Greg O’Brien

Some of life's most important decisions aren't simply financial or medical—they're both.

Greg O'Brien founded Medicare Caddy with a vision to transform the way people experience Medicare.   Rather than treating Medicare as an insurance transaction, Greg believes it should be approached as a critical component of a client's overall health and wealth strategy—one that protects both financial security and long-term healthcare access.

For more than 15 years, Greg has guided hundreds of individuals and couples through the complexities of Medicare with a philosophy rooted in education, objectivity, and personalized advice. His role is not to sell a policy, but to serve as a trusted advisor—helping clients understand their options, avoid costly mistakes, and make confident decisions that align with their unique health needs and financial priorities.

The inspiration for Medicare Caddy comes from Greg's years as a golf caddy. A great caddy doesn't swing the club—they provide knowledge, perspective, and confidence so the golfer can make the best decision on every shot. Greg built Medicare Caddy around that same philosophy. His role is to guide clients through the Medicare journey with clarity, helping them navigate unfamiliar terrain while avoiding unnecessary risks.

Under Greg's leadership, Medicare Caddy has evolved into a Concierge Medicare advisory practice dedicated to delivering white-glove service before, during, and long after enrollment. Every client receives thoughtful guidance, annual plan reviews, and ongoing support designed to adapt as healthcare needs and retirement goals evolve.

Greg believes the future of retirement planning lies at the intersection of wealth and health. By combining strategic Medicare planning with an unwavering commitment to client advocacy, he and his team help people protect what matters most—both their financial future and their peace of mind.

When clients work with Greg, they gain more than Medicare expertise. They gain a trusted advisor committed to helping them navigate Medicare healthcare decisions with confidence, clarity, and integrity.



When Greg is not living, breathing, or contemplating Medicare in 2036, you will find him enjoying mountain life and the nearby golf course on Lookout Mountain, Georgia.