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Barry was born in Harare, Zimbabwe in Africa. After completing his schooling in Zimbabwe and Dallas, Texas, he moved to the United Kingdom in 2001, and then to Sarnia in 2004.

Barry worked regionally in healthcare and industry until 2012 when he left to work in air operations for the United Nations Department of Peace Keeping. He served in two missions in Africa: MONUSCO in the Democratic Republic of Congo and UNMISS in South Sudan.

In 2013, Barry joined Cargojet Airways as an airline pilot. He is now a First Officer on the Boeing 767. He flies domestically, regionally, and overseas to multiple destinations, including North America, Europe, and Asia. Barry also volunteered as a firefighter for 13 years, holding the rank of Training Officer/Captain for a county fire department before retiring from Emergency Services in 2020.