AFMG - American Financial Management Group

07/16/2026

07/11/2026

The HSA may be the most underused retirement-savings tool going, even though, strictly speaking, it isn't a retirement account.

If you're HSA-eligible (generally, covered by a qualifying high-deductible health plan, with no disqualifying coverage, and not yet enrolled in Medicare), you get a federal tax deal nothing else quite matches: a deduction when the money goes in, tax-free growth, and tax-free withdrawals for qualified medical expenses. A traditional 401(k) and a Roth each get two of those three. The HSA gets all three.

The flexibility in reimbursement might be the best feature. You can pay medical bills from cash flow, save the receipts, and reimburse yourself years later. There's no federal deadline, as long as the expense was incurred after the HSA was established and you can document it.

That timing control can turn the HSA into a retirement-income planning tool. You decide when to reimburse yourself with tax-free dollars, which can help you manage a tax bracket, a Medicare surcharge threshold, or another income-based cutoff. But the real value isn't just decades of tax-free growth. It's that the money isn't trapped.

A big reason people hesitate to fund an HSA is the worry they'll need the money before retirement. But qualified medical expenses can be reimbursed tax- and penalty-free at any time. So the account doubles as a health-emergency reserve: money earmarked for the future, but still there when a medical bill arrives.

There's another overlooked benefit. Even when a medical expense gets you no tax deduction, whether because you didn't itemize, didn't clear the 7.5%-of-AGI floor, or both, paying it from the HSA is still tax-free. The HSA benefit never depended on qualifying for a Schedule A deduction in the first place.

The fine print matters. You can contribute only while you stay HSA-eligible, and it's Medicare enrollment, not simply turning 65, that ends that. After 65, non-medical withdrawals are taxable, but the 20% penalty disappears, so the HSA can act something like a traditional IRA if you need it to.

And it's still a health account, not a retirement account, a distinction that shows up at death. A surviving spouse can generally keep the HSA as their own. A non-spouse beneficiary generally can't, and the account can become taxable income. That's the weight the label carries.

Overlooked, misunderstood, and one of the best deals in the tax code. Worth a real look.

07/08/2026

Yes, this is very funny sarcasm, but it does hint at a real retirement-planning problem: “never spend nuttin’” is not a strategy.

Planning is not about saying no to everything today in the name of some theoretically perfect tomorrow. It is about finding a reasonable balance between using your money now and protecting your future self.

Because the goal was never to win retirement by spending the least possible amount.

FRANKLIN, TN—Popular Christian radio host Dave Ramsey has released a brand new Magic 8-Ball that always answers in the negative when you ask it if you should buy something.

07/08/2026

Can claiming Social Security after 65 create a tax problem inside your HSA?

It can. And it is one of those annoying planning traps where every individual decision seems reasonable until you see how the pieces connect.

First, why it stings: HSAs are a triple threat — to the IRS. Money can go in pre-tax or deductible, grow tax-free, and come out tax-free for qualified medical expenses. Hard to beat.

But once you are enrolled in Medicare, including premium-free Part A, you are no longer eligible to contribute to an HSA. That is true even if you are still working, still covered by your employer's plan, and still enrolled in a high-deductible health plan.

Here's the trap: if you enroll in Medicare after 65, Part A can be retroactive for up to six months. Any HSA contributions made during those retroactive months can become excess contributions, potentially subject to a 6% excise tax for each year the excess remains in the account.

Now add Social Security. Applying for Social Security retirement benefits after 65 automatically enrolls you in premium-free Part A — including the same retroactive issue. You do not have to sign up for Medicare to end up in Medicare.

That is the part people miss. Social Security touches Medicare. Medicare touches HSA eligibility. HSA eligibility touches the tax return.

The good news? If this already happened to you, it is usually correctable — withdraw the excess contributions plus earnings by the tax filing deadline and the penalty stops. The sooner it is caught, the cleaner the fix.

Working past 65 with an HSA? Know how the dominoes fall before you file for anything.

