He's such an untalented, unfunny, obnoxious hack with a massive sense of his own brilliance and wit - how the *fuck* did this guy manage to earn over 60K/year pumping out the shit he does?
And he 'started out' as a 'Brony Analyst' with 'pony hypnosis' videos and instructions - how did *anyone* like this guy's stuff?
I don't think people cared a whole lot about his brony videos. The guy has a billion different channels.
As I remember it, he got very popular in the anime sphere because of his endless sperging on Sword Art Online, he made hours of content bitching about every aspect of SAO. This, along with his controversial views got him a spot as somewhat of an outsider in the anime community. There's a lot of other normie anime reviewers like Gigguk, Glass Reflection and Mother's Basement (What a stupid name) who typically have no issue with selling out. One notable example being Crunchyroll, Digibro more or less made fun of Crunchyroll while everyone else was endorsing Crunchyroll in some respect.
Digibro doesn't want to do things the "normal" way and at times it seems that he's a contrarian for the sake of it. On top of that, he's unable to shut up about his beef concerning other youtubers. It's really not hard to take this position. Mother's Basement (which he's ranted plenty about) puts out content that sounds like a college essay. I think that's a trapping that's easy to fall into. You need to fulfill the YouTube algorithm so you need to make videos talking about absolutely nothing to keep afloat. Let's take MB's recent video on Ascendance of a Bookworm where he talks for 20 minutes about how the worldbuilding in that show is an "art". In reality, it's just the guy reading too much into it. Wow, this content is bad, thanks Digibro.
When he showed up at conventions, he would always put up this arrogant villain persona. And when on panels with these other anime youtubers, he was often the guy giving an off kilt opinion or being portrayed as the villain of the hour.
He wanted to be a pedophile but also wanted to get away with it so he become trans.
Being familiar with anime conventions, I can say I'm not surprised. Plenty MtF kid diddlers who pretend to be trans, but then also try to groom other awkward loser guys into being MtF as well. Wasn't new in 2010, isn't new today.
I am not sure if this is a behavior that's exclusive to anime though. Furry conventions garnered a nasty reputation for degeneracy in the 90ies they never recovered from.