OP
To be honest, I am not sure how to feel about Sargon of Akkad (the speaker). I think he might sometimes makes sense, but I do think he is more of an anti- everything (SJW/feminist/socialist/etc), and a bit of a provocateur. His internet history is controversial, as you've pointed out. Some of his critiques are probably okay for particular arguments, but I think he can miss the nuance, and is not the best at building things back up holistically.
This is the same issue I have with Jordan Peterson. I have no problem with him worrying about men (because I worry about women). It does concern me that under the guise of a warped idea of "intersectionality" (which I do believe has been hijacked from the original lens that Crenshaw meant) we are building new hierarchies to punish the old ones, instead of abolishing them... I am not sure I can agree with how Peterson views feminism and women, because I reckon that he genuinely is arguing an "evolutionary psychology," relatively essentialist, position of women's interests and character being more "neurotic" and "agreeable". I don't really mind research into the subject, but it rankles because historically women have always been described as "hysterical" or "irrational," usually to support viewpoints like not allowing women to own property or vote. My argument is that even if some psychological differences are broadly present, as they may be, there is very little way real way of telling what exactly is nature and what is nurture. Because unless we dump a whole bunch of people into a desert island from birth without any outside influence, how do we tell? Broadly speaking we ought to accept that men and women are different, and there might be an element of innate psychology there. However, when we code certain personalities for certain sexes, this hurts everyone in the long run. If you don't code personalities for races, you shouldn't do so for sexes.
In my ideal world, we would strive to ensure equality of opportunity - but not necessarily equality of outcome, because individuals need to be able to influence their own outcomes. The problem is we have to find ways of creating a somewhat level playing field to start with, and here is where it gets murky. Because sexism is real. Racism is real. Prejudices are obviously real.
I am genuinely conflicted about the best way forward. In principle, I am instinctively against "positive discrimination" initiatives as there is something that doesn't sit right with me about choosing someone for a role based on characteristics they cannot change (sex and ethnic background being some of them), but at the same time I do get fed up with, for example, watching all male comedy panel shows all the time. And there is a huge problem if we ignore the fact that women actually need maternity leave in order to give birth to the next generation of people. I am not sure that enforced quotas or ratios is necessarily the right path forward, but I do think there ought to be careful consideration of things like programs to empower people (and this applies to economic background, etc as well). Because the honest truth is that people do pick up on societal messages that certain career paths/futures are simply not for them, and I believe that representation very likely plays a role in that.
I guess my argument boils down to this: I don't need STEM fields to be 50% female any more than I need 50% of the fishing industry to be female. But I want 100% of females to feel like they could go into STEM or fishing if they wanted to, and that these fields would be as easy for them to enter as it would be for any male. Likewise, if males want to go into nursing, for example, they should be allowed to, and not face structural discrimination from society. That doesn't mean I need nursing to be a 50% male field.
On the trans thing, I believe that there's a fundamental misunderstanding of sex, which is the problem. Trans ideology is an extension of the idea that males and females have "different brains," which is categorically untrue. There are brains in male and female bodies, but they mean as much to me as the assertions that there are kidneys of those who have male or female bodies. In other words, it means nothing. If you can say that you have a "female brain" in a male body, it means you're saying you can have a "female kidney" in a male body. Which is absolute horse s**t.
Basically, if I had a magic wand, we'd all move back to the centre so at least we could all talk to each other and hash these complex ideas out. I am a huge fan of meeting in the middle, if only to try and understand things.