About Us

The Medicare program is confusing, complex and constantly changing. We understand that Medicare plays a significant part in the lives of many Americans – who are also living longer. We call this “longevity” – and with longevity comes many rewards and challenges. The Medicare Caddy team believes that Medicare should not be sold to you as an insurance product – it should be provided to you as ongoing advisory services that significantly benefit both you AND your family.

You need a trusted advisor who will proactively help you make wise healthcare choices related to Medicare and the longevity aging process. Medicare Caddy wants to be your trusted advisor.

Our Team

Greg O’Brien

Greg O’Brien spent the past forty-seven years of his life being immersed and infatuated in the history, structure and excitement surrounding the game of golf. He started as a practice range golf ball “shagger” at age eleven and each year grew more deeply involved in the “caddy shack world” of an exclusive private golf club located on the stately “Main Line” of Philadelphia, PA.

He learned to play golf on “Caddies Day” – each Monday when the course was closed to Members, but 50+ active caddies were allowed to enjoy the hallowed golfing grounds. Many early lessons of life were learned in the caddy yard, as well as from toting the bags of distinguished and some not-so-distinguished members and guests.

The lure of watching individually unique golf swings, hearing the swoosh and the click of a golf club contacting a ball, then seeing the white sphere fly across beautifully manicured green grasses towards a distant flag was captivating. The cast of characters and etched memories the game constantly generated fed his addiction.

Greg’s high water mark in his heavy golf inebriation period was quitting college after two years, buying a red, 1969 Ford Econoline conversion van and crisscrossing the United States from tournament town to tournament town, living the vagabond life of a PGA Tour caddy from 1979 – 1981.

Greg learned what it takes to evaluate the layout of a golf course, measure ever-changing conditions – to identify opportunities and avoid hazards. The real challenge was to then succinctly communicate the proper information so that his player could make informed decisions – and hopefully execute a successful golf shot. Whether it was for a club member’s $2 Nassau bet or a PGA Tour professional playing for his livelihood and tens of thousands of dollars – the importance of sound knowledge and prior experience in the game of golf became deeply rooted.

Later, as a J. Wood Platt Caddy Scholarship recipient (awarded by the Golf Association of Philadelphia) and armed with a Business Administration degree from the University of Richmond, Greg spent five years in the oil exploration business in Texas, until the “bust” of 1986 left Houston and the oil patch in a state of economic depression. Greg set his sights on another “course” and relocated to Atlanta, GA, married, raised a family and enjoyed 27 years in the commercial real estate business. Throughout his business career, the game of golf has played an important role in developing mutually respectful business relationships – as well as a favored pastime with friends and family.

After the Great Recession decimated the real estate industry, including the 1,500-acre master-planned golf course community in St. Augustine, FL where Greg was a Founding Member, he joined national Medicare insurance wholesaler Ritter Insurance Marketing. Greg spent five years recruiting, training and motivating Medicare health insurance agents and educating Medicare eligible beneficiaries, their families, CPA’s, financial planners and investment advisors as to the peculiarities of the Medicare system. And so emerged Greg’s unique relationship with the game of golf and the “game” of Medicare.

In early 2017, Greg, with his wife and business partner Julie, launched Medicare Caddy, LLC with what has been called the first Longevity Solutions for Seniors platform. Live longer, Better. And it begins with Medicare……

Julie O’Brien

Julie joined the Medicare Caddy team in January of 2017 as Executive Director. Julie’s career includes experience as a life, health and disability insurance agent working in Florida, where she grew up. After relocating to Atlanta, Julie spent over twenty years as an Executive Assistant in the financial services arena and commercial real estate industry. Julie managed the many administrative responsibilities for over $75 million of industrial warehouse and retail developments across North Georgia.

Julie further developed her executive management skills spending the last ten years working for “C” level executives. Julie’s disciplined work ethic, her sunny disposition and warm smile help clients, partners and co-workers feel welcome and cared about!

Working as a husband and wife team brings many challenges but more rewards. Julie and Greg are excited about developing long term relationships and helping as many people as possible with their Medicare and longevity needs. They consider it a privilege and a calling.

Julie was recently awarded the title of Certified Senior Advisor (CSA®) by the Society of Certified Senior Advisors. This certification provides a broad-based knowledge of the health, social and financial issues that are important to seniors, and the dynamics of how these factors work together in seniors’ lives. This will help Medicare Caddy better serve their clients in providing options and solutions as they age so that they can live better, longer.