I started my tech career around the turn of the century, and made the mistake of putting a ton of money (at least for me, at the time) into Global Crossing. My thought was that while there were all these "fluffy" doomed dot coms at the time, Global Crossing had billions in real, physical infrastructure they built. Obviously I didn't quite understand debt at the time, never mind the actual fraud that Global Crossing committed (I remember thinking "Wow, stocks really can go to zero and never come back.")
Sure, you could argue I made every newbie investor mistake in the book, but the worse consequence for me was that it "spooked" me early in my investing career, such that I became very reticent to want to invest in things when I felt they were overvalued. E.g. I was one of those people who thought there was a giant tech bubble when Facebook bought Instagram for a billion dollars - in 2012...
So sure, you may think I'm an idiot, but I can quite guarantee I was far from alone. It was only at the point where I really, truly believed "I'm definitely not smarter than anyone else in the market" (and hardly anyone is) that I just put my money in index funds, did regular rebalancing, and otherwise forgot about it.
We may be in an AI bubble, we may not, but I've seen way too many "vastly overvalued" companies continue to be "vastly overvalued" for over a decade (and then only briefly coming down before shooting back up again) to think that Tim Bray has any special insight here.