As a student leader in June 1969 he met John Lennon and drove him around Ottawa while he was hosting him for a "peace conference" he was holding.
In 2001, Ian moved to Ottawa and served as senior policy advisor to three federal cabinet ministers; Minister of Industry, Allan Rock; Leader of the Government in the Senate, Jack Austin; and David Emerson, Minister of Industry.
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The group usually targets Canadian politicians, and has pied former Prime Minister Jean Chrétien, provincial premiers such as Jean Charest and Ralph Klein, and cabinet ministers such as Stéphane Dion, Allan Rock and Pierre Pettigrew, among other political figures.
He wrote that he had supported Martin up to and through the 2003 leadership race, but that Martin had alienated faithful Liberals like Herb Dhaliwal, Allan Rock, John Manley, Sheila Copps, "and even poor little Don Boudria." "Don't push people around as you'll need them later on," he warned Martin.