Besides the obvious answer of firing him or making his life so miserable he'll quit, etc., here's an out of the box idea (I don't know if the preceding 38 comme

Besides the obvious answer of firing him or making his life so miserable he'll quit, etc., here's an out of the box idea (I don't know if the preceding 38 comments touch on this - if they did, that validates my idea a bit): What about the idea of selling the company to him or firing yourself with a nice, generous severance or golden parachute? One possibility is that you don't yet respect yourself as much as you could. Another is he may be more important than you right now. A third is that you will start messing up at work if you keep him around, so you are future value add will at some point be less than his. Any of these three possibilities suggest that the company is better off with him staying and you leaving. That said, my first suggestion for you is to get a good therapist. Get some help from your real friends and family (parents? siblings?) And when you man up, fire his ass. Good luck. You seem like a good person intent on doing what is right for all but it may be time to do what's right for yourself.