Michael Saylor is the cofounder of MicroStrategy (now Strategy) and one of the most well-known Bitcoin maximalists worldwide.

In 2020 he changed his view on Bitcoin and began large scale investing as protection against inflation.

Strategy built its position of roughly 650,000 BTC through bonds, convertible notes, and capital raises.

Saylor views Bitcoin as the ultimate digital property and promotes it worldwide through media, conferences, and education.

His strategy is praised for its vision but also criticized for high debt financing and risks during price declines.

📍Michael Saylor’s Background

Michael J. Saylor was born on February 4, 1965, in Lincoln, United States, and grew up in a military family. From a young age, discipline, strategy, and long term thinking played a central role. With an Air Force ROTC scholarship, he was able to study at the prestigious Massachusetts Institute of Technology (MIT). There he completed two majors, aerospace engineering and the history of science. Thanks to this analytical and mathematical foundation, he later applied these principles to entrepreneurship and eventually to his views on Bitcoin.

In 1989, Saylor founded the software company MicroStrategy together with his classmate Sanju Bansal. During the 1990s the company grew into an important player in business intelligence and data analytics. MicroStrategy continued to grow and was listed on the stock exchange in 1998. Though it was not always smooth sailing. In 2000 the company had to restate financial figures, leading to a sharp stock decline and a settlement with the SEC. Despite this setback, Saylor remained the head of the company and built MicroStrategy into one of the most recognized firms in the United States.

📍Strategy’s Bitcoin Positions

Strategy’s Bitcoin investments are some of the largest in history. While many companies take only small Bitcoin positions, Saylor is building a strategy fully focused on Bitcoin as a long term store of value, similar to the HODL mentality in the crypto space. Strategy achieved this through:

issuing bonds and convertible notes

repeated capital raises

a long term plan to invest tens of billions

This has resulted in the largest corporate Bitcoin holding. As of November 2025, Strategy owns roughly 650,000 BTC. This means Strategy holds about 3 percent of the total maximum supply of Bitcoin. With such a massive position, Strategy is considered a true crypto whale in the market. Strategy is by far the largest corporate Bitcoin holder in the world.