About Wes Chapman
I got into Medicare for one reason. I had done it myself. And I got ripped off.
People making one of the biggest decisions of their adult life were doing it alone, with no benefits department to call. If it happened to me, it was happening every day to people who deserved better. Nobody should get ripped off accessing benefits they paid into their whole working life.
So I built this practice to be the opposite of that experience. No high-pressure pitches. No fine print designed to confuse. No quotas pushing me toward a product that fits me better than it fits you.
A few years in, I noticed something. Medicare solves the health coverage problem. It does nothing about the income problem. For freelancers, business owners, anyone who built their own road, the income side is the bigger one. Medicare keeps you alive. Income keeps you living.
So I got licensed in annuities to handle that side too.
I have served clients on Medicare for years across 48 states. Appointments with more than a dozen carriers, including Aetna, UnitedHealthcare, Cigna, Humana, Anthem, Kaiser, and Wellcare. The household names a 65-year-old already trusts.
The work itself is mostly translation. Medicare paperwork is written for actuaries. The job is turning it into English you can act on.
The annuity license came after years of watching Medicare clients ask the same follow-up question. The health coverage was sorted. The income side was not. And long-term care was a question nobody had a clean answer to.
Annuities solve both at once. They are insurance products that pay you monthly for the rest of your life, the same structure pensions provided a generation ago. The modern versions can also pay extra income if you need long-term care, the same protection a standalone LTC policy provides at a fraction of the cost and risk.
For most of my clients, an annuity is the closest thing they will ever have to the pension their grandfather had. With a long-term care safety net built in.
My degree from Dartmouth taught me how complicated systems work. Medicare is a system. Retirement income is a system. Once you see the parts, the choices feel a lot less scary.
Four Things Your Money Needs to Do
Philosophy
Here is how I work. I explain your options. You make the decision.
The reason that matters: I have been on the other side of an insurance conversation that did not have my best interest in mind. It is a bad feeling. It is also avoidable.
No product of the month. No quotas. No artificial scarcity. The clients I have had longest are often the ones who said no to something I suggested. They came back later when the timing was right. That is the relationship I am after.
Retirement planning should not require a finance degree. If I cannot explain something to you in ten minutes, I am not doing my job.
Who I Serve
Three groups, mostly.
Medicare Enrollees and People Approaching 65
Once the health coverage is sorted, the next question often surfaces. What about the income side? Glad to help.
Self-Employed People and Entrepreneurs
You built your own thing. Nobody handed you a 401(k) match or a pension. You have IRAs, business equity, savings, maybe a brokerage account, but no plan to turn any of that into a paycheck. That is the work.
American Expats in Latin America
I have spent real time in Panama, Mexico, and Costa Rica. The friendships are real. The questions are familiar. Medicare rules abroad. Income planning across borders. Currency questions. These conversations are not theoretical to me.
If you want to understand your options in Medicare or retirement income or both, the door is open. No presentation. No obligation. Nobody selling you anything you do not need. One conversation.
helps people all across the United States, Mexico, Costa Rica and Panama