I’ve always been fascinated by money. Ever since I was a little kid growing up in Chicago, I wanted to know how much money everyone had.
“Dad, how come they have Atari and we don’t?” I’d ask.
“They must be rich,” my dad would say sarcastically, not really knowing what Atari was or why I wanted one so badly.
“Dad, how come they have a car with AM AND FM radio?” I’d ask.
“They must be rich,” my dad said, not seeing the point of listening to anything other than AM stations for news and sports.
“Dad, how come they have the new Addias Top Ten basketball shoes?” I asked after Isiah Thomas, Randy Whittman and the Indiana Hoosiers made Top Tens must-have gear for any 10-year-old with hopes of playing in the Big 10.
“You think those will make you a better player?” dad asked, knowing no matter the shoe, I’d still be shooting every jumper from the side of my hip for at least another three years.
As I got a little older, my fascination with how much money people had continued to grow. Since no one tells you how much they have, I created a system for knowing who was a millionaire and who wasn’t.
If you had a Betamax in your house in 1984, you were a millionaire.
If you wore Polo shirts to school, millionaire.
If your parents drove an Audi, BMW or Mercedes, obviously millionaires.
If you were allowed to sleep over at a friend’s house on Friday and Saturday nights, your parents were super cool so they must be millionaires.
If you went to Cabo San Lucas for vacation and you casually told people at school, ‘We’re going to Cabo,’ millionaires without a doubt.
In fifth grade, I was pretty sure 100 percent of my friends’ parents were millionaires. I had no idea what people actually did for a living or what those jobs paid. I just knew everyone was a millionaire.
And here’s the sad thing. That misperception has stayed with me pretty much for my entire life. Of course, now I know not everyone is a millionaire. I know the median net worth of the average U.S. household is $97,300. But for some reason, I always tend to think people have way more money than they do.
Every Investment And Every Wager For the Rest Of My Life
Because there is always so much secrecy about how much money people have and what people do with their money, I’ve decided to create a site where I’m totally transparent with what I’m doing with mine. I can’t give you the exact dollar figures, because my wife won’t let me, but I’m committed to logging every investment I make, and every bet I place, from this day forward.
I’m doing this for a few reasons. First, I’m turning 50 and it’s part of going through a mid-life crisis. My back hurts, my penis is shrinking, I grew this weird bump on my wrist called a Ganglion cyst (wtf?) and who the hell knows how much longer I’ve got. There’s a very good chance I will not make it to see my 100th birthday so why not just share everything I know with the time I have left.
After 50 years on this earth, I would say I’m a pretty good investor and a pretty bad gambler. And I’m fascinated as to why that is and the psychology behind both.
As an investor, I’m strictly buy and hold. I read all the Peter Lynch books in the 90’s and I bought into the whole ‘find good companies that you believe in and never sell.’ That philosophy has done really well over time. The thing I like about long-term investing is you don’t have to be very smart and you don’t have to be particularly good at math. You just have to be consistent and patient, two annoyingly boring qualities that I’ve been blessed with.
For example, I bought Anthem in 2007 at $74, Apple in 2010 at $11.42 and Facebook in 2012 at $38 to name a few. And that’s it. I didn’t do anything else. No day trading. No Robinhooding. No puts. No calls. No options. Just buy and hold.
I don’t plan to ever sell these shares unless global warming brings on the apocalypse. Then I will sell five minutes before a tsunami overtakes the city just so I can feel the joy of realizing the gain right before my death.
As a gambler, I’m the exact opposite of a consistent and patient investor. I make poor decisions, chase my losses, bet way too many moneyline parlays and, though I know it’s foolish, am influenced by former teams, coaches and players that have nothing to do with the current iterations.
So why is that? Why am I able to do the right thing consistently as an investor and just as consistently do the wrong thing as a gambler? Is it the nature of sports gambling itself, the need to bet every day or every week? Is it the adrenaline rush I so desperately crave that leads to poor decision making? I honestly don’t know the answer to that question but I’m hoping that by writing more about it, I’ll be able to figure it all out.
So that’s it. I plan to write a little every day about life, sports, investing, gambling and whatever else comes my way and chronicle it all for anyone who cares to listen.
Nothing too fancy. Nothing too serious. Just one man exposing his financial life for the world to see because growing up no one wanted to talk openly about money.
I hope you’ll join me along this journey. Because it’s always way more fun to win, and lose, with friends.
Sincerely,
The Bad Gambler
