My uninformed opinion on this is that he is so immensely rich that Twitter doesn't really need to be profitable in the long term anyway. Kinda like how YouTube usually operates at loss, but on Hitler's drug cocktail. It may bite him in the ass eventually because his whole house of cards of "real life Tony Stark" seems to be waning, but I think he's about as likely to become bankrupt as Yankee student loans are to be forgiven.