General (Ret.) Holland was born in West Virginia. He entered the U.S. Air Force Academy and graduated in 1968 with a BS in Aeronautical Engineering. He received Masters Degrees in Business Management from Troy State University in 1976 and in Astronautical Engineering from the Air Force Institute of Technology in 1978. He completed several professional military education schools to include the Industrial College of the Armed Forces in 1986. In addition, he completed the Program for Senior Officials in National Security in 1990 and the National and International Security Management Program in 1998, both at Harvard University.

During that assignment he was responsible for all special operations forces of the Army, Navy and Air Force, both active duty and reserve. Prior to the culmination of his active duty military career, he commanded a squadron in the Philippines, two Air Force Wings, served as Deputy Commanding General of the Joint Special Operations Command, and was Commander of the Special Operations Command, Pacific. Prior to commanding USSOCOM, he commanded the Air Force Special Operations Command and was the Vice Commander of U.S. Air Forces in Europe. He was a Command Pilot with over 5000 flying hours which included over 100 combat missions in multiple C-130 and SOF aircraft to include a combat tour in the AC-130 Gunship at Ubon RTAFB, Thailand during the war in Southeast Asia.

Upon retirement, he now serves as a Director or Advisor on multiple corporate boards and acts as an independent consultant for several companies to include the USAF and the Lawrence Livermore National Laboratory (LLNL). For the past fourteen years, he has provided executive level counsel for Air Force wargame design in a joint, combined, interagency and multi-level security construct while over the last seven years serving as a Strategic Advisor for LLNL. Beyond these duties, he is a volunteer Director Emeritus on the Special Operations Warrior Foundation Board which provides college educations to the children of fallen special operations personnel and if severely wounded, the foundation ensures that loved ones have immediate funds available to travel to be bedside when they are needed most.