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.”

• 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?

In this very special solo episode of My Favorite Mistake, Mark Graban breaks down the gloriously ridiculous — and surprisingly instructive — mistakes made by the characters in his all-time favorite film, This Is Spinal Tap.

With the long-awaited sequel, Spinal Tap II: The End Continues, now in theaters, Mark explores why Spinal Tap endures not just as a cult comedy classic, but as a brilliant satire of human behavior, team dysfunction, communication breakdowns, and leadership gone sideways.

And yes — these mistakes still matter, even four decades later.

From the Stonehenge measured in inches… To the foil-wrapped “courgette” in the pants… To the pod that wouldn’t open and the drummers who keep dying…

…these moments are funny because they’re true. And they’re great reminders that how we respond to mistakes matters more than pretending they never happened.

• Why This Is Spinal Tap is more than just a comedy

• The iconic “Stonehenge” prop mistake and what it teaches us about communication

• How real-life rockstars refused to drum in the sequel (because of the “curse”)

• Why remembering the courgette as a cucumber is itself… a mistake

• The brilliance of “We don’t have time for that” and the backstage loop in Cleveland

• Why doing what you’re told isn’t the same as doing what’s right

• Mark’s personal story of seeing the film 100+ times — starting with a VHS in high school

• 🎬 This Is Spinal Tap on IMDb

• 🎥 Spinal Tap II: The End Continues – Now in Theaters

• 📘 The Mistakes That Make Us by Mark Graban

• 💻 SpinalTarp.com – A curated list of character mistakes from the film

If you enjoyed this episode, make sure to subscribe, leave a review, and check out past episodes of My Favorite Mistake — where we talk to leaders, authors, entrepreneurs, and creatives about the mistakes that made them who they are.

🎙️ Listen on Apple Podcasts, Spotify, or wherever you get your shows.

My guest for Episode #324 of the My Favorite Mistake podcast is Trevor Schade.

Episode page with video, transcript, and more

Trevor began his career as a Lean Six Sigma Black Belt with a strong background in coding and process improvement. He consulted on business efficiency and outsourcing before shifting into real estate in 2008. After earning his license, he quickly built a top-performing team of 26 agents with zero turnover over five years. By leveraging a virtual admin team in the Philippines and innovative automation, Trevor’s group generated over a million dollars in commissions.

In late 2023, Trevor stepped away from leading that large team to focus on investing, advising, and teaching. Today, he speaks on topics including negotiation, time freedom, and real estate strategy, and he has launched Life Wealth courses to help others pursue similar goals.

In this episode, Trevor shares his favorite mistake: jumping into a multi-level marketing business at age 19. The venture wasn’t financially successful, but it transformed his mindset. For the first time, Trevor developed a daily reading habit that exposed him to classics like Dale Carnegie’s How to Win Friends and Influence People and Robert Kiyosaki’s Rich Dad, Poor Dad. Those books gave him a foundation in psychology, leadership, and long-term thinking that continues to influence his work.

We also explore:

• How lessons from Nebraska football and martial arts shaped Trevor’s resilience
• What Lean Six Sigma taught him about efficiency, quality, and leadership
• Why he focused on psychological safety and belonging to keep his team intact
• How he used outsourcing and automation to scale without burnout
• The importance of setting trajectories instead of rigid goals in business and life

Trevor’s story is a reminder that sometimes the most unprofitable ventures provide the richest education — if we’re willing to learn from them.

• What’s your favorite mistake?
• How did joining a multi-level marketing company at 19 shape your growth, even if it wasn’t financially successful?
• Did you ever think about leaving earlier, and was staying too long its own mistake?
• What lessons did you take from Nebraska football and sports about resilience and bouncing back?
• How did you first get into Lean Six Sigma and continuous improvement work?
• In what ways did Lean and coding skills help you scale your real estate business?
• What did you learn about leadership from running a 26-agent team with zero turnover?
• How did you create a culture of psychological safety and belonging for your team?
• Why do you emphasize inspiring people instead of “beating them over the head with metrics”?
• What role have outsourcing and automation played in your business success?
• You’ve said you set trajectories instead of rigid goals — what does that mean in practice?
• Looking back, how do you connect these mistakes and lessons to your current focus on investing, advising, and teaching?