By Joseph E. Seagle, Esq.

👋 Happy Friday! Today is National Mole Day, which chemistry classrooms mark from 6:02 this morning until 6:02 tonight in honor of Avogadro's number, 6.02 x 10^23. The mole exists for an unglamorous reason. Chemists needed one agreed way to say how much of something was actually there.

Which suits this issue. All three legal stories turn on the gap between a thing on paper and the thing actually there. The IRS says an IOU isn't a payment. One signature can license a dead person's face. And an exemption only answers the question you asked it.

1 big thing: The IRS says an IOU isn't an annuity payment

The IRS wants $614 million in gift tax and $122 million in penalties from a Nashville couple over three trusts, two of which moved roughly $200 million into trusts for their daughters. The Wall Street Journal reported on September 21 that Chuck and Trisha Elcan are fighting the assessment in Elcan v. Commissioner, Tax Court Docket No. 3405-25, over trusts the Journal says held about $1.5 billion in HCA Healthcare holding-company interests.

The vehicle is a grantor-retained annuity trust, AKA “GRAT.” Fund it with assets you expect to appreciate, take back a fixed annuity for a set term, and whatever grows faster than the IRS hurdle rate will pass to your children free of additional gift tax. The hurdle rate resets monthly; the IRS published 5.4% for September and 5.6% for October. Two-to-ten-year terms are a practice convention, not statute, and short terms are popular for a reason: die during the trust’s term and IRC § 2036 pulls all of the assets back into your gross estate.

Why a routine technique is suddenly in play

The fight isn't about whether GRATs work. It's about how one payment got made. Trisha Elcan put assets into her GRATs, then bought assets back from of the GRATs using interest-bearing promissory notes she owed the trusts. But the trustee then satisfied her annuity by forgiving portions of those notes.

Treas. Reg. § 25.2702-3(d)(6)(i) says that for a trust created on or after September 20, 1999, the instrument must prohibit the trustee from "issuing a note, other debt instrument, option, or other similar financial arrangement" in satisfaction of the annuity obligation. The IRS reads the forgiveness as doing exactly that. If the agency wins, the annuity interest never qualified under IRC § 2702, and every dollar put into the GRATs becomes a taxable gift at 40%, including the dollars in the third GRAT that failed on its own. As you can see from the penalties that were assessed, these trusts held huge sums.

The Florida piece nobody mentions

Florida levies no estate or inheritance tax, so the federal exemption, $15 million per person in 2026, is the whole budget a Florida family works with. That's why appreciation-shifting tools come into play here.

But a GRAT is a transfer-tax tool, not a creditor tool. Under Fla. Stat. § 736.0505(1)(b), a settlor's creditor may reach the maximum amount that can be distributed to or for the settlor's benefit, and a GRAT's whole design is a mandatory fixed stream coming back to you. For the entire term, that stream sits inside a creditor's reach. It stops there, though. It doesn't follow the remainder your children take at the end. And subsection (1)(c) isn't a workaround: it only keeps a discretionary tax-reimbursement power from exposing the trust, which GRATs usually omit anyway.

Keep in mind that these types of trusts aren’t used by people with estates with a net worth less than $30 million. But if your net worth exceeds that amount, it may be something to think about — especially for certain equities and other growing assets.

What to execute

For real estate investors and private lenders — a GRAT only pays on assets that outrun the hurdle rate. A stabilized rental rarely does; a development entity or a note portfolio might. Pull the instrument on anything already running and confirm the note prohibition clause is in it.

For licensed professionals — physicians, dentists, attorneys, pharmacists: if the practice is your appreciating asset, a GRAT moves future growth out of your estate. It does nothing about a malpractice judgment, and the annuity coming back to you stays exposed while the term runs.

For home services businesses — HVAC, plumbing, electrical, painting: the growth a GRAT captures is the growth between today and your exit. Starting one after a letter of intent to buy your company is starting too late. If you think your company could sell for an amount that will put your net worth north of the current estate tax exclusion (currently $30 million), then you could move at least some of your interest in the company to a GRAT so that future appreciation happens there instead of in your estate.

Where people go wrong: papering a substitution after the fact. The Elcans' notes were real documents in the right sequence, but the IRS still called it a “step transaction.” Backdating is a worse version of the same problem.

Out-of-state readers: § 736.0505 is Florida's creditor rule, and states differ on it. The Treasury regulation and § 2036 are federal.

