Gregory has been practising law since 2009 in the areas of business, trademark and entertainment law. He is also a co-host of the Legal Cut Pro entertainment law podcast and has been a sessional instructor at MacEwan University. Before his law career, Gregory worked in film and television for five years in various roles from being a locations PA to being a business coordinator in marketing/distribution. While Gregory takes his clients' matters seriously, he believes in having fun with the law by running panels and mock trials at the Calgary and Edmonton Comic Expos and participating in Nerd Nite.