The Ultimate Guide to Winning More Often at Gambling

By in Gambling Guides on
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Jackpot and Money

This ultimate guide to winning more often at gambling is aimed largely at recreational gamblers. Professional and advantage gambling are different animals, and some of the information here will apply to both kinds of gamblers.

But most of this post is aimed at someone who’s just gambling for fun and wants to maximize his winnings while minimizing his losses.

Most of the tips in this guide to winning at gambling relate to choosing the bets with the lowest house edge, but there’s more to the equation than that. I’ll cover the other factors you should consider when deciding which bets to make, too.

My best advice for most gamblers is to track their losses and make sure they’re getting a fair amount of entertainment for the money they’ve lost.

Keeping a Gambling Diary

The first and most important suggestion I have for someone who wants to win more often at gambling is to start keeping a detailed gambling diary. This is a good idea for multiple reasons.

For one thing, if you do win a big jackpot, you can deduct your losses from the year from the amount you’ve won for tax purposes. You can only do this if you have records, though. (And you can’t deduct more than you’ve won.)

The other – possibly more important – reason for keeping a gambling diary is so you can track how much you actually win or lose. Clarity is key when trying to win at gambling.

I have a friend – Steve – who plays the lottery regularly.

And he spends a lot of money playing – sometimes as much as $100 a week.

If you ask him how much he loses playing the lottery, he claims that he’s about even for the year.

But I know that the mathematical expectation for the lottery is -50%, so if he buys $100 worth of lottery tickets in a week, he’ll see a loss of $50 on average.

Whether you’re winning or losing, you need to know how much you’re winning or losing.

Sticking With a Budget

The next step to becoming a winning gambler is to set a bankroll budget and stick with it. In fact, I want you to make a resolution right now:

Promise yourself that you will never gamble money that you need for any other legitimate expenses.

This means if you’re behind on the child support or haven’t paid all your utility bills for the month, you should get those bills caught up before placing even a single bet at the casino or on a lottery ticket.

Dice and Playing Cards

You should have a bankroll set aside specifically for gambling, and it should be considered part of your entertainment budget – just like your cable TV bill.

Casino gamblers generally lose money because they usually play negative expectation games.

You can beat the odds some of the time, but most of the time, you won’t.

So don’t play with money you can’t afford to lose.

It’s that simple.

Find Low Variance Bets – Even If the House Edge Is Higher Than a Similar Bet With a Higher Variance

Volatility is one subject that gambling writers don’t spend enough time on. They focus more on comparing the house edge of games.

But the house edge only tells part of the picture.

Here’s an example:

You might be playing a progressive slot machine game where the jackpot is so high that the house edge is 0%.

In fact, it might even be in your favor – you might be playing with a mathematical edge against the house.

But if your probability of hitting that jackpot is 1 in 100,000, it might make more sense to stick with a lower volatility bet.

Here’s what happens in a situation where you have a huge jackpot with a positive expectation:

You lose money until (and if) you hit the jackpot. As most people know, that doesn’t usually happen. Some games offer bets with the same house edge different volatilities.

Roulette is the best example. In an American roulette game, all the bets (save one) have a 5.26% house edge. But a single number bet only wins once out of every 38 spins on average. An even money bet (like a bet on black) wins almost half the time. You’re better off going with the lower variance bet in the short run.

Most of the Time, Winning at Gambling Means Playing in the Short Run

Think of the house edge for a casino game as being similar to your long-term return in the stock market.

If you’ve ever invested in the stock market, you probably already know that sometimes you’ll see days where you get a return of 20% on a single stock.

But over time, that return evens out and gets closer to the average that you’d expect.

This is true of casino game bets, too. The more casino bets you make, the closer your actual results will start to resemble the mathematically expected results.

And if you’ve ever considered the size of the electric bill at one of those fancy casinos, you probably already know that the mathematical expectation for the casino is strongly in its favor.

This means that the longer you play, the likelier you are to see a loss.

But it also means that if you want to win money, staying in the short run is the way to go.

What Does It Mean to Stay in the Short Run?

An Englishman named Ashley Revell sold everything he owned to place a single roulette bet in Las Vegas. This means he bet $135,300 on a single spin of the roulette wheel.

He bet it all on the color red, and he won.

His goal was to get a fresh start in life, so he thought he’d either start off rich or poor. Either way was a fresh start.

But if you think about it, betting your entire bankroll on a single spin of the wheel is the ultimate example of staying in the short run.

I’ve seen this called the “maximum boldness” strategy.

Roulette Wheel

The idea is that you make fewer bets that are larger in size.

