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by voxy_dale 3846 days ago
I did this exact thing last year, so a couple of things to be aware of. Firstly, many companies will not allow you to sell the shares to another party without their permission. You can talk to them about this but realistically, unless they generally allow this, they are unlikely to make an exception for you since it sets a precedent within the company, but you can try. Might be good to talk to a lawyer about this. Secondly, by exercising you will very probably expose yourself to Alternative Minimum Tax (AMT). If you don't know what this is, look it up as this can be VERY expensive. So, before doing any of this I would really talk to an accountant and possibly to a lawyer.
1 comments

On the flip side of this, it's very unlikely that the agreement bars you from _talking_ to the other shareholders about buying you out.

The employee does have some leverage here, to wit, he/she can just ask corporate to make an offer, and if the offer isn't appealing, can canvas all existing investors and say the shares are going to the highest bidder. Someone will buy them, whether the company, to get the headache dealt with, or an investor who's happy to add some common at a nice price.

Whatever the ROFR says, corporate legal will think many times before going toe-to-toe with a recent large investor who wants to buy some more stock.

You are usually not legally allowed to sell stock from exercised options to anyone without explicit permission from the company. It has nothing to do with ROFR.
But, you miss my point. If Peter Thiel wants to buy your shares and holds N% of the existing company, that deal will get done, regardless of the company's legal rights. It's social.
Actually, this isn't correct. Sure, you can talk to whatever shareholders you want, but if the stock is still privately held the company can actually dictate whether you can sell the stock or not, and to who. Company does not have to buy it back, and doesn't have to allow a sale if it does not want to buy it. Trust me, I've been there.

Now, some companies might not restrict sale, but that'd be somewhat unusual.