My last boss was a bit like this.
He owned a small company with 7 employees, paid himself less than he paid us, and was in more debt than his house was worth.
So on paper he had less income and a lower net worth than me.

But he still lived in a big house while I was renting.
And the company was growing as well.
I still wouldn’t want to trade places with him.
I like my 30 days off plus sick days, where I can turn my phone off.