Michael Saylor’s rise from tech startup to Bitcoin billionaire

Michael J Saylor is no stranger to the ups and downs of the business world.

He is the co-founder and former CEO of MicroStrategy, a business intelligence company which was recently rebranded as Strategy. Saylor was born in 1965 in Nebraska, U.S. Part of a military family, he often moved around various U.S. Airforce bases. 

Saylor graduated first in his class from high school and went on to study at MIT on an Airforce Reserve Officer Training Corps scholarship. He graduated with a dual degree in Aerospace Engineering and History of Science. During his time in MIT, Saylor was also a member of Theta Delta Chi, a well-known social fraternity.   

Beginnings of MicroStrategy

Michael Saylor created MicroStrategy in 1989 at the age of 24. Prior to this, he worked as a Venture Manager at EIDP, Inc from 1988 to 1989. He became a billionaire at the height of the technology boom in the 90s. Saylor lost billionaire status after the SEC filed a case against him and his two partners—Sanjeev Bansal and Mar Lynch—for overstating revenues from June 1998 to March 2000. The case was settled with $11 million in fines. 

In 1999, Saylor established the Saylor Foundation, a philanthropic organization that has donated millions to various causes including refugee assistance, education, and environmental preservation. The Foundation runs the Saylor Academy which offers free education to students globally. 

He authored a book titled “The Mobile Wave: How Mobile Intelligence Will Change Everything” which was published in 2012. 

Saylor continued to run MicroStrategy until August 2022 when he stepped down from the role of CEO. He became chairman after stepping down. 

Involvement with Bitcoin, rebranding to Strategy

Closer to 2020, Saylor started heavily investing in Bitcoin and focusing MicroStrategy’s long-term strategy on holding BTC. A disclosure in October 2020 showed that he bought 17,732 BTC at a value of $175 million. In 2021, he was recorded as one of the 50 richest people in crypto by business magazine Entrepreneur. 

Michael J Saylor remains extremely bullish on Bitcoin. He regularly posts about Bitcoin on X and delivers keynote speeches. He is recognized for triggering the institutional investment boom in Bitcoin due to Strategy’s heavy involvement with the asset. 

Saylor’s connection to Bitcoin goes beyond what any traditional investor would commit to an alternative asset class.

His comments in a recent interview with New Zealand Herald is perhaps a telling hint as to his personal motivations. 

“I’m a single guy, I have no children — when I’m gone, I’m gone. Just like Satoshi left a million Bitcoin to the universe, so I’m leaving whatever I’ve got to the civilization,”

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