Did You Lose Money Gambling? I Did. This is My Story

I get it, it’s not fun to lose money gambling. It’s one thing to spend money on things that give you joy and value but it’s another for the money to be gone into thin air. Just like that without a trace. I’ve been there before. I lost about $20,000 gambling my money away, and when I was only 23/24 years old.

$20,000 felt like a billion to me at the time. It was enough money for food, water, and rent for an entire year for me. However, instead of spending that money over a year, I lost all that money over a couple of months. Just like that at the blink of my eye. I didn’t get anything in return for it.

It was demoralizing to see the dealer grab away the last of my $100 chip and simply place it in their own chip rack. Then they emotionlessly looked at me like, “next bet?”. It isn’t their fault, all they’re doing is just dealing out their cards. It’s my fault that I lost all of that money. No one forced me to drive 2.5 hours to the casino.

I did it all on my accord. Therefore, I know firsthand what it feels like to lose money gambling. Not just any amount of money, but a very significant amount of money. It was life-changing money. I have no idea how much more that money would have grown to had I kept that invested in the S&P 500.

I could have easily added something like $30,000 to my net worth by now, but I didn’t. Instead, I enjoy nothing in regards to the money. There’s no way to change my decision.

Do Gamblers Lose Money?

So before we get into the juicy details of when I lost money money gambling, let’s answer the question do gamblers lose money? The answer is a big, fat, and resounding yes. Casinos are mathematically designed to ALWAYS win over the long term. No matter what. Anything can happen in the short term.

However, in the long run, gamblers do not win money. The system is literally designed for gamblers to lose money gambling over the long term. Now, can you still win over the short term? Absolutely. Anything can happen in the short term. The casinos know this. Therefore, they play various tricks on you to get you to playing longer.

They know that the more time you spend sitting down and betting on the cards, the more likely you are to lose. The easiest trick they use is they put the casinos in a dark part of the hotel with zero natural light coming in. They want you to lose sense of time when you gamble. They don’t want you think “oh wow, it’s getting dark already?”

Now, there is a way for YOU to stack the deck against the casino. However, they require doing intricate things that the casinos will sue you over. Phil Ivey won 8 figures from casinos from a process called edge sorting. The casinos thought that he did something wrong so they sued him over. The judge agreed with the casinos.

The law favors casinos over the player. It doesn’t matter what the dispute is. In general, the courts favor casinos over players. There’s too much tax dollars at stake for the government to not favor the casino. Therefore, it’s stacked against the gamblers, both ways. Mathematically and in legal terms.

When I Lost Money Gambling Part 1

So now, let’s get into the juicy story. I never thought that I would lose money gambling. Things were going so well. I was 23 at the time and getting tired of my $20,000 salary, after all of my tax advantaged account contributions.

I needed a side hustle to make more money on the side because I was sick and tired of living close to poverty. The casino was only a 2.5 hour drive and I could just go there during the weekends! I’m not going to be greedy. If I can make a couple thousand dollars per month, then that’s plenty of side hustle money!

That was my thought process. And guess what? I was successful. I was so successful that I didn’t think there was a way that I would lose money gambling. After 5/6 short months, I turned a $2,000 bankroll into… $20,000. Not even including the free hotel rooms, the free food, free air fryers, clothings, etc. You name it, they gave me.

I thought, “ha! all these people talking about how bad gambling is are just flat out wrong! I figured out the system!”. Six months in, I took a day trip on a Thursday by taking PTO from work for the day. How much did I win on that trip? $11,000. I still remember the condescending look my dealer gave me when she started dealing me the cards.

And the surprised look she gave me when she saw how much I cashed out for. More money I ever made in a single day, ever, in my entire life. I was literally on top of the world..!! The thing about being in the top of the world is that it becomes easy to go back down.

When I Lost Money Gambling Part 2

Then comes… the crash down. The thing to remember is that I never gambled in the everyday floor. I gambled in the high limit rooms where the rates were $100 per hand. Therefore, I needed a good enough bankroll to withstand the high variance that can happen. The very next trip after winning $11,000, I brought $4,000 into the casino.

For reasons that I didn’t understand, I lost that money in the first day that I made the trip. I usually at least make my bankroll last to the second day, at a minimum. Usually, a $4,000 loss would devastate me into oblivion. It would hurt my psyche so much that I would question why I gambled in the first place.

However, when I went back after winning a five figure profit… it didn’t. I actually didn’t care. I thought, “well, that doesn’t matter, losing comes with the territory. $4,000 loss after $11,000 win is understandable”. That’s the most dangerous mindset you can ever get into when gambling.

In the next trip, I won $2k, then the trip after lost $4k, and so on and so on until my bankroll dwindled down. Until it went down… to $0. The biggest difference between my psychology was that I started to feel like I couldn’t lose. I felt invincible, even as I was losing. Then it didn’t take long until I started tapping into my money reserves to gamble.

So by the end of my gambling journey, I ended up losing $20,000 in winnings and another $20,000 of my money. I never thought that I could lose money gambling because I thought I was “too big to fail” in relation to what I was playing. It hurt and put in a low that I never felt before in my life.

What to do After You Lose Money Gambling

Below are 4 things you can do after you lose money gambling. Not all hope is lost and there’s a way to bounce back better than ever before.

1) Do NOT EVER Chase Losses

The term used for chasing losses is called “revenge gambling”. When you’re gambling the most important thing is your psyche, emotional resilience, and psychological health. Nothing else matters. Why? People are emotional about money. Money is an emotional subject for us.

