Failing My Way to Success: Phillip Cantrell on Scaling vs. Scrambling in Business

My Favorite Mistake: Business Lessons from Failures and Success

My guest for Episode #325 of the My Favorite Mistake podcast is Phillip Cantrell, EVP of Strategy at United Real Estate, founder of Benchmark Realty, and author of Failing My Way to Success: Lessons from 42 Years of Winning and Losing in Business.

EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE

Phillip reflects on more than four decades of entrepreneurial ups and downs across printing, real estate, and related ventures. He openly shares how devastating mistakes—including putting “all his eggs in one basket”—forced him to reinvent his approach. What looked like a catastrophe in 2007–2008 became the turning point that fueled Benchmark Realty’s rapid growth to nearly 2,000 agents.

“Failure is going to happen. If you don’t make mistakes, you’re not doing anything.”

In this conversation, Phillip and I talk about the difference between scaling vs. scrambling, the dangers of playing “not to lose” instead of “playing to win,” and why documenting processes is essential for growth. He also explains why your only real competitor is “the man in the mirror” and how daily reflection helps him learn from mistakes and avoid repeating them.

This episode is packed with timeless lessons on leadership, resilience, and learning from failure—whether you’re in real estate or any other industry.

“If you play not to lose in business, you’re already losing.”

Questions and Topics:

• What’s your “favorite mistake” from your career?
• How did putting “all your eggs in one basket” impact Benchmark Realty?
• What did you learn from losing agents and clients during the mortgage crisis?
• How did you develop the flat-fee brokerage model, and what risks did you see at the time?
• Did you ever doubt whether that new model would work?
• How did you rebuild Benchmark from five agents to nearly 2,000?
• Why is it important to look outside your own industry for best practices?
• What do you mean by the difference between scaling and scrambling?
• How does documenting processes create better outcomes?
• Why do you say your only real competitor is “the man in the mirror”?
• What role has reflection and journaling played in your leadership growth?
• What advice would you give younger entrepreneurs about learning from mistakes?