On the surface the strategy as he's talking about it makes sense and works but he's only operating at the surface level
Nobody's "stigmatized" and "doing it for other reasons" doesn't exist when there's only one reason to do it, everybody does it for the same exact reason. Expose flaws in the #1 and take market share
The problem is at some point you have to actually deliver on sentiment you're putting out or people grow tired of the act. Companies highlight weaknesses of leading brands and their solutions to the problem, ie "I'm a Mac/I'm a PC". The benefits of the challenger brand are clear and the consumer has to make a choice.
Between sophomoric jokes, sassy side commentary from Tony and his wrestlers, or complaining about WWE doing business as far as tampering that they obviously have done as well, what choice has Tony Khan presented fans other than "We're not owned by Vince & here's a bunch of matches"?
Not to mention the analogies given weren't the best because Pepsi & Coke don't exchange jabs, if they both weren't colas you wouldn't think about them tribally. And Pepsico has the leverage of being a lot more than just beverages, which is why most food places carry Pepsi over Coke. He has a lot more going on outside wrestling but he doesn't or clearly can't leverage that into his wrestling business model.
I don't doubt he was given a book but he clearly didn't read past the first few chapters. That new kid on the block, challenger, let's go after the top and shyt on them turns into insulting people's intelligence if the brand doesn't follow through. This is where he is now with ratings that have been stagnant but also now his ticket sales following suit