3 Things You Can Learn From My Gambling Mistakes

Gambling-Mistake-Sad Man

I’ve been gambling in one form or another for close to 40 years. The first 20 years, I gambled in a lot of private poker games and bet on sports with people I knew. I even played a regular euchre game for money for several years.

I rarely went to a casino, and when I did, I didn’t really know what I was doing. I made many mistakes over the years and didn’t start learning from them until the last 20 years. Now, I know which games I can beat, the house edge on most games, and concentrate on the areas where I can play with an edge.

In hopes of helping you not waste years learning from your own mistakes, I’ve put together some of the blunders I’ve made over the years.

1 – Lack of Research

This is a painful thing to admit because I love to read and do research. But, for the first 20 years of my gambling activities, I didn’t read a thing to try to improve. I learned how to win playing euchre for money by personal experience, and I did okay betting on sports because the people I bet with weren’t any better at it than I was.

I played a lot of poker because I liked it, but my results weren’t very good. I won sometimes and lost sometimes, and I didn’t track my results. My guess is that I lost quite a bit more than I won over the first 20 years.

Eventually, I decided I was going to see what I could do to improve my results. One of the first books about poker I bought was The Theory of Poker by David Sklansky. I tried to read it and didn’t understand most of it. I put it on a shelf and read some other books. The internet existed at the time, but it didn’t have much in the way of useful information back then.

I eventually went back to The Theory of Poker and suddenly, things started clicking. I wasn’t ready for the advanced concepts of expected value and odds when I tried reading it the first time, but it changed everything about my gambling activities the second time.

Now, I look at almost every gambling decision I make using expected value. This has improved my results and gives me a way to compare games and decisions in almost every area.

While I strongly suggest learning as much as you can about expected value, that isn’t the point of this section.

The thing you can learn from my mistakes in this section is you need to do as much research as possible if you want to improve your gambling results. If I’d stopped doing research when I didn’t understand the Sklansky book, I’d still be a losing gambler. Instead, I kept learning and reading and improving until it started to make sense.

You have access to more research, strategy books, poker articles, and videos than ever before. If you want to be a winning gambler, all of the information is easily and readily available. All you have to do is put in the work.

2 – Playing New Games

Several years ago, I was on a trip for a business conference and it was held in a hotel with a casino in Indiana. I won a drawing at the conference and received a $100 chip. So, after the conference finished for the day, I marched down to the casino and was disappointed to learn they didn’t have a poker room.

I walked around the table games and found a Let It Ride game. At the time, this game was new to me and I didn’t know how to play. The dealer was quite helpful and exchanged my $100 chip for a stack of $5 chips, which was the table minimum bet at the time.

I was able to play for several hours before I lost the $100 and had a great deal of fun. The problem is that I played a game that I knew nothing about and didn’t have any idea of the best strategy to use. As it turns out, Let It Ride doesn’t offer a good house edge, and I was lucky to last as long as I did.

Now, I never play a new casino game unless I know how to play and understand the best strategy for the game. I rarely play new table games because they usually have a house edge worse than blackjack.

You do have some advantages now that I didn’t have when I first played Let It Ride. You can use your smartphone to quickly look up information about casino games, including strategy. I don’t even remember if I had a cell phone at the time, but this has been so long ago that if I did have one, I just used it like a house phone.

Casinos introduce new games because gamblers are always interested. The casinos also know that players don’t know the best strategies for new games and it can give them a profit boost.

I highly recommend learning about the house edge, rules, and strategy before you try anything new. While my experience didn’t really cost me any money because I won the $100 chip, it still taught me a valuable lesson.

When I see a new game now, I make a note and follow up with research when I get back to my computer. Unless a new game has a house edge under 1%, I rarely play. I still like to play Let It Ride from time to time, but the edge is so bad that when I want to play, I play for free at an online casino.

3 – Understanding Bankroll and Bankroll Management

I always gambled with the money I had in my pocket during the first 20 years of my gaming history. If I had money, I’d find a game or something to bet on. If I didn’t, I waited until I got paid. This is the way many gamblers handle their gambling bankroll.

While there’s nothing wrong with this method, it’s far from the best way to tackle your habit. When I started setting aside a gambling bankroll, segregating it from the rest of my money, it gave me a way to start tracking my results.

Eventually, I started tracking everything I did, including my poker results. In hindsight, how could I know how I was doing if I never tracked anything?

I used to go to the dog track and make $2 bets on each race. Sometimes, I’d like a dog so much that I’d make a win-place-show bet, which is simply three $2 bets. So, the most I ever bet on a race was $6. I know for a fact that I lost money on the dogs.

Eventually, I figured out that I wasn’t going to put in the time and effort to learn how to win betting on dogs and gave it up. This was still during the time when I didn’t have a bankroll.

Different gamblers have different goals. They all want to win, but most don’t take the proper steps to give them a real chance at profit. If you just want to gamble for entertainment, you don’t really need a bankroll. But I still recommend having one so you know exactly how much you’re losing.

If you seriously want to learn how to win, you must start using a bankroll. Don’t make the mistake I made and just play with money in your pocket. Set aside a bankroll and only use it for gambling. You can use your bankroll for expenses related to gambling like travel if you want, or you can use your other money for expenses.

Tracking your play and results is just as important as having a bankroll. I didn’t start improving my results at the poker table until I set aside a bankroll and started tracking everything. I tried new strategies, and my bankroll and track record showed me if they were working or not. You can use this same system with any gambling activity.


I’m still making gambling mistakes, but it’s sad that I waited 20 years before I started learning from them. You don’t have to wait years to avoid the mistakes I made early in my life.

Use the resources you have available to learn as much about your favorite gambling activities as possible. You might learn that your favorite game can’t be beat, so you need to find a new one. Don’t make the mistake of playing new games until you know the house edge and the best strategy.

If you’re not using a segregated bankroll now, set aside some money to start your gambling bankroll. You can add to it when you have extra money. If you don’t have a separate bankroll in place, you can’t accurately track your results.

One of the biggest turning points in my gambling career was when I started tracking everything I did. Using a bankroll makes this easier, and if you simply start doing this, it can quickly help you improve your results.