I'll give Lil Bean credit for this much: He's one of the only lolbertarians who stuck to his guns. That might make him out of touch and stupid, but at least he has more integrity and a more solid worldview than most other e-celebs, whose only ideology is getting retweets.I think Matt Christman from Chapo Trap House summed it up best: Ben Shapiro is a conservative ideologue for when there is plenty. He spruiks The American Dream that all you need is hard work. I think this is largely the reason why he had to leave Brietbart. He didn't get the memo that entire large swathes of the economy STILL hadn't recovered from the Global Financial Crisis, many of jobs were automated, swallowed up by huge corporations like Wallmart or moved offshore.
The conservative politics that were in vogue during the 2016 election were those of anger, betrayal and the motivation to actually do something. The only time Ben Shapiro shows any sort of conviction is when he's refusing to use a trans persons pronoun which honestly, even if you don't believe it just makes you come off as being an asshole. Even his most ardent conservative followers know this. All the funny YouTube video titles are funny but they're just videos of an autist being a cunt at the end of the day.
Disagree with you on the pronoun thing, but you're right that the videos of him owning SJWs just aren't that impressive.
SJWs (especially the ones in the compilations, who are such caricatures I'm starting to think they might actually be plants) are really, really dumb. Pretty much anyone with a half a brain can own them. I think it reflects kinda poorly on Ben that these are the only people he bothers debating, like he won't go up against anyone that doesn't melt down at the sight of him.