John Bird’s Cool History

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Welcome! We are here to serve you.

Cool Insurance Group, LLC  was founded by John Bird, a Lexington, Kentucky native and veteran insurance industry executive. John had been in the business 30+ years including more than 20 years at the highest level with Blue Cross and Blue Shield plans in Kentucky and Louisiana and ten years working with Humana in Kentucky and Tennessee. Sadly, we lost John in early 2018, and Cool Insurance Group, LLC is now being ran by his wonderful family Claudia Bird and Claudia’s son, Timothy Chancellor, both of which are also Cool agents..

Before John (nicknamed “Daddy Cool”) left us, he managed to pull together an experienced team of professionals who are nationally focused to provide advice to clients about Medicare products, health insurance, life insurance, annuities, retirement income, debt elimination, wills and trusts and estate creation and protection strategies. In just a few short years, Cool Insurance Group, LLC has grown to represent the top companies in the industry,and, after we get to know you as a client, we can match the right options to suit your specific circumstances.  Finance and insurance doesn’t need to be stuffy.

Meet Our Cool Group of Agents


We are Your Hometown, VIRTUAL Solution

Each year, Cool Insurance Group, LLC, through it’s 30+ licensed and appointed agents, serves 1,000’s of Kentucky, Ohio, Indiana, and West Virginia clients under and over sixty-five years of age. This is our family. We love them as such. Sadly, our nation is currently at war with a deadly virus and none of us know what is going to be the long term outlook of this war. Because of that we just do not know where our society is going to be come October, when our family has to take a stop; take a moment; and make a decision about their Medicare for 2021.

So, we are making decisions, and working on strategy for our Cool Agents and clients. You need to see us this year just like every year. We need to see you. We want to serve you. And we know your history and your case. We are proud to serve you. The question is, what do we do? The thought is; we need a “Plan B” in the event that during open enrollment this fall, it may not be possible to see every client in a face to face meeting. We just may not be able.

This does not mean we cannot do the exact same work for you that we do every year. We still can and we will. We will be offering three options for meeting with you this fall.

Sure, it is possible to fall asleep reading some insurance documents, but we take pride in presenting technical subjects in plain language.  We help you understand how it works and, then, insurance doesn’t have to be boring.  In fact, it can be very cool. For more information on our COVID-19 plans, go HERE!

We Invite You To Contact Us So That We Can Tell You What We Are All About

All through the site, there are simple links to connect with us. You may give us a call or chat with us during regular business hours, register to receive our  periodic newsletter, or make a request for someone to contact you.