I recommend that any decision you make should be within a regret minimization framework. For each decision you could take think of the worst case scenario and g

I recommend that any decision you make should be within a regret minimization framework. For each decision you could take think of the worst case scenario and go in with the full acceptance that this scenario can really happen. The things you might regret are. * Not taking the deal when it was presented * Taking a deal where the valuation was low * Not being able to work on your ideas * Being cheated * Regrets that go with being employed(there are limitations) * Being stuck in a bad situation for 4 years As far as the specific circumstances you mention, the deal somehow sounds dodgy, what with them controlling the vesting period and having the ability to terminate your employment as well. One real possibility is not selling, because you already have a pretty good idea of how the future is going to be down this path and from your post, you seem to be happy where you are. Another factor you might consider here is, How long would it take, for you to accumulate personal wealth at a similar level to what you get from being acquired and what is the level of independence you'll have to work on your ideas.