How to Win at Gambling

Whenever you talk about gambling, people tend to have very strong feelings towards or against it.

For some, they think about trips to Las Vegas with their friends, good times, and a little wagering to spice things up. For others, they think about folks wasting their money on scratch-offs and weekly Powerball lottery drawings.

Whatever gambling means to you, today I am going to show you how to win at gambling.

First, when you think about “winning at gambling,” you have to separate it into very different objectives:

  • Are you playing for fun?
  • Are you playing to make money?

These are two very different goals. If you’re playing for fun, it’s about maximizing excitement and having a good time. If you’re playing to make money, you have to approach games far more strategically and much of the “winning” happens before you even play the game.

Table of Contents
  1. Playing for Fun? Go for Big Wins
  2. Playing for Money? Find an Edge
    1. Take Advantage of Promotions
    2. Stack the Deck in Your Favor
    3. Find an Inefficiency in the System

Playing for Fun? Go for Big Wins

A couple of years ago, my buddy Jeff, me, and my wife are just hanging out at the bar of a sportsbook chatting and “playing” video poker.

Much like watching a baseball game, the game itself is really just something to do while you sat around, enjoyed adult beverages, and spent time catching up with your friends. The game marks the passage of time more than offers up entertainment itself.

That’s when Jeff, who is actually the same friend who enjoys horseracing from a previous post, shared his approach to video poker. His horseracing tips were golden so I trusted his advice on these matters.

If you are put to a decision where you have to pick between a low probability of a big win or a large probability of a small one, always go for the big win. He didn’t get into boundary cases or expected value math but I took it at face value and did it. .

I gave that approach some more thought over the years and I’ve come to this conclusion – his approach is both correct and NOT mathematically sound.

But that’s OK because neither is gambling!

When you’re gambling, you are giving up odds to the casino in return for entertainment. With video poker, you get free drinks too.

You’re trying to maximize entertainment, not return on investment. Your expected return in gambling is negative so if you want to make money, the best thing to do is not gamble at all. Do something else.

If you’ve chosen to gamble, you’re not maximizing return but entertainment. You should maximize what will give you the greatest high – for that fleeting moment between when you decide to go for the big win and when you press “Deal.”

That moment is what you’re paying to enjoy.

And if you hit something big, which you will more often than you expect, the little rush you get after that is what you’re paying for. If you end up positive, even better – free entertainment and free drinks! You win!

We sat at the sportsbook of the Cosmopolitan for only a few hours and I hit five four-of-a-kinds (on a max bet of $1.25 per game – always play max bet on these games)

Thanks Jeff!

Was it fun? Yes.

Was it profitable? Yes. (this time!)

Did we win? Double yes!

That’s what matters.

As an aside, you could make the argument that you should always make the higher expected value choice. In those boundary cases, where the expected value of going for the big win is sometimes greater than the smaller one, so the math supports you. But we almost never have perfect information and I’m willing to wager that going for the big win probably has a lower expected value than the smaller win. Plus I’m sitting there with friends and not looking to calculate anything. πŸ™‚

Playing for Money? Find an Edge

If you’re gambling to win money, then all your hard work happens before you show up to the game. You have to find an edge that you can use repeatedly to maximize your earnings and avoid bad luck.

You have to research games so you pick ones with positive expected returns (hint: they’re almost always not going to be inside a casino).

Take Advantage of Promotions

Back in college, one of my craziest side hustles was casino promotions. This was when online casinos were more of a thing but they would give you a bonus based on your deposit. Deposit $100, get $100 in free cash.

The only catch was that you had wager a multiple of the bonus before you could withdraw your money. In the beginning, the multiples were like four times or six times. Eventually, the casinos got as high as twenty and twenty-four times before I stopped doing it because the edge was gone.

I tracked my wagering in a spreadsheet (I wish I kept it!) very closely and it felt more like work than entertainment!

A promotion can give you an edge since you get to play with some of the house’s money. In casino promotions are usually quite terrible, a few bucks that you need to wager multiple times in a slot machine, but other wagering platforms (like fantasy sports) still offer up deposit bonuses.

Stack the Deck in Your Favor

The only other way to win at gambling is to improve your odds through knowledge or tactics.

