 Although he had limited education, Macdonald quickly showed an entrepreneurial spirit and, joined by his brother Augustine, he organized himself as a broker to handle the shipping of American-made goods to merchants in his native Prince Edward Island.However, after a ship carrying some of his merchandise sank in an ocean storm, the venture had severe problems and Macdonald closed the business and left Boston.The Macdonald brothers moved to the then Province of Canada where they settled in Montreal, a city that was then undergoing an economic boom.