And it's not like he just flat out didn't invest all the money he wasn't putting into Geocities and Lycos. He was just putting it into other things, mostly stuff that was less the hot new thing, and therefore less in demand, and therefore more favorably priced.
I don't think he regrets his conservatism. From 1990 through now, BRK.A is up 4,200%, while the NASDAQ composite is up only 1,500%.