Caleb's show is just Judge Judy reborn under the guise of financial advice, which is why he gets Judge Judy levels of viewership. Pick guests that will outrage the viewer, then berate them to their face for being stupid. In the same way Judge Judy would comp legal expenses for appearing on TV, Caleb comps these people by raising their social media profile. If Josh didn't have to be so cagey about how much money he has in his warchest, it would be top-tier TV watching Caleb's jaw drop to the floor hearing everything Dear Feeder has done to keep in operation.