You have several options in this situation as far as I can see: 1) Get a raise in equity - this is the option that you boss offered you. Say, that you negotiat

You have several options in this situation as far as I can see: 1) Get a raise in equity - this is the option that you boss offered you. Say, that you negotiate a better offer (2%-3%). In this case, if I judge the numbers correctly, that will match your current salary to what other companies on the market are offering (the 30-50K). However, that will ONLY match those offers - your risk in this case so you would have to negotiate a lot more to take into account the risk difference (30-50K fixed vs 30-50K potential). Even if you do that, you will still have the insane work hours, the feeling that you are not appreciated enough and the risk hanging above your head whether you will hit the target salary. 2) Get a raise with both equity and money - you could negotiate a 1% equity + a decent cash raise. It will be difficult if your boss is so stingy but it is worth the shot. Keep in mind again your risk vs reward. I would at least want a raise of 20K + the 1% equity. That would give you more than what the market is offering you. However, the point above applies here as well although you will be in a better position this time since you will have some stable cash increase. 3) GTFO from there I have dealt with bosses like that and, in my opinion, you run a good risk of not being happy there, burnout, loss of motivation, etc. Your boss seems not to value his employees very much and this will most probably never change. I can imagine that you will always need to chaise the market average (just like now) and negotiate to actually be paid an amount which you could easily receive elsewhere (judging by your offers). Granted, my views on this are a bit extreme (I think that an appreciate boss should offer you a raise instead of you having to ask for one) but that is my opinion. My advice: go and check out some of your other offers - it is very likely that you will find a better paying job with less working hours. If you have worked heavy hours until now, this change will do wonders for you. Once you find a nice place, leave. Edit: last paragraph