The aspiring jockey signed his apprentice papers six months before leaving school.
During his time in the Rogerson stable, Oliver received his first big thrill in racing.
"At just my third race day ride, Rogie put me on Bijoux at Taranaki and we were so far back at the 800 that we were out of shot of the Trackside cameras," Oliver said.
"Getting to the home turn I gave the horse a kick and she took off to rattle home through the middle to give me my first winner.
"Being in a big stable, I was well down the pecking order and was receiving few rides, so after 18 months I started looking for new opportunities."
A transfer of papers to a Te Puke trainer around 18 months ago, resulted in Oliver travelling to the Gate Pa course in Tauranga, to ride trackwork. At that stage of his career the young apprentice jockey had ridden just a handful of winners.
During the time of his commute to ride fast work, local Tauranga trainer Brian McKeagg was looking for a replacement trackwork rider.
"Our stable needed a track work rider and Josh was looking to transfer to a bigger centre to get more opportunities, so in February of this year Josh transferred his indentures to me," said McKeagg.
Oliver's permanent move to Tauranga coincided with rich vein of form from the McKeagg team. On March 12, Oliver kicked home The Link for McKeagg, followed by Running Scared and On Parole also from the stable.
With fresh enthusiasm, Oliver finished last season with six winners to his credit.
Another highlight was winning the most improved apprentice jockey award for the 2013/14 season at the Waikato Apprentice School. Sydney superstar jockey James McDonald is a previous winner.
The extent that Oliver's career has taken off is shown by his workload last week.
Tuesday trials at Matamata were followed by race rides at Avondale, Woodville and Tauranga on successive days, with another good book at Rotorua on Saturday.
Just ten weeks into the new season, Oliver has ridden 10 winners to sit in fifth place on the national apprentice jockeys' table.