YouTuber, ex-philosopher 
Business email: info@contrapoints.com
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You demonstrate fluency with their jokes, their memes, their whole way of thinking. Then you begin to unravel the worldview that you've, at first, pretended to share. Only once that's accomplished do you start building up a new way of looking at things.
The point of the initial fake-out is that it's warm and inviting. If the video is framed as "Why You're Transphobic"—no one likes that, no one listens to that. They're dead against you from the start.
People have this expectation about what an "SJW" is like: that you're angry, always outraged, humorless, tiresome, earnest to a fault. The point of ContraPoints is to have SJW-type talking points presented by a host who's nothing like that.
If I come right out of the gate with guns blazing, shouting "YOUR SHITTY MEME GETS TRANS WOMEN KILLED"—no one listens. I'm just a hysterical wacko in the eyes of everyone who isn't already woke about this.
3: "Would you do a video with the n-word in the title?" No, I wouldn't. I'm not black.
4: "If trans women see the phrase 'Are Traps Gay?' without a warning, that could be triggering/upsetting to a lot of them." I'm not someone who disparages safe spaces. I think it's incredibly important to have spaces like that. But my channel is not designed to be a safe space.
You don’t have to be warm and inviting tho? They don’t have to like it?
Also: It doesn’t have to be a binary inviting/hostile
This is pretty obvious to me and it baffles me some people don't get it. There are enough outrage channels around that tackle shit straight up, they all preach to the choir. It's futile. The left needs to understand that optics are a tool, not a compromise.
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