Our Editors’ Biggest Mistakes (And What They Learned)

Listening to my wife.

Let me preface the story by saying she’s very smart and did a great job for us on an investment property that we bought and sold last year.

But during the dot-com boom, I bought a very speculative stock that I knew had no fundamentals. When the stock doubled, I wanted to sell half and take our risk off the table. She wanted to let it ride.

When I disagreed, she challenged my manhood. 

So we let it ride… and lost all of it.

The good news is she no longer challenges my manhood, and I handle our family’s investments with no interference.

The year was 1984. Companies were merging and buying one another out at a record pace.

And there was a ton of money being made… At least there appeared to be.

I was still flying for the Navy, and several of our reserve pilots flew for Western Airlines, which was in the process of being bought out. The reserve pilots were certain they knew the price per share of the buyout.

So I took some of the few dollars I had managed to save – on the slave wages they paid us back then – and bought a big chunk of Western Airlines stock.

Then I sat back and waited for the big check to come! Yeah, right.

The buyout was half the price that my so-called experts said it would be. I lost 50%, and my wife at the time gave me the dreaded “you idiot” stare.

Would I buy a company’s stock now based on expert advice from its employees? Never… no… no way. It’s a one-way trip to the poorhouse.

Fundamentals… fundamentals and no shortcuts!

The most important advice I could ever dispense to a young investor would be this: Marry well.

And by that I don’t mean “marry up” or “marry money.” I simply mean “marry well.”

Marrying badly is often the single most expensive “trade” anyone – including me – could ever make. Because of my divorce, I lost half of my accumulated wealth and spent several years “losing” a large chunk of my earnings, which made it VERY difficult to accumulate capital.

These direct losses of wealth and earnings amounted to a kind of “wealth tax” that created an even bigger problem: opportunity cost.

Specifically, my divorce forced me to sell my house at an inopportune time and not participate in the appreciation that followed that sale.

My divorce also forced me to say no to lots of investment opportunities that later excelled. I even had to say no to buying bitcoin when it was trading at $10 apiece. Today, it is trading at $2,800.

Now, don’t get me wrong: I’m not crying in my soup. Despite the financial impediments my divorce imposed, I still managed to achieve a high level of financial success.

But having said that, marrying badly was the worst “trade” I ever made.