Jamie Whincup is one of the most successful drivers in Australian motorsport history — a seven-time Supercars champion, four-time Bathurst 1000 winner and winner of 125 Supercars races. But his journey to the top was anything but straightforward.

Jamie joins James H Stewart to talk about starting out in karting, winning the Australian Formula Ford Championship at just 19, being hired — and then fired — by Garry Rogers Motorsport at 20, and fighting his way back into professional racing.

He shares the story of joining Triple Eight Race Engineering, racing alongside Craig Lowndes, winning three consecutive Bathurst 1000s together and building one of the most successful careers in Australian motorsport.

But this conversation isn't just about racing.

Jamie discusses becoming a shareholder in Triple Eight, what he learned from Roland Dane and some of the successful businesspeople around the team, and the very different challenge of retiring from full-time racing and becoming Triple Eight's Managing Director and Team Principal.

We explore the economics of running a professional racing team, the role of data versus instinct, managing elite performers, transitioning from individual competitor to business leader, and Triple Eight's major decision to move from GM to Ford in 2026.

It's a conversation about resilience, competition, leadership and what happens when your job changes from winning yourself to creating an organisation

capable of winning without you.

Disclaimer: This podcast is provided for general information and entertainment purposes only. The views and opinions expressed by guests are their own and do not necessarily reflect those of James H Stewart, What I Learned in Business (That Didn’t Kill Me!), or any associated organisation. Nothing discussed in this episode should be regarded as financial, investment, legal or other professional advice. Listeners should make their own enquiries and seek appropriate professional advice before making decisions based on matters discussed in the episode.

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