Cowboy received his initial film production training in Los Angeles, California at the NMTN American Indian Summer Institute at UCLA, Loyola Marymount University, USC-Zemeckis and FOX Studios in 2006-2007. Cowboy also completed the Full Circle: First Nations Performance Ensemble Training Program in 2007, then went on to graduate from the Independent Indigenous Digital Filmmaking program at Capilano University in 2008. Cowboy has gone on to write, produce and direct various works in live theatre, music video, documentary and narrative film, which earned him awards both in Canada and the United States. Cowboy is currently hosting and producing "The Silent X Podcast." Cowboy splits time between his traditional Blackfoot territory in Alberta and Vancouver, British Columbia.