With video poker, there isn’t much you can do to improve your odds. You can pick the machines with the best payouts or the lowest house edge, but after that, it’s just you playing the game. Through knowledge, you will know to play a game a certain way to improve your odds.

For example, if you have three of one suit, don’t try to keep them to make a flush (unless it’s the straight flush). If you have three of a kind with an Ace kicker, don’t bother keeping the Ace. You want two shots at the fourth card in the four-of-a-kind. Stuff like that is pretty simple and takes just a few minutes of reading.

There are other games, more complicated ones, where you can significantly improve your odds but sometimes that means playing in a way that the casino might not like. πŸ™‚

For example, my friend Colin runs a membership site called Blackjack Apprenticeship. He used to be on a card-counting team and tilted the odds in his favor with more information by playing on a team. Those teams worked well because they knew when to bet big when a deck was favorable to the players and casinos hated it.

He now teaches card counting, which on its own can improve your adds, and card counting on its own is enough to give you a small edge over the casino depending on the rules of the game.

You can win if you change your tactics… until the casinos kick you out. πŸ™‚

Find an Inefficiency in the System

One of the best parts about games is that they’re imperfect. This is especially true of casual games among friends or loosely affiliate people. I’m talking about Fantasy Football, March Madness brackets, and pick ’em leagues – casual games that won’t make you rich but can self-fund the entertainment.

Sometimes these games have quirks that you can use to get an edge.

For example, I’m in a football pick ’em league where you have to pick ten games a week. You pick the winner of each game (with the spread) and the person with the top three players (by wins) at the end of the season takes home a prize.

I’m going to start you off by explaining I’m not well versed in sports betting but there is one quirk about this league. The point spreads are set at noon on Tuesday but you have to submit your picks by noon on Thursday. That’s two days for the point spread to move and you can use that to find games where the spread has moved a few points in your favor. You can see how this would be helpful. πŸ™‚

There are inefficiencies everywhere in life, not just in gaming, and this is a useful skill to nurture!

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About Jim Wang

Jim Wang is a forty-something father of four who is a frequent contributor to Forbes and Vanguard's Blog. He has also been fortunate to have appeared in the New York Times, Baltimore Sun, Entrepreneur, and Marketplace Money.

Jim has a B.S. in Computer Science and Economics from Carnegie Mellon University, an M.S. in Information Technology - Software Engineering from Carnegie Mellon University, as well as a Masters in Business Administration from Johns Hopkins University. His approach to personal finance is that of an engineer, breaking down complex subjects into bite-sized easily understood concepts that you can use in your daily life.

One of his favorite tools (here's my treasure chest of tools,, everything I use) is Personal Capital, which enables him to manage his finances in just 15-minutes each month. They also offer financial planning, such as a Retirement Planning Tool that can tell you if you're on track to retire when you want. It's free.

He is also diversifying his investment portfolio by adding a little bit of real estate. But not rental homes, because he doesn't want a second job, it's diversified small investments in a few commercial properties and farms in Illinois, Louisiana, and California through AcreTrader.

Recently, he's invested in a few pieces of art on Masterworks too.

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  1. steveark says

    Playing negative sum games involving my hard earned money just seems not at all fun. Plus what if I won $1,000 or $100,000? Neither of those is going to impact my net worth or lifestyle enough to notice. While I still will feel some pain from losing money I don’t feel much gain at all by increasing my stash. I guess this will be put to the test again in a couple of months. An old college friend wants my (also non-gambling) wife and me to go to a casino with him and his wife for a weekend. I have no moral qualms with gambling, its just entertainment, it just isn’t very good entertainment compared to playing tennis, going for a hike, fishing or just about anything else we do for fun. But if someone does enjoy it, then its probably a great hobby for them. We’ll try to act like we are having fun. And the food will probably be good.

    • Jim Wang says

      I don’t play everything my friends like to play. I’ll hang out and play video poker while enjoying a few beers and the occasional hand of blackjack or Pai Gow. I’ll chip in a few bucks on horse races at the sportsbook while we kill time and even play some craps.


      I stand on the sidelines for roulette.

      My friends will play that and I’ll just stand and enjoy the ridiculousness of that game. πŸ™‚

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