Aspinall was born in Prestatyn, North Wales and grew up in Liverpool, England. He was an Accountancy student and lived with the Best family, renting a room in their house. Eldest son Pete Best was a drummer who played for the Beatles. Aspinall owned a van, and began driving the band to their shows, and setting up equipment. In time, they began to pay him for this, and he gave up his studies to be their official road manager.