The MicroStrategy CEO, Michael Saylor, is most renowned for losing $6 billion in a single day in the past when the software company he created at the age of 24 almost went bankrupt.
Saylor is once again at the heart of a tense discussion two decades later, owing to his extraordinary acceptance of bitcoin. Saylor has purchased almost 100,000 bitcoins valued at billions of dollars using a combination of debt and almost all of MicroStrategy’s capital — and he shows no signs of stopping down anytime soon.
While other high-profile tech executives have put corporate money into cryptocurrency — Elon Musk of Tesla and Jack Dorsey of Square are two of the most well-known — no one has tied their firm’s fate to bitcoin as Saylor does. According to analyst Kamil Mielczarek, only 20% of Microstrategy’s value is related to the firm’s core software product.
Saylor’s re-emergence as a crypto king is one of the most intriguing comeback narratives in the technology industry. Saylor has more than twice as many Twitter followers than the US Federal Reserve and nearly ten times as many as Gary Gensler, the Securities and Exchange Commission head, who has promised to monitor digital currencies more carefully.
The bitcoin price boom sent its shares skyrocketing. Insider spoke to some former people that worked with the executive in the past, as well as current and old friends, analysts, investors, and corporate-governance specialists, to determine whether the man behind the high-stakes bitcoin bet is demonstrating brilliance or repeating a risky practice.