MicroStrategy
Using the funds from DuPont, Saylor founded MicroStrategy with Sanju Bansal, his MIT fraternity brother. The company began developing software for data mining, then focused on software for business intelligence. In 1992, MicroStrategy won a $10 million contract with McDonald's to develop applications to analyze the efficiency of its promotions. The contract with McDonald's led Saylor to realize that his company could create business intelligence software that would allow companies to use their data for insights into their businesses.
Saylor took the company public in June 1998, with an initial stock offering of 4 million shares priced at $12 each. The stock price doubled on the first day of trading. By early 2000, Saylor's net worth reached $7 billion, and the Washingtonian reported that he was the wealthiest man in the Washington D.C. area.
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 Saylor was also listed by the MIT Technology Review as an "Innovator Under 35" in 1999.
On March 20, 2000, MicroStrategy announced that it would restate its financial results for the previous two years. MicroStrategy’s stock price, which had soared from $7 per share to as high as $333 per share over the course of a year, plummeted 62 percent, dropping to $120 per share in a single day. This significant decline is considered one of the key events marking the burst of the dot-com bubble. By August 2000, approximately two-dozen class action securities fraud actions against Microstrategy were filed in the United States District Court for the Eastern District of Virginia against the company. In December 2000, the U.S. Securities and Exchange Commission filed fraud charges against MicroStrategy and its executives. MicroStrategy ultimately settled with the SEC, agreeing to hire an independent director to ensure ongoing regulatory compliance.
After his leadership was criticized by several major investors in 2014, Saylor opted for a symbolic one-dollar salary without any cash bonuses, but with stock options. According to Bloomberg, Saylor exercised those option for around $400 million in the first quarter of 2024.
On August 8, 2022, Saylor assumed the title of executive chairman of MicroStrategy and appointed Phong Le, the company's president, to succeed him as CEO. Saylor said in a press release, "As Executive Chairman I will be able to focus more on our bitcoin acquisition strategy and related bitcoin advocacy initiatives, while Phong will be empowered as CEO to manage overall corporate operations."
As of November 2024, Saylor owns 19,998,580 shares (Class B common stock), about 9.9% of the total outstanding shares, and has approximately 45% of the voting power.
This increase in shares is mainly due to a MSTR stock split on August 8th 2024 at a 10:1 ratio for both class A and B shares.
In February 2025, the company rebranded from MicroStrategy to Strategy. The new logo was destined to include a stylized “B”, signifying the company’s bitcoin strategy. The brand’s primary color was also changed to orange, “representing energy, intelligence, and bitcoin”.
