Business Strategies Archives - Think Outside the Tax Box

Business Strategies

By Ted Stotzer

Turning Intellectual Property into Interest Deduction Capacity: Use of an IP Holdco After the OBBBA

Many taxpayers have lived with a frustrating mismatch since the Section 163(j) limitation tightened after 2021 – the business may generate plenty of cash, yet its interest deductions are limited because adjusted taxable income (“ATI”) is too low, e.g., due to capex. The 2025 restoration of depreciation and amortization addbacks makes ATI planning relevant again, especially for groups that own valuable intangible property (“IP”), and the choice of legal entity to house group IP may have very different tax consequences as discussed in this article.

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Do You Know U.S. Tax History?

In recognition of the 250th anniversary of the adoption of the Declaration of Independence on July 4, 1776, let’s review 250 years of tax history. Our nation’s tax systems have evolved over two and a half centuries as ways of doing business and living have changed. Also, expectations of services the public wants and needs from the government have grown, resulting in tax changes to generate increasing amounts of tax revenue. Along the way, lawmakers have considered principles of simplification, equity, fairness, economic growth and effective tax administration that have shaped our tax laws. This article offers questions and answers to cover a range of interesting aspects of our federal tax history.

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No Goods Or Services? Say It Explicitly: Tax Court’s Message In Martin v. Commissioner

Two recent Tax Court opinions , both about the same transaction, reinforce the importance of a contemporaneous written acknowledgement (CWA) to solidify charitable contributions. It is a good illustration of Reilly’s Fourth Law of Tax Planning – Execution isn’t everything, but it’s a lot.

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Perspectives on IRS Scrutiny of Captive Insurance Elections

The Internal Revenue Service has made no secret of its increased scrutiny of captive insurance arrangements, particularly those involving the small insurance company election. For taxpayers and their advisors, this has created understandable concern and, in some cases, hesitation about whether captive insurance remains a viable risk management and tax planning tool. Yet heightened scrutiny does not mean prohibition. The Internal Revenue Code continues to recognize captive insurance, Congress has refined it, and courts evaluate it based on well-established insurance principles. The real issue is not whether captives are allowed, but whether a specific taxpayer has a legitimate business need for insurance, has structured the arrangement properly, and has implemented it in a manner consistent with both tax law and insurance fundamentals. Understanding where scrutiny arises, how elections function, and what separates compliant captives from problematic ones is critical for CPAs advising closely held businesses today.

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Strict Substantiation: Why Being Right Without Proof Can Cost You Your Charitable Deduction

Reilly’s Sixteenth Law of Tax Planning – Being right without substantiation can be as bad as being wrong – is particularly apt when it comes to charitable contributions. The case law makes it clear that there is not much wiggle room in rules relating to substantiation and reporting of charitable contributions. We’ll dig into the rules here.

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Client Alert

The Growth-Minded Accountant: Rethinking Your Role in Client Success

At some point, accounting becomes more than compliance. It's years of watching businesses evolve, owners under pressure, and consequences unfold. We soon recognize the gap between what clients ask for and what they need. That quiet, steady understanding, grounded in experience, shapes the growth-minded accountant.

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A Court Just Bought Your Clients More Time on Clean Energy Tax Credits Here’s How to Use It

A federal district court just struck down an IRS rule that had been closing the door on a pretty compelling tax savings opportunity available to your clients today, the Section 48E Clean Electricity Investment Tax Credit. The ruling, handed down on June 6, 2026, reinstated a key pathway that allows investors to lock in credit eligibility for large-scale wind and solar projects a pathway the IRS had tried to eliminate just last year. The window is not wide open. July 4, 2026 is still the critical deadline, and the government will almost certainly appeal. But for advisors who act quickly, this ruling creates a genuine, time-sensitive planning opportunity. Here is what you need to understand, and what you should be doing right now.

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Client Alert

Your Summer Tax Practice Playbook: Three Moves to Make Before Labor Day

Tax Day is finally in the rearview mirror, and if you’re like many practitioners—with the phones quieter, the inbox manageable, and the September extension wave feeling comfortably far away—the temptation right now is to coast. Resist that temptation. Summer is the only stretch of the calendar when both you and your best clients have the bandwidth to think strategically; furthermore, this summer, there is a deadline-driven opportunity. In this article, I’ll walk through three moves every practitioner should be making between now and Labor Day. The first move has a hard statutory deadline of July 10, 2026. The second move is about turning your highest-value client conversations into billable advisory engagements. And third is about tending to the practice itself because a tax practice, like a garden, doesn’t survive without care.

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What Every Client Should Know About Partnership Distributions

Perhaps the most misunderstood aspect of partnership taxation relates to distributions. When a partnership distributes cash or property to its partners, the tax consequences can range from completely tax-free to significantly taxable, depending on how the distribution is structured and the partners' tax basis in their partnership interests. In this article, we'll explore the rules governing partnership distributions and how they impact partners' tax situations. More importantly, we'll look at strategies to structure distributions in the most tax-efficient manner possible – because the goal is not just to understand the rules but to use them advantageously.

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Client Alert
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