Habit Binge

How Michael Saylor rebooted his career and his company by becoming the world’s biggest

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Microstrategy CEO Michael Saylor
MicroStrategy CEO Michael Saylor

Michael Saylor is no stranger to the limelight. The MicroStrategy CEO is perhaps best known for losing $6 billion in a single day during the height of the dot-com bubble, when the software business he had founded at age 24 nearly collapsed.

Two decades later, Saylor is once again at the center of a jittering conversation, thanks to his unprecedented embrace of bitcoin. With a mix of debt and virtually all of MicroStrategy’s cash, Saylor has bought more than 100,000 bitcoins that today are worth billions – and he doesn’t show any signs of slowing his buying binge anytime soon.

While other high-profile tech execs have invested company cash into crypto – Tesla’s Elon Musk and Square’s Jack Dorsey are among the best known – none has lashed their business’s fortunes to bitcoin the way that Saylor has. As little as 20% of Microstrategy’s value is tied to the company’s core software product, reckons analyst Kamil Mielczarek.

Saylor’s re-emergence as a bearded crypto king is one of the most fascinating comeback stories in the tech business; a surreal second act as well as a striking manifestation of the popular forces reshaping the rules of business. With 1.5 million Twitter followers, Saylor has twice as many as the US Federal Reserve and nearly 10 times as many as Gary Gensler, the chairman of the Securities and Exchange Commission who has vowed to more closely regulate cryptocurrencies.

The bitcoin pivot has injected an element of flair into MicroStrategy, now the largest corporate holder of the cryptocurrency, and sent the company’s stock soaring.

Insider spoke to a half-dozen former employees who worked closely with the executive over the years, as well as current and former friends, analysts, investors, and corporate-governance experts to understand whether the man behind the high-stakes bitcoin gamble is showing a stroke of genius or repeating a reckless habit.

Read the full story here: He once lost $6 billion in 1 day. Now he’s a bitcoin guru. Meet Michael Saylor, king of ‘electric money.’

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