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I believe I'd pay out of pocket at a reduced rate, but I'm not 100% sure.

I think it's not standard that you have to pay (perhaps a symbolical $1 (one Washington) fee for legal details). I don't like it, but I hope that someone with more experience in this kind of arrangements can give a more authoritative answer.

Paying money to exercise vested options upon leaving a company is very standard.

> Paying money to exercise vested options upon leaving a company is very standard.

True; also very standard is cashless exercise, where you "pay" for your options using some of the optioned stock itself (really, taking fewer shares in a type of margin purchase). [1]

[1] See, e.g., http://www.investopedia.com/terms/c/cashlessexercise.asp

This is usually only available after an IPO or other "event". Not many brokers want to let margin plays happen with start-up options.

Perhaps I'm misunderstanding. I understand he has to pay now.

I've never seen an options agreement that didn't require a cash payout to exercise the option after leaving the company. The amount of time can vary but in the US it is very standard for that to be very soon after you leave the company.

Maybe you are thinking of a restricted stock grant?

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