From Failure to Legacy: Philip Cantrell on Business Growth, Nashville’s Future, and Lessons for Entrepreneurs

Philip’s Business Journey and Nashville Insights

In this episode, I sit down with Philip, an entrepreneur with an impressive track record of founding or leading 10 businesses across commercial printing and real estate. With a 4-4-2 record of wins, losses, and draws, Philip embodies the resilience every leader needs. Today, he’s the semi-retired CEO of Benchmark Realty, the largest real estate brokerage in Tennessee. Philip shares candid insights on Nashville’s explosive growth, its infrastructure challenges, and what the city needs to thrive in the years ahead.

Failure as a Teacher

Philip and I explore why failure should never be the final word, but rather a stepping stone. Drawing from his military background, Philip explains how mastering the mundane and making incremental improvements create lasting success. We both agreed that resilience is not about avoiding challenges, but embracing them as learning opportunities that sharpen your leadership and strengthen your business.

Growth Through Adversity

We dive deep into why true business growth rarely happens during comfort and ease. Philip and I shared stories of entrepreneurs who found creative ways to market themselves, including a startup cleaning business that used electrical tape as signage. These scrappy beginnings sparked a broader conversation about how society often fails to encourage entrepreneurs. Our conclusion: leaders must balance critical thinking with encouragement, because innovation thrives where support exists.

Stepping Outside the Comfort Zone

Philip offered a powerful reminder: success lives outside our comfort zones. He compared critics to chickens pecking at those who dare to stand out, urging us to see criticism as a sign we’re on the right path. He stressed that money is not the end goal, but rather the measure of how much value and service we bring to others. True business and life success, he explained, is rooted in serving people first.

Legacy and Lessons for the Next Generation

Our conversation closed on a reflective note. Philip shared why he dedicated two years to writing his book—a legacy project to pass down four decades of hard-earned wisdom to future generations. He wants millennials, in particular, to access the kind of business education he wished he had early in life. While he admits the book was never about profit, it’s about equipping others to sidestep avoidable mistakes and find their own success path. For those interested, Philip’s book and insights are available at phillipcantrell.com.

 

Failing My Way to Success
Lessons From 42 Years of Winning (and Losing) in Business

Book Description :

Success doesn’t follow a straight line—and failure isn't the enemy.

In Failing My Way to Success, veteran entrepreneur Phillip Cantrell shares a candid, no-fluff account of 42 years navigating the real-world highs and lows of business leadership. From building startups to scaling multimillion-dollar enterprises, Cantrell’s journey is a testament to the fact that failure, when embraced with clarity and courage, can become a strategic advantage.

With a personal record of 4 wins, 4 losses, and 2 ties across ten companies, Cantrell breaks down the often-unspoken truth: you don’t need an Ivy League degree, perfect timing, or a flawless resume to win in business. What you do need is grit, focus, and a relentless commitment to self-awareness and improvement.

Through stories both humbling and empowering, Failing My Way to Success delivers real-world insights on:

• Developing a resilient, high-performance mindset

• Building systems that scale sustainably

• Leading with integrity and emotional intelligence

• Learning from your missteps without letting them define you

This is more than a business book. It’s a leadership manual for anyone who’s been knocked down—and is ready to get back up stronger.

Whether you’re leading a team, launching a startup, or reinventing your career, this book is your reminder that setbacks are setups for the future you’re building.

Author Bio:

Phillip Cantrell is a tenacious entrepreneur and thought leader who knows firsthand that resilience is the cornerstone of success. As founder and CEO of Benchmark Realty, LLC, he’s led one of the Southeast’s most respected real estate brokerages, with offices across Tennessee, Kentucky, and Alabama.

In 2025, Phillip was named one of the 200 most influential people in real estate by the Swanepoel Power 200—a recognition earned through decades of leadership, innovation, and principled growth. He currently serves as Executive Vice President of Strategy for United Real Estate, where he helps guide a national team of over 25,000 agents and $35 billion in annual revenue.

Beyond titles and metrics, Phillip is a mentor at heart. He believes success is built on values, not vanity metrics—and he’s committed to sharing the lessons, losses, and breakthroughs that have shaped his career.

A proud alumnus of the Haslam College of Business at the University of Tennessee, Phillip lives in Tennessee with his wife Amanda. Together, they continue to invest in people, community, and a legacy of courageous leadership.