> Today, my base salary is $175K, no bonus, no stock refresh since the founder grant, fully vested stock, no severance, no indemnification. (Mainly because I just haven't asked for new comp b.c company is in a difficult spot) - In comparison, I hired a critical new C-Suite exec (COO) and gave her $285K/year

Here is your problem.

Some founders milk company directly on bonuses and pay, there is no "grand exit" when they go public. I think you may be subconsciously aware of that, maybe there is some hidden regret or self-hate etc... Continuing with this frugality may not be way forward.

I would suggest:

- get out of NY, some nice environment near sea or forest, work remotely

- prepare for your exit. Move out of NY to minimize income tax etc..

- can you actually become CEO? If not, it is not your business anymore, not your problem

- find way to increase your take-home money. For start you could pay yourself for overtimes. Maybe if you move out of NY, you may need office there and so on...

- personal brand is worth quite a lot. Maybe there is way to use this startup to build your own.