My favorite dot com crash story is second hand but I think it's true...a woman went tech crazy, buying all the hot dot coms, made a bloody fortune, and then cashed out in time. Paid the tax and bought long term treasuries with the balance, since she had enough money now.
But of course instead of being conservative...she made a bloody fortune riding the bond bull market for years and years. Just a complete, massive, total market timing success.
I really want it to be true.
I'm sure there are a a multitude of folks who have times things almost perfectly over the past generation.
Unfortunately, we all remember the folks who earned obscene money, but then wanted obscene^2. In the end they ended up with nothing but disappointment and a great life lesson.