What I found was there were usually one of two types of employments Witnesses had - construction/trades or janitorial. The Witnesses who had the wealth were not college educated. They are the ones that started their own construction or janitorial company and then employed fellow Witnesses. Often the business owners would take advantage of their fellow Witnesses whom they employed.
I remember working for one such company when I was 19. The elder who owned the company stopped by the job site late in the afternoon. He told me and the other Witness working there that the job needed to be finished that day. It was a meeting night. The elder went to the meeting. We stayed and finished the job.
Often such elders financially supported their adult children so their children could pioneer. It was common to find Witnesses in their early 20s living at their parents' home, sometimes married with children, so they could pioneer.