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John has been in communications since graduating from Creative Communications at Red River College Polytechnic in Winnipeg in 1992. He launched one of Canada's first digital-only local news sites called Winnipeg First in 2007, which led to digital editor postings with the Winnipeg Free Press and Edmonton Journal. In 2012 he joined Bankless Times as managing editor, later becoming president and CEO. He and the Bankless Media co-founders completed a sale and exit in August 2021.