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Josh Calaway – Medicare Guru

Josh Calaway – Medicare Guru

  • Where I’m From

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-year-old. I fell in love with the beach and never left (except for a few trips to India after college “namaste!”).

  • Hobbies

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 red fish caught and this former Michigander becoming a Floridian!

  • Career

I served as youth pastor at my local church for 7 years. In that time, I fell in love (deeper than with the beach!) with my lovely wife Rebecca. We are licensed foster parents and have our first born son Daniel.

After youth pastoring, I pursued my Medicare supplement insurance license. I held that in the background and made a foray into the banking work with Regions Bank. The past two + years I have focused primarily on insurance and specifically Medicare supplement and Medicare Advantage plans.

  • Current 

My goal day in and day out is to honor God and help people understand the Medicare maze. That mantra in 2016 led to me being a top Medicare producer for Florida Blue in the state of Florida. So far in 2017, I am in the top 170 with Cigna. In addition to Cigna, I also offer Aetna and Mutual of Omaha in over 40 states. I am also Authorized to Offer AARP Medicare supplement plans insured thru UnitedHealthCare.

How to reach me:

Direct: 1.888.857.0983 ext.206


Fax: 1.850.270.6708