Story - 3 Keys To Unlock A Better Investor/Entrepreneur

3 🔑s to unlock a better investor/entrepreneur

  • Cutting losses quickly
  • Understanding opportunity costs
  • Self-Awareness

👇👇👇 is a difficult to retell piece of my past but has helped my ability to weigh opportunity costs & cut losses QUICK.


We all have an internal story.

Growing up I had a broken internal story. I had a hard time describing what makes me, me. Part of that is understanding where your family is from. I didn’t know.

Some families came to the US a few generations ago. People take pride in being “Irish” or “Italian”, etc. Those individuals consciously/subconsciously fit themselves into a stereo-typical box. They have heritage.

I was born in a small rural area. There is no immediate lineage in my family to point to indicating where my ancestors were from. My last name is rare and not obviously any nationality. So I deduced I was a mutt.

This, among many, many other things, led to a distorted self image and poor self esteem. I felt like I should be with the other mutts in an animal shelter.

An incomplete (negative) internal story can lead one down this road.

To combat this incomplete story, instead of learning the reality and accepting, I decided to borrow other people’s heritage in college. I dated Asian women. Looking back, I might have had “yellow fever” but I think it had more to do with the fact these women had clear heritages.

To compensate for my perceived lack of heritage, I dove head first into theirs. Learning their mother tongues, cultures and different traditions was fun & new. Most Americans don’t care about other cultures, so my intense interest showed these ladies, their friends and sometimes parents I was one of them.

Then I took it a step further. I moved to one of the most ethnically/culturally homogenous places in the world, South Korea.

I absorbed everything Korea. Koreans took notice and would bestow an honorary “you are Korean” onto me. That sure felt good to a gentleman with low-self esteem with identity issues.

Through a friend I went on a blind date with a girl in Seoul. She too was surprised at my ability to speak Korean and understand the culture. Initially she didn’t want to date, but I was persistent.

Over the next 6 months we got serious and I met her parents over dinner. I made a powerpoint presentation about me, where I lived, who my family was and that I did want to marry their daughter - all in Korean.

Her father hated Americans. He told me so. But I proceeded to break his mental model on Americans. I spoke Korean and I executed all of the Korean customs. The father told me I must have been Korean in a previous life. I smiled.

Outside of work I spent countless hours with my girlfriend, her friends and family. I was determined to bring this girl to the US, marry her and start our lives.

We traveled to the US a few times and it seemed like this girl wanted to live in the US.

Not long after, we started the K1 (fiancé) Visa process. That was a couple $1,000 investment. Koreans go all out on wedding photos, that was ~$1,000. I bought an expensive ring.

It was a good portion of my net worth back then.

The relationship sure was rocky. There were red flags everywhere. The language/cultural barriers were HIGH.

But I invested HOURS and a good chunk of money into this relationship. I gave my word to this girl’s father. Not only that, my self-worth was now tied with “being” Korean.

I couldn’t give up on this.

We got the Visa & moved to the US. To save money we moved in with my family, at least temporarily.

It was fight after fight. But we had 90 days to marry.

I thought I couldn’t give up on this.

We had prepared a wedding celebration on a boat 2 months out. That was another couple thousand. I really didn’t have much money. But we decided to get officially married, with a justice of the peace, shortly after arriving.

The fights got worse. After one, the girl walked out of the house without a phone. I mean we were in the most rural area and she had no clue where anything was.

It was the most emotionally difficult time of my life, and probably her’s too. It was hell. But I had invested so much time, money and identity into this relationship. I was now officially married!

2 weeks later we were driving in the car. We were fighting AGAIN. For what, I don’t remember. The girl got so angry she started hitting me while I was driving.

We almost got into an accident.

Is this the life I wanted? I weighed my options. I could string it out, but I knew I didn’t want this. I knew anything would be better than this.

I checked my ex into a hotel to get out of my life. I felt horrible and selfish leaving her alone in a different country.

Literally the next day I went to a divorce attorney’s office.

I felt embarrassed. I was 25 years old and getting divorced after 2 weeks of marriage. There was no way to annul it. I was another divorce statistic. And it was MORE money.

But when she was out of my life, I felt like I had a new lease on life. I felt like I dodged a bullet.

I took control over building my internal story of myself.

Life is short. The amount of time already committed, money lost, or identity you tied to something should not affect your decisions.

If you feel something is bad, it is. Your gut usually will try to tell you. Listen. Don’t prolong the pain. Don’t compound the mistake.

Cutting your losses quickly is embarrassing.

Saying you are wrong is tough.

In reality, the opposite is usually true. Your future self will congratulate the decision.

I sure am.

Six months after getting divorced I met my now wife. I knew exactly what I wanted, which was my wife. I didn’t need another person to fix my broken narrative. I filled in the gaps. We’ve been happily married for nearly 6 years.

And my business and investing has benefited. Each decision has a failed 2 week marriage, with all of the losses cut, to compare against.

Additionally, my keen interest learning human cultures has helped me tune into the human cultural aspects of business. Culture is the biggest business moat of all.


If you enjoyed this, I occasionally send out a newsletter called the WoodShedd.

It contains:

  1. Digging hard into the mechanics of business, investing & leadership (like the above).

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