The $10 Million Mistake That Taught Me the Value of Trust-Centered Leadership

David Miller is an Entrepreneurs’ Organization (EO) member and the founder of Alchemy of Scale, where he helps entrepreneurs unlock both the method and the magic required for business growth, as well as understand the power of trust at the center of leadership. He previously scaled multiple companies and now coaches elite growth-seeking CEOs and their teams.

The buzz of networking conversations filled the air at a conference hall in San Antonio when my phone vibrated in my pocket. It was my chief of staff—my most trusted team member and the one who usually solved problems before I even heard about them. 

“David, I have some bad news.” 

Those words triggered a chain of events that would cost millions of dollars, transform my understanding of trust, and ultimately, reshape how I lead in business.

The moment trust shattered 

Our hedge fund trader had gone rogue. He violated the core strategy we’d meticulously built, ignoring safeguards, risk limits, and our playbook. The fund collapsed. In seconds, millions vanished, and there was no way to recover.

I immediately flew back to Atlanta. What followed was devastating: A cumulative financial impact well over $10 million in lost revenue, dozens of lawsuits attacking me and the company, millions in legal fees, and the pain of writing personal checks that eroded my family’s security because my conscience demanded I make clients whole. 

Most achingly, I watched relationships with employees and clients, many close friends I’d known for 15 or more years, disintegrate. In matters of money, when trust is violated, you rarely get a second chance. This component mentally and emotionally broke me and hard.

Emotions and the invisible infrastructure of business 

Over the next five years, I decided the solution was to work even harder to prove I was the invincible CEO. My rationale: Replace lost revenue with new revenue, so the firm would keep thriving. Delusional as it seemed, that’s exactly what happened. Our top line continued to grow, but everything else in my life went straight to hell. 

My maniacal work-first mentality pushed out everything in my life that had meaning. I was banned from coaching my son’s basketball team, banned at my country club, quit as den leader for my son’s Cub Scout troop, and quit my coveted weekly date nights with my wife. In short, I fell apart. 

The more I worked, the more I hurt inside. The more I hurt inside, the more I worked. Why was this vicious cycle happening? I was covering up the truth that trust in myself and others was fundamentally broken. 

I’ve always believed in the alchemy of both visible elements (processes, systems, and structures) and invisible elements (trust, energy, and resilience) of business growth. But I had failed to recognize how fragile that invisible infrastructure could be. In my eagerness to prove myself trustworthy, I overlooked warning signs and hadn’t properly verified the trustworthiness of others. 

The separation of self from enterprise 

This experience transformed my understanding of trust in business and life. Perhaps the most profound lesson was that the first trust broken was with myself. Eventually, I recognized that to preserve the company, everyone’s jobs, and the mental well-being of my family, I needed to take the bullet for the firm. While I may not have committed the act, this happened on my watch.

The government didn’t care about the proactive, voluntary, and expensive remediation measures I chose to make. As the owner and leader, I was held responsible. Rather than continuing to litigate, which would have financially benefited me, I chose to settle. 

Despite knowing my timing and leverage was inopportune, I also decided to sell internally to my employees. This decision taught me that sometimes the most noble leadership action is to step aside, allowing the enterprise to continue without you. It wasn’t about my ego or personal vindication, but about achieving an egalitarian outcome.

A framework for trust-centered leadership 

Looking back, I’m grateful for that catastrophic call from my chief of staff. It set off a cascade of events that let me separate from a company in which I was working 80 to 100 hours weekly while neglecting my family. It pushed me into a different industry, where I scaled another business to eight figures in 80 percent less time.

The healing process was anything but immediate. My self-care rituals and daily meditation practice, which I began in 2017 after a stress-induced health crisis, became crucial in processing the failure and finding a path forward. Through mindfulness, I learned to balance both the logical analysis of what went wrong with the emotional processing required for growth. 

Most important, it created space for personal transformation that shaped my approach to trust. I believe I am a microphone, and my painful lessons will help entrepreneurs build stronger businesses and teams. As you navigate your leadership journey, consider these trust principles that steer me today.

1. Cultivate both emotional and logical trust. 

Begin relationships with openness and vulnerability. Then, verify through clear, consistent actions. When asking questions, notice how people respond. Trustworthy partners will provide clarity rather than confusion. 

2. Recognize trust as a business asset. 

Many treat trust as a buzzword, but it’s actually your most valuable currency. Measure it, protect it, and invest in it as seriously as you would cash flow or inventory. 

3. Let go of ego when necessary. 

Sometimes, the most powerful leadership decision is stepping aside. The ultimate purpose of a leader is serving the organization’s greater good, not protecting personal position. 

4. Embrace your critics as guides. 

The path to excellence comes wrapped in cynically charged feedback that can feel like a personal attack. Train yourself to extract the valuable insights while filtering out the emotional noise. 

Finally, remember that the most expensive business education often comes from your most brutal failures. A $10 million mistake that nearly destroyed both me and my company has been my most valuable lesson in trust.

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