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[EDIT] I suggest looking at your situation from this perspective: $100,000 is a lot of money and can last you and your family over a year in certain places.
Keep your shares and consult with a lawyer who can ensure you are protected further down the line. PLEASE DO THIS.
I will guarantee 100% that the type of people that offer you 20 cents on the dollar (as a founder) are the type of people that will screw you. 100%.
[EDIT] I suggest looking at your situation from this perspective: $100,000 is a lot of money and can last you and your family over a year in certain places.
I would work out the difference between the salary at say Google vs what you took during your tenure at the startup then double it because of lack of upside. Aside: If the co-founder is an HN reader, then they probably know the throwaway account is you. That is going to skew this negotiation.
edit: of course, parent's comment regarding the other party is still sound and valid :).
[EDIT] I suggest looking at your situation from this perspective: $100,000 is a lot of money and can last you and your family over a year in certain places.
This is bad advice.
[EDIT] I suggest looking at your situation from this perspective: $100,000 is a lot of money and can last you and your family over a year in certain places.
Earlier quoted context omitted.
No reason to do this - you have the shares and the CEO wants to buy you out. Remember - the CEO wants to buy you out for a reason, and I guarantee you the investors want you bought out. Don't underestimate how much leverage "them wanting you bought out" is. It may even be a stipulation of the funding round.
Do the investors even know about the conversation? People paying good money for shares will jump at the chance to buy them cheaper. A CEO closing an investment round may have very different incentives, like not frightening the horses. [edit, clarity]
Earlier quoted context omitted.
Get the last 409A valuation. That's the price the shares should trade at and in fact will create problems for the company if they do not. If the CEO offered the last 409A valuation as a price, then there's little you can do if you're inclined to take an offer because the 409A is the "fair market value" of the common stock. Usually the 409A is a huge discount, like 60-80% less at the stage you've implied the company i…
Also, missing in this discussion is that the board likely has to ratify any change in ownership and the board (led by the CEO) has tremendous ability to just say no and/or dictate who and at what price can buy. All this discussion of the what the fair value of the shares might be to outside investors is somewhat irrelevant in that situation.