The Most Important Gambling Lessons I’ve Learned in the Last 25 Years

You might say I’ve been gambling since I was a kid. My mom taught me to play blackjack when I was 10 years old, but we never put real money on it.

I didn’t really start gambling with any kind of serious interest until I was in my mid-20s. When I took my first trip to Las Vegas, it was a gamechanger. I won’t say I was hooked, because that’s a cliché.

But I will say that I’m an enthusiast.

Writing about gambling for a living has been a blessing and a miracle.

Here’s what I’ve learned in the last 25 years from both gambling and writing about gambling. These are the most important lessons.

You Should Learn How to Play Poker

You might hate poker once you learn to play, but I just can’t imagine that. Poker is the greatest game ever invented. It has all the strategic complexity of a game of chess, but the lack of complete information and the random nature of the game make it even more challenging.

The best thing about poker is that it offers you a fighting chance of actually getting a mathematical edge while you’re gambling. This isn’t something you can do with most casino games in most circumstances. In fact, I have something to say about that, too.

Counting Cards Is Overrated

I used to work at a corporation with a corporate attorney, and during one of our water cooler conversations, he mentioned that he was a card counter. He was kind of a nerd, but I liked him a lot. He recommended a book to me about counting, and I devoured it.

Since then, I’ve written dozens of articles for the internet about how to count cards and how counting cards works. I’ve also gotten reasonably good at counting cards myself. I’ve even been on the other end of casino countermeasures against card counters. (I’ve heard that you’re not really a card counter until a casino has “backed you off.”)

Here’s what I’ve learned about counting cards.

It’s easier than you think, but unless you have a superhuman level of commitment bordering on obsession, it’s not that profitable.

After all, you’re only looking at getting an edge of 1% or so. Unless you’re playing for really high stakes, that just doesn’t amount to a high hourly win rate.

And pulling that off is tough. Counting cards at low stakes tables isn’t such a big deal. Casinos don’t like it, but it’s not going to hurt their bottom line.

Start playing for stakes that matter to the casino, though, and those are the stakes where you might actually win a life-changing amount of money. And the casino pays CLOSE attention.

This is why card counters organize into teams and come up with elaborate measures to avoid being identified.

To me, it’s more trouble than it’s worth. Just get a job that pays well and gamble as a hobby.

The Martingale System Isn’t as Bad as Experts Say

The Martingale system is a betting system where you double the size of your bets after each loss until you book an eventual win. When you do win, your bet is guaranteed to be big enough to cover your previous losses and show a small profit.

Traditionally, the Martingale system is something you’d use at a casino game where you’re making even money bets. Roulette is the preferred game for Martingale players because it has one of the highest probabilities of winning a single bet.

The probability of winning an even money bet at the roulette table is 47.37%. Compared to the 42.22% probability of winning a blackjack hand, real money roulette is a far superior game. (It’s more complicated than that, but for Martingale players, this matters.)

Here’s an example of the Martingale in action:

I took a date to the Winstar and sat down with $400 at the roulette table. We bet $5 on black and lost. Since we lost, we had to double the bet to $10 on the next spin. We lost again. So, on the next spin, we doubled up again to $20, and this time we won. Our $15 in previous losses were recouped, AND we had a $5 profit.

This went on for half an hour, and we booked several small $5 wins. We were up $30 or so after half an hour.

Then, we hit a serious losing streak.

We bet $5, lost, then $10, and lost again. Now, we had to bet $20. Then, $40. Then, $80. Then, $160, which meant we were betting with most of the chips we had left.

We won that $160 bet, which meant we were up $35 for the session, We called it a night after that.

Reasons the Martingale System Can Be So Much Fun

For one thing, my date that night had never been to a casino before, and she didn’t understand that in the long run, the Martingale is a losing strategy. Eventually, you’ll run into a losing streak that’s long enough that you’ll be unable to cover the next bet in the progression. We almost hit that point in the example anecdote I just shared.

Even if you have the bankroll to make the next bet in the progression, most casinos have a betting limit. This is the maximum amount you’re allowed to bet. Lose enough times in a row, and you’ll bump your head on the glass ceiling provided by the table limits.

But she didn’t know any of that.

She just thought I had a can’t-lose system.

Also, when it came time to bet $160 on the hand—most of the chips we had left—she was excited about placing such a big bet. Yes, I let her handle the chips and make all the bets. It was so much more fun for her that way.

Here’s what really happens when you use the Martingale system, though.

If you’re playing short sessions, you’re actually improving the odds that you’ll walk away with some profits. Suppose you stick with one-hour sessions. You’ll have a close to 80% probability of having at least some small profit after your session.

The only problem with the Martingale is that about 20% of the time, you’ll have a losing session. And that losing session will involve losing so much money that it will wipe out the wins from the other sessions, too.

Here’s an example.

You play five sessions of roulette on one weekend. Here’s how much you won during your four winning sessions:

• $20
• $30
• $25
• $20

That’s $95 in total winnings.

But on your fifth session, you lose $160 because you lost so many bets in a row. That wipes out all the winnings from the previous sessions.

Those numbers aren’t real. They’re just examples. Since roulette is a random game, you can’t predict your short-term results with any reliability.

As long as you understand that the Martingale system isn’t a can’t-lose system guaranteeing you a winning roulette career, it’s fine to use in the short term for giggles.

Craps Is a Lot of Fun

I have one topic I’m forbidden to write about here, and I’m not even going to mention it.

But I will say it’s the only thing I know that’s more fun than shooting craps.


Craps isn’t as popular as it once was. Slots have taken over most casinos.

But if you’re willing to spend 15 minutes learning how to play real money craps, you won’t regret it. Educated craps players know that the simplest bets at the craps table are also some of the best bets in the casino.

The basic bet at the craps table is the pass line bet. It has a closely related cousin, the come bet. If you learn those two bets along with the odds bet, you’ll be as good a craps player as anyone.

Just ignore all the other bets on the table, especially the bets that the stickman is constantly pitching like he’s the ringleader in some kind of bizarre circus where the dice are the attraction in the center ring.

No, craps isn’t a game of skill.

But it’s more fun than almost any other game in the casino.

Stay Away From the Slot Machines

No casino game will siphon money out of your wallet faster than a slot machine. Part of this is because the house edge on slot machines is high. In most casinos, the house edge is at least 6%. And 8% is probably closer to the truth.

But you don’t even know what the house edge is for slot machines because you don’t have access to the probabilities behind the game. Slots are the only game in the casino where you can’t calculate the house edge with any certainty.

I think that’s unfair in and of itself.

Almost everyone who plays slot machines puts far more money into action per hour than they expect. That’s because it’s easy to make a lot of bets per hour. Even if you’re only betting $1 per spin, if you’re making 500 spins per hour, you’re putting $500 into action every hour.

You’ll win some of those spins, so you probably won’t lose $500 per hour.


But you’ll probably lose 6% to 8% of that, so you’re looking at average hourly losses of $30 to $40.

That’s a lot of money to spend on a gambling game, especially when you can play a video poker machine with a house edge of 1.5% and lose just $10 per hour.


To me, video poker is more fun anyway. I get to make decisions on every hand that matter. I get to exercise my free will and my brainpower.

I have no such opportunity at the slot machines.

Conclusion

I’ve learned a lot in my 25 years as a gambler, and some of this might be advice you’ve seen before. I think my advice about the Martingale might be sacrilege to a lot of gambling bloggers, but it’s the truth of my experience.

I just hope you’ll remember to stay away from the slot machines! Best of luck.