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12 Ways to Gamble

By Randy Ray in General
| October 8, 2015 12:00 am PDT
Dice and Chips

Last week, a friend of mine told me she was going to trade in her other addictions for a gambling addiction. She was joking of course, but let’s assume that she wanted to get started as a gambler. It’s a big enough hobby that it might be hard to figure out where to start.

Below I’ve listed 12 ways to gamble. They include games you can play at a casino as well as activities available on the Internet. I’ve even included some options for placing wagers at home or in the office.

1. Start Hosting a Home Poker Game

Everyone knows how to play 5 card draw, so you could always start with that. But even if you don’t, hosting a poker night can still be easy. Just buy the equipment and read a book about poker variations.

Here’s the equipment you’ll need:

  • A table that seats 5 to 10 people. You can buy a real poker table if you have the money, but even a decent-sized dining room table will do the trick.
  • Clay poker chips. You can get a decent set of these for less than $50. They add an atmosphere to the game that’s impossible to match with plastic chips. Some people just use cash at the table, too, but that’s harder to manage.
  • At least 2 decks of playing cards. I like to buy plastic cards, like the ones made by Kem. When someone spills a drink on them, you can just wipe them off. Since they’re not made of paper, they’re hard to ruin.
  • A rulebook of some kind. This is strictly optional, but it can be nice to have some rules to refer to. If everyone there is new to poker, it’s a good idea to at least have a list of the standard poker hand rankings available for them to consult.
  • Snacks and drinks. You can’t host people without offering them something to eat and drink. I’ve played in home poker games that were potlucks, and I’ve also played in games where everyone threw in $5 or $10 toward food, with the host providing the meal from the proceeds.

An excellent book to buy and read before hosting your own poker night is called, aptly enough, Poker Night by John Vorhaus. You can buy it used at Amazon for $4, shipping included, and it provides detailed instructions for hosting your own home poker games.

Alternatively, you can look for someone else’s game to join. Local bars often offer free poker tournaments with cash prizes for the winners. Cigar shops also often host such events.

2. Set Up and/or Join an Office Pool

You don’t need a bookie to bet on sports. In a lot of offices, betting pools are already running, especially during football season. All you have to do is ask to get involved.

These contests can involve a certain degree of skill, or they can be completely random. For example, if you have to pick winners, a certain amount of knowledge and skill can help you get the edge over your opponents in the office. On the other hand, if it’s some type of lottery, like picking squares that correspond to numbers, there’s absolutely 0 skill involved.

The nice thing about office pools is that you’re almost never facing a house edge. Depending on the amount of skill involved, your odds of winning are as good as anyone else’s—maybe better. Any time you can get money into action without a house edge, then you’ve made a pretty good bet.

Here’s an example of an office pool where skill is involved:

You work in an office with a couple dozen people. It’s football season. Everyone throws $10 in the pot, so there’s $240 in winnings available. Everyone takes a list of the 16 or so pro games that are being played in the coming week and chooses the winner for each game. The player with the most correct guesses wins the $240. Players who tie get to divvy up the winnings between them.

Here’s an example of an office pool with no skill involved:

In the same office with two dozen people, someone sets up a table of 10 columns by 10 rows. Everyone has the opportunity to buy a square for $20, so there will be a total of $200 in the pot. After everyone has bought their squares and added their names to the chart, numbers from 0-9 are drawn for each column and for each row.

These numbers represent the 2nd digit of the final score of the game. The columns are for one team; the rows are for the other. So if a game ended with a score of 20 to 10, the player with the square corresponding to 0,0 would win the pot.

In some versions of this pool, there are winnings for the score at halftime and again at the end of the game. So you might have two $100 pots.

This game is entirely random. It’s like participating in a tiny local lottery where the numbers are determined by sports scores.

You’ll also find these kinds of betting pools available in your local bar.

