I would love to see a deeper analysis of how he went broke. I mean 8 kids is a lot, but still...
I do get the job difficulty, though. As many people found out during the 2008 recession, once you're out of work for a year or so, no one wants to touch you. It took a while for my brother to find a simple retail job after taking a year or two off, and his prior career was in retail management (albeit at a higher level). This poor guy had experience not one but two rapidly imploding industries (print magazines and scripted comedy TV), so it would have been even worse for him.