Let’s say the company you work for goes public and your stock is suddenly worth $1,000,000 (as an example). A wise investor, you normally put all of your other savings into broad market index funds. Now, do you sell your company’s stock that was given to you and took you four years to vest into, or do you hold on to it and hope the valuation keeps rising? (This is a rhetorical question btw)
If you had $1MM in cash, how much of it would you use to buy the company's stock?
I work at Google and it astonishes me how surprised people are when I tell them I use autosale, the company program where your stocks are sold immediately as they vest.
They always ask "Don't you think Google stock is going to go up?" And I always reply that yes I do think it will go up but
1) that's not the right question to ask, you should ask whether it will go up more/less than anything else you could invest in with that money
2) My future compensation, both in terms of stock and salary, is already heavily tied to Google's future performance, so I have even more incentive to diversify compared with someone who doesn't work there.