He wants to be everyone's friend but you can't be everyone's friend in the position he's in. It requires you to be a hardass who doesn't take any shit and who commands respect. Tony has no natural authority or charisma. Tony refuses to fire anybody or tell hard truths.

AEW will have problems going forward as Tony hires people to be his friend and then stops using them but also doesn't have the balls to fire them, and these people will begin to seethe in the locker room as they look for leadership which doesn't come. Punk's ego going out of whack due to the leadership vacuum was the first symptom of this problem, but there will be many more events like this going forward.