The bottom line: The strategy survived. One shortcut inside it may not.

Watch for: the ruling on the taxpayers' summary judgment motion, which Kiplinger reported was still undecided in late September. A decision for the IRS reprices every substitution that paid an annuity with a note, not just theirs.

Sources: The Wall Street Journal, September 21, 2026; Kiplinger, "IRS Is Taking a Closer Look at Trusts"; Treas. Reg. § 25.2702-3; IRS § 7520 rates; Fla. Stat. § 736.0505.

2. In Florida, any one spouse or child can license your face

Dolly Parton died August 25. On September 22, She's Alive LLC, the entity her estate plan created to hold and license her professional property, went into a Nashville court asking a judge to keep her own nephew away from its people and its business partners. The court entered a temporary restraining order the next day.

Fortune and the Associated Press reported that the filings describe escalating messages from Bryan Seaver, who ran Parton's security detail for roughly two decades and appeared in the video announcing her death. Davidson County Chancellor I'Ashea L. Myles granted the order, NewsChannel 5 reported, barring Seaver and his security company from interfering with the entity's business relationships or coming within 1,000 feet of its employees, attorneys, and business partners. According to the entity's own filings, Parton's trusts and estates attorney had already quit based on the threats received, She's Alive employees had resigned, and the entity was paying for private security at staff homes to protect them from Dolly’s nephew.

Seaver denies it. In a mid-October affidavit, he called the messages a private exchange between friends, denied threatening anyone with physical harm, tied his anger to money he says his firm was owed, and argued the order is written so broadly it puts much of Nashville off limits to him. The court hasn't resolved any of it.

Why it matters

What most people don't know

Florida has a statute on exactly that right, and its default is startling. Under Fla. Stat. § 540.08, nobody may use your name, portrait, photograph, or likeness "for purposes of trade or for any commercial or advertising purpose" without consent, and subsection (5) extends that protection 40 years past your death. Subsection (4) exempts bona fide news reporting, so it's a commercial-use rule, not a gag.

Read subsection (1) for who gives that consent once you're gone. First choice is whoever you authorized in writing to license it. If you never named anyone, consent may come from "any one from among a class composed of" your surviving spouse and your surviving children, and subsection (6) limits "children" to immediate offspring and legally adopted children.

Two things follow: One child, acting alone, can sign the deal for the rights to your face. But a nephew can't consent at all, which is worth noticing in a story about a nephew.

This reaches well past celebrity. If the company name is your family name, if your photograph sells the service, if your signature is the logo, that's licensable property under § 540.08. Leave the licensing authority unnamed, and you've handed the decision to whichever spouse or child moves first.

The yes-but

Naming one person in writing fixes the consent problem and creates a concentration problem. You've made one heir the gatekeeper over an asset the others have an economic stake in. The usual answer is to put the licensing power in an entity or trust with a named manager and a written removal path, rather than in a person, because the statutory route is slow. That’s what Dolly did. But alleged oral promises made prior to death to her nephew ended up in threats and resignations afterward.

Under Fla. Stat. § 736.0706, a settlor, cotrustee, or beneficiary can petition to remove a trustee for a serious breach of trust, or where the trustee is unfit, unwilling, or has persistently failed to administer the trust effectively. You prove those standards to a judge. Drafting your own mechanism is cheaper. In Dolly’s case, all of this was in place, but when one family member threatens to burn it all down after you’re gone because they feel they’re owed more, all the documents in the world can’t prevent the damage to your brand they can create.

What to execute

For home services businesses — if the trucks carry your last name, name the licensor in writing and say what happens if that person can't serve. Be clear in your company documents as to who continues to be paid, how, by whom, and for how long. Clear accountability and organizational charts for the business are vital to ensuring everyone knows their seat before you’re gone so they can continue to function.

For licensed professionals — your name is most of the practice's goodwill, and a buyer will want the right to keep using it. A succession sale with an unresolved name right brings a lower price if it brings a buyer at all.

For real estate investors and private lenders — the brand matters less here than the keys. Audit who holds signature authority on every entity and trust, and whether removing them takes a judge.

Out-of-state readers: § 540.08 is Florida's right of publicity. Most states have one, the post-death terms vary widely, and a few have none.

Bottom line: Parton's plan put the brand in an entity with a manager who could act. Copy that part. The part most people skip is naming, in writing, who speaks for their name after they can't, and how to reign in those who would try to harm the brand.

