Faces of crypto: Michael Saylor, executive chairman of MicroStrategy

A rocket scientist turned entrepreneur, Michael Saylor is one of the most famous and passionate Bitcoin bulls. The co-founder of MicroStrategy has had a rollercoaster career, with $6 billion lost in one day before a crypto-fueled comeback. Learn more about his unconventional life and success.

Childhood and education

Michael J. Saylor was born in Lincoln, Nebraska, in 1965. As a kid, he lived on US Air Force bases in different countries, as his parents were in the military. Later, the Saylors settled at Wright-Patterson Air Force Base near Dayton, Ohio, the birthplace of aviation and the home of the Wright brothers.

Michael studied diligently and finished high school first in his class. A class marshal and valedictorian, he was also voted most likely to succeed by his schoolmates.

Subsequently, Saylor entered the Massachusetts Institute of Technology (MIT), receiving a full Air Force Reserve Officer Training Corps scholarship. He graduated in 1987 with the highest honors and dual degrees in aeronautics and astronautics, along with science, technology, and society. A Theta Delta Chi fraternity member, Saylor played guitar in a rock band in his spare time. He also flew gliders, training at Lackland Air Force Base in San Antonio, Texas.

Michael Saylor in 1992. Source: Michael Saylor's Instagram account
Michael Saylor in 1992. Source: Michael Saylor's Instagram account

Saylor's obsession with computer simulation technology — specifically, its applications to business strategy and public policies — resulted in a thesis titled "A Mathematical Model of a Renaissance Italian City State." Saylor wrote it while studying system dynamics at the MIT Sloan School of Management.

By graduation, Michael Saylor had flight officer training under his belt, but a benign heart murmur diagnosis shattered his dream of becoming a pilot. Commissioned as a Second Lieutenant in the United States Air Force, he joined the Air Force Reserve and followed the consulting path, developing computer simulations used for strategic decisions at companies like DuPont and Exxon.

Founding MicroStrategy

At 24 years old and just two years out of MIT, Saylor created a company that now serves thousands of businesses worldwide. MicroStrategy, co-founded by him and his Theta Delta Chi fraternity brother Sanju K. Bansal, grew steadily.

Back in 1989, the firm aimed to help companies make intelligence ubiquitous. Saylor was fascinated with technology and business and keen on computer simulations. MicroStrategy's solutions combined client-server computing and graphical operating systems with a new, groundbreaking business intelligence method – relational online analytical processing (ROLAP).

ROLAP, which helps researchers answer questions by analyzing massive data sets, is crucial for data warehousing. This process involves cleaning, integrating, and consolidating data from heterogeneous sources. Saylor is credited with inventing relational analytics, and he is also a named inventor on 40+ patents.

By September 1997, MicroStrategy had over 400 employees and over $50 million in projected revenues. The Fortune magazine called Saylor a "real, honest-to-goodness visionary." He was determined to build the next billion-dollar software empire, and he did.

The following year, MicroStrategy went public (NASDAQ: MSTR). Saylor led it into the domains of web, distributed, and mobile analytics, cloud computing, mobile identity, and IoT. Under his leadership, the company became a global leader in enterprise analytics and mobility software. Today, it is the biggest independent publicly traded company in the business intelligence industry.

Losing $6 billion overnight

In early 2000, the US Securities and Exchange Commission (SEC) detected inaccuracies in MicroStrategy's financial results over the previous two years. The regulator charged Saylor and two other executives, who denied any wrongdoing but agreed to a settlement. Thus, the CEO left the 10-digit club. Following a revision of the financial results, the dot-com bust crashed the MicroStrategy stock.

Comeback through Bitcoin holdings

Two decades later, MicroStrategy's CEO rejoined the billionaire ranks after acquiring Bitcoin. He staked MicroStrategy's future on it, converting nearly all of MicroStrategy's cash into the coins. A stronger bull than Elon Musk or Jack Dorsey, he personally bought 17,732 BTC for $175 million.

The crypto winter of 2022 made a deep dent in Saylor's wealth — by June, he had reportedly left the billionaire club once again as his net worth plunged to around $500 million. Meanwhile, MicroStrategy lost $1 billion in investments. Yet the crypto king's belief in Bitcoin has never faltered. On June 13, he tweeted, "In #Bitcoin We Trust."

Saylor's tweet on June 13, 2022. Source: Twitter
Saylor's tweet on June 13, 2022. Source: Twitter

At the end of 2022, MicroStrategy recorded a net loss of $249.7 million, which resulted from its loyalty to Bitcoin. That was the eighth consecutive quarterly loss, but the company's stock doubled in value by early February 2023.

Remaining bullish, Saylor responded to Charlie Munger, Warren Buffett's right-hand man, who had called crypto a "gambling contract with a nearly 100% edge for the house." Saylor suggested Munger had not conducted sufficient research: "If he were a business leader in South America or Africa or Asia and he spent 100 hours studying the problem, he would be more bullish on bitcoin than I am."

From CEO to executive chairman

In August 2022, along with its second-quarter earnings, MicroStrategy announced that it had a new chief executive officer — Phong Le, who also kept his position as the company's president. Saylor became executive chairman, remaining on the Board of Directors. As head of its Investments Committee, he still oversees MicroStrategy's Bitcoin acquisition strategy.

The new role allows him to devote more attention to "innovation and long-term corporate strategy." CNBC quoted him as saying he would focus on "Bitcoin acquisition strategy and related Bitcoin advocacy initiatives," while Phong would "manage overall corporate operations."

Michael Saylor. Source: Michael Saylor's Instagram account
Michael Saylor. Source: Michael Saylor's Instagram account

Other businesses

In 2000, Saylor established Alarm.com, a trailblazer in home automation and security. Initially a part of MicroStrategy's R&D unit, it was later acquired by ABS Capital Partners and went public in 2015. Today, it offers a broad spectrum of integrated smart home and business software, including video monitoring and energy management.

Another Saylor's enterprise, Angel.com, is a pioneering provider of cloud-based interactive voice response solutions launched in 2002. From the get-go, this software company streamlined phone systems via speech-recognition technology, emphasizing its independence from MicroStrategy. President Michael Zirngibl told The Washington Post, "We have nothing to do with the core business."


Michael Saylor is a prominent philanthropist and educator. In 1999, he founded the Saylor Foundation, a charity organization supporting various causes, from refugee relief to the arts. It has donated millions to children's health, education, and environmental conservation.

Saylor Academy

The Saylor Academy, which the foundation runs, provides free college education and professional development courses around the world. According to the official MicroStrategy site, over 1.4 million students have used its services so far.

Bestselling author

In 2012, Perseus Books published "The Mobile Wave: How Mobile Intelligence Will Change Everything," a book by Saylor that landed on The New York Times and The Wall Street Journal Best Seller lists. Analyzing the impact of mobile intelligence, MicroStrategy CEO concluded that smartphones and tablets would form a global universal computing platform.

According to Saylor, this fifth wave of computer technology had brought such dramatic changes that humans could not fully fathom their scope. Anticipating the rise of giants like Apple, Facebook, and Google, he suggested that mobile computers could become an appendage of the human being.

A decade later, "What is Money?" was released. Aimed at helping readers grasp the historical significance of Bitcoin, this book documents Saylor's dialogue with Robert Breedlove in 2020. It covers the anthropological, energy, technological, and energy aspects of monetary systems throughout human history.