I understand where you're coming from, but we sometimes seem to forget that pretty much everything these guys say on stage is made-up material.
Of course, some might be based on fact, but let's not assume whatever he says happened to him did happen to him, or even happen at all!
Did you watch that interview about his "everything is amazing and nobody's happy" bit? He said that the bitchy guy "sitting next to him" in the plane was actually him!
This whole subthread is based on "things Louis CK said". Regardless: it's doubtful, given how well his tours seem to do, than Louis CK is anything less than "pretty wealthy".
Of course, some might be based on fact, but let's not assume whatever he says happened to him did happen to him, or even happen at all!
Did you watch that interview about his "everything is amazing and nobody's happy" bit? He said that the bitchy guy "sitting next to him" in the plane was actually him!