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Strategy Drunk

Strategy Drunk

A little Learning is a dang'rous Thing;Drink deep, or taste not the Pierian Spring:There shallow Draughts intoxicate the Brain,And drinking

Dec 15, 2019Updated Jan 27, 2026

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A little Learning is a dang'rous Thing;Drink deep, or taste not the Pierian Spring:There shallow Draughts intoxicate the Brain,And drinking largely sobers us again.

—Alexander Pope

Businesses do dumb things all the time. When it happens, a sort of ritual ensues: they get lambasted in the press, Twitter erupts, and at some point, inevitably, Matt Levine lifts his fearsome pen, and channels our collective bewilderment into the perfect sequence of words.

Some recent examples:

  • The financial misadventures of Adam Neumann and Masayoshi Son
  • The crypto madness of 2017
  • Robinhood “checking & savings” account
  • The Mac butterfly keyboard
  • “Funding secured”

Of course, these things really were dumb. They deserve to be called out. But in the midst of the mosh pit, few stop to ask: why did they actually do that?

The assumption is that these managers, unlike us, are just incredibly dense. I mean, what else could explain it? But I believe reality is more interesting than that. It’s not that managers are dumb—in fact, they’re often extremely smart. But something causes them to overlook basic problems at an alarmingly high rate.

It happens so often, I often wonder why. It’s an interesting question, but mainly: I don’t want to screw up!

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