[1] He attended the University of Tampa,[2] began his media career as a stringer for Time and the Chicago Tribune,[3] and retained close ties to the United States throughout his lifetime, including a second winter home in Arizona in his later years.
[3] Stirling was a co-founder in the Economic Union Party, a late-1940s political movement that sought closer ties to the United States for the Dominion of Newfoundland, which was then still independent from Canada.
[6] Stirling is regarded as an eccentric for both how he managed his businesses and for how he used his media outlets to promote a variety of personal interests such as eastern mysticism and intestinal health.
[7][8][2] For example, he devoted many hours of, often unscheduled, broadcast time to conversations with gurus such as Ram Dass and Swami Shyam and to a variety of esoteric subjects ranging from pyramids to unidentified flying objects, a practice which continues today as the station is run by his son G. Scott Stirling.
When he watched his own television station he would sometimes phone Master Control to order that a favorite tape immediately pre-empt the current broadcast or that the technician apply a particular effect to the screen.
Stirling appeared in the 1974 documentary film Waiting for Fidel about a trip he made to Cuba along with former Newfoundland premier Joey Smallwood and director Michael Rubbo.