You can't make observational comedy about being a young and hungry comedian/writer when you've spent the last decade being wealthy and out-of-touch.

If he was still clever, he probably could've threaded the transphobia needle and either figured a way to make it right or made it so funny that enough people would enjoy it regardless. But now he's cranky and spoiled by success so he's just going to get angry, which is even less funny.

Dude is a rich fuck who still bitches that other even richer fucks “stole” his money. And my poor ass is supposed to relate. He has been rich for most of his life but likes to pretend he’sa regular guy. He lives on another planet surrounded by bubbles of assistants and staff that kiss his ass