Tutorial Level

The Yellow Media Tutorial Level

Pre-Fanniegate. The lesson that changed everything.

I fumbled this one. Michael May was the one who knew what he was doing. But even fumbling taught me the most important lesson of my investing career.

Full Story Act III: Fanniegate

Michael May and the opportunity

Before Fanniegate. Before the GSE shareholder fight. Before eight books and three hundred articles and twelve years of showing up. There was Yellow Media, and there was Michael May.

Michael May spotted the Yellow Media restructuring opportunity. He understood the capital structure. He understood what the preferred stock was worth relative to where it was trading. He knew what he was doing. Glen got involved because Michael knew what he was doing.

This is important to say clearly: the credit for the idea goes to Michael May. Glen was along for the ride on this one.

The honest part

I fumbled it

Let me be direct: Glen did not play the Yellow Media restructuring well. He didn't optimize the timing. He didn't maximize the position. He made the kinds of mistakes that, in retrospect, are obvious but in the moment felt like reasonable decisions.

This wasn't a masterclass in restructuring investing. This was a guy learning on the job, making errors, and getting bailed out by the structural protections of the instrument he happened to be holding.

The preferred stock saved him from himself.

How it played out

Discovery

Michael May identifies the Yellow Media restructuring opportunity. Glen gets involved.

The Fumble

Glen doesn't play the restructuring optimally. Suboptimal timing, suboptimal sizing. Not his finest work.

The Save

Preferred stock does what preferred stock does — provides structural protection even when the holder makes mistakes.

The Lesson

Preferred > common in restructurings. Not sometimes. Not usually. Structurally. This becomes the thesis.

The Payoff

2016–2017: Glen moves from FNMA common to preferred shares. The Yellow Media lesson, applied at scale.

Four lessons from almost-failing

Preferred stock has structural protections

In a restructuring, preferred shareholders sit above common equity in the capital stack. They have contractual claims that common shareholders simply do not. This isn't an opinion — it's how corporate finance works.

You don't have to play it perfectly to win

Glen fumbled the restructuring. Made suboptimal decisions. Didn't maximize the opportunity. And still came out well, because the instrument itself — preferred stock — had built-in downside protection.

The tutorial level teaches more than the boss fight

Yellow Media wasn't the biggest trade. It wasn't the most profitable. But the lesson it taught — about capital structure, about preferreds vs. common, about structural protection — was worth more than any single return.

Find the people who know what they're doing

Michael May spotted this. Glen followed. Knowing when to follow someone smarter than you is itself a skill. The best investors aren't always the ones with the original idea — they're the ones who recognize a good one.

The through-line

Yellow Media → Preferred Stock Thesis → Fanniegate

The exact lesson Glen learned fumbling through Yellow Media — that preferred stock has structural protections common stock does not — is the reason he moved from FNMA common shares to preferred shares in 2016–2017.

That wasn't a guess. It wasn't a tip. It was the Yellow Media lesson, battle-tested through personal experience, applied to a much larger position. When you learn something by almost losing money on it, you don't forget it.

Michael May probably doesn't know that his Yellow Media call is the reason Glen ended up in Fanniegate preferred shares. But it is. The tutorial level taught the skill that mattered most in the boss fight.

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