Struggles to adapt CV, scattershot applications, just weird enough to put people off. I’ve known a few people like this (my self included). A lot of it is understanding that you’re providing a service to some company and they don’t really care about details of the technical bits most of the time. Companies care about impact and what you can do for them (ie. how much money are you going to make them). It isn’t enough to be a weirdo techy any more. Companies actually don’t like weirdos. They already don’t understand what you can do and if you aren’t personable, they won’t understand you, either. Sadly, the dude needs to learn how to mask and manipulate communicate.