It should be said that licensing the WordPress trademark to other companies would obviously be a massive cash opportunity. But since the Foundation and Automattic are already so inextricably intertwined, and controlled by one person, it raises some serious, potentially even IRS-level questions of where that money would be going, exactly. (I’m not a lawyer or a tax expert. It’s just that using a nonprofit to help create a monopoly that funnels money to your own for-profit company, which doesn’t have to pay the nonprofit like the other businesses do because you run both of them, just sounds like the kind of thing federal agencies might be interested in.)

Yeah this looks a lot worse and shadier than whatever Mozilla is cooking with their Foundation / Corporation split lol. At least from what I understand from Mozilla's structure, the money seem to always end up in the Foundation (so the Corporation is just another front to fundraise), while here it's the opposite