Route 66 Insurance
We opened our doors in 2010. At that time, we were the only independent agency in the building with the other captive agents. One of those agents was my dad, JD McCaw. He taught me the "ins" and the "outs" of the insurance business. He also taught me a lesson without really teaching me a lesson. What I mean is, he was an expert at being more than an agent. Most of his clients called him a friend. He did this by being available for them and showing an interest in their life and family, not just their insurance. He retired in 2017 and passed in 2020. I strive every day to carry on his legacy not only as an agent, but also as a listening ear and helping hand for our clients, friends, and neighbors.
Kimmie and I were married in 2016 and we have 4 children in total. We love our family and our community. We believe we are here to be more than just a place to buy an insurance policy. We believe God has placed us here to be a blessing to our community through relationships both business and personal.
God bless!
Justin McCaw, Owner of InsureBoss Route 66 Insurance
I have grown up watching my grandfather, JD McCaw, build InsureBoss and watch my own father carry on his legacy. Getting my license wasn't just for a job but to continue on in my father's footsteps. Watching how they cared for their clients and their families really inspired me to want to give that same peace of mind to others. Learning the ends and outs of insurance has really put into perspective on how important it is to protect those that we love and finding the best coverage possible. It means so much more now that I have a little family of my own. My beautiful wife, Reagon, and myself look forward to raising our son, Bentley, in Chelsea, OK and being a part of the Dragon Community.
-Daniel McCaw
ABOUT Chalkline Insurance
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I have been known as the ol’ ball coach for the last 20 years and have had the fortune of coaching high school softball and baseball at 5 different schools over those 20 years. With stops at Claremore Christian, Oklahoma Union, Chelsea, Lincoln Christian, and the last 4 years in Oologah I amassed over 500+ wins and impacted thousands of young people and families over that time period.
Justin McCaw, my brother-in-law, and owner of Insureboss, presented me with an opportunity to open my own agency in Oologah. After many prayers and discussions with my family we decided to jump onboard and open Chalkline Insurance Agency in August of 2022. This move has allowed me more time with my family and the ability to stay in the town and community that I love while still impacting people in a positive way by giving them a peace of mind by insuring their most valuable possessions and hopefully saving them money in the end. Our motto at Chalkline is “character creates connection” and it's my goal every day to make an impact in the Oologah and surrounding communities not only in the world of insurance but in the lives of each person I come across.
I am married to my wonderful wife, Jami. She is a personal trainer and owns her own business “All Things Fitness”. I also have two kids, Delainey (19) and Calvin (13). Delainey is everything art and dance. She has danced for K & Company Studio in Claremore for 16 years and is currently an instructor at the studio while also dancing on their dance team. Calvin is my video game star and future professional computer programmer. He loves to build games and build mods for several other games. I have been blessed beyond measure!