When I went to that conference in like 2011 where the guy who created Dogecoin made fun of it and said it was an indication of how idiotic crypto was, instead of thinking to myself, "Yeah, that makes sense," I should have bought as much of it as possible.
Jokes aside, I feel like the last 10 years have largely been like that. The more you took massive nonsensical risks, the more likely you were to be handsomely rewarded. So, basically, everything I did that I considered "prudent" 10 years ago, I'd do the opposite.