Rupert Grech is a first-generation Australian born of post-war Maltese emigrants. During childhood, he lived in the low-rent suburbs of inner Sydney, later moving to the western suburbs. Rupert graduated with a B.Ec and Dip. Ed. from the University of Sydney, during which time he also played A-grade Rugby League. He later completed an Honours degree at the University of New England while working as a High School teacher.
Rupert owned and managed a cafe in the Blue Mountains for six years. He returned to teaching and became a highly successful school principal in regional N.S.W. Rupert also farmed a 114-acre beef cattle property for ten years. At various times, he has performed as lead vocalist, guitarist and bass guitarist in bands. He has worked as a part-time radio announcer for a commercial station and wrote a weekly column reviewing bands for a regional newspaper. He lives alternately in Valletta, Malta and the Blue Mountains, N.S.W., Australia, for six months each year. 
He enjoys reading, writing, live music, trading equities and managing other financial investments.