Michael J. Saylor was born in Lincoln, Nebraska. His father was an Air Force master sergeant.

Saylor spent much of his childhood moving between Air Force bases around the world, including locations in Ohio and eventually settling at Wright-Patterson Air Force Base near Dayton. This upbringing instilled in him a sense of adaptability and global perspective.

Saylor graduated as valedictorian from Fairmont High School in Kettering, Ohio.

Saylor attended the Massachusetts Institute of Technology (MIT) on an Air Force ROTC scholarship. He earned dual degrees in Aeronautics and Astronautics, and Science, Technology, and Society (STS). He distinguished himself as a bright and ambitious student.

Saylor graduated from MIT and was commissioned as a second lieutenant in the United States Air Force. However, a medical condition prevented him from serving as a pilot.