Meet the guides
Josh Calaway

Contact Josh:

Direct: 850-807-0148


Companies Josh Works With:

More About Josh:

In Michigan, in 1981, my parents named me Joshua Calaway. I grew up in northern Michigan and moved to the Sunshine State when I was 16 years old. I fell in love with the beach and never left (except for a few trips to India after college, “Namaste!”).

Three Words That Describe Me:
Honest. Helpful. Dedicated.

Favorite Things To Do When Not At Work:
Beach fishing hooked me. I started off fishing from shore with shrimp bait. That wasn’t enough for me. The little fish I was catching were placed on much bigger hooks and kayaked out in hopes of hooking bigger fish. Result? I caught monster sharks and redfish, and this former Michigander truly became a Floridian!

Family is very important to me. My wife and I were married in September of 2012. We now have three sons, Daniel, born in 2017, Clark, born in 2018, and Elliot, born in 2020. When I’m not at work, I’m with them.

The most important part of my life is my faith. I try to mirror my life after Jesus Christ. He is involved in every area of my life – family, fishing, and work.

What I Like Most About Helping People Find the Right Insurance Plan Options:
Since I started offering insurance in 2014, the industry has changed tremendously. Government often comes out with new regulations. Medicare changes annually. Insurance companies have to keep up and make adjustments themselves.

Through it all, I have found insurance to be bittersweet – sweet because it can help people but bitter because it can be so complicated. Trust me, I know. I’m the nerd who read all 135 pages of the Medicare & You book. Navigating insurance should be sweet, not bitter. To help, I educate on insurance basics in everyday language, find people’s needs, and guide them to options.

My daily goal is to honor God and help people. In 2016, 2017, 2018, and 2019, that mantra led to me being a top Medicare producer in Florida. In 2018, I was also in the top 110 with Cigna senior insurance nationally. In 2019 and 2020, I was in the top 220 for Aetna senior insurance nationally. Most important to me, I’ve been able to meet many people’s insurance needs in a sweet fashion.