How to "Invest" like a "Gambler"

By Wayne Mulligan, on Thursday, March 30, 2023

When I tell people what I do for a living, I hear things like this: 

“The stock market!? That’s a real crap shoot!”

“You invest in startups? I’d rather play the lotto!”

“Oh, isn’t that like gambling?”

Comments like that used to bother me. But not anymore.

Nowadays, I take them as a compliment.

And once I show you why, you’ll see that investing like a “gambler” could be a good thing…

In fact, it could put more money in your pocket than you ever thought possible!

Try Your Luck!

Being called a “gambler” used to bother me because, by definition, it was the exact opposite of how I invest.

“To gamble” means to play games that are decided by luck, or to take a high-risk wager.

But everything Matt and I do — for our personal investments, and for the investment analysis we do here at Crowdability — is about eliminating risk.

When we make an investment, it’s based on a system… the type of system that enables us to make decisions based on facts, data, or math.

That’s why being called a “gambler” bothered me so much.

But here’s what I’ve come to learn…

Gamblers’ Multi-Million Dollar “Salary”

If you ever talk to a real gambler — a “professional” gambler — you’ll discover that they use systems, too, just like me and Matt.

And when I say professional gambler, I’m not referring to people who make an annual pilgrimage to Las Vegas to play the slots or a few hands of blackjack.

I’m talking about people who make their living through gambling.

And there’s one group of these “pros” we can learn the most from: Poker Players.

You see, with poker, the odds aren’t stacked in favor of the house. That’s because players aren’t competing against the casino… instead, they’re competing against one another.

And this is why I’ve spent time studying the most successful poker players:

Professionals like Vanessa Selbst, the Yale Law School dropout who earned $11.6 million playing poker…

Or, Fedor Holz who, according to Forbes, earned a whopping $23.3 million payday playing poker in his first four years alone.

The Gambler’s Edge

These professionals know that, to win consistently, they need an “edge” over their competitors.

This “edge” comes from knowing the mechanics of the game better than their opponents:

Being able to calculate the odds of each hand. Knowing how to place bets to optimize your “take.” Knowing when to call, raise, and fold.

Basically, they use a system.

And over time, by applying this system consistently, their edge adds up.

But one strategy to gain an edge gives them their biggest advantage…

And as it turns out, you can use the same strategy as an investor to make more money.

The One Rule You Must Follow

The strategy I’m referring to is known as “table selection.”

As it turns out, table selection — literally, the table you choose to play at — is the first and most important step in a professional poker player’s system.

Simply put, if an experienced player sits down at a table full of amateurs, he or she has an above-average chance of walking away with a profit.

And this is exactly how the pros earn a consistent living.

They wait. They watch. And when they see a table of amateurs — in other words, a table where their potential returns are inherently higher — they sit down and collect.

And like I mentioned, you can use this same technique with investing…

Choosing the Right Table

You see, when it comes to investing, there are different markets, different asset classes — stocks, bonds, currencies, etc.

Think of these markets as different “tables.”

And just like with poker, some of these tables offer you an advantage…

An advantage like bigger returns!

For example, consider the private market — in particular, the market for early-stage “startups.”

Multiple studies have shown that private-market investing offers outsized returns.

For instance, a 25-year study by Cambridge Associates — an investment advisory firm with clients like Bill Gates and the Rockefeller Foundation — found that a diversified portfolio of early-stage, private market investments generated annual returns of 55% per year.

That’s nearly 10x higher than the stock market average.

Again, simply by sitting at “the private market table,” you can put yourself in position to earn big returns.

But to be clear, “table selection” can’t be your entire private market investing strategy.

It’s just a first step…

To learn about some of the other steps we recommend taking, check out the free “Resources” section of the Crowdability website »

There, you’ll find multiple reports about the proven strategies and “tricks” for identifying the most promising private investment opportunities.

Happy investing!

Best Regards,



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