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I've done this before. Don't underestimate the opportunities that talking with the CEO (and board members) about your situation may present, especially if you'r

I've done this before. Don't underestimate the opportunities that talking with the CEO (and board members) about your situation may present, especially if you're on good terms with the company, have dutifully served for 7 years, and it makes sense for you to move on. Existing friendly investors in the company may be interested in owning more stock in the company and may purchase your stock in a transaction the CEO is okay with. You could explain the tax liability and that you've served dutifully for 7 years, and potentially exercise and sell enough of your options so that you have enough cash on hand to cover the tax liability for your further exercise. This is all in an ideal situation. How you communicate and play your cards with the CEO will matter a lot.

overdrivetg 11y ago
Also been there, done that. The other company ask if you have the relationship would be to extend your option period out for a bunch of years - see Pinterest as a precedent (7 years) [1] Start with whatever executive you have the best relationship with (ideally CEO/CFO). It may be hard though since this tends to require board approval. Oh yeah - you also don't get any cash out today either, but you don't have to track down and negotiate a private sale or deal with taxes, plus you get to keep any further upside if/when the company does eventually become liquid. The other benefit to the company with option extension is that you won't be on their cap table anytime soon - generally fewer shareholders == better for them too (pre-IPO). Your options would have to convert from ISO into NQSO, but you shouldn't really care about that since at least you get to keep them. Lots of nuances to any option (heh) and an accountant / tax attorney should be a no-brainer for you. Since you can't PM me and the HN guidelines don't prohibit referrals, my CPA easily more than paid for himself on my transaction: [2] Good luck, and congrats! [1] http://www.businessinsider.com/pinterest-will-let-employees-exercise-options-for-seven-years-after-leaving-2015-3 http://www.businessinsider.com/pinterest-will-let-employees-... [2] Kevin Rice at www.altumpartners.com

overdrivetg 11y ago

Also been there, done that. The other company ask if you have the relationship would be to extend your option period out for a bunch of years - see Pinterest as a precedent (7 years) [1] Start with whatever executive you have the best relationship with (ideally CEO/CFO). It may be hard though since this tends to require board approval. Oh yeah - you also don't get any cash out today either, but you don't have to track down and negotiate a private sale or deal with taxes, plus you get to keep any further upside if/when the company does eventually become liquid. The other benefit to the company with option extension is that you won't be on their cap table anytime soon - generally fewer shareholders == better for them too (pre-IPO). Your options would have to convert from ISO into NQSO, but you shouldn't really care about that since at least you get to keep them. Lots of nuances to any option (heh) and an accountant / tax attorney should be a no-brainer for you. Since you can't PM me and the HN guidelines don't prohibit referrals, my CPA easily more than paid for himself on my transaction: [2] Good luck, and congrats! [1] http://www.businessinsider.com/pinterest-will-let-employees-exercise-options-for-seven-years-after-leaving-2015-3 http://www.businessinsider.com/pinterest-will-let-employees-... [2] Kevin Rice at www.altumpartners.com