I SUSPECT its due to the people who have wronged him. The people jim used to be friendly with that turned on him like ralph or sargon their turning on him never really impacted him and just generated him more views than anything
Jim never had to go through the shit josh did, not a knock on jim since his cross to bare is his illness I'm just giving a description of their situations, having to flee the country and get banned from payment processors and being targetted by the entire internet infrastructure for his niche gossip site so *think* that's partially why josh has to have a far stricter view of these things IE with Juju. Also josh getting burned the time he did try to legitimately help, like Chris chan, probably sticks in his mind as well hardening his heart to these fuckups cause he's personally seen it up front. At some point you get the empathy burned out of you for these self destructive ingrates.
What's interesting with rackets is that both jim and josh have the perspective of someone who is seeing someone who basically handed a golden life on a silver platter, and in jim's case the life he always wanted with a loving family with kids, just burn it all down for coke and coom.