Amber avatar
Coin98 Insights
Nơi chia sẻ tất cả những kiến thức Crypto từ cơ bản đến nâng cao, kinh nghiệm đầu tư Bitcoin và các hình thức đầu tư tiền điện tử khác.

Who is Michael Saylor? From Anti-Bitcoin to a Bitcoin Whale

Michael Saylor is CEO of MicroStrategy, who once lost $6 billion in a day investing in technology companies. He also revived MicroStrategy and turned the company into one of the most famous names in the crypto world. How did Michael Saylor do that?
Amber avatar
7 min read
Published Feb 28 2022
Updated Apr 24 2024
Amber media

In the investing world, money talks, and over the past decade, the rise of Bitcoin has helped the early adopters join the new generation of billionaires. One of those billionaires is Michael Saylor.

Who is Michael Saylor? 

Michael Saylor was born in a military family. His father is an enlisted Air Force veteran and his mother is a daughter of a country musician. During his childhood, he lived in various Air Force bases around the world. After that, his family finally settled down at Wright-Patterson Air Force Base near Dayton, Ohio – the birthplace of aviation and home of the Wright brothers.

Michael Saylor graduated from high school first in his class and graduated MIT with the highest honors. He is a pilot, a technology entrepreneur and an inventor with 31 patents. He is currently the CEO of MicroStrategy, a leading company providing business intelligence, mobile software, and cloud-based services since June 1989.

Only 6 months after investing in Bitcoin, Michael Saylor owns $3 billion. He is ranked 4th on Forbes' list of “Bitcoin’s Recent Surge Creates New Billionaires” and 4th on Cointelegraph's list of “100 Notable People in Blockchain 2021”.


He was voted by his classmates as the most likely to succeed person and his colleagues view him as “wicked smart”. These are part of what made a Bitcoin billionaire.

A career turning point

Michael Saylor graduated MIT with the highest honors in 1987. Completed successfully Flight Officer Training at Lackland Air Force Base in San Antonio, Texas, he was commissioned as a Second Lieutenant in the United States Air Force.

However, a benign (and ultimately erroneous) heart-murmur diagnosis shattered his next ambition of becoming a fighter pilot or astronaut. He then decided to join The Federal Group, Inc, in 1987 and DuPont in 1988 as a consultant.

The birth of MicroStrategy

At the age of 24, after 18 months designing software and helping DuPont predict changes in the market, with the passions for technology and business, Michael Saylor quit and asked DuPont to fund him and his former classmate, Sanju Bansal, $100 million to start his own company. In the end, he received his required grant along with free office space and computer equipment. MicroStrategy was then founded in June 1989.

"Michael has a brilliant mind and a seemingly infinite capacity for detail and precision. Working with him over the long term takes a special person. There are some great people at MicroStrategy who have mastered that art. For me it was a mix of intellectual entertainment and mind-blowing frustration," Marge Breya, a former chief marketing officer who briefly served on MicroStrategy's board, told Insider.

The stock price doubled on the first day of trading because the investors believed MicroStrategy is purchasing a market that can only go up. Saylor owned over 39,521 units of the company, worth almost $5 million. In 1992, MicroStrategy got its first huge client when it signed a $10 million contract with McDonald's.

$6 billion lost in a day

In 1996, Saylor was named KPMG Washington High-Tech Entrepreneur of the Year. In 1997, Ernst & Young named Saylor its Software Entrepreneur of the Year, and the following year, Red Herring Magazine recognized him as one of its Top 10 Entrepreneurs for 1998. In 1999, he was featured by the MIT Technology Review as an "Innovator Under 35". By early 2000, Michael Saylor was reported as the wealthiest man in Washington D.C. by The Washingtonian.

Michael Saylor had helped MicroStrategy made billions of dollars from the dotcom craze thanks to his adventurous and determined personality. The company grew rapidly under his direction.

“Nobody has really grasped yet the great wealth that can be made selling data over the Web, there are 100 million potential customers out there," – Michael Saylor told the Washington Post in 1996.

However, it did not last long. On Monday, March 20th 2020, Michael Saylor lost $6 billion, more than anyone had lost money in history. The dotcom bubble had caused the MicroStrategy stocks to collapse from 226.75 USD to 86.75 USD, the company then had to restate its financial-earning reports, revealing two consecutive years of losses. Michael Saylor then became a hot topic in Washington DC with his confidence and bravado saying “The loss feels like nothing, actually”. However, his colleagues revealed that he was shocked by the event.

Hundreds of employees were laid off, MicroStrategy’s shares were reduced, Michael Saylor continued to run MicroStrategy years after. Even though “The company should not have survived. It should have died," said a former executive who worked with Michael Saylor.

