An age-old question. If you look at Larry Ellison or Bill Gates, they would not be where their are without holding a whole lot of stock when the could have sol

An age-old question. If you look at Larry Ellison or Bill Gates, they would not be where their are without holding a whole lot of stock when the could have sold. Personally, in the case of your first liquidity event, it is a great time to take enough off the table to never have to worry about money again. Beyond that, it is a matter of risk tolerance and what you find entertaining. Here are the wise words from the CEO of the first start-up that I worked at, which went public (but I was too junior to make much money): "Remember, at an IPO, the people that know the company best think that it is a very good time to be selling stock."