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How I Made 377% Betting on the Super Bowl

Written By Alexander Boulden

Posted February 15, 2023

Dear Reader,

After a long weekend of sportsbook and casino ads on the TV and radio to entice people into the dark and dirty world of sports betting, I thought I’d offer up my personal experience with it over the weekend.

Now, it was only a few years ago that I started dabbling in sports betting, and I gotta tell you, nothing feels like the first time…

The date was November 23, 2018.

A friend and I had to travel to a smoke-filled casino in a different state.

Ah, the good old days before COVID…

The game we were betting on?

Phil Mickelson versus Tiger Woods in a heads-up match play at the famous Shadow Creek Golf Course in Las Vegas, dubbed “The Match.”

At the casino where we were gambling, you could only bet on the winner no side bets.

So we entered our tickets into the betting machines (this detail will be important to remember at the end of the story).

The oddsmakers had Tiger winning by a large margin, so following the crowd, I bet $50 on Tiger to win.

My friend, being a more experienced gambler, put $100 on Phil to win — 1) because the odds were better and 2) because he thought he’d win anyway. (I know now that in gambling, you always want the odds in your favor. Otherwise you have to risk more money to get the same payout.)

If you know the Vegas match I’m referring to, then you know that the two pros battled it out all day over a $9 million purse.

They were even mic’d up so you could hear them trash-talking each other.

We were on the edge of our seats.

The match ended with Phil sinking a put on the 22nd hole to defeat Tiger.

I’d lost my 50 bucks, or so I thought.

My friend had tripled his money, or so he thought…

We went to the cashier to cash out his ticket and it turns out the betting machine hadn’t taken our bets.

Thankfully, I hadn’t lost any money on my ill-fated bet, but my friend wasn't happy!

He’d been slighted, swindled, cheated.

They never really offered up an explanation as to what happened, which was definitely strange.

We had a good laugh and eventually got over it, talking about the match over a beer.

But here’s the problem with sports betting: If you like watching sports, have a knack for predicting outcomes, and have knowledge of the games and players, you start thinking you’ve got things figured out.

And maybe you do, at least for a while.

Then you start to see the potential of bets you didn’t place.

For example, last year I studied up on the Preakness Stakes that take place here at Pimlico Race Course in Baltimore.

Apparently, back in the day, everyone bet on the horses.

I picked out my horses and jockeys.

I even wrote them all down in this order: Early Voting, Epicenter, Creative Minister, Secret Oath, Simplification.

I don’t have a time stamp to prove it, so you’ll have to trust me.

Had I bet on this race, I would have walked away with the superfecta — four horses in a row.

I calculated it, and I honestly wouldn’t be writing to you today had I placed even a small bet.

Alas, that's the world of sports betting.

Fast-forward to this year’s Super Bowl, and I decided to download DraftKings — the company was running a promotion where you got $200 in free bets if you spent $5.

So I got my free bets, placed some speculative plays on the Eagles, hedged my bets with the Chiefs, and I walked away with 377% more than I had put down.

As you can probably tell, I’m not a gambler, and I’m no Adam Sandler in Uncut Gems, betting all the money I have, betting someone else's money, and doubling down every time.

That’s because, like most of us, I absolutely hate losing money.

And with so many new investors and gamblers in the market today, a lot of them conflate investing and gambling, so let’s set the record straight.

Here’s my first point.

Investing and gambling are not one in the same.

There are three reasons this is the case…

Investing Is Not Gambling

First, you can almost always take your money out of a stock.

With gambling, your money’s locked up until the action you bet on occurs.

If the action doesn’t go your way, that’s it. The money’s gone.

But with investing, you’re in control.

You choose the length of time your money’s at risk.

You decide when to put the money in and when to take it out.

No one's forcing your hand.

Not to mention, unlike in the casino, long term, the investing odds are in your favor.

You’re 100% in Control 100% of the Time

Second, you can use a stop-loss strategy with your investments.

Only want to risk a certain amount of cash?

No problem!

Most brokerages offer trailing stop services that automatically sell a security if it drops by a certain amount.

Or you can manually keep track of your investment and sell it if you think the play is turning against you.

The industry standard is 25%, but you can choose what you want — 15%, 10%, 5%…

You’re in control.

There are no stop losses in gambling; you either win or lose.

With the stock market, you can even hedge your investments by playing options, buying inverse-leveraged ETFs, or purchasing bonds or Treasurys.

Investing Perks

Finally, you get to reap the benefits of being an accredited investor.

Some companies will literally pay you cash on the nail to merely hold their stock.

It’s a wonderful thing when you realize you can utilize compound interest to boost your portfolio.

You can also dollar-cost average your investments.

That is, if you get a little too excited and buy a security at its peak, you can just buy it for a lower price later to lower your cost average.

And you even get certain tax breaks for adding money to your tax-advantaged and tax-deferred retirement accounts.

Try getting those perks at the casino.

In fact, if that big jackpot ever hits, you’ve got to pay a hefty tax on your winnings.

Not to mention the psychological impact gambling has on you  constantly trying to time your hands or plays or horses, whatever it may be.

With investing, it’s common knowledge that timing the market isn’t important; it’s time in the market that matters.

That’s why I want to point you toward my publisher, Brian Hicks, who’s been in the market longer than any of us here at Wealth Daily.

He’s warning his readers that something big is going down in Washington, D.C.

I hope he’s wrong, but if not, he says this sinister move from our lawmakers will affect anyone with a brokerage account, retirement account, or plain old cash.

Check out his urgent report before it’s too late.

Stay frosty,

Alexander Boulden
Editor, Wealth Daily

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After Alexander’s passion for economics and investing drew him to one of the largest financial publishers in the world, where he rubbed elbows with former Chicago Board Options Exchange floor traders, Wall Street hedge fund managers, and International Monetary Fund analysts, he decided to take up the pen and guide others through this new age of investing.

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