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  • Lessons from the Dot-Com Bubble: Are Today’s Tech Valuations Repeating History? – Kavan Choksi / カヴァン・チョクシ

Lessons from the Dot-Com Bubble: Are Today’s Tech Valuations Repeating History? – Kavan Choksi / カヴァン・チョクシ

Michael Thompson
May 30, 2025May 30, 2025 Comments Off on Lessons from the Dot-Com Bubble: Are Today’s Tech Valuations Repeating History? – Kavan Choksi / カヴァン・チョクシ

The late 1990s are remembered as one of the most dramatic periods in stock market history. The dot-com bubble saw the rise—and spectacular fall—of internet-related companies that promised to revolutionize the world. Investors poured billions into startups with little more than a website and an idea, driving valuations to unsustainable heights. When reality set in, the market collapsed, wiping out trillions of dollars in value. Here is what some experts like Kavan Choksi / カヴァン・ チョクシ say:

Fast forward to today, and the question many investors are asking is: are we witnessing a similar moment? With soaring valuations in tech, artificial intelligence, and digital assets, echoes of the dot-com era are becoming hard to ignore.

The dot-com bubble was fueled by excitement over the internet’s potential. Investors believed traditional business models would be disrupted overnight, and many bet big on companies without profits—or even revenue. Stocks like Pets.com and Webvan became infamous examples of hype outpacing fundamentals. The Nasdaq Composite index, heavily weighted with tech stocks, more than doubled between 1998 and early 2000, only to crash by nearly 80% over the next two years.

Today, we see similarities in how investors approach emerging technologies. Companies involved in artificial intelligence, cloud computing, and digital infrastructure have seen rapid share price growth. Some have strong revenue and proven products, but others are still early-stage ventures with lofty promises. Just as the internet promised to change everything in the ’90s, AI and automation are seen as transformative forces today.

In both eras, innovation is real—but investor expectations can get ahead of reality. One key difference, however, is that many of today’s tech giants are highly profitable. Companies like Apple, Microsoft, and Alphabet generate massive cash flows and dominate their industries. These firms didn’t exist in the same form during the dot-com boom, or they were still in their infancy.

Still, froth can build around newer sectors. In 2020 and 2021, for example, many startups went public through SPACs (special purpose acquisition companies), often with unproven business models. Their rapid rise and equally fast decline in value feel reminiscent of dot-com excesses. Similarly, some AI-focused firms now trade at price-to-earnings multiples that suggest extreme optimism.

What history teaches us is that technological revolutions don’t guarantee investment success. The internet did change the world—but many of the biggest winners came after the bubble burst, not during it. Amazon, for instance, survived the crash and emerged stronger, but only after losing over 90% of its value.

For investors today, the lesson is to separate the excitement of innovation from the discipline of investing. Pay attention to fundamentals: revenue, profitability, leadership, and market demand. Be cautious of hype, and don’t assume every new technology trend will produce instant winners.

History doesn’t repeat exactly, but it often rhymes. The dot-com bubble offers a valuable reminder that while technology evolves, investor psychology remains remarkably consistent. Staying grounded can help investors benefit from innovation—without getting caught in the next crash.

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