Hi, 2.5 years ago I joined a startup in SF as one of the very first employees. The offer was quite ridiculous, but after doing tons of work and becoming a key element I was able to negotiate again my compensation, and now I have north of 1% ISOs and 165k salary. My role is heavily technical, I built most of the core at the beginning and now I spend my day leading a few teams in the company (the company size is 35 people). The main problem is that I feel this inner conflict that is deepening every day: I can witness that my productivity and my contribution to the company is huge, but I don't get any satisfaction out of it because I feel like my slice of the pie is way smaller than what I think I deserve. Also, I feel very lonely in this matter, because all my coworkers are either more junior, less talented or less ambitious than me, and so for them the simple joy of working on interesting problems and getting an equity of 0.0x % is more than enough. Some solutions I can think of might be: 1) Get a better title (VP of engineering): this is going to be absolutely hard. The founders are extremely stingy and so are the investors, and I've been repeatedly told that in order to aspire to a VP role for a company with our traction you need to have a previous curriculum, which obviously I don't have since this is my first startup experience (I'm 28). 2) Leave: this one would make sense if it wasn't for the ISOs. If I had to leave and exercise my vested share of options, I would have to pay an incredible amount of taxes (because our valuation increased) for a liquidation event that might happen years from now, or never. 3) Ask more money/equity: knowing myself, this would make me genuinely happy for about a year or so, and so might be reasonable. The problem is convincing the founders (and the investors) would be very draining, since I'm already the highest paid technical person. Have you ever gone through something like this? Thanks for reading.