My Portfolio Changes Toward Resilience

Ravi Gupta asks: What if the greatest risk in markets today isn’t missing out on AI—but believing it can never crash? In this solo deep dive, he unpacks why today’s trillion-dollar bets on artificial intelligence may mirror past manias—and why, with pensions, private equity, and passive index funds all in the mix, the next downturn could look less like Silicon Valley in 2000 and more like Japan’s lost decade. All of these arguments build toward a single point: how Ravi is rethinking his own portfolio, and why he believes resilience—not hype—is the smarter path forward.

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• Read more from Ravi on Substack: https://realravigupta.substack.com 

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• Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/