In 1988 Machine was sent to Alston House Approved School, Rochester, for the theft of scrap material, and the following year to Dover Borstal for young offenders, after burgling a greengrocers in Leysdown (Isle of Sheppey).
[2] He spent time claiming benefits and running the family business, an amusement arcade in Leysdown, as well as breeding Rottweiler dogs and working as a bouncer in South London night clubs.
He has described creativity as the way out of the background in which he felt trapped: "Painting and writing have been far better for me than any of the mistakes I made in stealing and fighting.
"[2] In 1999 he was one of the 13 original founder members of the Stuckists, an anti-conceptual art group co-founded by Billy Childish and Charles Thomson.
My Grandfather Will Fight You depicts a gaunt older man with clenched fists and blood-spattered shirt, painted on two wooden boards nailed together.