His mom's a witch (as in "literally practices magic", she laso runs a cattery) who pulled him from public school to "unschool" him, which is a fancy term for letting your kid do whatever they want. Cicierega is what happen when a dorky kid has absolutely no oversight, endless free time, and a small army of people online who will praise him for everything, the only difference between him and you or I is that we can hold jobs and function in society and interact with people outside of singing novelty songs and making Harry Potter references.
The same people, just without the advantages of computer-guided weaponry or the medical advancements to deal with the resultant injuries. Basically gangrenous hippies with sticks.
Unschooling is not letting your kids do whatever they want all the time. Even if it was, most kids naturally want to play, learn, explore and be creative. It's the other process that drains that out of them.
Five stars for this guy making tons of money via dumb internet videos. Twenty years ago he would be a homeless guy giving witty observations to people outside a coffee shop.
There was a point where I stopped thinking "Wow Neil Cicierega's sister makes funny comics" and started thinking "Wow Emmy Cicierega's brother makes funny videos"