Ten More Lessons from Ten Years

December 27, 2023

Last week, I shared 10 things I wish I knew when I became a millionaire at 33.

One of our sayings in the fighter squadron was, “Criticism keeps us alive.” When debriefing a flight, we wouldn’t focus on the things we did well, because that was the standard. We would pick apart every little misstep in order to improve for the next flight.

And there is definite value in holding that line.

But often, as entrepreneurs, we can be so focused on improving, learning, and iteration that we forget to celebrate the wins and the things we did well. We forget that there can be as much learning from the things that went right as from the things that didn’t.

So in that spirit, here are 10 things that I’m proud of from the early days that served me well:

1. Experiences > things.

While my friends know I do love my luxuries, I had a nearly unlimited budget for adventures. Surf trips, heli-skiing, epic family vacations, I experienced an incredible amount in my 30s and I’m glad I did. I said yes to almost anything that I thought might create a memory that would last a lifetime. As an old mentor used to say, “They can’t repossess a good time.”

2. Family is the most important thing you can invest in.

I saw a lot of peers burning the candle at both ends, sacrificing for a future outcome that wasn’t guaranteed. Hustle culture is a trap, full stop. I was deeply involved in raising my children from birth, and I was known as the dad pushing the kids in the stroller at 2 in the afternoon. They grow up fast and I’ll always cherish those memories.

3. Your integrity is your most valuable asset.

In those days a lot of folks in my industry played it fast and loose. Our motto was that we would never put investors in a deal that we wouldn’t buy ourselves. And while that may have slowed us down a bit, we created lasting relationships, and those same relationships paid untold dividends when things slowed down.

4. I hired the people I loved.

I built my company with my best friend and we hired my two brothers because those are the people that I wanted to do life with. I loved going to work every day, and our office was often filled with laughter. I often look back on those days as some of the best. For deeper insight into building a business with friends and family, I talked about it at length in my episode of My First Million.

5. There are no emergencies in business.

This was our motto because my business partner and I flew jets in combat, and nothing about business compared to the stress of getting shot at. When others were losing their heads over a deal not closing, we carried a certain calm that only the experience of life and death brings. Trust me, it can wait until Monday.

6. Don’t be afraid to defy convention.

Because I felt like an outsider, I brought a certain rebel energy to the oil business and it served me well. If things had always been done a certain way, that was the place I looked to shake things up. This allowed us to be first movers in what would wind up being one of the most prolific areas of the Permian. The bulk of our wealth was generated from that one single bold decision.

7. Give selflessly.

I wasn’t afraid to donate to causes that I cared about. This led to me being an early investor in psychedelic medicine for veterans and to this day this is one of the things I’m most proud of. I often talk about using our wealth to serve our values, and I can’t think of a better example than investing in areas that change lives at scale.

8. Constantly seek growth. No one has it all figured out.

I found personal development in my mid-thirties, and needless to say, my life took a very different path. I’m deeply grateful for the opportunity to learn from some of the best coaches on the planet. I wouldn’t be where I am today without their guidance. When we find success, especially if it seemingly comes easily, we can fall into the trap of Midas Touch Syndrome. Finding someone who can challenge your deeply held beliefs is the true gold.

9. Always bet on yourself.

Through all the trials and tribulations, we were never afraid to swing for the fences and bet on ourselves. We always said we were buying call options on ourselves. This helped me cultivate a deep sense of self-trust that I rely on today.

10. Enjoy the ride.

There will always be more money to be made, new business opportunities, and new technologies to learn. But there will never be another first business. The personal growth, the sleepless nights, the mistakes, I’m deeply grateful for all of it. What a wild ride.

It really is all about the journey,


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