Jackson was born to Rose, a Cree mother, and Marshall, an English father on the One Arrow Indian Reserve in Saskatchewan, Canada. At the age of seven, his family moved to Namao, Alberta, moved with his family to Winnipeg, Manitoba at age fourteen. A year or two later, he dropped out of high school and left home. He spent seven years voluntarily living on the back streets of Winnipeg. That experience gave him the determination to be successful as well as a compassion to help others.