Michael Saylor

The Conscious Contrarian
2 min readOct 11, 2024

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If you have not already heard of him, this may be a good time to familiarize yourself with Michael Saylor.

Michael Saylor is the CEO of the publicly listed company Microstrategy (MSTR) which, until a couple of years ago, was a little known data analytics company with a market capitalization of about 1 billion dollars.

Today, Microstrategy is worth 41 billion dollars (that’s 41x) and it is the only US company to have outperformed NVIDIA over the last 4 years.

The reason? Microstrategy adopted Bitcoin as a treasury asset in August of 2020 and has since acquired 252,220 Bitcoin, or over 1% of the total supply.

The company’s performance and Bitcoin acquisition strategy in themself are notable.

However, here is where it gets crazy: Michael Saylor has no intention of stopping to acquire Bitcoin, let alone selling any. Instead he is pursuing an aggressive strategy to obtain dollars cheaply by issuing more stock and convertible bonds — and buying more Bitcoin.

Here he is in a recent interview with Bernstein:

Most analysts think this is the craziest nonsense they have ever seen and that this works until it doesn’t.

What they do not realize is that Michael Saylor is essentially running a speculative attack on the whole, overpriced stock market. He is essentially saying: My stock, like all your stock, is overvalued and I’m going to keep selling it to acquire more Bitcoin until that is no longer the case.

In my view, we are witnessing one of the most extraordinary cases of financial engineering in history. How it will turn out is anyone’s guess. But either way, it will be fascinating to watch.

Hendrik Gerritsz Pot’s “Flora’s Wagon of Fools” (1632/1642)

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The Conscious Contrarian
The Conscious Contrarian

Written by The Conscious Contrarian

The Conscious Contrarian challenges conventional wisdom to uncover new, more attuned principles and perspectives for navigating the future.

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