Wealthy Advisor Mindset

47 | Dennis Hall | From Commando to Compassionate Planner: The Mindset Shift That Changed Everything


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What happens when a battle-hardened Royal Marine Commando steps into the cutthroat world of financial sales - and realizes something’s deeply off?

In this gripping episode, the founder of Yellowtail Financial Planning, Dennis Hall, peels back the curtain on his extraordinary 40-year journey through financial services. He shares how he went from pushing products in a high-pressure sales culture to building a purpose-driven business grounded in trust, integrity, and authentic human connection.

You’ll hear raw, heartfelt reflections from Dennis on the identity crisis after leaving the military, the power of early self-help principles, and the moment he stumbled upon a like-minded community that helped him redefine success on his own terms.

This episode will hit home if you’ve ever felt out of place in your industry

  • What Dennis learned from serving in the Royal Marines during the Falklands War—and how that shaped his risk tolerance and resilience.

  • The 1980s financial sales machine and why it left him questioning everything.

  • The exact moment he stopped selling products and started changing lives.

  • How the right community helped him align his business with his values.

  • Powerful advice for advisers who feel stuck, misaligned, or ready for something more meaningful.

This is more than a business story—it’s a masterclass in mindset, identity, and building a life (and business) you actually believe in.

🎧 Press play. This one might just change how you see your work - and yourself.

Connect with Dennis:

🔗 Yellowtail Financial Planning

Connect with Nina:

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Wealthy Advisor MindsetBy Nina Cooke

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