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Josh Calaway – Medicare Specialist

Josh Calaway – Medicare Specialist

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 on pompano rigs. That wasn’t enough (law of diminishing returns at its best). The little fish I was catching were placed on much bigger hooks and paddled out past the sandbar in hopes of hooking bigger fish. The little fish I used for bait grew to be bigger fish. Result? Monster sharks and redfish caught and this former Michigander becoming 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. He is involved in every area of my life – family, fishing and my work.

What I like most about helping people find the right Medicare plan options:

Over my five-plus years of being licensed to offer health insurance, there have been numerous changes. Medicare itself has changed deductibles, coinsurance and premiums regularly. The Medicare Advantage insurance industry as a whole has also changed dramatically with plans being discontinued, premiums adjusting, state-specific rules, etc.

Through it all, I have found Medicare to be bittersweet – sweet because it can be a great help to 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. There are many companies offering Medicare Supplement insurance plans, many different styles of plans available, and many rules strung like red tape from Medicare. Navigating Medicare should be sweet, not bitter. To help, I educate on Medicare basics in everyday language, find people’s needs, and guide to options to meet needs with the best company for them even if it’s not a Medicare Supplement company I work with.

In the state of Florida, I am appointed with Florida Blue Cross Blue Shield (offering Medicare Advantage and Supplement Plans). In other states, I work with Medicare Supplement plans from Mutual of Omaha, Cigna, and Aetna. I am also authorized to offer United Healthcare.
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.

Companies Josh works with:

Florida Blue Medicare



Aetna Medicare



Cigna Medicare



Mutual of Omaha Medicare

mutual of omaha medicare supplement in texs


I welcome your call or email!

Contact Josh:

888-857-0983 ext.206

email: [email protected]