Purely speculation, he seems to be somewhere on the autism spectrum. He was weird his whole life and fairly oblivious to how other people think and act. His parents were well-off and spoiled him, driving him to Walmart at 8 AM to buy video games on launch day and dropping large sums of money to support his pet passions. He was raised to think he was a genius destined to do Great Things, but was never instilled with the work habits to meet his goals. He didn't want to code, but wanted to be a coder. He didn't want to animate, he wanted to be an animator. He didn't want to develop a game, but he wanted to be a game developer. That, and he identifies people based on the most superficial traits. He stereotypes most of his male peers as being dumb jock dudebros and that's the only fathomable reason why they don't support him. It's his go-to rationalization for every dissenting opinion, even in his steam posts he immediately assumes that the bad reviews come from Gamergators and people who only like shooters. The game itself is good, they just hate it for what it is. Just like how people only argue with Brianna due to her gender
And he doesn't see himself as a dudebro, hence he must not "really" be a man. From his perspective women are more pleasant, more sensitive to the needs of others, and more insightful. And when they get sloppy drunk, it's silly and endearing! He admired them going back to his original comics.
But he's also a narcissist, because narcissists can never link their failures to their actions, only their identity. This is crucial. To them, identity defines behavior and not the other way around. And because he's autistic, he was inflexible to changing any ingrained habits. So when John Flynt failed in every capacity, the only remaining explanation was that he must not "really" be John Flynt.