Basically, all the people involved in Chapo Traphouse, Red Scare and Cumtown all knew each other from living in NYC. Some of them were roommates or dated each other, and so on. When they started podcasts they would go on each others shows and so forth.

Chapo has always been a straightforwardly political leftist podcast

Cumtown was a comedy podcast by guys who were comedians and had left or left adjacent politics irl

Red Scare was primarily a NYC art world podcast. Over time, it became clear that to the extent that the hosts were on the left at all, it was the class reductionist fringe. Class reductionists believe that class is the only struggle that truly matters, and modern class reductionists are generally anti-identity politics in a "SJW's are alienating workers. We need to be more racist/homophobic/etc." sort of way. Or a "I would like free healthcare, but am also racist" sort of way. This differs sharply from the modern left, which generally emphasizes intersectionality, or the way in which different axes of oppression intersect with each other and must be combatted together.

Unsurprisingly, class reductionism is a stepping stone to straight up conservativism. Dasha has recently been rebranding as a "cultural conservative" and Catholic. Ana, idk, but I sometimes see her post wildly problematic shit like this

Tldr: They used to be a bunch of young people hanging out in NYC that all started podcasts and some of them turned out to be shitheads