#378 Rupert Guinness, legendary sports writer and ultra-endurance cyclist, on choosing growth and opportunity and discovering untapped physical and mental capacity through extreme adversity

Dec 1, 2025
1h 1m

Episode Description

"As human beings we have a lot more physically and mentally than we give ourselves credit for. When we think we're done, I don't think we're near."

In this episode of The Inner Chief podcast, I speak to Rupert Guinness, legendary sports writer and ultra-endurance cyclist, on choosing growth and opportunity at every turn, and discovering untapped physical and mental capacity through extreme adversity.

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Rupert is a Sydney-based sports writer, author, public speaker and media consultant, as well as an accomplished ultra-endurance cyclist, adding extraordinary personal experience to his storytelling.

Rupert spent nine years living in Belgium and France covering the Tour de France from up close in inside the tent. Since then, he has written for major publications including The Sydney Morning Herald, The Australian and The Daily Telegraph. 

Across his career, Rupert has reported on an exceptional array of sports, covering many of the world's biggest events, including the Rugby World Cup, four Olympic Games and an extraordinary 31 Tours.

Beyond journalism, Rupert has held senior media and communications roles with the Australian Rowing Team, the NSW Waratahs and the Rolex Sydney Hobart Yacht Race. He has also written 15 books, including Power of the Pedal, Overlander, and The Tour.

In this Masterclass, we talk about:

✅ The harsh reality of life inside the Tour de France and the unseen battles at the back.

✅ His personal accounts of mental toughness, setbacks and breakthroughs in finishing ultra endurance races.

✅ How he used resilience and composure to reframe weaknesses into growth areas, and

✅ Why seizing opportunity, embracing uncertainty and pursuing adventure matters more in midlife. 

Stay epic,

Greg

Connecting with Rupert Guinness

You can connect with Rupert via LinkedIn or Instagram.

Books and resources

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