>It seems to me there's a parallel to someone like Moxie Marlinspike who's vaguely in the same field, but seems to be doing very well for himself.

Moxie Marlinspike was doing well for himself when he was squatting in pgh and train-hopping, too. Some people are just better at coercing life into doing what they want to do. I think it helps that Moxie is probably a few standard deviations more intelligent than most humans, but that's just a bonus.