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by uahal 4143 days ago
A huge percentage of stock options expire worthless (one common assumption is that 90% of options bring no value to the holder).

That's offset by the fact that a meaningful fraction of the 10% that have value to the holder can sometimes generate life changing wealth.

To me, substitution of stock options for cash is a function of how much financial risk you want to take or can afford.

If you have fewer financial obligations (eg. unmarried, no mortgage, no kids, no or low debt) and want to take a risk at a company by taking options in lieu of cash, do so.

If, on the other hand, you have financial obligations (any of the Big Financial Four above), it's probably better to get a salary that keeps your nose above water, take the token sign on equity they offer and then earn more shares by being awesome.

In any case, it's wise to objectively evaluate the value of your equity every six months or so. If it seems to you that it's got a lot of value, try to get more (ways to get more include being awesome and asking). If you think it's not worth much on two consecutive bi-annual reviews, see if there's another place where you could get a better deal.

It's no one's job to manage your career but yours.

2 comments

I don't suspect most people have any problem with worthless options. Quite the opposite, those are easy to deal with. What most people have a problem with is the requirement to exercise the options for real money when leaving a company before there is any proof that they are worth anything.
Seems to me that if a person is leaving a company for a different opportunity, they're making a clear comment on their perceived future value of the company.

That is, who would leave Google in 2002? Dell in 1993? Facebook in 2006?

In my opinion, the best stock exercises are cashless, one time events, paying full short term capital gains. Those trades represent almost no risk to the exerciser (exercisor?) and are pure financial upside.

I wonder how options stack up against just getting a higher salary, gathering all the extra money and taking it to the casino for one big spin?
This is an excellent suggestion. Alternatively, you could invest the extra money in stocks, which have a somewhat better average return.