imho if you're at a company, and they're having layoffs... it's generally better to be laid off, get some severance, and end up at some other company that is hiring / growing, rather than a "survivor" who now has more work to do with fewer people at a company that is possibly troubled, unlikely to give any good pay increases any time soon, etc etc.

re #3 - no, "jack of all trades" tends to be a career trap / dead end. companies hire for specific skill sets.

The only reason to accept the negatives of working at a startup (stress, below market remuneration, workload) is the potential upside (rapid growth and an eventual liquidity event).

If the startup is contracting, it sounds like the only potential upside has disappeared. I’ve been in a similar situation before and made the mistake of sticking around, to the detriment of my physical, mental and financial health. Obviously businesses pivot and turn around, but that’s the exception rather than the rule. Most startups fail, and if your startup is starting to falter, I’d say it’s about to prove the rule.

I’ll give you the advice I wish I had:

Run. Start interviewing like crazy and get another job. Good luck.

Have you tried owning 40% or more?