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Confused about employee stock options: How do I afford these?
ISOs (incentive stock options) can be closed out in a cashless transaction. Say the first round vests, 25,000 shares. The stock is worth $7 but your option is to buy at $5 as you say. The broker executes and sells, you get $50,000, with no up front money.  Edit based on comment below - you know they vest over 4 years, but how long before they expire? It stands to reason the longer you are able to hold them, the better a chance the company succeeds, and the price rises.  The article Understanding employer-granted stock options (PDF) offers a nice discussion of different scenarios supporting my answer.