Winston was born in Auckland, New Zealand and moved to Canada to follow his heart. His most recent play, Outward, was on stage as part of the Toronto Queer Theatre Festival. Winston was a finalist at the Newmarket National Ten Minute Play Festival with his play Parent/Child, which was also staged at the The Coming Out Play Festival in St. Louis, Missouri. He was the publicist for Bakersfield Mist at the Toronto Fringe Festival and stage managed and produced Point and Click at the Toronto Queer Theatre Festival. Winston now lives in Toronto with his dog.