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Re:Ask HN: When do you sell your stock grants? by burnallofit on Thursday October 26, 2017 @09:11PM (#15564771)
It totally depends on the company you work for.

I work for a company whose stock is going up. This makes it a great company to hold stock in. Unless, some other company's stock is going up faster. Which there always will be, but I don't necessarily know which one. I could be making more money. The trick is knowing which, unfortunately reading tea leaves is difficult.

So I diversify. I leave some money in my company, I put some money in other investments. That way, if my own company goes down in flames, I am not totally lost, and if they continue going up, then I gain.

What you need to do is understand your company, its products, its history, likely future, and risk factors. Yes that is a lot of stuff to research, but it is the way to sleep better at night while feeling good about yourself and your investments.

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