After the last tech bubble burst in 2000, I developed a classification system for the people I knew and or would meet that were shaped by this.  It was a two by two matrix to deal with how people handled their stock (including options).    There were four possibilities:

1) Those who had stock that they could sell and sold it

2)       Those who had stock that they could sell and did not sell it

3)       Those  who had stock they could not sell and sold it

4)       Those who did not have stock and did not sell it.

The first group (by the way, I am a member of that group fortunately) were pretty happy people.  The second group were pretty unhappy people.  The third group was truly miserable.  They were the people who because of greed, hubris or ignorance sold stock that they did not really own like unvested stock, borrowed money using stock as collateral, exercised options and held the stock creating major taxes issues, or exercised stock options in companies which they managed knowing that their companies were not performing as well as the market thought.    Recently there were to examples of this that I would like to point out.  The first is that of Joe Nacchio, the former CEO of Qwest  which you can read about here and the other is that of David Hayden former CEO of Critical Path which you can read about here. They are very different stories of two executives in category 3.   I do not sense that we are in the same kind of bubble as we were in last time.  Certainly this is not a public market bubble but I thought I would share my little matrix and the dangers of being in category 3. By the way, many of the people in the last category we miserable when so many were getting rich (at leapt on paper) and felt a lot better when the whole thing came tumbling down.