#8 Trading

I am a natural born trader. The only problem is that I didn’t discover this until I was 68 years old in 2020.

I’ve always been good with numbers. My high school math teacher Mr. Curtis asked me to teach the Calculus course because I was bored with his teaching. He gave me a shot one day. He sat in the back of the classroom and let me do my thing. I also got 700+ scores on the math SAT exam with no preparation. I just took the exam cold. Probably could have scored close to 800 with a little preparation like kids do nowadays.

But it takes more than math skills to be a good trader. It requires patience, discipline, research-time, and a bankroll.

When I resigned from the WCA in May 1998, I was way too young to be retired, and we had just enough money for me to start playing with. I didn’t have a large trading portfolio back then and I really didn’t have much of a strategy. I just bought and sold stocks I liked. We lived off Liz’s salary, so I had no pressure on me to make much money. It was just a way to fill time and learn my craft.

All this changed when Liz stopped working in 2019 and her last check was cashed in early-2000. All of a sudden, for the first time since we were married, we had no income and I felt tremendous responsibility to manage our nest egg. I fired our investment manager at Merrill Lynch and moved all the money to Fidelity where I had been trading for years. I now had a very important job to do. Trade for a profit AND manage our nest egg AND earn enough money to travel the world.

Fast forward five years later. I trade everyday M-F. I am having my best year ever in 2025. We’ve been on the road over 100 nights per year for the last five years. Life is good. And I still have a lot to learn. It doesn’t feel like a job. I simply wake up every day and react to what the stock market is doing. Up, down, sideways. It doesn’t seem to matter much. I continue to find opportunities to make short-term trades that are profitable. I rarely hold a position for longer than three months.

Trading is a lot like gambling which I’ve also done my share of. The only difference is the odds are in my favor as a trader unlike Vegas where the house has a 2+% advantage on every bet. Starting a trading day is a lot like sitting down at a new blackjack table. You get excited and hope to do well. The BIG difference is I expect to win 90+% of my trades whereas in blackjack I just hope to break even.