Jarrett Caldwell

Branch: Air Force

Duty Station: Joint Base Langley-Eustis

Number of Deployments: 2

Number of PCS's: 5

Share your military spouse story:
My name is Jarrett Caldwell. I have been married for 14 years to my wife Major Kerrin Caldwell. We met at Scott Air Force Base while at church. She signed up to sing in my "Singles Choir"... and the rest was history. After 6 months of dating, We got married... I got "kicked out" of my singles Choir and started this road as a military spouse to an United States 2LT. I knew nothing about the military... I knew nothing about being an officers spouse. I knew very little about LIFE as whole. I knew whatever the challenge, we were going to face it together. From stratifications, to promotion boards... Her life became my goals. From Del Rio TX, to FL to Illinois to Korea, to Virginia... The unmentioned TDY's and Deployments.. Her success became my mission and her wins felt like "Our Wins".. but then... the 20 year active duty time frame comes and you realize that this doesn't last forever and its time to prepare for what comes after. I embraced this turn and became overzealous in carving the path of our future. My wife carried the torch up to this point and now its my turn to finish the anchor of this race. I dove into Real Estate and I hit every bump along the way all while feeling the support of my wife saying "you got this" and "I believe in you"... as we are now stationed at her last duty station preparing to retire after 25 years of active duty to the United States Air Force, I can proudly say... I GOT THIS. I am now a top 5% agent in Hampton Roads, VA and continue to educate other entrepreneurs and home owners alike on my journey and showing those the path who desire to be a part.

Share an example of your leadership experience within the military community:
I am a local real estate agent. Over the last 5 years of being in business, I have positioned myself as a top 5% agent in Hampton Roads, VA. My business was built off of my expertise of the PCS Experience. 75-80% of my clients are Military Veterans. I assist them through the VA Home loan process... Getting them qualified to use their VA benefits, negotiate deals, connect with subject matter experts to bring a level of comfort to the home buying experience from someone who can "speak the military language"... Who has personally purchased homes using military benefits, who understands PCS Seasons and all that goes along with that entire experience. I also provide monthly first time home buying seminars for new buyers to continue to educate buyers on the home buying process in hopes of developing new future home owners.

Describe your involvement in the military community:
I have served over 300 families in either buying or selling real estate. I have over 3000 clients/customers in my database/sphere located all over the United States. 75-80% of my clients are Military Veterans. I assist them in the PCS process, buying/selling a home/ first time home buyers seminars and referrals to other military agents across the country. I educate military investors on how to purchase at every duty station the are PCS to and grow their real estate portfolio and generational wealth...Typically without downpayment and utilizing their military benefits fully and effectively.

Describe how you support your community:
Over the last three years, I have pledged a portion of the profits from my company back into the community to assist with feeding the homeless, clothing drives, education scholarship assistance, grocery assistance, mortgage assistance and more. This amount is well into the $100,000 range and now has become a staple within our business outreach ministry.

What do you advocate for? Why?
I advocate for education and equality. I believe that the lack of knowledge is a large cause in the disparity between different people. I have placed myself into a position to be at more tables and advocate for the under represented. I resided as the chairman DEI Trainings for Keller Williams Elite Peninsula- Newport News, VA as well as my wife being the Regional Representation for Keller Williams Virginia to assist in bringing understanding to communities on home ownership disparates among the black and brown community. My communication with clients is education based... I have social media platforms dedicated to "First time Home Buyers".

How have you spread the message of your platform/advocacy?
I am not very flashy in my giving initiatives in which I create. Many times, a part of our request when "giving" is it must be done without our names being attached to the gift. I don't give for fame or kudos. I give because there is a need and I must do my part. I have been blessed to be a blessing to others and I don't need to stand in between the need being completed. On the other hand, I educate as loud as possible. I have around 5K plus instagram followers, 3K Facebook followers, and Tiktok and Youtube slowly but surely growing as well. I educate freely to those who want to learn about wealth building through the vehicle of real estate as well as educate entrepreneurs on how to set up the business appropriately through LLCs and all that it entails.

What do you hope to accomplish with the AFI Military Spouse of the Year® title?
I learned so much through my time as a military spouse that came through many heartaches, headaches and tears... Deployments are tough, especially with young children. Moving and becoming reestablished in each location is not for the faint of heart... but with appropriate mentorship and guidance, it is doable and possible. I believe being a black military male spouse to an officer placed me in a unique experience that is also under represented at most military institutions. I would like to have the opportunity to bridge that gap for others and provide assistance on a more personal level for those who might be struggling to make it over that hump. I too wanted to quit... I too struggled to find myself and my footing. It took a mind shift and prayer to get me where I am today and I would like to reach back and pull those who desire to come through this door I have left cracked.


Jarrett is a loving and supportive husband, man of faith and the best big brother you could have in this military life. I had the pleasure of meeting Jarrett in Del Rio, TX at Laughlin AFB. Him and his wife Kerrin made that base in the middle on no where feel like home to so many. Everywhere they go they are a light as they open their homes to single Airmen and young couples to mentor, feed and encourage them. I remember the tough conversations, wise advice and countless laughs he has personally brought to my life. Jarrett serves military spouses through informing and connecting them with needed resources like MyCAA. At church and in his personal walk, Jarrett shares his faith and services as a worship leader. As an entrepreneur, he is inspiring others though his accomplishments and helping the local and military community find their dream homes. It is my honor to nominate Jarrett for AFI's MSOY and I am grateful to call him a friend.
- by Bree Carroll