I have been in similar shoes, and had a huge impact as a founding engineer (#2 employee) at a startup (now unicorn). I wouldn’t say I had tremendous niche skill

I have been in similar shoes, and had a huge impact as a founding engineer (#2 employee) at a startup (now unicorn). I wouldn’t say I had tremendous niche skills, it’s more that I took so much direct ownership and accountability of so many problems that I was able to have outsized impact for the first few years until the company became too large for me to keep track of all of it (many years later). The founder knew my personality traits (we worked closely before) and chased me very hard in the hiring process. Many new employees and customers would ask me, after seeing me operate: “Why aren’t you the CTO and the founder is, since you are the de-facto technical authority here of every system?”. I had a successful career at that company but I never really brushed off the exact resentment you talk about, so if I were to do it again I don’t know if I would. It was a very hard emotion to deal with. You build something great one day or enable a massive new customer deal, get a rush of endorphins because you single-handedly made it happen via heroic efforts, then you remember your financial outcome will be a tiny fraction of the founder’s. My equity will be valued at best ~$10M (or more likely the ~$2M I already cashed out and the rest $0, we’ll see if they survive this downturn), whereas the founder will easily take $1B+ from this (and has already cashed out $xyzM). These days I’m generally “happier” at FAANG being a good team player and just helping everyone around without a “grandiose” mentality, I am at peace with being a small cog in a large machine. I don’t think I will ever do a startup as a non-founder again, I don’t want that feeling to surface ever again. From a cursory read, it seems like you may be in for a similar path with similar inner demons.