Holliday was born in Providence, Rhode Island. He watched Star Trek as a child, and wanted to become an astronaut. He grew up in Scarsdale, New York. Holliday studied mechanical engineering at Carnegie Mellon University, where he was one of only fifteen African American engineers in his class. During his studies he became interested in robotics, as the nuclear meltdown at Three Mile Island resulted in the launch of a Carnegie Mellon spin off company called RedZone Robotics, with Red Whittaker as the Chief Scientist. Holliday worked with Red Whittaker who was designing robotic systems to explore the contaminated reactor. He was selected to attend the International Space University in 1991 and reached the finals of the United States astronaut corps in 1994 and 1996. Holliday withdrew his application to NASA after the Space Shuttle Columbia disaster.