Playing Full Out

May 20, 2024

I sat in the hot seat in front of the room, and I could feel myself sweating.

I was in a quaint fishing village on the west coast of Ireland at a retreat led by my dear friend and long-time mentor, Philip Mckernan.

I had just revealed to the group of 16, who were intently staring at me, something I had never admitted to myself, much less to another human being. In that moment, I admitted my deepest desire and the source of my greatest shame.

I wanted to know what it felt like to play full out.

​For the last 40 years or so, I had been living a lie.

​Sure, everything looked like it was going great. I had done all of the things that society told me I was supposed to do.

​I went to a prestigious college, flew fighters in the Navy, and tested myself in combat. I was an accomplished endurance athlete, built and sold a company, and was a multi-millionaire.

But I was dying inside.

The day I sold my company, I thought I would never be unhappy again. I had done everything I was supposed to. Each new success, each new victory, was supposed to fill this hole inside of me.

​But they didn’t. Each one was emptier than the last. Of course, I pressed on trying, desperately seeking the validation and approval that were supposed to come with such success.

Despite all of the external success, the admiration of my peers, and the entrepreneurial accolades, I had a secret. And it was eating me alive, gnawing me from the inside out.

​My dirty little secret? The one that kept me up at night?

I had never truly tried at anything. 

My whole life, I was running an elegant ego defense mechanism. Legendary mindset coach Elliot Roe calls this program Too Smart to Try.

(This is the third and final installment in a three-part series. If you want the backstory, you can catch up by reading Part 1: When Talent Runs Out and Part 2: Too Smart to Try)​

This detrimental subconscious program forms when we are young and consistently told that we are smart and can do anything that we put our minds to—and we begin to believe it. The problem comes when we begin to identify our intelligence as an innate personality trait, part of who we are. When we tie our self-worth to this trait, the subconscious creates a program to avoid any situation that might call our intelligence (and, therefore, our worth) into question.

This is exactly how I had been operating my entire life.

Each success was a calculated bet, one that I knew I could achieve before I even started. Sure, they might seem impressive to the casual observer, but I knew otherwise.

​They had come easily. Worse, in every case, I subconsciously limited my efforts (and, therefore, my success) to engineer out any chance of failure.

To put it bluntly, I always played small. 

I would do just enough to get by, just enough to achieve anything that I wanted to do. But anytime the going got really tough, or the path to the next level would require me to step into unknown territory, I would decide I didn’t really want it, and I would quit.

The truth is, I lived in constant fear.

​I was terrified that if I really went for it, really went all in on a massive goal or dream, my talent would run out, and I would come up short.

​This last idea was almost unthinkable. If I tried and failed, it would mean the loss of the adoration and praise that I secretly coveted. It would mean that maybe it was all a fluke, and maybe I wasn’t as smart as everyone thought.

It would mean that I wasn’t special after all.

​And the shame of that potential reality was too much to face.

​The irony was that I was already facing that shame every day in everything that I did. I lived with the constant shame that I was playing small and that there was a deep ocean of potential that I was afraid to tap. The guilt would come in wave after wave, knowing that there was so much more I could do, but that I was too afraid to try.

I was trapped, and I wanted out. 

And so I lived for decades, a prisoner of my own mind, living a grandiose, Instagram-worthy life on the outside but afraid and ashamed on the inside.

​Until I found a way out.

Why do I always have a briefcase?

After I sold my company, I began coaching fellow founders. At first, I focused strictly on business, but over time, I developed a more holistic approach, integrating aspects of mindset, relationships, limiting beliefs, and, well, life. (I still despise the term life coach.)

​Just as my coaching career began to pick up steam, a new deal came across my desk. Here was the opportunity I had been waiting for – a chance to prove how smart I was, once and for all.

I decided to pause my coaching and purchase a distressed company on the brink of bankruptcy.

