Michael commenced real estate work at 18 when he joined the Cantwell family's real estate business in Hawthorn, Melbourne. From 1991 to 1999 he worked in residential property, trust management and commercial and industrial property management with a portfolio ranging from 20-storey office buildings and large factory complexes to prime retail and cafes. After enjoying a career change working for Action Sports Industry as a national product manager, Michael and his family moved to Castlemaine in 2011. He returned to the family tradition, joining his sister Genevieve to establish Cantwell Property Castlemaine in 2012.