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Success leaves clues—but only if you're willing to learn from someone who's lived through decades of wins, losses, failures, and comebacks.

In Episode 368 of The Real Business Owners Podcast, Trevor Cowley and Rick Trimmer sit down with Rick’s stepfather, Kendall Prisbury, a businessman with more than 50 years of entrepreneurial experience.

From losing everything and starting over to building, growing, and eventually selling a highly successful company, Kendall shares the lessons, sacrifices, mindset shifts, and hard-earned wisdom that helped him navigate decades of business ownership.

This conversation goes far beyond business tactics. It’s a raw discussion about resilience, delayed gratification, leadership, personal development, financial discipline, and what success really looks like after a lifetime of building businesses.

If you're an entrepreneur chasing growth, working through adversity, or questioning whether the sacrifices you're making today will be worth it tomorrow, this episode offers a perspective that only decades of experience can provide.

Because success isn't built in a year—it's built through the decisions you make over a lifetime.

Key Topics in This Episode:

Why most businesses fail and how to avoid common entrepreneurial mistakes

Lessons learned from losing everything and rebuilding from scratch

The dangers of lifestyle inflation and trying to look successful

The difference between persistence and stubbornness in business

How leadership must evolve as a company grows

Why personal development is essential for long-term success

The sacrifices required before freedom and financial independence are possible

Navigating difficult seasons in business and life

How the definition of success changes over time

The relationship between wealth, freedom, happiness, and fulfillment

What 50+ years of entrepreneurship teaches about building a meaningful life