The Journey Never Ends

I’ve been trading since the early 90s. I got my first chunk of money when I was 18 via an annuity that was structured for me by my mother after a lawsuit settlement following the murder of my father in 1981. She had a choice of whether to take a lump sum then or 5x the amount when I hit 18.

We weren’t very smart with the money, divvied it up and spent it almost in a manner on par with idiocy. Unlike my mother and sister, I chose to invest it in stocks because I was obsessed with them, always had been since the crash of 1987.

I’ve made plenty of mistakes with money and my relationship with it has always been contentious. I fear losing it and don’t want to revert back to not having any, not now and not ever. My behavior reflects this in my trading; but it wasn’t always this way. When I first became a stockbroker in ’97 I dabbled in junk bonds and early stage internet stocks with all of my money, because I wanted to be rich. With my money, I had plans, especially since I had my first son when I was just 21. In a sense, I have always been a father, for all of my adult life. I never went on benders or adventures with friends, but to the train and to an apartment in Bay Ridge Brooklyn to my wife and son. I wanted everything to be perfect. After all, I had always known that I was good at picking stocks and I could rely upon my instincts to guide me into the wonderful world of Wall Street.

After just 1 year in the business, I was making more money than my mother made over a 10 year period and didn’t know what to do with it. My wife wanted to buy real estate; but I shot down that idea because I had always rented and preferred to invest my money in stocks. It was in stocks where I’d make my fortune, visions of Gatsby and the Count of Monte Cristo, depending on my mood.

But after the dot com crash in 2000, all of my talents and “innate skill” was for nothing. With zero risk management experience and inability to see the forest thru those very dense and thick trees, I lost all of my money. It was during that experience that I grew into what I am now: a person conscious of risk and the gumption to act upon it. Those of you who traded with me inside Stocklabs and before that Exodus and before that The PPT understand that I am not patient and am always looking for downside surprises.

As a person, it might surprise you to learn that I am extremely bullish on people. Politics aside, I believe in the human evolutionary spirit like the best of them and it is this evergreen feeling coupled with my fear of losing money that I balance myself as an investor. You can be two things at once, long and short, depending on the arb and the timeframe. Investing is all about timeframes. You miss a trade whilst in the bathroom but an investment because you thought the President would ruin the nation.