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