Yep, he's definitely a self-hater. On top of that he is also an opportunist who goes where the money goes. There has been a boom in the manosphere section and he recently realized that embarrassing women for their standards is a lot more profitable than coming for both men and women. In the past i'll admit he did used to insult men just as harshly, but he hasn't produced content like that for over a year. Insulting women is what draws the crowds and that should tell you everything.
You're right. He preys on the insecurities of women and goes straight for the jugular attacking their age or looks and gives them zero hope. Apparently, if you are an average looking woman with some baggage but earns 6 figures you have no right to demand someone in the ballpark of your income bracket, looks or life experience. He makes these women feel like they are wrong for wanting what other women from other groups also demand. They give this man a carte blanche to tear them down and sadly look to him for validation. He's also bitter, twice married and not in a long term relationship at present so his advice can't be taken seriously. He also steals some of his content from other madow women YouTubers and repackages their material for his red pill/manosphere audience. This man calls himself masculine and high value but he's got a low value character and wreaks of toxic effeminate energy (this goes beyond his image consulting and manner of dress but is focused on his destructive delivery).