3. Sign Up for a Season-Long Fantasy Sports League for Money

I’ve played in a lot of different fantasy sports leagues, mostly football, and some of them are just for bragging rights. But the more interesting fantasy sports leagues are the ones where there’s money on the line. It’s a lot of excitement over the course of a season for a relatively small investment.

It’s common for a fantasy football league, for example, to consist of 12 managers. Each manager drafts a team of players. They then start a roster each week and earn points based on how the members of their team perform during their games. The commissioner for the league sets up a schedule for whose team plays whose.

The playoffs are usually determined by a manager’s winning record. The winner of the playoff is the champion.

A common entry fee for a season-long fantasy sports contest is $100. That’s $1200 in prize money. Some leagues pay the entire amount to the winner. Others have prizes for 1st, 2nd, and 3rd place.

Scoring systems and results are generated differently depending on your league rules. I’ve played in leagues where the winner for the year is the team that accumulated the most points all year, regardless of their record versus other teams. I’ve also played in leagues where every team played every other team every week. (Yes, that set-up really is as complicated as it sounds.)

Season-long fantasy sports are a lot of fun, and it is considered a game of skill. When the U.S. federal government passed the UIGEA (Unlawful Internet Gambling Enforcement Act), they specifically exempted fantasy sports from the restrictions. It’s a hugely popular way to gamble.

4. Try Daily Fantasy Sports on the Internet

If you watch professional sports on television, you’re almost certain to have seen ads for websites like DraftKings and Fanduel. These are sites which take the concept of fantasy sports but reduce the time frame for a league to a single day or week. These games are almost always played for money.

The buy-ins for daily fantasy sports contests can be as low as $0.25, but I’ve also seen contests with buy-ins as high as $5300. The number of players involved in each contest can vary dramatically, from head-to-head leagues, where you’re facing a single opponent, to huge tournaments with 400,000 entrants.

Daily fantasy sports are arguably a game of skill, but when you’re playing in a tournament with 400,000 people, even if you’re twice as skilled as the next guy, your odds of winning are akin to that of winning the lottery. Yeah, the top 80,000 or so places get some kind of payout, but the really big payout at the top is a 1 in 400,000 shot. Assuming you’re twice as skilled as the average player, you’re still looking at a 1 in 200,000 shot.

5. Sign Up at an Online Casino and Try the Casino Games There

Depending upon where you live, this might or might not cross certain legal boundaries. I’d never advise anyone to break the law, but if you live somewhere with legal online casino gambling, getting started on the Internet can be a lot of fun. The Web-based games can be remarkably similar to the games as they’re played in an actual casino.

Slot machines and video poker games are the two biggest draws in the online casino world. The former require no skill at all, but the latter do. Some of the online slot machines are even more exciting and visually compelling than their land-based counterparts. Video poker games are easy to learn, too, especially if you have a little bit of experience at the tables.

Some of the more interesting opportunities at online casinos these days are the live dealer games. These are games like blackjack and roulette, only played via Webcam. They’re almost exactly like their land-based casino game counterparts. Some players enjoy seeing a real deck of cards or a real roulette wheel in action. Webcam casinos cater to those players.

6. Find a Local Bookie and Place Some Sports Bets

This one skirts the law for sure, since taking bets over the phone on sporting events is illegal at the federal level. Enforcement activities always focus on the bookie, though—I don’t know of any bettors who’ve ever been arrested or prosecuted for putting some money down on a football game.

Finding a bookie is the tricky part. Because of their outlaw status, bookies don’t run ads in the newspaper, on the radio, on television, or in the yellow pages. The best way to find a bookie is to become a regular at a bar where people watch a lot of sports. Usually the bartender or some of the regular patrons there will be willing to refer you to someone—once you’ve gotten to know them.

It’s a good idea to learn about the different kinds of sports bets and how the vig works. Neighborhood bookies tend to operate similarly to professional books, although they usually offer a smaller variety of bets.

