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?
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Cardiac Cowboys
The heart was always off-limits to surgeons. Cutting into it spelled instant death for the patient. That is, until a ragtag group of doctors scattered across the Midwest and Texas decided to throw out the rule book. Working in makeshift laboratories and home garages, using medical devices made from scavenged machine parts and beer tubes, these men and women invented the field of open heart surgery. Odds are, someone you know is alive because of them. So why has history left them behind? Presented by Chris Pine, CARDIAC COWBOYS tells the gripping true story behind the birth of heart surgery, and the young, Greatest Generation doctors who made it happen. For years, they competed and feuded, racing to be the first, the best, and the most prolific. Some appeared on the cover of Time Magazine, operated on kings and advised presidents. Others ended up disgraced, penniless, and convicted of felonies. Together, they ignited a revolution in medicine, and changed the world.
The Joe Rogan Experience
The official podcast of comedian Joe Rogan.