While the apprentice programs were not as advanced as what they are now when Boss debuted in 1986, he made it work.
He would often approach senior jockeys on race day in the rider’s room, he explained, and would ask they why they were doing what they were doing or just ask for them to explain things further to him.
Even to this day at 51 years of age, Boss says he is still learning and was keen to speak to the teenage apprentices on Monday to see if he could pick up something new and fresh from them.
Being able to watch thousands of races a day online and on television, Boss believes apprentice jockeys these days are light years ahead of where he was when he was starting out.
“I was always one of those guys that would sit back and watch, observe, not just jockeys, lots of different sports people and athletes,” Boss said of his younger days.
“I asked a lot of questions and the guys I learnt the most from Shane Dye, who is regarded as one of the best tacticians ever to ride and was well before his time.
“He imparted his knowledge, gave me tips and said go watch how I do these things and how I ride.
“Jimmy Cassidy was an amazing influence on me, he used to be a live by the sword guy in races, really back himself.
“Those things that I was taught as a young guy, I still use them today.”
Boss is sure to have inspired the entire room of apprentice jockeys on Monday, but there was one emerging rider that he had already put on the path to becoming a hoop.
Toowoomba-based apprentice Isabella Rabjones has long idolised the Melbourne Cup winner.
“Glen is actually the reason I became a jockey, I was always into horses and my grandparents sponsored the local races,” Rabjones revealed.
“It happened to be my first time ever going to the races the day he won the Melbourne Cup in 2003 on Makybe Diva, for the first time.
“I had a little bet on him that day, $2 maybe, and then I followed him throughout his career from that moment on.
“I was the only one in my family who thought he could go three in a row in the Melbourne Cup and he did.”
The 25-year-old Rabjones says the entire apprentice contingent, with almost 30 on hand, were honoured to learn from Boss.
“It was a huge opportunity for all of us, he is such an idol to all us as apprentices and riders in generally for all that he has done in the industry,” Rabjones said.
“I think it is great from Racing Queensland to get him involved and for all us apprentices to learn and listen to him.
“I met him at Magic Millions last year and to come here today and spend a day with him, it is an honour.”