He made his senior AFL debut in 1993 with the Bombers and enjoyed a quick rise that year.

Olarenshaw was traded to Collingwood (instead of his preferred club, the Kangaroos) at the end of 1998 after agreeing to leave Essendon.

Olarenshaw was disillusioned by the new surroundings at Collingwood and suffered injuries that restricted him to just five games with the club.

In October 2024, it was revealed that Olarenshaw was linked to a Bali massage parlour that was allegedly offering illegal sexual services through its employees.

[3] Following the 2009 AFL season, he was removed as Channel 7's boundary rider in favour of Matthew Richardson.