I needed money. I was working my first job out of college and it was not a particularly well-paying job. I was living in Manhattan paying rent and I needed to find a way to make some more money. I started researching, and one thing led to another… about eight years later it became my career.

I sing in a band and I have a side hustle as a ring announcer in boxing. When I’m not doing those, I enjoy playing poker and traveling.

A lot of our readers do, in the fact that they’re willing to look outside of the mainstream wisdom for financial advice and ideas. One of the things that I think is really cool about our readers: In the emails I get, especially if they’ve had a big win or made a lot of money, it’s almost never, “I made all this money and bought a new car.” Or “I bought these new toys.” It’s almost always “This will be the best Christmas for my family.” Or “My wife or husband and I can sleep better at night.” It’s very family-oriented. It really is about improving their lives, reducing their stress, and creating memories vs. being rich for the sake of being rich and having all the toys. I really love that. I feel like our Members are doing it for the right reasons.

My favorite book is called The Power of One. It’s a novel about a young kid growing up in South Africa during World War II. It’s an amazing story, and they’ve turned it into a movie with Morgan Freeman. I have a few favorite investing books as well. Get Rich with Dividends… kidding (not kidding)! I’ve talked about this in various columns - The Richest Man in Babylon by George S. Clason. It’s about 80 pages and you can read it in an afternoon. It’s a book of fables that take place in ancient Babylon but focuses on money: making wealth, keeping wealth, and doing it the right way. It’s so simple, clear, and entertaining. I recommend it to everybody. When I was first starting to learn about investing, I read a great book called Understanding Wall Street by Jeffrey Little. It really explained how stocks, bonds, options, everything, works in very easy-to-understand terms. For people a little more advanced, my favorite book is called Contrarian Investing by David Dreman. It’s more academic and takes longer to get through than the other two, but it really is a great book about understanding investor psychology and when you should go against the crowd.

There have been a lot, especially when I was younger. Overconfidence is an easy mistake to make. You get a couple of wins in a row, and you think you’ve got it all figured out, but you don’t. The market will keep you humble whenever you start to get overconfident. The most important lesson I’ve learned is to use stops. There was an investment I made a long time ago during the dot-com boom and I bought too much of the stock, so I was in over my head. It doubled and I wanted to sell it, but for various reasons I didn’t. I watched it go down more and more but thought, “If it just climbs back up a few points, I’ll sell it.” It never did and I actually rode it all the way to zero and lost everything I had invested in that stock. If I had a trailing stop in there I would have gone out with a profit. A big one.

Yes, but it’s not a famous quote. A longtime friend of mine said that the two lessons he wants to impart to his kids are 1) Stay hydrated and 2) Never leave a party to go to another party. It sounds silly, but I think it's profound because it means take care of yourself, take care of your health, and live in the moment. You shouldn’t always be thinking about the future and what could be better. Enjoy what you have and are doing now. That’s especially relevant for me because I am always thinking about the future, so it’s a great reminder.

Do whatever you can to take emotion out of investing. It is absolutely your worst enemy, and trailing stops are the best way to do that. Don’t ignore the stop. A lot of people try to find a justification for why they should stay in a losing investment, and that will bite them almost every time. The more calculated and unemotional you can be about your investments, the better. Don’t get married to a stock; it’s just a vehicle for making money and that’s all it should be.