Couple of strategies to consider: If the CEO is suggesting vesting for this equity position ask for highly accelerated vesting schedule Negotiate for protecti

Couple of strategies to consider: If the CEO is suggesting vesting for this equity position ask for highly accelerated vesting schedule Negotiate for protection against dilution if additional rounds of investment are needed. In the end, 8% undiluted might be better than 15% post dilution. Another strategy that occurred to me is to take the CEO's offer and discipline yourself to take the $25K difference in cash and invest it in small cap stocks. Obviously it won't actually be $25K after taxes but you get the idea. This strategy enables you to diversify your risks. Of course if this start-up is the big hit you are hoping for the return from small cap stocks will pale in comparison to the returns from start-up equity. Finally, you could ask for something in the middle - how about 10% / 115K If it is more about the respect and co-founder status than the money itself ... ask yourself what other things communicate co-founder to you?