If you have trouble understanding how that works, think about the probability of doubling your money on a single spin of the roulette wheel compared to 2 spins of the roulette wheel.

Gambler A has $100, and so does Gambler B.

Gambler A bets it all on red. 18 out of 38 times, he’s going to double his money. That’s a 47.37% probability of doubling your money.

Gambler B bets half of it on red with the intention of betting $50 on red on the 2nd spin, too.

The probability of winning BOTH spins, which is what he’d need to do to double his money, is 47.37% X 47.37%, or 22.42%.

Obviously, you’d rather have a 22.42% probability of doubling your money, if that’s your goal.

Stay Away From the Slot Machine Altogether

No game will take more of a toll on your bankroll than the slot machines. That’s because slot machines force you into the long run faster than you think possible.

The trick to winning at casino gambling is to quit after a short session so that you’ve taken advantage of short-term variance.

For example, an average roulette player might make 30 or 40 bets per hour, which isn’t nearly as statistically significant has hundreds of spins.

On the other hand, a slot machine player, on average, spins the reels 600 times per hour.

You can lose a lot of money making 600 bets per hour – even if those bets are small in size.

Switching to video poker is one solution, but video poker requires skill to play well. The house edge is so much smaller on video poker that it’s ridiculous.

A better option, though, is to learn how to play a couple of table games. Even the table games which a high house edge cost you less in the long run because the rate of play is so much slower.

Losing 6% on average on a slot machine with 600 bets per hour is far more damaging to your bankroll than losing 5.26% on 35 bets per hour, even if you’re betting more money.

Gamble on Something Where You Might Be Able to Get an Edge

You can only get a mathematical edge on a handful of gambling activities. Poker is one of these. Sports betting is another. As far as casino games go, you’re limited to blackjack and video poker, probably.

Each of these requires a skillset that 95% of gamblers don’t have.

Here’s why:

You’d think that poker would be a break-even game most of the time. After all, you’re probably an average player playing with other average players.

If that were true, you would be playing a break-even game – at least when you weren’t facing more skilled players.

The problem is that if you play poker at a casino – or even in an independent cardroom – you’re facing a rake. The house takes an average of 5% from each pot to pay for them hosting the game.

Not only do you need to be better than the other players at the table to show a profit, you must be of such a high caliber that you make up for the 5% rake.

Gambling With Casino Chips

Sports betting has a similar problem. The bookmakers do a good job of setting up the point spreads so that you’ll have a 50% probability of winning, which would make for a break-even proposition.

Except bookmakers charge something called “the vig,” which is comparable to the rake in poker. Instead of wagering $100 to win $100, you have to wager $110. This means that you have to win a little over 52% of the time just to break even.

I’m sure you already know about the house edge for casino games, but in case you don’t, the casino sets their games up mathematically so that they always win in the long run. The amount they win on average from each bet over time is called the house edge, and it’s expressed as a percentage.

Blackjack and video poker are exceptions, but for different reasons.

Real money blackjack is a game where you can get an edge if you count cards. That’s not something the casinos allow. If you get caught counting cards, the casinos will ban you from playing there. They might even trespass you from the casino altogether.

With video poker, you can get a tiny edge, but only on specific games with specific pay tables. But you must know how to play each hand perfectly to achieve those results. Sometimes you can get a small edge by combining a tiny house edge with the rewards program from the slots club.

I’ve also read that you can get an edge at horse betting if you know how to handicap, but I consider that similar to sports betting, which I’ve already covered.

But you should learn how to participate in some of those gambling activities.

What You Shouldn’t Do If You Want to Win More Often

You probably shouldn’t fool around with betting systems, although you can if you want to. I also recommend against some of the zanier ideas related to money management.

A betting system is a strategy for raising and lowering the size of your bets based on whether you won or lost on the previous bet. You can have fun using betting systems like the Martingale, but they can’t overcome the house edge.

The usual money management advice is to set a win goal and a loss limit and quit when you’ve hit either of those numbers. The idea is that you can stop losing sessions sooner and quit winning sessions while you’re still ahead.

That’s true to a certain extent, but not to the extent of changing your odds on the game. The house edge remains in place.

With most betting systems, especially the Martingale, you’re just creating more volatility rather than changing the odds.

That can be fun as long as you’re willing to weather the occasional big losing session – and if you’re willing to settle for frequent small winning sessions.


Winning more at gambling involves being more aware of what you’re doing. I’m a big fan of mindful gambling.

Understanding what you’re doing and what odds you’re facing is the most important thing you can do to win more often.

Really, the rest of the tips are just details.

Without the initial knowledge, you’re trying to fly an airplane in the dark without lights.

Michael Stevens

Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for since early 2016. ...

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