I think you are probably right. When starting the project, creators value their work very little, but value any attention given to their project very highly, thus a permissive license makes sense. Only after success hits do they regret it.
Even so, if someone was seeking fame and fortune through OSS (a somewhat foolish mission, but whatever), I would still probably recommend they release their software with a permissive license as companies are far more willing to get on board with MIT/Apache licensed software. I mean just look at the incredible amount of hate Facebook got for having the gall to offer a free patent grant with gasp a condition that you not sue them.
The best way to personally profit from OSS is very oblique. Assuming you make a kind of software useful to businesses like Redis (not end user software), it can look very good on a resume, can help you land some speaking gigs, maybe a book deal, and so on. If you build up your reputation like that, it should be possible to land a cushy, high paying job at a tech company somewhere or high paying support consulting.