Kicking Myself For Dumb Mistakes

My first big fiscal mistake was during the last dot-com boom. Like everyone else I bought into it - big time - and lost a fortune. If I had known a few basic investing rules I would have cut my losses and still come out substantially ahead, instead of losing 90% of my value. But I was young, right out of college, and had no experience or knowledge to draw upon. Now I am a very conservative investor but I will never make that mistake again.

My next big mistake was about a year ago. I was involved with a start-up company from the beginning and they gave me equity in it. Through some complex financial maneuvers I had the opportunity to cash out for a pretty high value. Due to restrictions I couldn't have cashed all of my equity in at that high value, but I still would have been sitting pretty. I didn't sell because the value had been going down pretty much consistently since it had value and I expected it to go back up.

Now that equity is virtually worthless and I kick myself every single day for not selling more of it when I had the chance. It wasn't a lot of money I could have made but we could have bought my wife's dream house with it - in cash no less.

Maybe this is why I get so angry when I hear about Zuckerberg turning down billions of dollar worth of offers. A friend of mine put it best - do you still wear a seat belt even though you are a good driver? Yes you do, because you would rather be safe than dead, and if I was Zuckerberg I would have sold to Yahoo in a heartbeat, taken my money and gone home and counted it.

The moral of this story is - if you ever have anything worth money you need to take steps to ensure that you don't lose that value. Set limits and stick to them.