Cisco’s John Chambers lived through the dot-com crash. He says the AI bubble is harder to navigate

In today’s CEO Daily: Diane Brady interviews John Chambers, who knows bubbles, about the AI boom.

The big leadership story: Kalshi and the SCOTUS case that could determine the future of gambling.

The markets: Down in Europe as tanker attacks threaten a fragile ceasefire.

Plus: All the news and watercooler chat from Fortune.

Good morning. Are we in a stock market bubble? If you go by the so-called Buffett Indicator, as my colleague Shawn Tully reminded readers in this piece yesterday, the answer is yes. The ratio of total stock market capitalization to GDP now stands at 232%, exceeding 1999 levels and the 200% threshold where Buffett said investors were “playing with fire.”

But is today’s bubble comparable to what we saw during the dot-com boom from 1995 to 2000? For insight on that, I spoke yesterday with John Chambers, who was CEO of Cisco from 1995 to 2015. Under his watch, it became the most valuable company on earth, with a market cap of $576 billion in March 2000, dropping to a low of around $60 billion by October 2002. Today, it’s around $340 billion. For almost a decade, Chambers has bet big on AI through JC2 Ventures and continues to advise founders, government leaders, and CEOs on market trends. (I co-wrote a book with him and find his annual tech predictions prescient.) His take:

What’s similar: “The driving force was the internet, and growth was almost completely out of control. The limiting factor was supply chain: lead times stretched out and nobody wanted to cancel orders, which can disguise a lot of problems. The most valuable companies were the technology companies, and there was a 50% increase in (annual) productivity gains. I do see........

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