Olson was the first Navy SEAL ever to be appointed to three-star and four-star flag rank, as well as the first naval officer to be USSOCOM's combatant commander.

His overseas assignments include service as a United Nations military observer in Israel and Egypt, and as Navy Programs officer in Tunisia.

The commander in charge of all Navy SEALs during Desert Storm, Ray Smith, hand picked Olson to be on his staff.

[5] Olson earned a Master of Arts degree in National Security Affairs at the Naval Postgraduate School in 1985 and studied at the Defense Language Institute.

Olson is an Advisory Board Member of Spirit of America, a 501(c)(3) organization that supports the safety and success of Americans serving abroad and the local people and partners they seek to help.