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AI’s Y2K Moment

Posted February 25, 2026

Matt Insley

By Matt Insley

AI’s Y2K Moment

I asked — you answered. And the range of fears you sent back was as thought-provoking as anything we debate during Paradigm’s editorial calls.

Douglas D. laid out a sweeping set of concerns which mirror many of our own: “Obviously, I’m afraid of any devastating market crash or similar extreme turmoil that harms millions of middle-class Americans and creates a crisis for the country.

“I worry about the monetary system crashing and being replaced with a tokenized dollar that the government fully controls, allowing them to completely monitor citizens, using it to punish political dissent, freeze assets at the government’s discretion, resulting in an Orwellian nightmare.

“I do worry about AI progress accelerating too fast, leaving millions behind, forcing some kind of universal basic income. This would trap a vast segment of our citizens in a snare of government dependency that would be hard to escape otherwise.

“Still, I’m an optimist who hopes these fears are less likely to occur, at least to their worst extremes,” he says. “Appreciate all the opinions, analysis and insight provided by the Paradigm team!”

Next, Barry H. writes: “I am most worried about all assets falling at the same time, including stocks, bonds, precious metals, private debt and real estate.”

“What scares me most?” asks Tom V. “Long term it’s the effects of AI on the economy and the workplace; short term it’s the pending engagement in Iran.”

David G. quips: “What I fear: That I am on the wrong side of capital rotation.”

And Kevin G. concludes: “I would NEVER bet against Elon.”

To Douglas, Barry, Tom, David, Kevin — and the many other readers who took the time to write in — thank you. This newsletter is better for your perspectives.

Your Rundown for Wednesday, February 25, 2026...

HALO Stocks

Here’s a thought experiment I can’t shake: What if we’ve already been here before?

Assuming you’re old enough, cast your mind back to 1999. The internet was going to rewire everything — commerce, communication, the entire architecture of daily life. And, yes, it would.

But first, it gave us Y2K. A civilizational panic about whether computers could survive a date change.

It was, in retrospect, a collective anxiety attack dressed up as a technical problem — the market’s way of screaming that it didn’t fully understand what it had built. Billions were spent. Midnight came and went. The lights stayed on.

I think we’re living through AI’s Y2K moment right now.

The freakout crystallized on Sunday in the form of a 7,000-word post at a Substack account called Citrini Research — a small outfit with a massive following that depicts macro scenarios.

Their post imagined a near future, dated June 2028, in which AI doesn’t just disrupt industries — it dislocates the top-of-the-foodchain role that human intelligence has commanded throughout all of modern economic history.

The Dow dropped 800 points. Software firms cratered. DoorDash fell 6.6% after Citrini called it “a poster child” for how AI agents would hollow out companies that profit from transactional friction.

DoorDash co-founder Andy Fang even capitulated on social media: “The ground is shifting underneath our feet, and the industry is going to need to adapt to it.”

  • The market’s response to this shifting ground has been fascinating. Investors are piling into what Ritholtz Wealth Management CEO Josh Brown — who coined the term — calls HALO stocks: Heavy Assets, Low Obsolescence.

Think McDonald’s, Exxon, Deere, Freeport-McMoRan. Companies you cannot disrupt with an AI prompt.

Meanwhile, Goldman Sachs formalized their thesis this week, noting that stocks in capital-intensive industries — companies whose value is anchored in physical assets like machinery, infrastructure and energy networks — have outperformed their capital-light counterparts by about 35% since the start of 2025.

Capital-light businesses, by contrast, derive their worth primarily from human talent, software and digital systems — exactly the kinds of inputs AI is now threatening to replace.

Translation: When in doubt, according to Goldman Sachs, buy the thing that can’t be coded or downloaded.

So here’s the Y2K parallel that haunts me: In 1999, the panic was premature. The disruption was real, but the timeline was wrong. Maybe that’s true again? Maybe it never arrives at all.

Or maybe — this time around — there’s no midnight reprieve.

Market Rundown for Wednesday, February 25, 2026

S&P 500 futures are up 0.30% to 6,925.

Oil is up 1% to $66.25 for a barrel of WTI.

Gold’s up 0.55% to $5,206.30 per ounce.

And Bitcoin is up 2.85% to $66,290.

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