Valuation and percentage aside, let me ask you this question -- now that the company is raising another round, where do you think the equity for the new investors is going to come from?
Say the company is trying to take on another 20mil at 100mil valuation, that's 20% of the company that will have to come out from the current shares, i.e. dilute all the current owners of the shares. That means to raise that money right now, the company is going to have to dilute you, but also all other employees and founders and investors. So you will lose ~20% of your shares, in exchange for XX-growth of the paper value of your shares.
Imagine that right now your shares are worth 1 million, but for absolutely no cost to you, those same shares will be worth 20 million tomorrow (minus the 20% that investors end up taking). This is not "exact" math, but it illustrates the point.
You can sit on your shares today, and make a ton of money overnight by doing _nothing_.
If you sell your shares today, for any amount less than what you would get in the above scenario, you're losing money. The hardball-CEO is just going to take your shares, and immediately resell them to new investors at 100X the price.
Unless you absolutely need the 100k today and can't live without it, your best bet is to hold on to the shares and take the gamble on them growing multiples. If the company does great, you win. If the company shuts down, all you lose is x-months worth of salary equivalent. If the company needs to raise more money later, then you can always offer to sell your shares at the later price.
If someone came to you and demanded your house for a small price of $20 dollars, would you yield and sell?
In the same way, the hardball CEO can offer whatever she wants, but in this case the ball is completely in your court. You can ask for 10 million, if you want, or a 100.
An ass-hat CEO could technically issue a billion shares to herself and new investors and completely dilute your value in the company, as a last resort.
Say the company is trying to take on another 20mil at 100mil valuation, that's 20% of the company that will have to come out from the current shares, i.e. dilute all the current owners of the shares. That means to raise that money right now, the company is going to have to dilute you, but also all other employees and founders and investors. So you will lose ~20% of your shares, in exchange for XX-growth of the paper value of your shares.
Imagine that right now your shares are worth 1 million, but for absolutely no cost to you, those same shares will be worth 20 million tomorrow (minus the 20% that investors end up taking). This is not "exact" math, but it illustrates the point.
You can sit on your shares today, and make a ton of money overnight by doing _nothing_.
If you sell your shares today, for any amount less than what you would get in the above scenario, you're losing money. The hardball-CEO is just going to take your shares, and immediately resell them to new investors at 100X the price.
Unless you absolutely need the 100k today and can't live without it, your best bet is to hold on to the shares and take the gamble on them growing multiples. If the company does great, you win. If the company shuts down, all you lose is x-months worth of salary equivalent. If the company needs to raise more money later, then you can always offer to sell your shares at the later price.