Therefore, when you lose money gambling, you should never EVER chase losses. You shouldn’t think about going back and making all the money back. The more you chase after something, the more it doesn’t want you. The more you chase after your losses, the farther your losses become. If you lost $2,000 for the day by gambling, let it be.

Give up. Stop thinking about it. Enjoy the amenities of the hotel. Maybe go to the pool, work out a little, enjoy the pricey restaurants. There’s other things to do besides gambling in the hotel. This is the number one thing to do. You should never ever chase losses when you lose money gambling. If you remember one rule, remember this one.

2) Get Back to Your Normal Mindset

I get it. When you lose money gambling, your psychology is completely out of whack. You feel low, lower than you ever felt. Like why did you even step in the casino in the first place? Why didn’t you leave when you were up? Am I going to live through this? This is more money than I ever thought in my life.

How do I know you’re asking these questions? I asked the exact same questions when I lost money. The exact same. I would mope around in the hotel bed thinking how stupid I was that I didn’t get up and leave when I was up a couple thousand dollars. I felt mad. That’s when you just need to let time pass.

It’s easy because you don’t control time. Whether you want it to or not, time is going to pass anyway. You return to your normal mindset eventually. Even if you think that the world is over for you, it isn’t. It took about 3 months before my psyche returned to normal after I lost money gambling. Now, it’s just a distant past.

I feel nothing now.

3) Take a Break from Gambling

The last thing to do after you lose money gambling is to go right back at it. It’s VERY IMPORTANT that you take a break from gambling, possibly forever. I haven’t gambled in almost three years and I intend to keep it that way. Unless you’re a billionaire and you can afford to lose $20,000 without feeling anything, you need to stop gambling.

Don’t have the YOLO, “live everyday like it’s your last” mentality.

Casino games are mathematically designed for you to lose money over the long term. No one’s been able to win against math, except people like Phil Ivey who learned edge sorting. After you lose, it’s more important than ever to take a step back and focus on other things for a while before you even consider going back.

Don’t worry, the cards will ALWAYS be there. The casino will always deal the cards and will exist for the rest of your life. There’s no need to return to the casino the day after to try and win your money back. The casinos run 24/7/365 and will continue to run until they physically are barred from doing so.

Which they won’t be, lawmakers salivate over the gambling revenue it brings the state.

4) After Time Passes, Consider Walking Away Altogether

After you lose money gambling and you got back to your normal psyche, consider giving gambling up completely. There are more proven ways for you to build wealth like saving and investing your money into the stock market. In fact, the S&P 500 has been the biggest wealth creator for me in the past five years.

I don’t think the S&P 500 will ever stop help build wealth for me, either. After I gave up gambling, my net worth skyrocketed to new heights. I expect to continue to skyrocket to even higher heights as long as I just keep saving and investing my money.

It’s never a bad idea to stop putting yourself in situations that’s mathematically designed for you to lose. It’s not a bad idea to keep gambling as a part of “fun money” budget. However, be honest with yourself. Can you really afford to gamble?

Do you already have next generational level of wealth that losing thousands of dollars literally doesn’t matter? If you did, you wouldn’t be in the casino in the first place. Therefore, for the vast majority of the population, gambling is a bad thing to do.

It’s Expected For You to Lose Money Gambling

Every single game in the casino is designed for the house to have a slight edge. The edge may be small as 0.5% or as large as 8%. However large the edge is, the house only needs a 0.5% edge to win billions of dollars from people. Therefore, if you do lose money gambling, don’t beat yourself up.

All that’s happened is that what was expected happened. The long term expected value for a gambler is always negative. There are exceptions, of course, for advantage players such as card counters. However, the vast majority of people do not know how to count cards correctly. I don’t know how to.

The movie “21” is a horrible example of card counting because it dumbs it down. The casinos allowed the movie to go forward because they knew that people are not going to put in the work to actually know how to card count. They were right. Card counting is a skill that many people cannot master without putting in hours of work.

Therefore, it’s expected that you would lose money gambling. It’s not a surprise or anything special that you actually did lose money. All that’s happening are statistics working its magic like it should be. The free perks you earn from gambling can make everything worth it, though.

I’ve gotten to eat frog legs, alligator meat, crab meat, and more because of the free buffet tickets they give me. The pit bosses said that they don’t mind giving away free food just because of how much they throw away already. Therefore, you might as well take advantage of it.

If You Lose Money Gambling, Don’t Gamble Again

There are people out there who can consistently win money gambling. However, 99.9% of people do not know how to do so. Why is that? First, they have day jobs that are distracting them from focusing on the game in the first place.

Second, even if they do go all in, they don’t have enough of a bankroll or the knowledge on how to master the statistical advantages. Don Johnson is a gambler who won $15MM from the casinos coming out of the financial crisis. However, casinos gave him rules the likes of which I haven’t ever seen.

When you actually run the numbers, Don actually had the advantage over the casinos. It takes something special like that to actually win the big money from the casinos. Meaning, for 99.9% of people, it doesn’t work. Therefore, if you lose money gambling consistently, just don’t do it.

The best way to save money is to never spend it in the first place. The best way to not lose money gambling is to not gamble in the first place. There are more proven ways for you to build wealth and generate additional sources of income. Ways that may take longer than gambling but have a very high chance of success.

The first rule of building wealth is to not lose money and the second rule is to never forget rule number one. When you find out that the S&P never returned a negative return over any 20 year period, then you should become intrigued. There’s no reason to bet against that kind of results.

If it’s good enough for Warren Buffett, it’s good enough for you.