I think there are two ways it can happen:
1) You show how they are under attack, how the current climate is increasingly about redistributing men's value away from them on virtue of being a man and being told all the world's problems are their fault at the same time. Given the situation you could try dropping in the
Dave Foley divorce video. Drop it in without any context. You could try dropping in a few other things and see where it leads. The likely reactions are:
a) He'll start to see certain things as a threat and become more receptive to more info
b) He'll associate with the side of women as he finds safety there, which is very likely as a beta of the year
2) You completely break his persona, Full Metal Jacket style.
I red pilled one guy pretty quickly by sending him a lot of material the radical feminists produce. At the time he was under a real tyranny and would make numerous comments (which I saw in some ways as cries for help) regarding how he had to get permission to do pretty much anything. Now the same girl is saying she wants to be a stay at home mother.
Other guys I sent the same material to have ended up going really far left, because they associate with the tribe of feminism and all the other left wing mobs that use emotional manipulation to extract resources from their out-groups and beta providers.
One of these guys has had a long history of slandering any area of male endeavour and becoming very submissively combative when exposed to male energy. He has no place in this world, so he will always side with women who give him zero respect for his pedestalling persona and outlook. And he's paying the price. He's with a bat-shit cray leftist, tax avoiding hypocrite with razor blade cuts all down her arms and he's constantly worrying that she will find out what an idiot he is (his own words). The only solution for such people is to be utterly broken by a woman who they gave everything to and she will, of course, take it all + stunt cocks.