The Old Story of Investing in New Technology: Why 2026 Looks Like 1999

Deja Vu All Over Again: The Dot-Com Playbook is Back, and It's Digital.

The pattern is unmistakable. A revolutionary technology emerges, dismissed by incumbents as a fad. Early adopters get labeled speculators. Then, the infrastructure gets built, the use cases explode, and the skeptics are left scrambling. Sound familiar? It should. We've seen this movie before—only this time, the ticker symbols have more letters.

From Browsers to Blockchains

Replace 'internet' with 'blockchain' and the parallels get eerie. The early web promised to democratize information. Digital assets promise to democratize value—cutting out the middleman, bypassing legacy gatekeepers, and creating entirely new economic models. The initial volatility? Just the sound of a new financial system being forged in real-time. Remember when Amazon was just a bookseller?

The Institutional Tipping Point

The real signal isn't retail FOMO; it's the quiet, systematic accumulation by institutions that once scoffed. They're not buying the meme; they're buying the infrastructure—the decentralized rails that could underpin the next half-century of finance. It's a hedge against obsolescence, the ultimate 'if you can't beat 'em, join 'em' play.

A Cynical Footnote for the Finance Bros

Sure, the space has its charlatans and its absurd valuations. But let's be honest: so does the legacy market—they just wear better suits and charge higher fees for their actively managed underperformance. At least here, the code is (usually) open for audit.

The old story isn't just repeating; it's accelerating. The question isn't if you believe in the technology, but how long you can afford to watch from the sidelines.

Invest like it’s 1999?

In 1999, Warren Buffett warned that world-changing technologies are often ruinous for the investors that correctly predict them. 

The auto industry was one example: “If you had seen at the time of the first cars how this country WOULD develop in connection with autos,” he told the annual gathering of VIPs at Sun Valley, ID, “you would have said, ‘This is the place I must be.’ But [out of] two thousand [auto] companies, as of a few years ago, only three survived…so autos had an enormous impact on America, but in the opposite direction for investors.”

Airlines were another: “Imagine if you could have seen the future of the airline industry back there at Kitty Hawk. You [would] have decided, this is the place to be.”

But “as of a couple of years ago,” he noted, “there had been zero money made from the aggregate of all stock market investments in the airline industry in history.”

That was Buffett’s way of warning his VIP audience they could be right that the internet would change everything — and wrong that investors would profit from it. 

The dotcom bubble popped eight months later.

Today, artificial intelligence is the obvious candidate for the next world-changing technology to ultimately disappoint investors: It probably will revolutionize everything; but which companies, if any, will capture the value it creates remains anyone’s guess.

Crypto is another.

The news this year was shockingly good — the SEC flipped from anti- to pro-crypto, the GENIUS Act legalized stablecoins, prediction markets went mainstream, TradFi institutions scrambled to get involved — but token prices have been shockingly bad.

That might just be because expectations got ahead of reality.

But it might also be a sign that, however much value crypto ultimately creates, little of it will accrue to the investors that funded it. 

People are excited about the tokenization of real-world assets, for example. But if most of those assets are tokenized by Robinhood, BlackRock and the DTCC, the crypto investors who financed the infrastructure that made tokenization possible won’t capture much of the value it creates. 

Similarly, the crypto industry has devoted billions of dollars to developing zero-knowledge proofs, and it’s easy to imagine how these could be great for the world — they may be humanity’s last line of defense against AI slop. 

But they may also be terrible for investors: ZK proving is math that doesn’t need a tradeable token to function.

There are many more such examples — likely because the value that crypto set out to create was not meant to be captured.

Just the opposite: Composable, open-source, decentralized crypto was meant to disintermediate the rent seekers of technology and tear down the toll booths of finance.

At the end of a disappointing year for token prices, it’s tempting to conclude that crypto is progressing too slowly toward those goals.

But if crypto turns out to be as good for the world as bicycles, no one should complain if it’s also as bad for investors.

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