A caveat of the popular "would you invest in this company?" question: it's not a good litmus test for "should I work at this company?" because you're not a VC.

A caveat of the popular "would you invest in this company?" question: it's not a good litmus test for "should I work at this company?" because you're not a VC. If you're considering employment, it strongly suggests you don't have as much money as an angel or VC, which puts you in a different position. Losing $100,000 might not make a VC with $100MM of other peoples' money bat an eye, but what about you?