Which is fuckin' weird, 'cause who cares, right? this isn't sales. the man can program.
Now, he does have a handful of real problems. First, he takes interviews seriously; like he stops looking for work when he gets a serious one. He doesn't look for work while he's working. And he wants a job where he has experience with the languages and frameworks, rather than practicing his "I've got hands, I'm sure I can figure it out" that the rest of us do. To be clear, he's worked with me before, and I have seen him pick up new stuff. He's a smart guy and picks up new stuff faster than most, he just doesn't want to be deceptive.
(If anyone is looking for a smart C++ dude, preferably someone using QT, lemme know, I'll hook you up.)
The funny thing is that I just got off of working for my own company for a long time (not ten years... about half that) and yeah, it's harder to get back in the game working for other people; I'm making less than several of my ex-employees, and I had to do way more interviews than I usually do (though, as I said in another post, that might be because I was confused about what 'devops' meant, in a job description)
So... working for yourself at a company that wasn't venture backed is a disadvantage, but not one that can't be overcome. Lacking that "bro attitude" - that confidence - that willingness to push and shove and to say what is expected? that's a disadvantage... well, that's a disadvantage that it's really hard to overcome.