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The potential downside here is that you have to pay to exercise, which is lost money if the company folds.

As long as the strike is low this makes total sense.



Negotiate additional compensation to pre-exercise?


Isn't that just a needlessly complicated version of a stock grant, instead of stock options?

What benefit would this have over negotiating for a stock grant instead?


It should be an easy negotiation - the money just goes back into the company, less the taxes you would have to pay on the additional compensation.

In practice, you need to be a fairly significant employee to drive this kind of abnormal transaction.




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