Through Empire Company Ltd., Sobey purchased a local drive-in theatre (renaming it Empire Theatre) and later built a chain of movie theaters, in addition to substantial commercial and residential real estate holdings. In 1971, while still active in the business, Sobey handed over formal control of the company's operations to his three sons, Bill, David and Donald. In the late 1950s, Premier Robert Stanfield appointed Sobey as president of Industrial Estates Limited with a salary of $1/year; Sobey is credited with guiding IEL to make investments in the 1960s that significantly expanded and diversified Nova Scotia's economy. Sobey was also one of the investors behind Peter Munk (chairman of Barrick Gold) in founding Clairtone.