Michael J. Saylor was born in Beirut, Lebanon, to a father who was an Air Force Sergeant, and spent much of his childhood moving between Air Force bases around the world. This nomadic upbringing likely instilled in him a sense of adaptability and a global perspective, traits that would later prove useful in his entrepreneurial ventures.

Saylor demonstrated exceptional academic prowess at the Massachusetts Institute of Technology (MIT), earning dual degrees in Aeronautics and Astronautics, as well as Science, Technology, and Society. Initially, he had aspirations of becoming a pilot in the Air Force, but his colorblindness prevented him from pursuing that path. This setback led him to explore other avenues, ultimately shaping his career in technology.