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Glen Boss

Triple Melbourne Cup Champion Jockey, Media Contributor & Keynote Speaker

One of Australia’s most accomplished jockeys, Glen is renowned for his skill, professionalism, and iconic victories. Since retiring, he has become a respected media contributor, commentator, and sought-after speaker, bringing insight, star power, and inspiration to events nationwide.

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Glen Boss, affectionately known as “Bossy,” is one of Australia’s most accomplished and successful jockeys. Born in Beaudesert and raised on his family’s cattle property in Caboolture, Glen left school at 15 to pursue a riding apprenticeship, quickly establishing himself as a standout talent in Brisbane before moving to Sydney in 1994, where his career flourished.

Over his illustrious career, Glen has won 96 Group 1 races, highlighted by three consecutive Melbourne Cup victories aboard the legendary Makybe Diva (2003–2005), four Cox Plate wins, and two Golden Slipper triumphs, capturing three of the four legs of Australian racing’s Grand Slam. He was inducted into the Australian Racing Hall of Fame in 2015.

After a stint riding in Singapore, Glen returned to Australia in 2019 and continued to secure victories in marquee events such as The Everest (2019), The Golden Eagle (2019), Cox Plate (2020), and George Ryder Stakes (2021) before retiring from professional riding in November 2021.

Since retirement, Glen has worked as a media contributor for Entain Group’s Ladbrokes and as a key commentator on Channel 10’s coverage of the 2023 Melbourne Cup Carnival. A celebrated guest speaker, celebrity panellist, and host, Glen continues to inspire audiences with his insight, professionalism, and first-hand experience at the pinnacle of Australian horse racing.

Topics

  • Turing Dreams into Trophies
  • The Day My Life Ended … and Started Again
  • Working for Kings, Sheiks and Billionaires
  • Winning All You Can Win and Remaining Focused
  • Me and the Diva
Glen was truly inspirational. He has an amazing drive and focus and has overcome major setbacks in his career to come back to win his 3rd Melbourne Cup on Makybe Diva proving that with determination and strong will you can achieve anything … Glen spoke from the heart, was honest and humble and received a great reaction from my team. His presentation was uplifting and enlightening. SONY BMG is one of the most important and influential companies in the music industry, and in my position I have worked with the leading figures in the music and entertainment industry. Glen was able to make connections to our industry with his story to inspire and motivate my team and we intend to use him again. SONY BMG
His contribution to our conference was tremendous and went well beyond just his beautiful address to over 200 delegates … his country chat mixed with a very interesting ‘Life in racing’ made everyone hang on every word … I have seen many a good speaker in my time at conferences and I for one was not disappointed at all. On the contrary my expectations were already high from your recommendation and Mr Glen Boss exceeded that expectation. Glen made the audience feel and believe that they were actually riding on Makybe Diva to the finish. Total Financial Solutions Australia
Glen was well received by the audience, told a great story about a comeback against the odds and gave an insight into a great racehorse, was very open about his style and spent considerable time after the address having photos taken with members of the audience. The feedback post the event was very complimentary. Rural Press
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