When a loan goes unpaid, the lender may be able to deduct it, but only after answering several questions first. In the first of two episodes on bad debts, Jeremy follows a $75,000 loan to a family member’s struggling business. He explains how to tell real debt from a gift or equity, when a debt becomes worthless, and why the lender’s own trade or business, not the borrower’s, decides whether the loss is ordinary or a short-term capital loss. He also covers shareholder and employee loans, loans to a single-member LLC, and payments under a loan guarantee.

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Your client paid his entire tax bill by January 15th, so why does his return still show an underpayment penalty? Jeremy explains why the estimated tax penalty works as a timing rule that tests each installment separately, and he walks through the safe harbors, Form 2210, and why withholding gets better treatment than estimated payments. He also covers ways to shrink the penalty, like annualizing uneven income or running more S corporation wages through withholding, and why getting it waived is nearly impossible.

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Clients increasingly show up with tax positions backed by blog posts, podcasts, social media, and AI, but how much of that actually counts? Jeremy walks through the closed list of sources the regulations recognize as authority, from the Code and Treasury regulations to court cases and revenue rulings, and explains why IRS publications, form instructions, and even other tax professionals’ opinions don’t make the cut. He also covers how to weigh supporting and contrary authorities against each other, and why that matters for the Section 6662 substantial understatement penalty.

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Jeremy unpacks the "no tax on overtime" deduction created by the One Big Beautiful Bill Act, explaining why the name is misleading since qualified overtime compensation is still taxable income subject to withholding, FICA, and (in most states) state tax. He walks through how to isolate the FLSA overtime premium from gross overtime pay, calculate the deduction on the new Schedule 1A, and apply the filing status caps and MAGI phaseouts through real client examples. He also flags the reporting changes coming in 2026, when employers must correctly report the amounts on Form W-2, Box 12, Code TT, and the relaxed 2025 transition rules disappear.

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In part two of his series on protecting taxpayer information, Jeremy shifts from who can see client data to how firms actually have to secure it. He walks through the Gramm-Leach-Bliley Act, the FTC Safeguards Rule, and what a written information security plan needs to cover, then explains how SOC 2 reports help firms vet software vendors. He closes with the IRS Office of Professional Responsibility's new AI guidance under Circular 230, and what it means to treat AI like a junior staff member rather than an unsupervised practitioner.

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Jeremy opens a two-part series on taxpayer confidentiality by breaking down IRC Sections 7216 and 6713, the rules that govern how tax professionals can use and disclose tax return information. Using a case study of a solo firm owner weighing seasonal hires, an outsourced bookkeeper, and a possible merger, he walks through what actually counts as tax return information, when taxpayer consent is required, and the exceptions that let firms share data without it. He also covers what a tax return preparer and auxiliary service actually mean under the regulations, since those definitions decide whether consent is even needed in the first place.

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Jeremy closes out his partnership series by tackling outside basis, how partnership liabilities affect that basis, and what happens when a partner exits. Using a case study of two LLC members with mounting losses, he walks through abandonment, a buyout by the remaining partner, a partnership redemption, and a sale to a third party, comparing the tax results of each. He also covers Section 751 hot assets and why unrealized receivables and appreciated inventory can turn part of a capital gain into ordinary income.

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