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Grass is always greener...

It can be a tough decision, but I have been through it enough times that I don't really care what the options package is. I just want one if everyone else gets one, but otherwise I look at salary and benefits. Because most likely the shares will become worthless, and if not, I most likely won't be around to see the liquidation event. I never exercise unless I know for a fact a liquidation event is coming.

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Thats different than being an uber early employee and knowing your private equity is worth a ton. I also wouldn’t exercise random startup shares unless they were real cheap and I wanted to roll the dice. The uber example is clearer. I’d always rather be a paper millionaire than not a millionaire at all. At least you have the choice to exercise some if you leave, or all if you can afford the loans. Also uber is a bad example since people DID sell their private shares as there was enough of a marketplace for it.

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