Stuart Jolly

Managing Director

Stuart Jolly is a veteran political strategist, retired LTC, and political advisor, having spent the past 16 years advising national and state entities, businesses, and political campaigns.

Stuart Jolly is a long time political operative and advises clients on matters relating to political risks and U.S. government engagement. Prior to joining Cool Springs Financial Group as a Managing Director, Mr. Jolly served as the Founder/CEO of Command Solutions LLC, as well as, President of Sonoran Policy Group (SPG) and named partner at Grieboski Jolly Caraway Corp, two private diplomacy groups representing several countries and organizations with unique political, national, and international concerns. He also served as Southeast Regional Political Director and promoted to National Field Director in the 2015/16 presidential campaign, securing 22 critical State Primary wins. Mr. Jolly has also served in multiple political positions including Senior Advisor and Political Director for several state, senate and congressional campaigns and 3 Super PACs.

Stuart was also Executive Director of the Education Freedom Alliance for 4 years, where he promoted choice in education and advocated and lobbied for good public policy in all 50 states on education freedom issues. And as Professor and Adjunct Professor at East Carolina University and University of Central Oklahoma, Stuart taught Finance, Leadership, Tactics, and Strategy for over 14 years. In 2010, he was the recipient of the “Adjunct Professor of the Year Award.”

From 2006-2013, Stuart helped launch the conservative political advocacy group called Americans for Prosperity (AFP) in Oklahoma, where he served as Oklahoma’s State Director for over 6 years.

Stuart’s also a retired Lieutenant Colonel from the U.S. Army where he served as an aviation officer flying UH-60 Blackhawks in the 101st Airborne Division at Fort Campbell, KY and 3rd Infantry Division in Europe. He served with distinction as a Company Commander in Germany in an Apache Attack Helicopter Battalion and as a Foreign Area Officer in the Defense Attaché Office in the US Embassy in Brussels, Belgium. LTC Jolly is also a Veteran of the Gulf War where he earned a Bronze Star and two Air Medals for his service in Iraq.

LTC Jolly is a graduate of The Citadel in Charleston, SC (BA - Political Science) and holds a Masters Degree in International Studies in Business from East Carolina University in North Carolina. And from the military, Stuart graduated from the Defense Language Institute (DLI) at the Presidio of Monterey, California in French & Dutch, the US Army Flight School at Fort Rucker, Alabama, and the Command and General Staff College (CGSC) at Fort Leavenworth, KS. Stuart and his wife Marcia are blessed with two daughters and a son.