Annuities

Protect your retirement savings from market volatility, ensure you never outlive your money, and build a reliable funding source for future healthcare needs.

Licensed in Virginia & North Carolina

Helping hundreds of families secure their assets since 2014

Coordinating seamlessly with Estate Planning Attorneys and Financial Advisors

What Exactly is an Annuity?

The financial industry is full of conflicting advice, and annuities are often misunderstood. To put it simply: an annuity is a contract between you and an insurance company. In exchange for your premium, the insurance company provides a guaranteed stream of income for a specified period of time—or for the rest of your life.


It is often described as the opposite of life insurance. While life insurance protects your family if you pass away too soon, an annuity protects you from the financial risk of living a very long time.

What an Annuity is NOT:

At Midtown Financial, we focus on protection and predictability. We do not focus on aggressive, high-fee variable annuities that put your principal at risk in the stock market.


Instead, we focus on Fixed and Fixed-Indexed Annuities. These are insurance instruments designed to protect your principal. If the stock market experiences a major downturn, the money inside your fixed annuity does not lose value due to market performance. It is a contractual guarantee of preservation and income.


For retirees looking to fund their later years or help pay for in-home care without the stress of watching the daily stock ticker, this predictability provides significant peace of mind.

Why Annuities Matter for Retirees

To understand why guaranteed income matters, you have to look at the reality of aging.


If you are forced to withdraw large sums to pay for care right after a market downturn, you could lock in those losses and significantly reduce your portfolio’s longevity.


Annuities help mitigate this risk. Here is how they protect you:

  • Protection from Market Volatility

    Your principal is protected from market downturns. You aren't forced to sell investments at a loss to pay a medical bill.

  • The Medicaid-Compliant Strategy (Spousal Protection)

    If one spouse requires a nursing home, Medicaid rules often require a "spend-down" of assets. This can threaten the financial security of the healthy spouse (the "community spouse"). A specialized tool called a Medicaid-Compliant Single Premium Immediate Annuity (SPIA) can be used to convert exposed cash into a protected income stream for the healthy spouse, helping them maintain their standard of living.

Is an Annuity Right For Your Portfolio?

Annuities are not meant to replace your entire financial strategy, but they serve as a critical anchor for many. You should consider exploring annuity options if:

  • You Want to Ensure You Don't Outlive Your Money

    An annuity provides a literal "paycheck for life."

  • You Want to Protect a Healthy Spouse

    If you want assurance that if one spouse needs care, the other maintains a guaranteed monthly income.

  • You Have "Lazy" Cash

    If you have funds in low-yield accounts because you are afraid of market risk, a fixed annuity offers safety with better growth potential and tax-deferred advantages.

  • You Cannot Qualify for Traditional LTC Insurance

     Certain asset-based annuities offer guaranteed acceptance and can still provide funds for care.

How Annuities Work to Build Your Defense

Willie Jester believes in an education-first approach. We guide you through the mechanics so you can make an informed decision. While there are many variations, we generally focus on these core insurance strategies:

  • 1. The Accumulation Phase (Growing Your Money Safely)

    With a Fixed or Fixed-Indexed Annuity, your principal is protected from market losses, and your money grows tax-deferred until you are ready to use it.

  • 2. The Annuitization Phase (Creating the Paycheck)

    When you retire or need to fund care, you "turn on" the income stream. The insurance company begins sending you a guaranteed monthly check. You can choose to have this check last for a set period or for the rest of your life.

  • 3. Long-Term Care Multiplier Riders

    Many modern annuities offer a Long-Term Care (LTC) Rider. For example, if your annuity pays $3,000 a month in retirement income, and you suddenly require assistance with two activities of daily living (like bathing and dressing), the contract may double your payout to $6,000 a month for a set period to help pay for your medical care.

It is critical to understand that an annuity is an insurance tool; Extended Care Planning is the overall strategy.


At Midtown Financial, we view annuities as defensive fortifications for your Long-Term Care strategy. We use them to build a financial moat around your castle.


If you require care, you need predictable capital. An annuity ensures that capital is there and immune to stock market crashes. Furthermore, it helps ensure that your healthy spouse is not left financially vulnerable. By integrating an annuity into your broader strategy alongside asset protection and life insurance, Willie Jester helps you achieve clarity and control.

The Moat Around Your Retirement

Secure Your Income for Life

You worked hard to build your retirement. Do not leave its survival up to the whims of the stock market. Sit down with Willie Jester for a clear, no-pressure conversation about how annuities can fit into your overall Extended Care strategy.