The company's executive chairman has compared it to a bitcoin spot leveraged ETF,[9] though it's not a regulated investment fund.

Saylor was soon joined by company co-founder Sanju Bansal, whom he had met while the two were students at Massachusetts Institute of Technology (MIT).

[10] The company produced software for data mining and business intelligence using nonlinear mathematics,[7] an idea inspired by a course on systems-dynamics theory that they took at MIT.

[14] On March 20, 2000, after a review of its accounting practices, MicroStrategy announced that it would restate its financial results for the preceding two years.

[19] In December 2000, Saylor, Bansal, and the company's former CFO settled with the SEC without admitting wrongdoing, each paying $350,000 in fines.

[14] The company introduced OLAP Services with a shared data set cache to accelerate reports and ad hoc queries.

[22] In 2010, the company began developing and deploying business intelligence software for mobile platforms, such as the iPhone and iPad.

[25][26] In January 2014, the company announced a new feature of the platform called PRIME (Parallel Relational In-Memory Engine), co-developed with Facebook.

[27] In October 2014, the company announced plans to lay off 770 employees, a month after reducing Saylor's salary from $875,000 to $1 at his request.

[33] MicroStrategy said the case is "a personal tax matter involving Mr. Saylor" and called the claims against the company "false" and it would "defend aggressively against this overreach.

In a press release announcing the transition, Saylor said that he would focus on the company's bitcoin acquisition strategy and that Phong would manage overall corporate operations.

[9] In August 2020, MicroStrategy invested $250 million in bitcoin as a treasury reserve asset, citing declining returns from cash, a weakening dollar, and other global macroeconomic factors.

[38] After bitcoin's price fell to about $20,800 in June 2022, the company said that it had not received a margin call and that it had enough capital to withstand further volatility.