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Better Safe Than Sorry? The Choices We Make

January 2, 2026

Close Brush With Riches

A friend of mine told me a story about his father’s close brush with real riches. My friend is in his eighties and has quite a unique life himself. But his father’s story is a unique lesson in choices. He was given a choice of two options. One option would make him well off. The other option could make him the richest man in the world. When faced with such a choice, how do you decide?

It was the 1920’s. My friend’s father had invented a device for railroad cars. One of the major railroad companies wanted his invention and made him an offer. Both options were good offers so he knew he was about to win.

Option 1

Option 1 was safe and secure. $50,000. As you can imagine a hundred years ago that was enough to set him up for life in modest comfort. That’s over $800,000 in today’s money.

Option 2

Option 2 is to me an irresistible offer. When the railroads were built, the company would go across the US buying up land. In many areas they owned thousands of acres on both sides of the tracks. They paid pennies per acre for most of this land. Option 2- Instead of the $50,000 one time cash payment he could opt to receive ownership of thousands of acres in the Permian Basin area of West Texas. That included all the sub-surface rights (aka mineral rights). If you’ve watched shows like Landman or movies like Giant you know the area I’m talking about. The railroad probably considered it to be worthless land and probably hoped he would take Option 2.

Before oil was discovered in the Basin the land was nothing but desert covered in mesquite brush and tumbleweeds. And a lot of sand, rock, and wind. And a railroad running through it.

He chose the one time cash payment and did well with it. He put that money to good use with other land investments. But he never reached great wealth and riches.

Intuition & Timing

Had he taken Option 2- Soon after he sold his invention to the railroad oil was discovered in the Permian Basin. Oil was discovered there in 1923 and the first well in Odessa was completed in 1926 - right in the heart of where he would have owned his land had he taken Option 2. The Permian Basin is now the largest oil producing region in the United States. It accounts for 45% of all US oil production. He would have easily become one of wealthiest people in the world if not the wealthiest.

Today Midland Texas has more millionaires per capita than any other city in the United States. This is why I have operated my commercial real estate brokerage there for the last 15 years. It’s a place of great opportunity.

It all came down to one choice. Take safety and security or take a chance on an offer that on the surface appears to be a bad deal but in reality was a once in a hundred lifetimes offer.

What choice would you have made? It’s easy to say Option 2 now of course. But imagine being given a choice like this. These choices are offered to us for a reason. Sometimes the risk of loss is worth it. How do we know? Intuition? Life experience? A gambler’s mindset? Yes to all three I suppose. Some of the world’s greatest fortunes were made by taking the big risk. Burn the ships and win or die. What does your gut tell you?

That’s the exciting part about being an entrepreneur. It’s an adventure. And I believe it’s an adventure worth taking and a life worth living. So when you find yourself making choices over this new year, remember this story about how one choice could have created the richest man in the world. But even the wrong choice that he made gave him a good life. Is it better to be safe than sorry? We can’t know that in advance. We can’t let ourselves be afraid of making choices or of taking risks.

Which option would you have taken?

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That's it for this time. See you next week!

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