What's next: the hearing on a longer injunction, which was moved from October 9 to October 20, has reportedly slipped again.

Sources: Fortune/Associated Press, September 23, 2026; NewsChannel 5 Nashville; CBS News; Fla. Stat. § 540.08; Fla. Stat. § 736.0706.

For those who missed Wednesday evening’s livestream, or for those who didn’t get a high-quality connection, you can watch the re-run in clear high-def, or listen to it. I’ll be the first to admit that this one had a lot of visuals, so if you’re just listening to it on a podcast app, it won’t always make sense. So try the YouTube link when you get a minute.

 Listen in or watch on your favorite streaming platform.

3. Practice Pointers: The same asset, three different exemption tests

John Vandergriff argued in Kiplinger that estate planning starts in the wrong place. A will governs what's left, and nobody asks the prior question of whether anything will be left to govern. He names three pillars that determine it: your investment strategy, your tax strategy, and your long-term care plan.

He's right, and in Florida those pillars hit something specific. Florida protects a great deal of property. It does not protect the same property from every claim.

The big picture: Florida's exemptions are claim-specific, not asset-specific. Run one retirement account or one annuity past a judgment creditor, a divorcing spouse, and a Medicaid caseworker, and you can get three different answers about the same dollars.

Why it matters:

What most people don't know: the annuity is the cleanest illustration. § 222.14 keeps a judgment creditor away from the cash surrender value and the proceeds. Medicaid is indifferent to that. Under 42 U.S.C. § 1396p(c)(1)(F), buying an annuity counts as a transfer for less than fair market value unless the State is named remainder beneficiary in the first position for at least the total Medicaid paid on the individual's behalf, or in second position behind a community spouse or a minor or disabled child. Same contract, same dollars. Shielded from one claim and disqualifying for the other.

Key takeaways:

Where people go wrong:

Out-of-state readers: chapter 222 and § 409.9101 are Florida law and unusually generous by national standards. The 60-month look-back and the annuity rule are federal.

The bottom line: Build the financial life first, then document it. And when you paper it, make somebody tell you which claim each exemption is actually answering.

Go deeper: Read the full long-form article on aspirelegal.com or download our Florida Exemptions Claim Guideline.

Sources: Kiplinger, John Vandergriff, June 15, 2026; Fla. Stat. § 222.21; Fla. Stat. § 222.14; Fla. Stat. § 409.9101; 42 U.S.C. § 1396p.

4. Coaching Thoughts: Block an hour to see what everyone else missed

Most small business owners don't have an idea problem. They have an input problem. Every week looks like the last because the information coming in is the same, from the same five sources, about the same three competitors.

Kamya Marwah wrote in Inc. that her best marketing ideas never came out of a brainstorm. They came from watching what other brands did and asking a different question. Not "was this good?" but "why did they do this now?" She blocks an hour every week with no intention of posting anything, and she reads deliberately outside her own industry, on the theory that a beauty brand can learn something from a food startup.

EOS already named this, and most owners skip it anyway

Gino Wickman built it into the Entrepreneurial Operating System as the Clarity Break: a standing appointment with yourself, out of the office, with a blank pad. Wickman is specific that it should never happen at your desk and isn't a chance to catch up on work. It's the first thing to fall off a busy week, because an hour that produces no output looks like the most expendable hour you own. It's the opposite. It's the only hour you spend working on the pattern instead of inside it.

Make it a To-Do, not a good intention

Then feed it into the Level 10

A Clarity Break that only produces a nicer Friday is a hobby. Write what you noticed onto the Issues List, where it gets IDS'd with people who can act on it. If a pattern you spotted can't earn a line on that list or a Rock next quarter, it wasn't a pattern. It was an interesting article.

Bottom Line: The owners who see a shift early aren't consuming more than you. They're the ones who put the noticing on their calendar.

This Week's Challenge: Block 60 minutes before next Wednesday. No posting, no inbox, no competitor dashboards. Read or watch three things from industries with nothing to do with yours, write one sentence on each answering "why now," and bring the best one to your next L10 as an issue.

Sources: Inc., Kamya Marwah; EOS Worldwide, Gino Wickman on Clarity Breaks.

We hope you found this helpful — any feedback is appreciated and can be shared by hitting reply or using the feedback feature below.

Be on the lookout for our next issue! 👋