The road leads to Bitcoin

None of the former MicroStrategy employees remember their boss ever mentioning Bitcoin except for a tweet he posted in 2013: “Bitcoin days are numbered. It seems like just a matter of time before it suffers the same fate as online gambling.”

In July 2020, because of the confluence of macro factors affecting the economic and business landscape that Saylor believes is creating long-term risks for MicroStrategy treasury program, Saylor announced his intentions for MicroStrategy to explore the purchase of alternative assets instead of holding cash reserves. After researching, he found out that Bitcoin price has gone up 100% every year for the past decade and has the ability to store and move assets without being dependent on any one party.

The following month, MicroStrategy announced stock buyback plans as well as the plans to purchase $250 million in bitcoin. The company purchased 21,454 bitcoin. In September, Saylor announced the purchase of an additional $175 million worth of bitcoin.

MicroStrategy used a total of $3.8 billion to buy 125,051 Bitcoins at an average price of $30,200, owning 0.5% of Bitcoin's total supply. Michael Saylor, who currently holds 75% of MicroStrategy, denied that he is turning MicroStrategy into a Bitcoin investment company or an Exchange Traded Fund.

Michael Saylor began to change his Twitter profile picture along with the “laser eyes” (indicating the people who are bullish on bitcoin) and posted status that support bitcoin like “Bitcoin is "money that isn't broken" behind a "wall of encrypted energy"” or famous quotes with the hashtag #Bitcoin.

In October 2020,  Saylor revealed that he currently holds 17,732 Bitcoin which he bought at $9,882 each on average and up to now, he has not sold any Bitcoin.

Investing in bitcoin has now paid off Michael Saylor wonderfully. Only 6 months after he announced his investment into bitcoin, MicroStrategy stocks surged 971% from 135 USD to 1,312 USD. The bitcoin price increasing has made him another 2.3 billion USD, helped to bring his name into the crypto tycoons on Forbes’ 2021 billionaires list.

Despite becoming a billionaire, money is not Michael Saylor's top goal. He believes that he is here to change the world, to give everyone the opportunity to improve their knowledge. In 1999, Michael Saylor used $100 million to establish Saylor Academy - providing 100 free courses from top universities such as MIT, Carnegie Mellon… for students.

The Bitcoin believer

Many former MicroStrategy executives praised Saylor’s business acumen, the ability to analyze vast amounts of information and focus intensely, citing numerous examples of the times he was ahead of the curve.

Classic examples would be his early investments in Amazon and Apple as well as Saylor’s timely embrace of mobile computing – Michael Saylor provided iPads to MicroStrategy executives in an effort to fasten the development and adoption of mobile software, or when he invested early in Amazon and Apple, to the time he read 100 books of architecture when he was buying land in Virginia. He also knew the importance of mobile in the future and wrote “The Mobile Wave: How Mobile Intelligence Will Change Everything” in 2012.

At the moment, he keeps calling people to buy Bitcoin with tweets like:

"Bitcoin is oxygen".
"Buy Bitcoin when you can, not when you must".
"Bitcoin is the price of Freedom".
"Bitcoin is technology that everyone needs and no one can stop".
"Don't wait until you lose 93% of your wealth to buy Bitcoin".
"Inflation is the problem and Bitcoin is the solution".

With a strong belief in Bitcoin, Saylor persuades everyone to trust and buy Bitcoin as a hedge against inflation. He also advises people not to worry too much about Bitcoin's price fluctuates as he believes in the long-term benefits Bitcoin offers.

The future of MicroStrategy and Bitcoin

Even though Bitcoin is currently down nearly 45% from its ATH in November 2021 (around $68,000), Michael Saylor said that MicroStrategy plans to hold Bitcoin for the next 100 years without selling any Bitcoins. He believes Bitcoin is the best collateral in the world and he sees bitcoin's market value reaching $100 trillion one day.

MicroStrategy is looking for ways to generate yield on its massive Bitcoin holdings.

There may be opportunities to either put a mortgage against it and generate long-term debt under favorable circumstances, which we could leverage up against the Bitcoin, or we think that we could lend it to a trustworthy counterparty. hat could become a good source of income for us, or we could develop it with some kind of interesting applications,” Michael Saylor shared.

Furthermore, Saylor is also seeing the possibility of a market developing to eventually issue bonds backed by Bitcoin.

After MicroStrategy went public with its investment in August 2020, a number of giants jumped into the game. Tesla, Paypal, Mastercard, Square, MassMutual, BNY Mellon and many others have poured billions of dollars into Bitcoin. Even legendary investor Stanley Druckenmiller started investing in Bitcoin, although a few months ago, he said he did not want to own Bitcoin. Billionaire Bill Miller – one of the Wolves of Wall Street also decided to invest 50% of his fortune in Bitcoin.

All of the above proves Saylor's vision of the Bitcoin future as he is once again ahead of the time.