in the development of the low floor bus, CNG deployment and hybrid technology. Only poor health slowed this corporate dynamo!

Mr. Sheardown was the earliest corporate supporter of the New York Public Transit Association. His firm sponsored 100% of the State Roadeo for many years. He and his staff attended every meeting of the New York Public Transit Association.