[In today’s special guest essay, Paradigm’s income expert Zach Scheidt shares one of the most valuable investing lessons he ever learned — not on Wall Street, but at the poker table.

Drawing on his experience as a semi-professional poker player, Zach explains why the best investors don’t chase certainty. Instead, they look for asymmetric opportunities where the potential reward far outweighs the risk. Read on for his full essay.]

Recently, my wife Angela and I headed up to Harrah’s Cherokee. She was there for a Rotary conference. I was there as her “plus one” … which, for me, meant two straight days at the poker table.

Some of you may not know this, but in a former life, I was a semi-professional poker player. It wasn’t my full-time job, but I earned reliable income at the tables — enough that I had a business partner living in Las Vegas and logged literally thousands of hours on the felt.

Looking back, that experience shaped the way I think about investing far more than any finance textbook or Bloomberg terminal ever could.

And the single most important lesson poker taught me was this: The best investors don’t look for certainty.

They look for asymmetric opportunities.

The Edge Most Investors Ignore

An asymmetric bet is simply a situation where the potential reward is far greater than the potential risk.

In other words, instead of risking $100 to make $100, you might risk $50 to potentially make $200. The odds are tilted in your favor before the outcome is even decided.

That concept changes everything.

Here’s a simple poker example:

Imagine you’re holding a promising hand and facing a $50 call into a $200 pot. You don’t need to win every time to make that bet profitable. In fact, you only need to win more than 20% of the time to come out ahead over the long run.

If you’re winning that hand half the time, the math works overwhelmingly in your favor.

Now flip the situation around. Suppose you have to risk $200 to win a $250 pot. Suddenly, you need to be right nearly half the time just to break even.

Even skilled players struggle to overcome those odds consistently.

That’s why successful poker players stop obsessing over individual wins and losses. Instead, they focus on expected value and long-term edge.

Your Rundown for Wednesday, July 8, 2026...

How to Build Asymmetry Into Your Portfolio

There are several ways investors can stack the odds in their favor. Here are three of the most important…

1. Find Stocks With Outsized Upside Potential

The first place to look for asymmetry is in a company’s underlying story.

Think about a small defense contractor bidding on a major Pentagon contract. If the company wins, the stock could soar 50%, 100% or even more.

But if it loses, the stock might simply drift back to where it started or decline modestly.

That’s not a balanced risk/reward setup. It’s an asymmetric opportunity where the upside meaningfully outweighs the downside.

Biotech companies awaiting FDA approval can create similar setups.

So can small technology firms launching breakthrough products, energy companies making major discoveries or businesses preparing for transformational earnings announcements.

The key is identifying situations where a positive outcome could dramatically reprice the stock higher while the downside remains relatively limited.

2. Structure Trades With Defined Risk

The second layer of asymmetry comes from how you manage the position itself.

Before entering any trade, I always ask myself two questions:

Where am I wrong?

And what does success realistically look like?

If I believe I could lose $5 per share if I’m wrong but potentially make $30 per share if I’m right, that creates a 6-to-1 reward-to-risk setup.

Think about what that means mathematically. I could be wrong five times in a row and still come out ahead with just one successful trade.

That’s incredibly powerful.

Unfortunately, most investors approach the market backward. They spend all their time thinking about how much money they could make, but very little time defining how much they’re willing to lose.

That’s dangerous.

One of the most important habits I developed during my poker years was deciding my risk before the cards were even dealt. Good poker players know exactly how much they’re willing to lose in a hand before they put chips into the pot.

Investors should approach markets the same way.

Defining your downside in advance won’t eliminate losses entirely. But it can keep small mistakes from turning into catastrophic ones.

3. Use the Right Investment Vehicle

Even when you find a great opportunity and structure the trade thoughtfully, the investment vehicle you choose still matters enormously.

Personally, one of my favorite tools for asymmetric investing is in-the-money call options.

Now, I know some investors hear the word “options” and immediately think of reckless speculation. But when used properly, options can actually help control risk while increasing upside efficiency.

When you buy shares of stock outright, you must commit the full amount of capital upfront. But an in-the-money call option often allows you to participate in most of the stock’s upside movement while putting far less money at risk.

At the same time, your maximum loss is generally limited to the premium you paid for the option.

That creates a naturally asymmetric structure.

Of course, options do involve a learning curve. Investors need to understand expiration dates, strike prices and position sizing before using them.

But once you understand the mechanics, options can become one of the most effective tools available for creating favorable reward-to-risk setups.

Patience Matters More Than Perfection

Even the best asymmetric strategy will still produce losing streaks.

That’s normal.

A fair coin, for example, will land on tails three times in a row about 12% of the time.

The same thing happens in investing.

You can make smart, disciplined and mathematically sound decisions and still experience periods where multiple trades go against you in a row.

That’s part of the process.

The goal is not to win every trade.

The goal is to make far more when you’re right than you lose when you’re wrong — and let probability work in your favor over time.

That lesson was drilled into me across thousands of poker hands over the years. And it continues to guide every investment decision I make today.

The real edge in investing doesn’t come from being right all the time.

It comes from being positioned correctly when you are.

Market Rundown for Wednesday, July 8, 2026

S&P 500 futures are down 0.54% to 7,510.75.

Oil is up 2.11% to $71.20 for a barrel of WTI.

Gold is down 1.68% to $4,087.70 per ounce.

And Bitcoin is down 2.01% to $62,056.40.