Entertaining read. It takes a while, in any business/other relationship to learn to stick to your guns. Reading this, and somewhat projecting, I would say you

Entertaining read. It takes a while, in any business/other relationship to learn to stick to your guns. Reading this, and somewhat projecting, I would say you lack confidence in some of your decisions. You therefore seemed opened to discussion. I'd personally never quit a job for a startup with no money. But if I did, I believe that would be on me and I'd be walking into it with the idea that this would be an interesting experience which might not pan out. Regarding the wedding/holiday. You just need to be firm about what you think is right. "I need to take this time off", "we need to reschedule/cancel as I have an important prior engagement". If that kills the relationship, well it probably wasn't going anywhere anyway...