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Okay, so people are pointing out that First Headmaster looks a LOT like canon Shadow Milk; even more so than Fount. And, looking at what we see in the academy and what little we currently know of the Headmaster, it got me wondering:

What if after his "fall", Fount went undercover in his academy?

It's highly implied cookies attempted (or likely succeeded) in executing him, and the story we're being given seems skewed to making Shadow Milk look more menacing and evil after the fact. He is seen as manipulative, violent, a fraud, and a deceiver; and that weirdly plays into the narrative Shadow Milk has been cultivating around himself all this time.

But time and time again, it becomes evident that's not how Shadow Milk operates. He shows odd softness and curiosity towards the Brave Trio in the Spire (up until the point where they threaten his hold on Pure Vanilla, and then they have to go), he is consistently acting like a teacher to cookies who are willing to indulge him, he trusts deeply and looks for understanding in anyone who will accept his logic, and he still seems to hold Knowledge in a high regard even after all it did to him.

Plus, a lot of what deeds he's "done" seem to be at best correlated and overly exaggerated by Elder Faerie on behalf of the Soul Jams and Silent Salt. And at worst, they're completely fabricated to keep cookies from looking into what happened with the Beasts. The only truth we actively see is that the Virtues abandoned their roles and vanished before Salt, and Shadow Milk seems to be discussing what happened in a more studious disguise w/ Black Sapphire.

But now, looking at the design of First Headmaster and the academy, I'm not so sure that's the truth at all. In fact, I'm starting to think after his execution the Milk of Knowledge went into hiding, and he built up the academy as a place to teach exclusively the willing and worthy. This would make sense with his character, because it is a very possible step between exhausted Emissary who is not cared for, and the chaotic jester that leaves the tree.

A few pieces of evidence here:

First Headmaster is portrayed with a full-face mask in almost every depiction, and is in fact the ONLY Shadow Milk we've seen who wears one. Why would a self-described "incredibly handsome" and "beloved" cookie do such a thing unless he was explicitly trying not to be recognized?

The Blueberry Yogurt Academy seems to be located in a realm both bordering Tartrus and the Dark Side of the Moon, both being locations that would be hard for any cookie to access already, but then added onto that we also see that the only way across the river is via the Ferryman. What need would an academy have to be so hard for any regular cookie to get to? It seems directly designed to keep any unauthorized cookies from being able to enter the grounds at all

On top of that, there's an extra level of security with the sheer amount of eye motifs on every surface. It's highly implied that Shadow Milk can see through any eye in the Spire, so why would he not set up such a thing in the academy? And yet, there is no sign the eyes are seen as a frightening or oppressive thing at all. In fact, Pure Vanilla incorporates them into his bedroom in the Vanilla Castle, showing that they weren't ever seen as dangerous. Which implies that the eyes were meant to look for something other than the students. But, again, why would Shadow Milk be afraid of other dangers outside of his academy?

The most damning thing to me though is that the teachers seem very trained to protect against threatening cookies, but not intense monsters. They laid between the balance of life and death, and yet the most powerful and knowledgeable teachers in all of Earthbread barely could hold back the monsters. That means the Headmaster never wrote out the protocol for how to fight monsters invading the school; monsters that were under very real risk of attacking. So why is there a protocol to attack the Brave Gang and any other cookies when they enter? And why does it only seem to activate when non-students arrive? It's as if every teacher was trained to eliminate any possible cookie on sight that didn't belong. But that would only need to exist if the Headmaster believed there would be a possibility of cookies attempting to enter for the sake of hurting something within

These are just the bare few ideas I can scrap together off the top of my head, but all of them show a pattern of surveillance and secrecy designed to protect any cookie authorized to be there, and eliminate any unwanted guests before they could even arrive. And that level of safety is only warranted if Shadow Milk believed that cookies would be willing to attack his academy if they knew he was there. Which can only set the founding/Headmaster period of the academy post-execution, as prior to that moment he'd have no reason to believe they'd get so violent towards the Virtue of Knowledge.

If this is true, it means Fount did not corrupt as violently or frighteningly as he was implied to, but rather he simply took on another form that allowed him to spread his knowledge in a way that felt safer. It means that Shadow Milk did not abandon his virtue at all, and instead took to learning more about his creators and teaching cookies to become self-sufficient. It means he was objectively doing his job more effectively than he had been as the Fount of Knowledge, which is the exact opposite of what we would have believed.

And if that's the case? I can only imagine his fury when he was imprisoned/tortured by the "witches" and Elder Faerie for things he'd never done; and even more so because those same claims took the last pure thing he had made, and erased him even from his best work.