> This person signed a vesting agreement that agrees to a 36 month vesting schedule with a 12 month cliff. This was agreed to in advance by all parties. I have

> This person signed a vesting agreement that agrees to a 36 month vesting schedule with a 12 month cliff. This was agreed to in advance by all parties. I have no qualms with him retaining what was earned under the agreement. I'm curious about how the vesting agreement was written. I think that many people write these assuming that any shares not vested will be due to someone separating voluntarily. In this case, was it specified what happens if the separation was involuntary? Assuming that involuntary separation was not specified in the vesting schedule, then I think that you should just move on. Maybe talk to him to see if the separation can be on better/nicer terms. As a thought/empathy exercise, how would you feel if it was you who was being ousted? Keep in mind that you certainly wouldn't think you would deserve to be let go (just like he thinks). What would you think is fair? On a more constructive note, I suggest you ask your mentors/investors about expanding the share pool (esp. if you get more funding). It is not uncommon for founders who are no longer affiliated to get diluted quite a bit (imho rightly) when compared to the founders who stayed and built the business. This perfectly reasonable dilution can be done in a professional way or a spiteful way -- I suggest taking the high road. In the event that you reach a liquidity event, I think that you will be very happy with what you get, and you will probably be happy with what the person who left gets (i.e., a relatively small windfall for getting a business off the ground in its most fragile stage).