Harry has been playing trumpet since the age of twelve and learnt to scat from listening to the Jazz greats. Harry went to primary school at Malvern Primary School, where he would often perform as a vocalist at school assemblies. Harry went to high school at McKinnon Secondary College and was taught by Ian Orr in Melbourne before studying at the Victorian College of the Arts. In 2006 he appeared twice as a panelist on the ABC Australian Music Quiz show Spicks and Specks. Harry is also part of The Conglomerate, a four-piece Melbourne jazz band.