You join a startup, they give you $100k “valued” of ISO per year. After two years you decide to leave somewhere else. You keep the ISO in hopes the company still IPO’s one day, correct? At any point you most likely can sell on the secondary market if allowed. Does the company ever buy back? What do most people do with their startup ISO? Sell, hold on, or something else?
No. You usually get 90 days after leaving to exercise your ISOs (some companies give a few years, but that's rare). Even if you exercise them, no one guarantees that your shares won't be diluted at some point later on, especially if you have left the company.
Or cancelled because the investor class is cutting their losses and forcing an underwater sale...
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Most ISOs expire either 10 years after they are issued or 90 days after you terminate employment. In some cases, if you are terminated for cause, they are cancelled immediately. Most ISOs also include a clause that will cancel them if sold on a secondary market or transferred to any other person.