Frankly, if one takes out my time at Simuality, when we were all being paid the same minimal amount from "angel investor" funds, I've pretty much not had a "real paycheck" since when the agency went out of business after my car crash in 1993. Following that, I worked on building Eschaton Books for a decade plus, never quite making it to break-even (and hence, not paying myself anything), then went back to school for programming (sufficiently close to the "dot com bubble burst" that I never even got an interview, let alone a job), then was the "Marketing Director" for the Wife's tutoring franchise for a number of years, again unpaid (although I think we did make some money on that), before landing with Simuality. However, once the "angel investor" money ran out, we were back to being unpaid, which continued into the re-branding (and restructuring) as Liminati, Inc.
Since then, I've primarily worked on a number of boot-strapping start-ups, generally as the Communications guy, but none of them producing a paycheck (I was typically a 20% owner - working for equity that never appeared), and doing random freelance/consulting gigs that paid a bit here and there (see my NASCAR-like logo wall at btripp.com for those) while cranking out resumes for "real" jobs. From 2009 to 2015 (when my health issues started to put the job search on the back burner), I applied for over 4,000 jobs, and maybe got a half a dozen interviews. Which really sucks (I don't handle rejection well, or else I'd be in sales).
Anyway, I have an old high school buddy (she likes to tell people we've known each other since 4th grade) who has tapped me for projects over the years, and actually paid me. We work pretty well together, as stuff that triggers my panic attacks, she has no problem with, and the stuff she can't deal with I can do with ease. She has a couple of patents she's looking to market, and several things in the works more or less related to those, so there's a fairly constant flow of stuff for me to do. She has a budget, but we've not yet maxed out my allocation on that (at a very low hourly, but, hey, it's there).
I was up at her place today, helping with the organization of some paperwork, etc., and meeting with another person that's handling other stuff around her. One of the nice parts of this deal, is that it usually involves going out for lunch or dinner, and the three of us headed over to an Irish pub up by her for lunch. Not bad "being on the clock" while getting fed!
Unfortunately, even if I hit the total number of hours she's got set for my help, I'd not be making "an income", but it's sure better than nothing coming in.