To be honest, I think all founders are in some degree of pain. I mean, I say that hoping it will make you feel a little better, but it certainly won't solve any

To be honest, I think all founders are in some degree of pain. I mean, I say that hoping it will make you feel a little better, but it certainly won't solve any of your problems. For me, knowing I can quit whenever I want helps. I mean, I would literally quit and move on if things got too bad. There are plenty of opportunities. But as it turns out, either my pain tolerance is pretty high, or it's never gotten bad enough -- probably out of sheer luck. To me, your situation is straight forward. This is what you're missing. Well, two things. #1. You are burning out. Pretty standard, frankly. And anything could cause it. For some it's the mid-life crisis. For some it could even be diet. My mother took pills that caused night terrors. They stopped when she changed medication. The typical entrepreneurial cause would be "lost your passion". That thing that got you motivated before you went to work is no longer there. Your entrepreneurial mojo is gone. But of course, that makes for a good narrative, but in reality it could be anything. Even just plain fatigue. #2. I'm not sure how conscious entrepreneurs and founders are of this, but if you're a fan of first principles, you should be a fan of this one. An entrepreneur is someone that creates jobs. Though we can define it many ways, ultimately the core competence of an entrepreneur is in their ability to grow a company beyond just themselves, and... move on. So a successful entrepreneur is either serial - moves on from startup to startup, or is monolithic - they build one business but with multiple departments under one umbrella (a la Amazon or Microsoft or Apple, but head count still keeps growing). So #2 is your third option. This is what you need to do. > don't know how to make it work Figure this out, just like you did everything else. > The product is just too complicated (tons of domain knowledge required) for someone to come in and take over Simplify and document until you're out of paper, then train someone. > isn't that interesting Doesn't matter. Money is interesting. If they're being paid for work they agreed to do, it's just a matter of finding a professional worker. The thing about your third option is, at least to me, it's the obvious final step. If you're looking to get acquired successfully, then you are looking to be replaced, no? And the hurdles for your third option are exactly what would turn off anyone looking to take over. So for your own sake, and for the incoming new boss, you need to continue on with your third option. Anyway, hope that helps!