In an era where education opportunities were limited in small Maritime towns, Sobey left school after Grade 8. However, he had an entrepreneurial mindset, and at age sixteen enrolled in a business college. In 1924 he persuaded his father to expand the store to carry a full range of groceries and the family began expanding, opening stores in the nearby industrial towns of New Glasgow, Trenton and Westville, and the university town of Antigonish. In the early 1940s, the family wished to purchase a building on Archimedes Street in New Glasgow for a supermarket. The property was owned by a company named Empire Company Ltd. and to acquire the building, the family purchased the company itself. Empire was transformed into the family's holding company and was privatized in 1981.