It was 1999, we had just moved to Seattle, and all these people I had just met who were in their early 30's were retiring from Microsoft. Not just from MS -- they were retiring. Near the millenium, with the stock sitting at about $120/share, a good friend who had started at MS as a receptionist and moved all the way up to program manager (a rather common title, in those days) decided to call it quits. She cashed out, worth some $7.5MM, bought property on the Baja in Mexico and left town. Never saw her again.
Then, after the bubble popped in March 2000, I can recall people losing their million-dollar homes in Queen Anne because they had secured the purchase with options on IPO stock. All the sudden, their paper was worthless -- and a lot of people were left scrambling.
I remember stories of people who leveraged all this paper wealth, only to be left upside-down in the blink of an eye.
Such foolish times for people with resources.