Rich Gambler, Poor Gambler

Silhouette of a Rich and Poor Man With a Slots Background

What’s the difference between rich gamblers and poor gamblers?

And what’s the difference between people who build wealth when they’re gambling and people who get poorer while gambling?

This post looks at that difference so you can decide which category you fall into.

It’s Hard to Get Rich Gambling

I used to own a bookstore, and I like to tell people the secret to winding up with a small fortune after owning a bookstore for five years:

Start with a larger fortune.

The same humor applies toward most gamblers and most gambling.

If you’re the average recreational gambler, you’re going to lose money over time. That’s just how it works, regardless of whether you’re a casino gambler, a poker player, a sports bettor, or all three.

But even if you’re that rarest of breeds – an advantage gambler – it’s easy to go broke as a gambler.

An advantage gambler is someone who only gambles when they have a mathematical edge. This doesn’t guarantee success, though – gambling is still random. Even if the odds are on your side, you’ll still lose sometimes.

The experts gave Donald Trump only a 30% probability of winning the 2016 presidential election, but if you bet on Hillary Clinton, you saw what a run of bad luck really means.

The same holds true for any sporting event you can think of. There’s an upset every Sunday.

If your bankroll is small, you stand the risk of going broke even if the odds are in your favor all the time. It just takes a short string of bad luck to lose all your money.

That’s why it’s easier for rich people to get ahead as advantage gamblers – they have enough money to avoid going broke before their long-term mathematical advantage kicks in.

Rich Gamblers Get Different Treatment From the Casinos

If you want an eye-opening account of what it’s like to be a rich gambler in a casino, check out a book called Whale Hunt in the Desert: The Secret Las Vegas Of Superhost Steve Cyr by Deke Castleman.

Aria Las Vegas High Limit Lounge

It’s the story of Steve Cyr, the most revered casino host in Las Vegas. As a casino host, he caters to the biggest whales – the richest gamblers. You’ll be amazed at the kind of treatment big gamblers get at the casino compared to the rank and file working class gamblers like you and I get.

Unlike many of the books I recommend, Whale Hunt in the Desert doesn’t offer you any kinds of tips to make you a better gambler who wins more often. It’s just a look into the side of the business that makes literally almost anything available to casino gamblers who are willing to bet life-changing sums of money on a single hand of blackjack or a single roll of the dice in craps.

It Is Possible to Get Rich Gambling

You can get rich gambling in different ways. The easiest but least likely way is to get really lucky and win the lottery or hit a progressive jackpot. The problem with that approach is that you’re more likely to get struck by lightning than you are to win the lottery or a progressive jackpot. Most people who play regularly their entire lives just lose the money they’re wagering on such games.

One way to get rich is to find a gambling activity where you can get an edge and then repeatedly leverage that edge to win money over the long run. This seems like a fun, romantic way to get rich, but it’s less exciting than you probably think.

Most professional gamblers might as well be actuaries or accountants for all the excitement they get out of their chosen profession.

And I have some friends I’m close with who are accountants. Lively, exciting people they are not.

How to Get Rich Counting Cards in Blackjack

One of the only casino games where you can get an edge over the casino is blackjack.

But it’s not enough to just play every hand correctly. That’s a good first step, but you need more than just the mathematically best way to play every hand in every situation.

That’s called being a “basic strategy” player, and it minimizes the house edge.

But it doesn’t eliminate the house edge or put the math in your favor.

To get a mathematical edge at blackjack, you need some kind of advantage play technique. The most common way to get an edge at blackjack is to learn how to count cards.

Even if you’re good at counting cards, you’re only looking at a 1% edge over the casino. That sounds small, but it applies to every hand you play – which is between 50 and 350 hands per hour.

That adds up.

The more you’re able to wager per hand, the faster you can make your fortune in blackjack by counting cards.

But you need a big enough bankroll that you can avoid going broke because of a streak of bad luck before your edge kicks in.

You can learn to count cards from any number of books on the subject. Look for something by Sanford Wong or Arnold Snyder. It’s easier than you think, and no, you don’t need to memorize an entire deck of cards. (Even that’s easier than most people think. It just requires some focus and attention.)

How to Get Rich by Becoming an Expert Poker Player

Most real money poker players wildly overestimate how good they are at playing. If you truly want to get rich playing poker, you need to start by keeping careful records of how much you’re winning and/or losing in the long run.

I read somewhere that you know you’re a serious poker player when you start keeping written records. That’s easy. Just by a spiral notebook, write down what you started with at the beginning of each session, how long you played, and how much you wound up with. You can subtract one from the other to find out how much you won or lost.

And you can divide the amount of time you spent at the table by your loss or your win and calculate your win or loss rate per hour.

Closeup of a Poker Player Handling Their Chips

In the short run, this won’t accurately reflect how good you are at poker.

But as you gain data, you’ll start to see a long-term pattern for how much you’re winning or losing per hour.

There’s more to playing winning poker than just keeping records, though.

That’s critical, but there’s a lot more to learn.

You should constantly be reading books about how to improve and watching videos. You might consider investing in some coaching or mentoring, too.

95% of the player at the table are losing money in the long run.

If you want to be profitable – if you want to be in the top 5% — you’re going to have to put in the effort.

How to Get Rich as a Sports Bettor

I suspect that the 95% to 5% ratio of losing sports bettors to winning sports bettors is also accurate. I’m not as sure about that number as I am the poker number, but I am convinced that most sports bettors are losing money in the long run.

How do you turn that around and become a winning sports bettor?

The first step is understanding how the vig works and how sports betting is just a marketplace for various bets with varying values. The brilliant thing about sports betting, though, is that you don’t have to take every bet.

If you have the discipline to only take those bets you think are mathematically in your favor, you’re well on your way to profitability already.

The other trick is to come up with some strategies and systems for choosing winners that will overcome the book’s vig. You need to win 52.4% of your bets just to break even because of the vig.

51% won’t cut it.

You’re still losing money at that rate.

Getting Into the Biz

Of course, the surest way to get rich as a gambler is to own the casino. You don’t have to worry much about the odds being in your favor when you own the casino because that’s how the games are designed.

Owning a big Las Vegas casino is beyond the means of most people, though. But even if you only own a gas station or a neighborhood bar, casino style gambling is something you can offer.

Just be wary of the gambling regulations where you live.

Gaming Machines in a Gas Station

I’m in Texas, and every bar and convenience store in the state has slot machines, but none of them are operating entirely legally. They seem to get away with it, but it will be a drag when that ends.

Other states are probably more draconian in their enforcement of gambling regulations.

This doesn’t mean you can’t get rich from the gambling business unless you own your own business.

You can also go to work in a casino in various capacities and get rich the old-fashioned way – keep your expenses below your income and save the difference.

After that, the power of compound interest will make you rich.

You just have to wait.


If you want to be a rich gambler, it helps to start off being wealthy in the first place.

If you want to make your fortune gambling, blackjack, poker, or sports betting is the way to go.

But 95% of the gamblers who play those games lose money.

Gambling isn’t an easy or sure route to riches, but it can be a lot of fun.