EAs, Emmys, and… Enlargements

Josh and Shannon get into what actually separates a business deduction from a personal one.

Shannon reports back from the Brass Tax EA Bootcamp and the first year of at-home EA exam proctoring (the metal detector stories are real). Then: why an unlicensed preparer cannot represent you before the IRS no matter what the Facebook group says, how to tell whether a CE speaker actually knows the material, and §162 versus §262 by way of an influencer who deducted the Grammys, a dancer who depreciated her chest, and two business partners who were very sure the Rolexes were ordinary and necessary.

Plus: why the adversarial posture toward the IRS is mostly bad strategy.

CASES

Sami v. Commissioner, T.C. Memo. 2026-69 (Aug. 18, 2026) — An IT manager/social media influencer deducted roughly $97,000 in celebrity meet-and-greets, Grammys and Emmys tickets, and signed Kobe Bryant shoes. The celebrity expenses went down, but the result wasn't a complete wipeout: the court allowed portions of several business expenses under Cohan and credit-card processing fees in full.

Hess v. Commissioner, T.C. Summary Opinion 1994-79 — Yes, that case. Cynthia Hess, stage name “Chesty Love,” successfully treated her surgical implants as depreciable business property. And much of what tax professionals repeat about this opinion is wrong.

WELL, ACTUALLY…

• Hess is not T.C. Memo. 1994-79. It's a nonprecedential small-tax-case summary opinion.
• “Not precedent” does not mean “not citable.”
• She was 56FF in the tax year before the court; the later 56N implants came afterward.
• Sami was a mixed result, not a complete denial.
• Calling Sami “the first influencer case” may be premature.
• The Dinah Shore gown deduction appears to be tax folklore, not a reported case.
• And Suleiman Sami is one person. Suleiman is his first name.

Code: IRC §§162, 262, 7463(b), 67(h)

MENTIONED

Brass Tax Presentations — brasstax.com
AskTomG — asktomg.ai (Disclosure: Josh has a financial interest.)
Tom Talks Taxes — tomtalkstaxes.com
U.S. Tax Court — ustaxcourt.gov

Full show notes, citations, source documents, links, and corrections: wellactually.tax

This podcast is general commentary on federal tax law and procedure, not tax, legal, or accounting advice. Tax outcomes depend on facts. Views expressed are the hosts’ own.

Two enrolled agents who just survived the Tax Court exam sit down to compare notes on a summer of conferences, a vendor hall full of AI products, and the disclosure rule nobody wants to talk about.

Josh and Shannon open the first episode of Well, Actually with the small talk (105 degrees in Texas, an angelic glow in Long Beach) and get to the substance quickly: what they'd change about every tax practice in the country if they had one wish, why "our lawyer says 7216 doesn't apply" is a red flag, how to actually vet an AI vendor, and what OPR's guidance on artificial intelligence does and doesn't say about billing.

Then a detour through ghost tours, continuation school, GEDs, acting degrees, and whether you need a master's in taxation to sit for the USTCP exam. (You don't.)

The episode ends on the first official well, actually of the series, courtesy of a five-hour research spiral in a rented house in the desert: an IRS publication is not primary authority. It has never been primary authority. It can also, it turns out, simply be wrong.

Interested in the USTCP Exam? Check out www.taxcourtexam.com