In a significant shift from its origins as a software firm, MicroStrategy has redefined itself under the leadership of co-founder and chair Michael Saylor, evolving into a prominent player in the cryptocurrency space. The company, now known simply as Strategy, has made headlines by adopting Bitcoin as its primary reserve asset and embarking on an ambitious acquisition strategy aimed at bolstering its corporate treasury.
Established in 1989, MicroStrategy initially focused on creating business intelligence software solutions to help companies analyze data effectively. The company quickly gained traction and went public on the NASDAQ in 1998. However, it faced challenges early on, including an SEC settlement in 2000 for allegedly overstating revenues. After two decades of relative stagnation in its stock prices, everything changed at the end of 2020 when it made headlines with its first Bitcoin purchase.
In a pivotal move in 2020, Strategy recognized Bitcoin’s potential amid concerns about inflation and currency devaluation, leading to an initial investment of $250 million in the cryptocurrency. Saylor emphasized at the time that Bitcoin represented a reliable store of value with substantial long-term appreciation potential compared to holding cash. Since then, the company has grown increasingly reliant on innovative financing methods, primarily utilizing short-term convertible notes to fund its Bitcoin purchases.
This financing strategy has attracted interest from other publicly traded companies, including firms like Marathon Digital Holdings and Riot Platforms. Saylor likened his approach to the real estate development in Manhattan, commenting that as values rise, developers issue more debt to fund further growth. In pursuit of expanding its Bitcoin holdings, Strategy announced plans in late 2024 to raise up to $42 billion. Following that, in January 2025, the company approved a significant increase in its Class A common shares, positioning itself to acquire additional Bitcoin.
Under this aggressive strategy, the firm introduced a newly named stock, Strike (STRK), and announced intentions to raise funds via various preferred stock offerings to enhance its Bitcoin treasury. As of early 2026, Strategy claimed its status as the “World’s First and Largest Bitcoin Treasury Company,” reinforcing its commitment to this digital asset.
Michael Saylor’s beliefs about Bitcoin have transformed dramatically since he once viewed it as a fleeting trend. After dismissing Bitcoin in 2013, he eventually embraced it, famously stating a commitment to buying at peak prices. His vision includes predictions that Bitcoin will represent an increasingly significant portion of global capital, perhaps reaching valuations of $13 million per coin over the next two decades.
Nevertheless, this approach has not been without its critics. Analysts have highlighted the risks inherent in Strategy’s debt-fueled Bitcoin acquisition model. Concerns have arisen that if the share price falls significantly, the company may be compelled to liquidate Bitcoin holdings to satisfy billions in convertible notes—potentially triggering a downward spiral in prices. This worry has intensified as shares experienced a substantial decline alongside Bitcoin in early 2026, prompting Saylor to dismiss these fears as unfounded and assuring stakeholders of his capability to refinance debt as necessary.
To mitigate the risk of forced sales, Strategy established a reserve of cash amounting to $1.44 billion and later increased this fund to secure over two and a half years’ worth of debt and dividends. As of February 2026, the company holds an impressive 717,131 Bitcoin, valued at nearly $48 billion, although it faced a reported $6.5 billion loss on its lifetime purchases.
Looking ahead, Saylor envisions transforming Strategy into a “Bitcoin bank” valued at a trillion dollars, proposing capital market instruments linked to Bitcoin for investors. Despite opposition from some industry giants, including Microsoft, which declined to adopt Bitcoin onto its balance sheet, Saylor remains undeterred in his pursuit of Bitcoin advocacy and expansion of Strategy’s influence in the cryptocurrency realm.
