If you are ready to level up personally and professionally, go to joinrbo.com

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

If you are ready to level up personally and professionally, go to joinrbo.com

Most entrepreneurs think their biggest problem is their business—but it’s not.

In Episode 367 of The Real Business Owners Podcast, Trevor Cowley sits down with entrepreneur Rick Trimmer to break down one of the most overlooked reasons businesses stall, struggle, and fail: the owner stops evolving.

Through real stories from their mastermind, practical business examples, and lessons from scaling companies, they explain why growth isn’t just about better marketing, better employees, or better systems—it’s about becoming a better leader.

If your business feels stuck, this episode will force you to stop looking outward and start looking inward.

Because in most cases, the ceiling of the business is the ceiling of the leader.

Key Topics in This Episode:

• Why most entrepreneurs delay or avoid making critical decisions
• How overthinking kills momentum and slows business growth
• The difference between companies that adapt and companies that disappear
• A real-world breakdown of turning a stagnant business into a thriving one through leadership
• Why culture issues are almost always leadership issues
• How to spot opportunities hidden inside your existing business
• The role of standards, accountability, and data in scaling
• Why great leaders never stop evolving
• How to become the type of person your business can grow around
• Why execution always beats intelligence in business

If you are ready to level up personally and professionally, go to joinrbo.com

In Episode 366 of The Real Business Owners Podcast, Trevor Cowley sits down with entrepreneur Rick Trimmer to discuss a radically different approach to entrepreneurship, wealth building, business ownership, and financial freedom.

After losing everything during the 2008 recession—including his home, vehicles, and business—Rick was forced to rebuild from the ground up. But instead of chasing more revenue, bigger assets, and endless growth, he focused on something most entrepreneurs overlook: buying back his time.

What followed was a complete redefinition of success.

By building systems, developing leaders, and sharing ownership with key team members, Rick created businesses that could thrive without his daily involvement. The result? Nearly a decade of traveling the world with his family while his companies continued operating and growing.

This episode challenges traditional ideas around control, leadership, scaling a business, and what true freedom actually looks like for entrepreneurs.

Because the ultimate goal isn’t building a business that needs you forever—it’s building one that doesn’t.

Key Topics in This Episode:

* How losing everything during the recession led to a better business and life

* The hidden cost of building a business that depends entirely on the owner

* Why most entrepreneurs are chasing the wrong definition of success

* The importance of delayed gratification and living below your means

* How to build systems that create freedom and scalability

* Why ownership creates leaders while salaries often create employees

* The unconventional strategy of sharing equity to grow a business faster

* How to create passive income and long-term financial freedom

* Leadership, accountability, and developing people who can run the business

* What it takes to build a company that gives you your life back