My theory is that he just doesn't understand technology. He probably grew up in a world where his parents/family/friends had steady income from "lifer" jobs and tried to apply the same concepts to his income.
He doesn't know how to set up capture cards, use software, build a computer, edit videos, use proper passwords, manage his internet connection(s) properly, use a VPN, use a mail service besides fucking Yahoo, order groceries online or pretty much anything. He can't even manage to play or stream PC games properly (!).
He can't even set up his microphone properly, he can't figure out how to use discord, he can't use chat properly.
So it is perhaps more realistic that however intelligent Phil may actually be, it is definitely not in the world of computers or technology.
This would explain his naive attitude when it comes to YouTube-bucks and his failure to adapt to the changing nature of YouTube in any capacity.
YouTube was actually second-wave when it came to changes in advertising revenue. The wave before YouTube was people's websites that relied on Google's search algorithm and/or revenue generated from ad views due to their search rank/popularity.
If Phil was at all tied into any of these concepts, then he would've been able to adapt far more effectively. He obviously doesn't posses any intrinsic understanding or appreciation of the inner workings of online-based advertising.
What Phil calls "street/book smarts" I prefer to call "being astute". It defines the ability to pick up something and learn it rapidly, without having to refer to basic instructions.
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Some people just aren't astute by nature. I would say Phil is one of those people. He might do great in some other environment, but being that he relies on the internet, it is not the arena for him.
If he was actually astute, he would have all those skills I mentioned above as well as perhaps areas like webdesign, SEO, programming and video editing. He'd be able to get a job with those, even if it was a junior position.
Not everyone is destined to be a rocket scientist. He'd probably do well for himself if he moved off the internet entirely and got a job in another industry.