As someone who identifies with the IDW and also agreed with Cathy Young’s article, I think you are right about the problems with Dave Rubin’s approach. I think classical liberalism needs to be more than just about anti-IDPol and free speech. I mean, these things are important, but they must be situated in a larger and more positive agenda, which people like Rubin seem to miss.
Even on YouTube, the far-left is now winning converts, because people like Rubin haven’t been up to the task of making their movement (our movement?) attractive enough. If this continues, BreadTube will win, and we will lose. This is what has caused me to re-assess my own direction on YouTube, here on Medium, and in other places earlier this year, and right now I am exploring a new approach to ‘revive classical liberalism’, making it bigger than just SJWs and free speech, as it should be.