One of the biggest problems with the dissident right now, something that everyone from Millennial Woes to Jared Taylor have noticed, is that it attracts people who revel in being socially outcast.
The left has been winning because they were "fitting in" and then very subtly and incrementally subverting the culture once they got into positions of power. That's how they took over academia, by fitting in socially, getting into hiring positions, then hiring SJWs who frame the key message in terms of acceptable discourse and giving no room to the right. Same with the mainstream media, same with the social media, same with journalism….etc.
Rather than taking a look at Reddit, Youtube, Facebook, Twitter…etc and saying "Hey, we should fit in and become mods there and then take over by removing the left wing posters by enforcing rules and pushing our own message in subtle, intelligent ways", the right retreats to /pol/ and jerks itself off on how gay mainstream sites are and how cool you are to be the few in this echochamber, too in love with the image of itself being some enlightened misfit class apart.