Michael Saylor: 15 Frequently Asked Questions

Michael Saylor (born 1965) is the executive chairman and former CEO of MicroStrategy (now branded as Strategy), a business intelligence software company he co-founded in 1989. He earned dual undergraduate degrees from MIT in aerospace engineering and history of science, and led MicroStrategy through its 1998 IPO. His most consequential public role, however, began in August 2020, when he announced MicroStrategy would convert its corporate treasury reserves into Bitcoin — initiating what became the largest publicly disclosed corporate Bitcoin holding in the world. He stepped down as CEO in 2022 to focus on Bitcoin strategy as executive chairman, and has since become arguably the most prolific and rhetorically forceful Bitcoin advocate among public-company executives, giving hundreds of interviews and speeches framing Bitcoin as superior to gold, real estate, and equities as a long-term store of value.

Saylor's central contribution was demonstrating, at scale, the corporate Bitcoin treasury model. Before MicroStrategy's August 2020 move, no major public company had openly converted significant treasury reserves into Bitcoin. By executing repeated purchases — funded by cash flow, convertible debt issuance, equity issuance, and operational restructuring — Saylor accumulated hundreds of thousands of BTC over five-plus years, providing a template that several other public companies subsequently emulated. He also pioneered the issuance of convertible bonds explicitly tied to Bitcoin exposure, creating a new category of fixed-income instrument that gave traditional asset managers a regulated, equity-like vehicle for Bitcoin allocation. His Bitcoin advocacy through Saylor Academy and his prolific media appearances has shaped corporate boardroom conversations about Bitcoin as a treasury asset.