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Let me answer a question you haven't asked but that is very relevant:

Q: How can I mitigate the risk of holding startup shares that are illiquid and whose value can drop to zero?

A: There are investment firms that will help you buy employee stock options and then split the proceeds with you. One of these is ESO Fund (esofund.com) and they are very nice people. They can help answer your other questions as well.

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