Bernie didn’t have his first job till he was 40 has ALWAYS worked for government!!!
I just checked his biography on Wikipedia (FWIW). It's not exactly true that he didn't hold a job until he was 40.
His biography is rather disturbing. He was not a run-of-the-mill protestor against the war. It would bear investigation to determine just how radicalized he was. That was his MO during and for a time after college. He did work during those after-college years, in NY then in VT. It's described as a variety of odd jobs. Enough of them are specific enough that they can be verified. It looks as if his first career-type job was mayor of Burlington at age 40. Before that, it seems he was just doing the VT partner with the earth NYC hippie dropout kind of thing.
I don't see anything in Sanders job history or accrued wealth that would be anything but counterproductive to criticize. But those radical early years....that needs lots of scrutiny.!