I'd be wary about 4. I've worked at a fintech startup before where the founders boasted about how they had moved all their net worth onto the platform. Some time later over a casual chat and drinks, it turned out this was far from the truth. Don't just take people's word for it, I may be biased about startups now, but "trust but verify" is a good motto to go by.
Hell no. The startup I was working for fired me on a Friday, no notice, effective immediately. We had a team meeting the previous week about how macro environment was tough but everything was fine.
I'm so done bending over backwards to satisfy rich people who will dump me as soon as things get slightly bad.