I don't think he nor potential hiring managers perceive it as a hole in his cv. He is pretty smart, could get a coding or tech lead job in a number places. Instead he decided to benefit from other human beings not knowing how to live life in their chosen developer careers and he entertains dreamers and monetized others' wants and imaginations. He is smart but not that smart. I watched his episodes where he walks through "hard interview questions". First of all they were not hard at all, and secondly his proposed algorithms were several times not optimal.
He tried his hand at trading and blew his account. His intent was to invest/trade his ESOP liquidation. It didn't work that way and now has a hole in his resume so he's resigned to YT revs.