The New Side Hustle Netted $1,091.44 In One Day

I almost didn’t write about this hustle. Does anyone need yet another story boasting about how the author spotted an opportunity, jumped in and out, and already has over $1,000 for her trouble via our friends of the Pals of Pay?

Probably not.

And yet I have reconsidered. You won’t be able to duplicate the exact hustle, but you may get a similar opportunity in the not-too-distant future. More likely, you will have an “opportunity” dangled in front of you that looks like a good hustle — only you might be the one getting hustled.

You see, the hustle in question is online sports betting. You may have been profitably involved in this enterprise for years. In that case, carry on. You’ve got nothing to learn from my amateur effort.

This story is for two kinds of people:

* You’ve been sports-betting online for two decades, but that’s also how long you’ve been donating money. You’re doing it wrong.

* You’ve never placed a sports bet, but the online game has been legalized in your state, and a lot of ads keep targeting you to invite you to play, and, hmm, it sure seems like they’re giving away money.

Your perception is correct. The new online sportsbooks are giving away money. Let’s see if we can get you some without turning you into a donator.

What I Did

I live in Louisiana, as regular readers already know from my semi-frequent photographs of these guys:

As a result, in recent weeks, my Twitter feed has been absolutely crammed with promoted posts to remind me that online sports betting in Louisiana was about to go live at any minute. Multiple books were therefore offering free bets to anyone who signed up.

I like free. Who doesn’t like free?

So I tried to sign up with four of them. They all test your location to check and see if you really live in Louisiana. One of the four came back and said I lived in New Jersey.

Dude, I’ve been living in southeast Louisiana since the 1970s.

Since I already have too much money to be highly motivated — don’t get old, kids — I didn’t worry about that offer anymore. A determined person could have probably got it fixed by kvetching to customer service. But, these days, when it comes to side hustles, I’m looking for three things — easy, fast, and profitable.

Two out of three doesn’t count.

So now I’m signed up for three books. Two of those three are subsidiaries or at least carry the names of casinos that have asked me not to be their customer thanks to my previous life on a blackjack team. At this point, I don’t know if they’ll actually let me play or cash out.

I mean, they’re going to know who I am if they want to know. I’m living in the same place under the same legal name, address, and Social I had thirty years ago, so it doesn’t take Sherlock to figure out I’m the same person they didn’t like before.

But if I don’t spend too much time and angst on it, what do I have to lose?

So I get free bets from the three books for $200, $250, and $300. So far, so good.

Of course, you can’t just sign up, nab the free money, and then cash out. The books aren’t stupid. You have to have enough gamble in you to place at least one bet. Otherwise, they don’t need you coming around.

What I know about American football is only what I need to carry on some barroom small talk, and I’m not going to suddenly learn more. So, to save too much thinking, I put a ten-minute time limit on choosing where to place my free bets.

In late January, everybody already thought it would be Bengals vs. Rams in the Super Bowl. Might as well bet on that. Plus I made some other random bets around the January 30 games. They weren’t any more deeply thought out. Heck, I forgot what they were almost before I placed them.

Late on the evening of January 30, it occurred to me that the issue had been decided. So I logged into my accounts to see the settled bets at my three books. I’d won $385, $381.82, and $324.62 — a total of $1091.44.

Way cool. But I didn’t get too excited yet.

Let’s see if they cash me out.

One of the sites was easy-breezy. The other two — the same two owned by entities who had expressed displeasure with my action in decades gone by — wouldn’t cash me out at first.

Uh-oh. I poked around a little.

Found out they wouldn’t cash me out because I’d never placed a deposit.

All right. I can do that.

I started with the one that had a minimum deposit of $10. A few hours later, I withdrew $334.62 for a profit of $324.62.

Encouraged, I then made the min deposit of $20 at the other one. They dilly-dallied for a few days, but they too eventually sent me the money.

Score!

I’ve scattered my receipts throughout this story for your viewing entertainment. Also to back up my bragging.

What You Should Do

My advice will vary depending on your location, your history, and your tendency to addiction. If you have a history of gambling or gaming addiction, back away from this hustle right now. You don’t need the quick sugar high of winning $1,000 if it’s going to cost you way more as you continue to chase future highs.

I will repeat: It makes no sense to risk an expensive addiction to pick up a few quick bucks.

As I said at the beginning, we’re here to make money from our hustles — not to get hustled by large corporations.

