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 I have had this same experience with this guy. Couldn't stand him when my parents watched him on Fox, thought it was all Boomer fear porn. Now I listen to a bunch of his shows.

I think people like Rogan and Mr. Carlson are the gateway drug to becoming an Anarcho capitalist. 

Rogan lead me to Lex, Lex lead me to Breedlove, and Breedlove Orange pilled me on the spot. 
 I'm not a big fan of greedlove, but I'm glad that he is orangepilling people. I have never understood the love for Lex either, he seems super fake to me.

I came by way of economics which was my major. I found Milton Friedman & Thomas Sowell, then Peter Schiff (who used to be great) & Doug Casey & Tom Woods, then Rothbard & Karl Hess & some others. And these days Part of the Problem & Bitcoin Audible & maybe Liberty Lockdown are my favorite regular listens. But Carlson, Joe, & a few others are often really good. 
 Likewise. The issue is there are very few journalists - which may be a generous description of Tucker - who are discussing these things.

If someone is addressing this topic, I don't care for their political persuasions nor do I (or should I) inherently trust them. It is the subject matter that is important.

If one cannot separate the two, then I suggest looking to other people doing the same, such as Jimmy Dore. Ultimately, they are having conversations and pushing the discussions into the open, which is what matters.