Michael May
The tutorial level Glen didn't deserve.
Before Fanniegate, before the preferred stock thesis, before any of it — there was Yellow Media. And before Glen understood Yellow Media, there was Michael May.
Michael saw what Glen couldn't see yet: that restructurings reward people who understand the capital structure. Glen fumbled the Yellow Media restructuring — didn't execute it well. But he owned the preferred stock, and the preferred stock still worked, because preferred stock has structural protections that common equity doesn't.
That one fumbled trade taught Glen more than most of his wins combined. The lesson embedded itself permanently. And the thesis that grew out of it became the foundation for everything after.
Glen says
“Michael was the one who knew what he was doing. I was the one who fumbled it. Give Michael the credit — he saw the restructuring clearly and understood the capital structure in a way I hadn't learned yet.”
“I came out okay because I owned the preferred stock. But that wasn't skill — that was the structural protection doing its job. Michael was the teacher for that lesson. The preferred stock thesis that defined everything after Fanniegate started right there, with a trade I didn't deserve to survive. Pre-Fanniegate, Michael May was the tutorial level.”
What Michael Taught Glen
Three lessons from one fumbled trade. Every one of them carried forward into Fanniegate.
Restructurings reward capital structure knowledge
Michael understood this intuitively. Glen had to learn it the hard way. When a company restructures, the people who understand where they sit in the capital stack come out ahead.
Preferred stock has structural protections
Common equity absorbs the damage. Preferred stock has contractual claims. Glen owned the preferred in Yellow Media and still came out well — even after fumbling the rest of the trade.
You learn more from one fumble than from most wins
Glen didn't execute the Yellow Media trade well. But the lesson embedded itself permanently. The thesis that came out of that fumble was worth more than the trade itself ever could have been.
Continue the Story
The Full Story
The complete arc — from Indiana to hedge fund to AI.
Read moreThe TradeYellow Media
The trade itself. How Glen fumbled and still learned.
Read moreAct IIAct II — The Thesis
How the preferred stock lesson became a full thesis.
Read moreAct IIIAct III — Fanniegate
Where the tutorial level paid off. The real thing.
Read morePeopleThe People
Everyone who shaped the story.
Read more