[1][2] At age 12, after his father had left the army and married a woman with three sons, Olle moved into their home in Melbourne and attended the local government Mornington High School.
He quit school aged fifteen, took odd jobs at an automotive spare parts shop and a Myer department store in Melbourne, and moved out of his father's home.
He and a friend were arrested after committing a break and enter (Olle later recalled that "We broke a showcase window full of sunglasses, with no concept of what we would do next – and were caught redhanded by the police."
[1][2] He married Annette Longfield Olle (née Marjason), a nurse, at St Thomas' Anglican Church, Toowong on 24 April 1969 and the couple had two sons and a daughter: Nick,Sam, and Nina.
[1][5] He then returned to the ABC where he initially worked once again on Four Corners (from 1985 to 1994, winning a Penguin Award for Best Current Affairs Presenter in 1987,[6] and anchored election coverage.
[7][10] His radio program was shifted from the morning to the late afternoon drive-time slot for the 1996 schedule, which he strongly preferred, though he died before this change was implemented.
[1][11] For the memorial service Australian composer Peter Sculthorpe wrote a special arrangement for cello and piano of his 1947 work Parting, dedicated to Olle, which was played by Nathan Waks and Kathryn Selby.