07/02/2026

Presented in time for your beach reading, the AFMG Summer Newsletter! https://buff.ly/UFQElxc

Most financial advice focuses on building wealth. Kevin Gaines of American Financial Management Group focuses on what comes next—turning it into reliable retirement income. Through tax-aware strategies, Social Security planning, and flexible income design, he helps you navigate the shift from savi...

07/01/2026

Trump Accounts may be a good idea for the kids in your life, but if you don't understand the rules and the purpose, it may be hard to decide among 529s, UGMAs and Trump Accounts -or even "none of the above"

In today's Slott Report, our Director of Education, Sarah Brenner, JD, breaks down the IRS's new safe harbor that addresses the gift reporting concerns surrounding .

Here's what the guidance says and what it means for contributors. Read more: https://bit.ly/44CBCv1

07/01/2026

And the subject of a great Take Back Retirement podcast episode: https://takebackretirement.com/podcasts/a-league-of-their-own-retirement-planning-lessons-from-a-baseball-contract/

Happy Bobby Bonilla Deferral Day: Bonilla is set to collect another $1.193 million from the New York Mets today, as he will each July 1st through the year 2035.

06/29/2026

The IRS has announced that qualifying contributions to Trump Accounts generally will not trigger gift-tax return filing under a new safe harbor.

Many expected this, but the clarification matters. Because a child generally cannot access the money during the account's growth period, some worried contributions could be treated as gifts of a future interest. Future-interest gifts do not qualify for the annual gift tax exclusion, which could have meant filing a gift tax return even when no gift tax was actually owed.

The IRS instead treats qualifying contributions within the safe harbor as completed gifts eligible for the annual exclusion. In plain English: a paperwork headache for many parents, grandparents, and others who want to help fund a child's account — now mercifully avoided.

The timing matters too. Trump Accounts officially launch on July 4, just as families start deciding whether and how to fund them.

You can find the details here: https://buff.ly/0zdD8QC

Taxpayers had raised concerns that Trump account donations would trigger gift tax reporting rules.

06/29/2026

You spent 40 years learning to save. Nobody taught you the second half.

There’s a survey making the rounds from the TIAA Institute and Nuveen — I came across it in ThinkAdvisor — and the short version is this: most workers have barely thought about how they’ll actually pull money out in retirement.

And honestly, if that’s you, you’ve got a lot of company.

The easy take is, “people don’t plan.” I don’t think that’s it. A lot of people did exactly what they were told to do. They contributed to the 401(k), took the match, tried not to panic when the market got ugly, and slowly built something meaningful.

They planned plenty. They just planned for the first half.

Here’s the part that really matters: nearly half of workers underestimate how long they’re likely to live after age 65. But the deeper problem is that nobody actually knows. Guess too short and you may clutch dollars you could have enjoyed. Guess too long and you may stretch thin for years that may not come. The point isn’t to land on the perfect number — you can’t. It’s to build a plan flexible enough that you don’t have to.

For decades, the retirement message was pretty simple: contribute, diversify, don’t panic, repeat. That’s good advice. It answers one question: how do I build the pile?

But retirement asks a different question: how do I turn this pile into income that lasts as long as I do?

That’s not the same question. It’s not even the same math. Spending in retirement involves timing, taxes, Social Security, market risk, required withdrawals, and the very human fear of running out of money. It also includes the quieter risk that doesn’t get talked about enough: being so afraid to spend that you never really enjoy what you worked so hard to build.

The pile was never the answer. The answer is the system that turns the pile into the life you wanted in the first place.

Saving for retirement is a plan. Spending in retirement is planning — ongoing, adjusted, revisited, and kept alive as long as you are.

Those accounts you’ve been guarding for 40 years? They were never really savings. They were future spending, waiting for now.

If you’ve got the number but no idea how you’d live off it, you’re not behind. You’re normal.

But normal was never the goal.

The goal was the life all that saving was supposed to buy.

That second half is the part worth getting right.

From ThinkAdvisor: https://buff.ly/9f4fBox

Only 22% of respondents to a recent survey said they had given the matter a lot of thought.