Ret Taylor: Your Childhood Taught You Money is Pain - Money Stories Ep 21

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Aug 1, 2025

Ret Taylor, a transformational coach and retreat leader, shares his compelling journey from a scarcity mindset to embracing a richer, purpose-driven life. He reveals how idolizing struggle shaped his early entrepreneurial pursuits and discusses the dangers of the 'follow your passion' mantra. Ret highlights a pivotal coaching moment that helped him face fears and realign with his true self, emphasizing the profound lessons found in challenges. Nature serves as a backdrop for rediscovery, as he advocates for simplicity, freedom, and genuine connections in a complex world.

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ANECDOTE

Bus Station Vow to Escape Scarcity

At 10 years old, Ret stood in a cold bus station and vowed to escape scarcity by excelling academically and financially.
He started small entrepreneurial jobs like raking leaves and washing cars to gain agency over his life.

ANECDOTE

From Saudi to Brazil Adventure

Ret moved from Saudi Arabia to Brazil after losing all his money and following a girlfriend's dream.
In Brazil, he co-founded the Brazilian Green Building Council while on a tourist visa, raising over $2 million for the nonprofit.

ANECDOTE

Denali Climb Mirrors Business Crisis

Facing a bank crisis and potential business failure, Ret left to climb Denali with debt collectors pursuing him.
The climb paralleled his business struggles, highlighting tough decisions about whether to push on or retreat.

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At 10 years old, he stood in a cold bus station and vowed to do whatever it took to escape scarcity.

He succeeded, founding, scaling, and exiting a natural remedies company.

But Ret Taylor’s real transformation began on a frozen mountainside on Denali, when he finally admitted the truth: he was idolizing the wrong thing.

In this episode, Ret unpacks the invisible script that drives so many entrepreneurs: the belief that value only comes from struggle. He reveals why the advice to "follow your passion" can be so dangerous, sharing how he built a purpose-driven company only to find himself trapped in a "zone of competence," staring at spreadsheets instead of living his truth. This isn’t just a story about exiting a company. It’s about identity, alignment, and the quiet courage to let go of the oars and trust the current.

We unpack:

• Why following your passion can be dangerous advice—and the subtle difference between passion and true alignment.

• How to stop idolizing "the hard thing" and finally let go of the oars.

• How a single coaching question helped him let go of worry and unlock the solution to save his business.

• Why your deepest lessons are found in your biggest challenges.

• How nature and discomfort can bring you back to yourself.

• Redefining what it means to live a rich life beyond the bank account.

About Ret Taylor:

Ret Taylor is a transformational coach, retreat leader, and recovering entrepreneur. He helps high-performing founders and leaders reconnect with what truly matters by guiding them into the wild—both outside and within. Through his practice Reconnect // Rise, Ret blends nature, challenge, and deep inner work to spark what he calls a “deep remembering”—of strength, clarity, and the wild man within. His upcoming book, The Misogi Challenge, explores how discomfort can bring us back to ourselves.

This is a conversation about success. But more than that, it’s about what it costs—and when it’s time to choose alignment.

Connect with Ret:

Website: https://www.rettaylor.com/

LinkedIn: https://www.linkedin.com/in/rettaylor/

Instagram: https://www.instagram.com/rettaylor_/

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