Archive

Writings

Essays and observations extracted from published works on contrarian investing, market survival, artificial intelligence, and the philosophy of capital allocation.

9 essays

Market AnalysisMr. Grumpy's Investing Survival Guide

The Quiet Shift in Capital Allocation

What matters is what those managing serious amounts of capital are actually doing with their money right now. Their actions are starting to diverge from the prevailing narrative in ways that tend to matter later.

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3 min
Contrarian ThinkingMr. Grumpy's Investing Survival Guide

There's Always a Recession Somewhere

Don't you realize there's always a recession somewhere? You just have to look around. And that's often a good place to start investing.

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3 min
Technology & AINotes on Intelligence and Infrastructure

The Illusion of Progress: Why AI's Biggest Wins Are Also Its Biggest Weaknesses

When we design systems to dominate benchmarks, we produce gold medalists. Deep Blue played chess at a superhuman level, yet it could do nothing else.

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3 min
Technology & AINotes on Intelligence and Infrastructure

The Ghost in the Machine: Why Emotion is the Missing Piece in AI

Emotion is not a decorative element layered on top of cognition. It is a fundamental component of reasoning itself.

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3 min
Institutional InvestingThe Yale Model is Dead

The Quiet Death of the Yale Model

The Yale Model died somewhere between 2018 and 2022. Not dramatically, but quietly. The arbitrage is gone, but the fees remain eternal.

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3 min
Institutional InvestingThe Yale Model is Dead

The Career-Risk Trap of Institutional Investing

Your job security depends on failing conventionally rather than succeeding unconventionally. I get it.

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3 min
Mental ModelsAn Analysis of Napoleonic Principles of Work and Strength

The Drawer System: A Framework for Mental Organisation

When I wish to interrupt one occupation, I shut its drawer and open another. They do not mix.

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3 min
Market HistoryThe Stock Market Doesn't Care About This Book

The Origins of the Stock Market and the Birth of the Investor

Two young fish are swimming in the ocean when an older fish passes by and says, 'enjoy the warm water today.' The two younger fish look at each other and ask, 'what the heck is water?'

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3 min
Investment PhilosophyThe Stock Market Doesn't Care About This Book

Investing vs. Speculating: A Fundamental Distinction

To put it in the simplest terms, it comes down to when the moment of selling occurs and when the moment of buying occurs.

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3 min