Most bets with your local bookie will be on point spread bets. These are bets where the favorite has to win by a certain number of points for the bet to pay off. For example, if New England is a 7 point favorite over the Dallas Cowboys, that bet only wins if New England wins by more than 7 points.

They’ll also usually require you to risk $110 to win $100. The extra $10 is the “vig”. It’s easiest to think about it as a commission on each bet that the bookie takes. The book’s goal, even a local bookie, is to get about the same amount of money wagered on each side of a game. That way they’re guaranteed to make a profit on every bet.

Here’s an example:

A bookie has 40 customers betting on a game between the New England Patriots and the Dallas Cowboys. Half of them take the Patriots, and the rest take the Cowboys. Assuming every bettor wagers $100 on the game, the book takes in $4400, but he only has to pay out $4000 in winnings to the winning side. He has a guaranteed profit of $400.

7. Travel to Las Vegas

There’s probably no better way to get started with a gambling hobby than to visit Sin City. Not only do they have the widest variety of casinos and casino games in the United States, but they also offer all kinds of things to do besides gambling. It’s also a great city to visit on a budget.

If you’re planning a trip to Las Vegas for the purpose of gambling, you should set aside a bankroll specifically for your gambling activities. For a 3 day trip, for example, you might take $450 to gamble with. Play with $150 per day. You can even break that down into “session bankrolls”.

This is especially important for beginners. It’s not uncommon for new gamblers to get so excited that they lose more money than they expected. You sure don’t want to get in a situation where you’ve gambled away all your money for food or other types of entertainment.

Of course, if you’re a high roller, $450 might be less than what you spend on a single blackjack or baccarat bet. If that’s the case, call some of the casinos beforehand to let them know that you’re coming to Vegas to gamble, and you’ve got a lot of money. They’ll make you all kinds of offers for free travel, free food, and free event tickets in order to entice you to their hotel and casino. They’ll want to know how much you plan to bet while you’re there and on what, so be prepared to discuss this with them. The perks for high rollers can be amazing.

8. Visit Macau

If you really want to get exotic, or if you think Vegas is a little too old-school, you might consider planning a trip to Macau. It’s possibly the biggest gambling Mecca in the world now. They play a lot of the same games that you’ll find in Vegas, but the number of people playing a specific game can be dramatically different.

For example, 85% of table game players in Macau are playing baccarat. Yeah, you’ll see baccarat at a Vegas casino, too, but you won’t see nearly as many people playing baccarat as you’ll see playing blackjack.

Pai Gow (with the tiles) is also popular in Macau, but it’s played a little differently there. For one thing, tradition in Macau requires you to set your hand while the tiles are in the table; you’re not supposed to pick them up. For another, players in Macau set their hands by feeling the tiles rather than looking at them. That’s a big change from how the game is played here in the United States.

9. Find a Casino Near Where You Live and Take a Road Trip

Of course, you might not want to take a long trip. Depending on where you live in the United States, you’re probably just a few hours’ drive from a casino. I live in Texas, and there are precious few casinos here. But Oklahoma is just an hour or two north of Dallas, and there are casinos aplenty there.

Different states have different laws about what kind of casino gambling is acceptable, though. For example, in Oklahoma, gambling is limited to certain types of slot machines. They’re also allowed to deal blackjack games, but they have to take an ante of 50 cents per hand from the player. That kind of rule completely eliminates your ability to get an edge by counting cards.

Some states have casino cruises. You get on a boat which travels out to sea far enough that they’re in international waters. Once there, you’re able to gamble on casino games, because there are no applicable laws that apply. The only problem with these kinds of casinos is that the odds aren’t as good as you’ll find in traditional land-based casinos in traditional gambling destinations like Las Vegas. Still, if it’s the only game in town, and you want to get into action, why not?

10. Play the Lottery

In some states, the lottery is literally almost the only game in town. I hate the lottery because the odds are so bad. I also hate it because I don’t think the government should be involved in running a casino type business. But you might try it and see if you like it.

