Sounds like a crappy situation. Hindsight is 20/20 but what I learnt from your story is that it's important to ask investors the minimum valuation and cash/equity split they will accept before engaging a potential buyer. In general, knowing your own limits is important going into any negotiation.
Before quitting and losing control over so many years of hard work, I would recommend putting your recent frustration with the VC aside and sitting down with him to understand what he wants from any future liquidity events. You say he has been a good investor so far, and may be he is under pressure from LPs or has something that would explain his strange behavior.
I can imagine it would be hard to work on a startup where your final outcome seemingly depends on a person who seems to be fickle and unreliable. Any clarity you can get on this may help align your interests with them.
Reminds me of something a very wise venture capitalist once told me in a cynical moment: "At exit, everyones' interests are misaligned". The only thing you can do to avoid this is try to 'hire' VCs who are also good people.
Sorry it has come to this. Hope it works out for you.
Thanks for the empathy with the situation. It is very good advice to make it perfectly clear what the intents of our VC is going forward. I sure will take the experiences from this process with me in future ventures.
Niels Bohr said that "An expert is a person that have made all the possible mistakes in a narrow field". Sometimes I feel like I'm getting there...
Before quitting and losing control over so many years of hard work, I would recommend putting your recent frustration with the VC aside and sitting down with him to understand what he wants from any future liquidity events. You say he has been a good investor so far, and may be he is under pressure from LPs or has something that would explain his strange behavior.
I can imagine it would be hard to work on a startup where your final outcome seemingly depends on a person who seems to be fickle and unreliable. Any clarity you can get on this may help align your interests with them.
Reminds me of something a very wise venture capitalist once told me in a cynical moment: "At exit, everyones' interests are misaligned". The only thing you can do to avoid this is try to 'hire' VCs who are also good people.
Sorry it has come to this. Hope it works out for you.