"I call him Gamblor!"

“I call him Gamblor!”

There are hundreds of different side hustles you could possibly do. You could sell your bodily fluids, some sexier than others. You could walk dogs or babysit larger, less smelly, more human dogs. You could even take pictures of your used underpants and sell them on the Reddit, a thing that actually exists.

Man, capitalism will never cease to amaze me.

For a while, during the Saturday/Sunday/Friday/Monday morning dumps, I was doing a gambling category. I’d pick three games to bet on, keeping track of my record. I eventually got it back to a little over .500 after spending the better part of a year in the hole. Luckily for me, I never placed an actual dollar on any of those games.

But just because I am a terrible gambler doesn’t mean you can’t make money gambling. Here are a handful of ways you could potentially make a little extra cash doing it, with their chances of success.


Back in the early days of this here blogening, I took a look at doing this using a computer program. Back then the programs were more basic than they are now, but many actually came with evidence that they’d be consistently profitable players at the lowest stakes, i.e. where the shitty players hang out.

The only problem is the poker websites hate poker bots. If you’re caught using one, your ass is gone than me finding an episode of Sex and the City.

So you’re probably going to want to play the old fashioned way. Poker isn’t nearly as popular as a few years ago, which means a lot of the crappy players have moved onto daily fantasy sports, or some other such nonsense. This is making it more difficult for average or maybe slightly above average players to make consistent money.

I know a couple of guys during my days as a casual player who make a decent amount of income playing poker. I also know more who downright suck at it, and shouldn’t even be trying.

Your chances of success: moderate


If you play blackjack properly, the casino’s edge falls to practically nothing. Assuming, of course, the casino gives you rules that aren’t terrible.

In a relatively standard game (one that lets you split aces, double down on any two cards, and pays 3-2 blackjack), the house’s edge is about 0.4%. Which means the house will win 50.4% of the time, while you’re winning 49.6%.

You can push this edge slightly into your favor by counting cards and betting more aggressively when the odds are in your favor. You can’t go nuts doing this, or the casino is going to kick your ass out. If you’re betting $5 at a time, going up to $500 is a no-no. But you could probably get away with $25.

But even if you’re playing optimally, Blackjack is still a losing proposition over time.

Your chances of success: low

Sports betting

If I were to try make money gambling, I’d probably try doing it with sports betting.

You have to be smart with it, unlike when I dabbled in the art. It involves doing a ton of research and being very selective in what games you happen to choose.

I’ll give you one system that has worked out pretty well. From 2000 until 2013, there were a total of 67 NFL games where the home team was a double digit underdog. Think of situations like the Packers going into Detroit back when the Lions were terrible. The home team only had a record of 26-41 in those games, but they covered the spread 82% of the time.

Depending on how generous your bookie is, you’ll have to hit between 52.5% and 55% of your games right to make any money betting on sports. But if you’re very selective on games you want to get on, I’d say it is possible to make money gambling on sports.

Your chances of success: moderate

Slots and other casino games

Uh, probably not. Definitely not with slots, anyway. Unless you find a way to screw the system. Here’s a fun story of two guys who found a way to screw the casino in video poker.

The best odds are with full-pay video poker, craps, roulette, and baccarat, all with a house edge of less than 2%. You’ll still lose money over the long-term, but hey. If you go to Vegas and play the minimums, you could maybe get enough in free drinks to do okay.

Fun fact: back when I used to drink the alcoholic beverages, I found a keno machine in Vegas that let me play a penny per bet. I got six drinks for a total investment of $7 before stumbling back to my hotel room.

Your chances of success: almost zero, unless you’re okay getting paid in booze

Investing in the casino

Okay, this isn’t technically a way to make money gambling, but it is a way to make money off gamblers. Which is really close, dammit.

There are several ways you can do this. One stock I’ve invested in is Dover Downs Entertainment (NYSE:DDE), which owns a single casino in Delaware. It’s only breaking even on an income basis, but it trades for a mere fraction of its replacement value and is cash flow positive. It’s waiting patiently for the state legislature to pass a bill that gives it some relief on slot taxes. There seems to be political support for such a thing, it’s just a matter of getting it done.

But Dover Downs doesn’t pay a dividend, and people might not like it because shares only trade at $1. A couple of Canadian options are Gamehost (TSX:GH) and Great Canadian Gaming (TSX:GC). Both own physical casinos.

Let’s start with Great Canadian. It owns 13 casinos in Canada and 3 in the U.S. It’s comfortably profitable, trading at about 17x earnings. It’s currently flirting with a 52-week low, as are most Canadian consumer discretionary stocks. But it doesn’t pay a dividend, choosing to put all of its income back towards paying down debt.

The more interesting one — at least to me — is Gamehost. It owns a grand total of three casinos and two hotels in Alberta. The casinos are located in Calgary, Grande Prairie, and Fort McMurray, three places which aren’t doing well right now. The hotels are attached to the casinos in Calgary and Fort McMurray.

Gamehost’s management owns about 40% of the outstanding shares, something I always like to see. And the company is also sitting on a fairly healthy cash hoard, with shares trading at a reasonable 12.5x trailing earnings. It pays a real nice dividend too, coming in at 8.7%.

Your chances of success: high to very high

Tell everyone, yo!