Frequently Asked Questions

What is Medicare Caddy’s primary purpose for being in business?

As reflected in our marketing materials, Medicare Caddy’s objective is to share our knowledge and experience to help you become an “empowered healthcare consumer,” no matter what your sneed may be. Medicare Caddy follows a phased process to Engage, Educate, Evaluate, Enroll – which leads to Empowering you to make educated and informed decisions.

How do I get started with Medicare Caddy?

The best way to get started with understanding how Medicare Caddy can help you and/or a loved one is to review the White Papers and downloadable information on our website As you read the materials, write down on a sheet of paper all of the questions and concerns that come into your mind. This will provide you a solid start in beginning to work with Medicare Caddy.

What is provided with my free initial consultation?

Medicare Caddy offers, at no cost or obligation to you, a 30-minute initial consultation to determine if your needs and Medicare Caddy’s solutions are a good match. If we don’t think we can help you or your family in a meaningful way, we will tell you so and also provide you with a vetted contact person we know that is better suited to meet your needs.

Is Medicare Caddy a licensed insurance agency?

Yes, Medicare Caddy, LLC is a licensed health & life insurance agency in the state of Georgia. Medicare Caddy is affiliated with Ritter Insurance Marketing, LLC , one of the largest Field Marketing Organizations (FMO) in the United States. Ritter specializes in providing Medicare related insurance services to agents and agencies across the United States, including accurate premium quoting, compliant communications and enrollment fulfillment.

When is the best time to engage with Medicare Caddy?

Medicare Caddy generally starts working with our clients six (6) months before their 65th birthday. There are clear advantages to review and understand your Medicare related alternatives prior to enrolling in Medicare, which can happen three (3) months prior to your 65th birthday.

Can Medicare Caddy help me with questions I have about Social Security?

Yes, many of our clients are confused about when to start receiving Social Security Retirement Income and reach out to Medicare Caddy for guidance. Medicare Caddy has access to very experienced consultants that work in the Social Security arena every day.   While Social Security income can start as early as age 62, the majority of our clients understand that waiting until full retirement age (or later) generally is in their best interests.

Do I have to be a golfer to use Medicare Caddy?

No, not at all. However, the golfer’s “caddy” analogy works very well in describing how Medicare Caddy approaches providing our services. Most people understand and appreciate the value of having an experienced and knowledgeable professional to guide you through the challenges of an uncharted course. As a former country club and PGA Tour caddy, our founder, Greg O’Brien, wants our clients to feel the satisfaction and enjoyment of having an honest and well intentioned “caddy” to carry the burden of knowing your Medicare options (which are constantly changing), as well as providing Longevity Solutions as you and your loved ones age.

Can Medicare Caddy help me if I have a problem with Medicare claims?

Yes, one of the key services provided by Medicare Caddy is the ability to manage claims – and to properly appeal medical and prescription drug claims that have been denied for payment. Through partnering relationships with Claims Security of America and Benefit Defender, Medicare Caddy can provide seamless attention to the aggravation of denied claims.

Should I consider Medicare if I (or my spouse) are turning 65 but still working and have group insurance?

Absolutely! Many mistakes that lead to lifetime premium penalties are made because people do not think they have to engage with Medicare until after they retire, leave the workforce or get off of corporate sponsored group health insurance. Medicare Caddy has a publication available titled 65 and Still Working? What to Do About Medicare that can provide some needed guidance.

Can Medicare Caddy help me with my Part D Prescription Drug Plan?

Without a doubt! The costs of prescription drugs vary greatly depending on a multitude of variables. Medicare Part D is an important part of many people’s life and well-being. Medicare Caddy helps many of our clients in this arena.

What information is needed from me to get started?

The basics for understanding your costs and benefits available through Medicare are:

  • Date of Birth
  • State, county and zip code of your primary residence
  • Effective Dates for Part A & B
  • Modified Adjusted Gross Income from past 3 years
  • Current prescription medications with dosage & frequency

Where can I learn more about Medicare?

There are ample websites to provide the basics about the Medicare system. To find out specific information about you and your Medicare benefits, Medicare Caddy suggests spending time looking around the primary government sponsored website, which is . For big picture viewing of the size and impact of Medicare within the United States economy, the Kaiser Family Foundation is an outstanding option. Visit and be prepared to learn.

How does Medicare Caddy provide access to so many varied services?

Medicare Caddy is active in our communities’ “senior services” sector, which is very vibrant with many people committed to helping seniors live better, longer. Our involvement includes developing relationships with many companies that provide specific services to seniors. Like a good golf caddy, Medicare Caddy is in the know with who is a “good” service provider – and those who need to improve. Medicare Caddy spends time researching various service providers and seeks to partner with those we would recommend to our own family members. And in return, many Medicare Caddy Members were introduced to Medicare Caddy services by their trusted advisors.

Can Medicare Caddy help us with Long Term Care insurance products?

Medicare Caddy is a firm believer that anticipating the need to provide funds for short and long term recovery and care is a fundamental feature of a well-structured Medicare and aging healthcare strategy. The added years of longevity significantly increases the risk of accidents, illnesses, and the wearing down of various body components. The funding of short, medium and long term care needs is changing dramatically from an insurance product to hybrid life insurance products with riders for long term care needs.

What is Medicareful? is accepted by the Centers for Medicare & Medicaid Related Services (CMS) and is a website designed to help interested consumers gather Medicare related information and support when considering enrolling or changing Medicare insurance plans, including Original Medicare (Parts A & B) benefits, Medicare Supplemental (Medigap) plans, Medicare Advantage (Part C) plans and Medicare Prescription Drug Plans (Part D). Many people use this site as a way to first contact Medicare Caddy.

How do you charge for Medicare Advisory services?

Medicare Caddy services are offered on an annual subscription (“Membership”) basis. There are three levels of services that address the various needs of our Members.

Service Level Annual Fee – Individual Membership Annual Fee – Couple Membership
Par $495 $595
Birdie $695 $795
Eagle $895 $995