> many startups have decent health insurance

About what kind of startup are we talking here? When we discuss #1 engineer compensation we are most likely talking about a very early stage company that likely lacks a profound company structure and employee benefits program. So I would assume that #1 engineers will most likely not be greeted with a good health insurance on the employer side.

I was employee #1 at a startup. Right out of the gate our medical was better than Google’s. Having been exposed to the financial side of things, the cost difference between shitty and decent insurance for employees was inconsequential in the overall cost of doing business.

I was engineering hire #1, and we had no insurance and pay was half market rate, but at least the founders were incompetent and abusive depending on the day.

And therein lies a valuable lesson: don't be employee #1 if you don't know the founders personally, or can otherwise make sure they have a good track record.