Scratch and win tickets are how most people start. The prize amounts are smaller, but you win more often. The big jackpots rarely pay off at all, but when they do, they can change your life. Unfortunately, the odds of winning one of those large jackpots are ridiculously low.

And when I say low, I mean 1 in 175 million. By way of comparison, your odds of being struck by lightning sometime during your life are 1 in 12,000.

I don’t mind the low odds of winning so much, but I do mind the overall payout percentage and house edge on the lottery. Even the worst slot machine games in Las Vegas have a return to player of 75%. Most of them are in the 90% or higher range.

That means when you bet a dollar on a slot machine game, over time you’ll see 75 cents in winnings on that dollar. That’s averaged out over thousands of bets. You’ll be up sometimes, but you’ll also be down sometimes.

But the payout percentage on the lottery, in general, is about 50%. It’s one of the worst gambling games in existence.

It’s a fun and stress-free way to get a little bit of gambling in, but mathematically, it’s one of the worst deals you can find in a gambling game. In fact, you’re probably better off playing keno games at the nearest casino.

11. Visit Your Local Bingo Hall

Bingo’s an interesting gambling game because it lacks the “sinful” reputation of other gambling games. When’s the last time you saw a church offering a blackjack game or a casino night? But you see bingo games being held at churches all the time.

In many states, bingo games are required to give a certain percentage of their revenue to charity. So not only can you get into action, but you can feel good knowing that at least some of the money you’re losing goes to help those in need.

Bingo is one of those games that involved almost no skill at all—except maybe for the ability to multi-task. You have to be able to keep up with what numbers have been called on the cards. Doing this for a single bingo card is easy, but most serious bingo aficionados like to play multiple cards at one time.

Bingo is also legal in a lot of states that don’t allow casinos. They usually fall into the category of “pari-mutuel” games, which are gambling games where all the payouts come from the player’s contributions. In other words, there’s a direct relationship between how much money people spend on bingo cards and how much money is available to be won.

12. Find a Local Bar that Offers Pool Tournaments

I mentioned earlier that you can find bars with free poker tournaments. You can often find bars which offer pool tournaments, too. These usually require an entry fee, though.

Pool isn’t the only game played in bars for money, though. I played in a weekly table shuffleboard tournament with a $10 buy-in for years. Those were some of the most enjoyable nights out I ever had.

You can also find bars which host darts tournaments. I’ve never enjoyed darts, but I know a lot of people do. And if you’re hoping to get some money into action, that’s probably as good a way to do so as any.

You can enter trivia contests with prizes, too.

Usually any of these types of tournaments have an entry fee which goes toward creating the prize pool. For example, in the shuffleboard tournament I used to play in, we spent $10 to play. We’d often have as many as 20 or 30 participants. The team that won first prize got to split the prize money. Second prize got a free entry to the following week’s tournament.

Sometimes bars will add money to the prize pool in order to make it an even better bet. It was not uncommon for the owners of the bar I used to frequent to add $50 to the prize pool.

Shuffleboard’s a game of skill, but we drew partners randomly, so everyone—even the worst players—had a shot at winning. When the bar added money to the prize pool, it created an “overlay” situation. Even if you were a bad shuffleboard player, you had a positive expectation if you got lucky and drew a good partner.

Bars hold pool tournaments and the like in order to attract customers. The more people who are in the bar, the more drinks they sell. It’s a simple and effective marketing tactic.


Gambling can be a fun hobby for people who don’t have impulse control problems. If you want to give it a try, you have multiple options available. Some require travel, but many can be done right in your own backyard, so to speak.

The main thing to keep in mind with any kind of gambling activity is this:

Never gamble with money you can’t afford to lose. Your gambling game bankroll should always be funds that are kept separate from your living expenses. If you spend the rent money playing slot machines, you could wind up on the streets.

That’s not a good way to gamble.

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  1. rebecca balutis January 23, 2020 at 4:37 am

    I want to win toudeds of dollars



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