​If my thesis was correct, I could restructure the debt, inject some capital, and turn the company around in 12-18 months, selling it for 3-5 times what I had paid for it. I had a plan and a world-class team, and I closed on the deal.

It was an abject failure.

Apple forced an algorithm change on Facebook’s advertising platform in a clash of tech titans. Tens of thousands of small businesses suffered as a result of the warring giants, and my fledgling company was caught in the crossfire.

Revenue was down 70% the month after I closed. I started injecting cash, plowing $100,000 of my own capital every month to cover payroll and inventory expenses. This went on for over a year.

​My bank account was dwindling towards zero at a breakneck pace, and with it, any hope of a turnaround. I was defeated, and I knew it.

​I was anxiety-ridden, depressed, and panicked, all at the same time. There were days I didn’t even want to get out of bed to face the day. I was staring down my first real failure, and the elaborate defense mechanism I had created for my ego was about to be shattered.

I sold the company for a massive loss less than 18 months after I bought it.

​The various parts of me: the undefeated investor, the brazen fighter pilot, the tough-as-nails athlete were all in tatters, lying on the floor covered in blood, sweat and salty tears.

​Then, something amazing began to happen.

I began to feel lighter.

​Over the next few months, I replayed the events in my head, analyzing my decision-making and questioning my every move. Instead of the shame and self-loathing that I expected, I found a new, unexpected emotion: self-compassion.

I was finally free.

​I had failed publicly and spectacularly.

​No longer would I have to fear the bitter taste of defeat; I now knew it well. No longer would I have to play small to keep my fragile ego intact; I knew that I could weather the storm and come through the other side stronger and with self-love.

​My teacher, Philip, often says that our greatest gifts lie next to our deepest wounds.

Today, I view my agonizing business loss as perhaps the greatest gift I have ever received. Before this loss, I carried a certain arrogance and lack of empathy that only someone who has never lost could.

And so, a few months later, in that sleepy Irish village, in front of my peers and my mentor, I made a new commitment.

I promised myself and those few witnesses that from that day forward, I would no longer live in fear. 

I promised to use my talents, gifts, and story to serve others to the best of my ability. I promised myself that when things were hard, or I was gripped with the fear of the unknown, I would push through on a path to become the best version of myself.

On that rainy day on the coast of Ireland, I promised to play full out.

​As I type these words, I am deeply proud to say that I have honored my commitment. I launched headfirst into sharing my message on stages, social media, and this newsletter despite the gripping fear that comes with building a personal brand. I built and launched the best coaching program that I possibly could, and it’s only getting better.

In the last year, I can unequivocally say that I have worked harder than at any other time in my life. In practicing this dedication, new gifts continue to spring forth far beyond my work.

​I am the healthiest and most fulfilled that I have ever been. After a twenty-year-long unhealthy relationship with alcohol, I gave up drinking 245 days ago for one simple reason: it was no longer serving the person that I want to become.

I don’t say any of this to brag or garner approval—thankfully, I am no longer addicted to seeking external validation. I am simply acknowledging and honoring a simple truth: that I have kept my word to myself. 

And I’m just getting started. Without the shackles of fear, I can envision the impact that I can create as a steward of my God-given gifts. For the first time, I know what that feels like. 

As I step into this new world, this new version of myself, I thank you with my deepest gratitude for being here and following my journey. I hope that you find these messages useful.

And if you want to identify and eliminate:

  • The money stories and narratives that are holding you back from creating the wealth and life you deserve
  • Patterns of behaviors and blindspots that are making you move so much slower than you could be
  • Areas where you are breaking your word to yourself
  • Inconsistent money and life decisions caused by a lack of a cohesive framework

​Click the button below to apply for Unbreakable Wealth, a program that leverages mental models, high levels of accountability, personal coaching, and tailored investment strategies – all designed to help you create a life that you never have to retire from.

Come Join Us

​I look forward to seeing you on the other side.

​To playing full out,


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