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What are the most common reasons for losing it?
The number one reason for folks who won the "IPO lottery" is they fail to cash out/diversify their stock, and at some point in the future the stock price drops dramatically. For example, during the 2001 tech boom/bust a lot of tech companies went bankrupt in a very short period of time. As a result a lot of tech employees saw the value of their stock/options drop to zero (effectively). The speed in which the bust hap…
There is no right way of doing it, you’ll never sell at the top. At least the right moment is when you can use the money for a project.