Olaiya was born in Ilesha, Southwest Nigeria, he was raised in colonial Nigeria and grew up in the Northern provinces. His father worked as a teacher and later as an accountant and the family moved quite often, living in Jos and Kano.
Olaiya's upbringing was shaped by his birth in Ilesha, his residence in colonial Nigeria, and his family's frequent moves between Jos and Kano due to his father's work as a teacher and accountant.