Fair Square Medicare

Hi, I'm Dan Petkevich, CEO of Fair Square Medicare.

I started Fair Square Medicare after watching my own parents struggle to understand Medicare. After a week of reading about Medicare Parts A and B, Medigap plans, prescription drug plans, and Medicare Advantage plans, my Dad exclaimed, "Medicare is a minefield!"

My parents were particularly frustrated that their only sources of advice for navigating this "Medicare minefield" were confusing documents from the government, insurance agents they didn't trust, and websites from the 90's that either list out all 100 plans available to them or take your phone number and call you every day for months.

Fair Square Medicare is the health insurance shopping experience I wish my parents had. Our website creates a personalized plan for when you should enroll in Medicare Parts A and B and a short-list of Medigap and Medicare Advantage plans to consider. We create this short list by algorithmically sorting through every plan available to you without any regard to how much commission we earn if you enroll in the plans it contains. Our goal is simply to find you the most comprehensive plan for your needs and budget. It's the right thing to do for you and the right thing for our business in the long run.

If you have any questions, please email me at daniel@fairsquaremedicare.com.

Our Team

Dan Petkevich, CEO

Dan Petkevich, CEO

Dan previously cofounded two financial technology companies: Trim and Octane Lending. He graduated from Yale.

Chris Dingess, Head of Brokerage

Chris Dingess, Head of Brokerage

Over the past decade, Chris helped more than a thousand people find the best medicare coverage - including Dan's parents!

Our Investors

We're backed by some of the top investors in Silicon Valley, including:

Fair Square Medicare


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Re-shop Your Current Medigap Plan for the Lowest Price

Virgil Insurance Agency, LLC (DBA Fair Square Medicare) and www.fairsquaremedicare.com are privately owned and operated by Help Button Inc. Medicare supplement insurance plans are not connected with or endorsed by the U.S. government or the federal Medicare program. This is a solicitation of insurance. A licensed agent/producer may contact you. Medicare Supplement insurance is available to those age 65 and older enrolled in Medicare Parts A and B and, in some states, to those under age 65 eligible for Medicare due to disability or End-Stage Renal disease. Virgil Insurance Agency is a licensed and certified representative of Medicare Advantage HMO, HMO SNP, PPO, PPO SNP and PFFS organizations and stand-alone PDP prescription drug plans. Each of the organizations we represent has a Medicare contract. Enrollment in any plan depends on contract renewal. The plans we represent do not discriminate on the basis of race, color, national origin, age, disability, or sex. Plan availability varies by region and state. For a complete list of available plans please contact 1-800-MEDICARE (TTY users should call 1-877-486-2048), 24 hours a day/7 days a week or consult www.medicare.gov. © 2022 Help Button Inc