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Who is bitcoin billionaire Michael Saylor? The MicroStrategy CEO’s net worth once dropped by US$6 billion in one day during the dot-com boom … will the same happen with his crypto investments?

Michael J. Saylor, CEO of MicroStrategy and an even bigger bitcoin bull than Elon Musk or Jack Dorsey, lost billions in the dot com crash but is confident the same won’t happen again. Photos: @michael_saylor/Instagram
Michael J. Saylor, CEO of MicroStrategy and an even bigger bitcoin bull than Elon Musk or Jack Dorsey, lost billions in the dot com crash but is confident the same won’t happen again. Photos: @michael_saylor/Instagram

  • He grew up on various US Air Force bases, went to MIT, and then founded MicroStrategy, providing business intelligence, mobile software and cloud-based services
  • Besides being a tech entrepreneur, the former multibillionaire is also a New York Times bestselling author, the founder of Saylor Academy – and used to throw great yacht parties too

It’s not every day that a person loses US$6 billion, so when Michael J. Saylor did exactly that in the 2000s at the height of the internet bubble, he definitely made a name for himself.

Michael J. Saylor lost US$6 billion during the dot-com boom. Photo: @michael_saylor/Instagram
Michael J. Saylor lost US$6 billion during the dot-com boom. Photo: @michael_saylor/Instagram
Two decades later though, the 57-year-old CEO and co-founder of business software firm MicroStrategy has ridden the roller coaster all the way back up again. He did so by staking his company’s future on bitcoin – showing even more passion for the world’s biggest cryptocurrency than such tech visionaries as Elon Musk and Jack Dorsey.
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So who exactly is Saylor, what is his current net worth and how exactly did he lose billions back in the day? Let’s take a quick dive into the crypto king’s distinctive background.

He had an unusual childhood

An early McMoment in Michael Saylor’s life. Photo: @michael_saylor/Instagram
An early McMoment in Michael Saylor’s life. Photo: @michael_saylor/Instagram

Born in 1965, in Nebraska, US, Saylor’s childhood was far from average. He grew up in a military family and lived on various US Air Force bases around the world. Graduating as the class valedictorian in high school, the sky was the limit for the young man.

Thanks to a full Air Force scholarship, Saylor obtained dual degrees in aeronautics and astronautics, as well as science, technology and society at the Massachusetts Institute of Technology (MIT). It was also in uni where he met his Theta Delta Chi fraternity brother and future co-founder of MicroStrategy, Sanju K. Bansal.

He co-founded MicroStrategy at 24

Michael J. Saylor, chairman and chief executive officer at MicroStrategy at the DC Blockchain Summit in Washington, in May. Photo: Bloomberg
Michael J. Saylor, chairman and chief executive officer at MicroStrategy at the DC Blockchain Summit in Washington, in May. Photo: Bloomberg