

jim o'brien
Founder, Osprey Arrow
COL(R) Jim O’Brien was commissioned a 2LT from the United States Military Academy in 1996 receiving a BA in History. His first assignment was to the 1st Infantry Division in Vilseck, Germany where he deployed to Bosnia and Kosovo. In 2000, he attended the Special Forces Assessment and Selection Course in the hopes of becoming a Green Beret.
After the Special Forces Qualification Course in 2002, he was assigned to the 7th Special Forces Group (Airborne) in Fort Bragg, NC whose primary Area of Responsibility is Latin America. In 2006, he was assigned to the United States Special Operations Command in Fort Bragg, NC. In 2009, Jim was assigned to the 5th Special Forces Group (Airborne) at Fort Campbell, KY whose primary Area of Responsibility is the Middle East. In 2016, he assumed command of Special Forces Qualification Course at Fort Bragg, NC and then was assigned to USSOCOM in 2020. There, he assumed the duties of the J3 Training and Education Division Chief, J3-International Division Chief, and the Deputy Director of Operations for the entirety of the 72,000-person strong USSOCOM Enterprise.
Since retiring from the U.S. Army, Jim was living his best life but ultimately getting in his wife’s way. After serving in a fiber optic construction management role, he joined a global security company providing risk management solutions for various corporations and families. Ultimately, he departed to pursue his passion: teaching, coaching, and mentoring others. Leadership development and training the next generation of commandos has been a constant thread and passion throughout his time in, and out of, uniform.
He has multiple combat and operational deployments to Europe, South America, the Middle East and south-west Asia as well as a few hundred airborne operations, all alongside our International Special Operation allies and partners. He has numerous U.S. decorations, such as the Combat Infantryman’s Badge, Special Forces Tab and Ranger Tab among others. His foreign awards include the El Salvadoran Gold Medal of Freedom, British SAS wings, Selous Scouts airborne wings, a score of various foreign Freefall wings, honorary membership in the Selous Scouts Regimental Association, and many other official and unofficial honorifics.
Jim was born into a military family as the oldest of six kids but spent most of his formative childhood in South Portland, Maine. There he skied, surfed, windsurfed, flyfished, hiked, biked, and grew up along the northeastern coast living a charmed life. He is married to his stunningly beautiful and talented wife Darcey and they have three sons, a daughter, a daughter-in-law and two grandchildren. His two oldest sons serve our Nation in the military and in Federal service while his 9-year old son is a budding commando and his daughter is his world. He stays young with a 1966 Mustang, an ever-growing honey-do list, and tending to a new brood of chickens – which he will quietly grumble about but enjoys the fresh eggs and how much his wife and kids love them.
29
Years of Army Service
25
Years as a Green Beret
5
Publications & Podcasts
13
Keynote Addresses









