In 1999, investors followed Prince’s advice and partied. The Nasdaq Composite soared as enthusiasm for the internet sent technology stocks, and many unproven companies, to extraordinary valuations. When the celebration ended, however, investors learned how quickly excitement could turn into painful losses.

More than two decades later, artificial intelligence is fueling another technological revolution. Stock prices have climbed, several dominant technology companies have reached enormous valuations, and warnings about a new market bubble have become increasingly common. But does today’s enthusiasm truly resemble the dot-com era?

In this episode of Coasting in Retirement, Josh Null compares the markets of 1999 and 2025. He examines differences in market performance, economic conditions, interest rates, and the companies leading each technology boom. While many dot-com favorites had little revenue or profit, today’s largest technology companies generally operate established businesses and generate substantial cash flow.

Still, familiar signs remain: lofty expectations, concentrated market leadership, speculative behavior, and confidence that a new technology will transform nearly everything.

Is artificial intelligence producing another period of “irrational exuberance,” or is the comparison to 1999 overlooking important differences? Listen to the full episode for the first half of Josh’s examination of modern market bubbles, and the setup for an even bigger question: Do bubbles still matter?



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