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It's possible your options expire 90 days after you leave the company's employment, or some such thing. I suspect that's the case. It doesn't make sense to ju

It's possible your options expire 90 days after you leave the company's employment, or some such thing. I suspect that's the case. It doesn't make sense to just walk away from those options, though. Ask the company's CFO or somebody if there's any way they can buy back some of your shares at or near market price. If they can do this, or if they can let you sell them to a third party, you can sell enough shares to raise the cash to cover your tax liability and hang on to the rest. Or, maybe the company can grant you an exception to the "exercise it or lose it" rule that kicks in when you leave. You won't know unless you ask. You have some leverage. With the number of shares you have, they'll probably need you to cooperate in any transaction they carry out. ESOFund is a possibility. But your company has to be a participant. And, they grab some of the upside and a lot of the downside. At any rate, you probably should get yourself a decent tax accountant (or maybe lawyer) to help you navigate this. It's worth paying for top-drawer advice. That person will know how to recommend an honest EOFund-like broker if that's the route you go. (Congratulations in advance, by the way!)

kevinpet 11y ago
To clarify, if you find a buyer who is interested in buying (would need to be a qualified investor), the company can exercise their right of first refusal to buy the shares from you at that price, but they cannot generally prevent you from selling. If I were in your shoes, I would probably want to have the deal lined up ahead of time before exercising. Consider going through the CFO or CEO to see if any of the company's existing investors would be interested in acquiring some of your stock. This has the advantage to the company of not bringing in an unknown outsider. Edit: I see further down that some companies have further restrictions beyond right of first refusal. I'd never heard of that before, but then, I'm only on my first startup where I think my options are worth anything.

kevinpet 11y ago

To clarify, if you find a buyer who is interested in buying (would need to be a qualified investor), the company can exercise their right of first refusal to buy the shares from you at that price, but they cannot generally prevent you from selling. If I were in your shoes, I would probably want to have the deal lined up ahead of time before exercising. Consider going through the CFO or CEO to see if any of the company's existing investors would be interested in acquiring some of your stock. This has the advantage to the company of not bringing in an unknown outsider. Edit: I see further down that some companies have further restrictions beyond right of first refusal. I'd never heard of that before, but then, I'm only on my first startup where I think my options are worth anything.