The window AI just opened isn’t going to stay open for long.
Chess is played on a perfect board of 64 squares, eight by eight, alternating black and white. Each player begins with 16 pieces: 8 pawns, 2 rooks, 2 knights, 2 bishops, 1 queen, and 1 king. Amongst 32 pieces, two kings stare at each other across an empty wasteland. Every game of chess begins from this exact same position, and every one of them ends in one of two ways: checkmate or stalemate.
Mathematicians estimate there are about 10120 possible games of chess. Just to put that into perspective, the estimated count of atoms in the observable universe is somewhere between 1082 and 1090.
The universe is roughly 13.8 billion years old. That’s about 1017 seconds since the Big Bang. Long enough for stars to form, burn, and collapse. Long enough for galaxies to drift apart. And still, if every second since the beginning of time, a new game of chess had started and finished, we wouldn’t even be close. Not by a hundred orders of magnitude.
And that’s with only 64 squares and 32 pieces.
The Chess Era of Business
There was a man who started a business in 1962 in a town of fewer than 4,000 people. He spent the next thirty years quietly turning it into the largest company in America.
Before starting his business, he had already spent 17 years apprenticing in others’ retail stores. He would wait another 17 years before he took his company public.
He didn’t move fast; he focused deliberately. He opened his second store two years after his first. He kept his expansion inside a four-state radius for the better part of a decade. Store employees told stories about catching him in their aisles, an unassuming man in rumpled clothes asking too many questions and jotting figures into a yellow pad. And he drove a beat-up Ford pickup truck to work long after he was the richest man in the country.
He studied his competitors obsessively. His own wife described family vacations when they would pass through a town, and she would sit in the car with the kids while he went into a store he’d heard about.
He built his own distribution centers because no one would deliver to the small towns where he opened. He built his own satellite communication network when nobody else thought a retailer needed one.
By the time he died, the playbook he had written was being studied in every business school in the country.
That is what the chess era of business looked like at its highest level.
That’s the world that built the Fortune 500.
It’s also the world the man with the yellow legal pad spent fifty years mastering. His name was Sam Walton, and he founded Walmart. The playbook he wrote, the playbook every Fortune 500 CEO has been studying for forty years, is now in the midst of a once-in-a-lifetime shift.
The board hasn’t changed yet. Business is still business. Customers, margins, trust, capital, and execution still matter. But the clock has changed. The time you have to make decisions is collapsing.
The Pickleball Era
I picked up a pickleball paddle in July of 2021 because of a man named Ron.
Ron is a retired dentist and inventor. He has the steady hands of a man who spent forty years working in millimeters. The first time I met him, my friend Ricky and I were in the weight room at our gym. Ron walked up to us mid-set with the gentle authority of someone who had decided, without asking, that he was going to teach us something.
“Come with me,” he said. “There’s a game I want to show you.”
We followed him out to the courts. I had never picked up a paddle before. I had never even played a racket sport in my life. Ron didn’t care. He gave me forty-five minutes of his time and a free lesson on the dink.
A dink, if you’ve never played, is a soft shot played at the kitchen line. It barely clears the net. It looks sooo boring, and until you master it, it kind of is. Ron taught it the way a dentist explains a procedure, patiently and precisely, as if Ricky and I were two grown men who needed to understand exactly what he was about to do to our molars.
“You’re not trying to win the point with this shot,” he said. “You’re trying to give your opponent nothing to attack.”
He hit a hundred dinks at me that morning. Maybe two hundred. None of them moved more than four feet. Ricky and I went home sore in muscles we didn’t know we had.
And we came back the next day.
Five years later, I realize The Game is built around the lesson Ron gave me on day one: don’t chase power, create the next opening.
The court is small, but nothing about the point feels simple. Every ball arrives with a different question: where it might land, what angle it is coming from, how much spin is on it, how fast it is moving, where your opponent is leaning, and what part of the court he just left exposed. Chess gives you time to think through those possibilities. Pickleball throws them at your feet.
A younger player tries to end the point with power, and Ron just waits. He reads the angle, absorbs the speed, shifts one step, and drops the ball into the space the other player just abandoned. Then he does it again. And again. By the third or fourth time, the younger player is reaching, lunging, pressing, and losing patience.
Mo Gawdat, the former Google X executive, recently described what made an entrepreneur valuable in the chess era:
That skill, he says, is over. The chess era has ended. He thinks we’re playing squash now, where the ball comes off the wall faster than you can plan a response.
Mo is right about the shift. He is wrong about the sport.
Squash was the metaphor in 2005. Pickleball is the metaphor in 2026, because the new game isn’t just faster. It is also lower to the ground and much more accessible.
The same shift is now playing out in business.
The Moat
Warren Buffett spent sixty years teaching the world that the most important feature of a great business is its moat: the defensive structure around an economic castle. The brand that a competitor cannot replicate. The network effects that compound. The regulatory complexity that takes a $100 million to navigate. Coca-Cola has one. Apple has one. Your local hardware store does not.
The moat is the chess-era dream. The reward for patience, capital, and seeing further than the person across the table. The Fortune 100 is essentially a list of the deepest moats in America.
But a moat only works if it keeps the competition out.
In its 2026 AI review, Morningstar’s equity research team examined 132 companies and revised moat assessments for roughly 40 of them. Several major software companies, including Oracle, Salesforce, Adobe, and ServiceNow, were downgraded from a wide moat to a narrow one.1
Why is the duration of competitive advantage less certain? Because AI is doing something the chess era did not anticipate. It is effectively operating as a bridge, collapsing the cost and risk involved in crossing the moat.
Brand premiums that once required a marketing department can now be approximated by a small team using the right tools. Operational efficiency that took a Fortune 500 company a decade to engineer is sitting in a stack that a five-person team can rent by the month. And the most valuable asset in any chess-era company, the twenty-year veteran’s judgment encoded in ten thousand small decisions, is now sitting inside a model that costs $200 a month.
I want to be honest about what we do not know.
We don’t know how long the moats will stay weak. We don’t know which crossings AI actually maintains and which ones are hype. New moats are almost certainly forming. My guess is that they will form around what AI cannot easily replicate: control over personal data, customer relationships, and the servers that store both. Some of the giants that look exposed today will adapt and emerge stronger.
That uncertainty is the whole point. The operator who waits for the answer loses to the operator who acts.
The moat that has protected your competitor for thirty years is the same moat that has kept you small. For some unknown stretch of time—a year, three years, ten—the cost of crossing has dropped. The window is open right now. Whether or not it stays open is somebody else’s problem. It’s up to you whether you walk through it before the next moat forms around someone else.
So the real question is one only you can answer.
Where are you still playing chess because that is how you were trained? Where are you waiting for certainty while the market rewards motion? Where are you defending a moat that AI may have already bridged?
These are uncomfortable questions, and they should be. The questions that make you uncomfortable are usually the ones you can’t afford to ignore.
I’ve sat across from operators who built real businesses by playing the long game. Most of them are still trying to play it. The ones I worry about aren’t the ones who don’t see the shift. They’re the ones who see it and decide they’ve earned the right to wait it out.
Mo Gawdat said the skill of an entrepreneur used to be foresight. That skill has been redistributed. For most of my career, I have watched the smartest in the room win. They had time. They had information. They had patience.
The room is faster now. Smart still matters, but so does speed. Either alone is no longer enough.
Originally posted on Substack