Completing his schooling in Form 5 (Year 11), his first job was as a production cadet at the Australian Paper Manufacturers.

Running until 1969, it provided a stepping stone for performers such as Debra Byrne, Rod Kirkham, Jane Scali, Peter Doyle, Patti Newton, Anne Watt, Vikki Broughton and Jamie Redfern.

Naylor also hosted the SSB Adventure Club in the early 1960s with Madeleine Burke,[4] and appeared as a regular on the station's daytime variety program Time For Terry in 1965.

[5] A patron of several organisations (the Variety Club in Victoria, the Dialysis and Transplant Association of Victoria and the Jack Brockhoff Reconstructive Plastic Surgery Research Unit of Royal Melbourne Hospital), Naylor also assisted with fundraising for the Macfarlane Burnet Appeal and Windana Society Drug Rehabilitation.

[6] Less than a year later, on 7 February 2009, Naylor and his wife Moiree were killed as one of the Black Saturday bushfires destroyed their property in Kinglake West.