I've been in a very similar situation myself. Being the lead developer from a very early stage, working with shaping the product and the business itself as well

I've been in a very similar situation myself. Being the lead developer from a very early stage, working with shaping the product and the business itself as well as actually making it happen by coding as well as heading the development team. However, in my case, a larger company group was the sole owner of the company and a significant part of the vision and goal went out the window after launch due to internal politics in the company group. This was demotivating because frankly, a large part of my purpose of getting on board disappeared. So this is one part to ask yourself, in terms of organisation/vision/company goals - has anything changed? In terms of tasks, I'm motivated by actually creating value - shipping things that made sense business wise. During the first 1-2 years this was the case, but when strategy was changed to cut costs (yet again due to internal company group politics of the owner) I felt I didn't really contribute on the level I wanted (e.g. architecting/developing large scale, heavy traffic modern web application versus copy/paste the nth banner network JavaScript code for yet another ad). Also, does the person have a niche in their role they particularly excel in and enjoy? Has it changed? In my case I very much was the bridge between business development and technical development. Getting tech people to understand business value of what to do, and work with business developers to leverage technology. When the company cut down on more or less all development and went into maintenance mode this opportunity kind of disappeared. Another take on this is that people may enjoy and thrive during different phases of a company. In the end I asked myself - in the end of the year, would I feel I've made the most out of it in terms of personal development, experience and pure happiness if I continued with this - or would it be better to leave.