Scouting for opportunities

There’s a general principle about promotional gambling opportunities. New gambling dens offer big giveaways to promote their new place. They know a certain number of people will come for the free money and stay at the party too long.

If you’re sure you know how to go home when a party’s over, you may now start cruising around for offers for new gamblers. Don’t necessarily pick up the first offer you see. For instance, one of the new Louisiana books suggested I tell all my friends to sign up at their place, and my friend will get $50 and I’ll get $50 as an affiliate fee.

Um. If the friend took a different sign-up offer directly from the site, they can get $200-$300 in free bets. So I’d be a real “friend” if I advised them to sign up on my link so they can get $50. Sheesh, people.

You will see no affiliate links in this story. I don’t need money that bad.

Executive summary: You’re only a new player at a new place once. Look over the sign-up deals carefully before you jump. Deals through your buddy’s affiliate link might cost you.

If your state doesn’t yet allow online sports betting

Keep an eye on your Twitter feed and/or NextDoor or any other online place where you share chitchat about local and state politics. They’ll let you know when your time is coming.

Don’t try to bet online from states where betting online is illegal. Don’t try to bet if you’re under 21. You know. Obey all the laws, and read all the terms and conditions.

That’s just common sense, but I’ll say it anyway. Because lawyers.

By the way, if you’re not in the state you claim, they’re going to test that stuff, so they’re probably going to know. Although I still can’t explain why anyone would think I’m in New Jersey.

Deciding what to bet

It doesn’t matter. You don’t win at sports betting by knowing a lot about sports. The books know a lot about sports. It’s their real job. Full-time. They move the lines around to make sure they profit.

One of my known associates had a big sports betting team. (Maybe he still does, but we fell out of touch years ago.) He didn’t win by knowing more about sports than the books. He won by knowing more about math and arbitrage.

You ain’t got time for that, and neither do I.

It’s a free bet. Throw a dart. If you sign up at multiple places and place multiple free bets, you’re going to have trouble walking away with nothing. Nobody wins them all, but almost nobody (knock on wood) loses them all either.

Cash out

There will undoubtedly be other profitable promotions in the future. However, the longer you hang around a gambling joint, the more likely you’ll be tempted to keep playing even when you don’t have an advantage.

Also, it’s a good idea to cash out just to make sure you can.

Make a note of what you earned. Gambling winnings in the United States are taxable income.

A Special Note for Long-Time Losers

Let’s go back to those of you who have been sports betting online since the days when they mailed you those silver CDs and begged you to gamble in their place in Antigua.

You say you’ve been donating money year after year? You say sports betting is a terrible money-losing hustle?

As I said before, that’s because you’re doing it wrong. You thought you were betting on sports. Winners don’t make money betting on sports. They make money placing bets ONLY where they have a huge advantage.

I hate to be the one to tell you, but your sports smarts are not any smarter than anybody else who watches a lot of games. I don’t care if you made the team in high school. Or even college.

Try this rule: Never place a bet without a matching or larger free bet from the house. Promotions come around all the time. So why bet when you’re not getting an incentive to bet?

Don’t bet money based on, I want to support the team.

The team is fine. The owner’s a billionaire. The players are multi-millionaires. And, anyway, your gambling money doesn’t go to the team. It goes to the book.

A Final Word of Warning

No one is telling you to gamble as a side hustle. No one. If you must, use your brain. You will not out-think professionals who have devoted their lives to this stuff. I don’t care if you’re the ghost of Albert Einstein’s smarter brother Stephen Hawking.

My side hustle was a form of advantage play. A very simple form. I accepted the free bets offered to me. I placed the bets. When I won, I made the minimum possible deposit required to cash out.

That’s it. That’s my whole system.

If you can’t follow instructions, or if the setup is different in your state, or if you’re banned from gambling online for any and all reasons, you should keep looking for a different hustle.

Sign-up promotions seem like easy money to the player and automatic losses for the house. And yet the house keeps offering them.

Know why?

Because so many of you will not stop before you’ve given it all back and more.

Don’t do that. We’re here to take money, not give it away.

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Author's Note: This story was originally published in The Side Hustle Club, a Medium Publication. I have republished it here for my Vocal readers. If you enjoy it, let me know by tapping that <3 button and/or leaving a small tip.

Here's a previous story about my silliest gambling system:

Here's a more serious story that might help you win more at poker and/or life: