Michael Saylor, co-founder of MicroStrategy, has redefined corporate strategy by transforming the company into the largest corporate holder of Bitcoin. In August 2020, Saylor initiated this shift by investing $250 million of the company's cash into Bitcoin, citing concerns over a weakening dollar and inflation risks. This move marked the largest Bitcoin acquisition by a publicly traded company at the time. Under Saylor's leadership, MicroStrategy continued to expand its Bitcoin holdings, reaching over $1 billion by early 2021 through strategic purchases and convertible-note issuances. By early 2025, the company held over 2% of Bitcoin's total supply, valued at over $50 billion. Saylor's approach, which includes dollar-cost averaging and leveraging structured finance tools, has set a benchmark for institutional Bitcoin adoption, despite concerns over potential debt and stock dilution. Saylor's strategy has not only transformed MicroStrategy's identity but also influenced broader corporate adoption of Bitcoin. As institutional interest grows, Saylor continues to advocate for Bitcoin as a corporate treasury standard, positioning it as a key player in reshaping business financing strategies.