What if the biggest risk in your career isn't making the wrong decision — it's leaving an opportunity unexplored?

In this episode, Alisdair Barr — founder of Striver, former banking executive, startup builder, and one of the profession's most passionate advocates for growing the next generation of advisers — joins Ben and Fraser to unpack the ideas that have guided every major fork in his career.

Ali shares the throwaway piece of advice that became a lifelong decision-making framework: opportunities not taken are lost forever.

From leaving a successful corporate career to building a business around a purpose bigger than himself, he explains why he refuses to die wondering, how he evaluates risk through the lens of future regret, and why the best decisions often sit just beyond your comfort zone.

Along the way: why most career decisions aren't tattoos, the question venture capitalists ask that instantly removes self-imposed limitations ("if money wasn't an issue, what would you do?"), how purpose became the filter for every business decision, and why playing the semi-final and the grand final requires complete focus on the game in front of you.

Plus, the surprising lesson Kokoda taught him about mental health, why walking became his daily reset button, and how family ultimately became the compass that keeps everything else in perspective.

A masterclass in building a life with fewer regrets and more deliberate footprints.

Connect with Alisdair here - https://www.linkedin.com/in/alisdairbarr/