If you are in a group that has the structural advantage of wages, safety, health and education – when you’ve basically already won the life lottery just by showing up – it is your responsibility to educate yourself. And really, don’t tell women to be nice. We’re angry. We have every reason to be. Frankly, you should be too.
This summarizes the attitude of the "Educate yourself" essay. The problem here is that you cannot put people into boxes called "winners" and "losers" based on their gender. That isn't to say there aren't structural advantages in American society that on balance favor men. There are. It's that the there are many kinds of advantages and disadvantages a person has based on their individual biography. Some of these depend on how their identity - their religion, class, ethnicity, gender, sexual orientation, regional dialect, etc. - is treated in society. Some are not.
There are all sorts of ways in which a man, even a white man, may be far more disadvantaged by his life and social position than a feminist woman he is interacting with. She may be the lottery winner by any reasonable interpretation of their life-stories. I don't think the author of this piece realizes how resentful this can make some men who are in that position and hear this. It's sexism to assume that a man has got it on relative easy-street by virtue of the fact he is a man to the point that any claim feminists make about male advantage shouldn't even require the beginnings of justification in conversation.
I grew up impoverished, in foster care, and with other disadvantages that by far wash out advantages I gained from being a man. To characterize me as a lottery winning member of an oppressor class, which she does in other parts of the essay, simply because I am the beneficiary of some discriminatory social mores borders on offensive. There are so many ways men and women can be socially advantaged and disadvantaged, that we are all part oppressed groups in one way or another. I don't think this means everyone should be so righteously angry that they can't ever even deign to explain themselves. While I don't think he'd ever admit it, someone like Droopy probably is pretty disadvantaged and probably resentful when he hears a message like this, even though he identifies with the sense of righteous anger.