Individual Strategies Archives - Page 4 of 20 - Think Outside the Tax Box

Individual Strategies

By Sean King, JD, CPA, MAcc

Kadau v. Commissioner and the Line Between Effective and Broken Captives

Captive insurance remains one of the most closely examined tax planning strategies in use today, not because it is inherently flawed, but because small missteps can carry outsized consequences. Many taxpayers assume that careful formation and proper documentation are enough to protect the intended tax outcome. A recent Tax Court decision, Kadau v. Commissioner, serves as a reminder that those assumptions deserve closer scrutiny. The court’s analysis did not hinge on whether captive insurance can work, but on how a specific arrangement actually functioned in practice. For tax professionals advising clients who rely on micro-captives, the case raises important questions about where structures tend to break down, why some arrangements attract IRS attention while others do not, and what really separates a defensible captive from one that invites challenge.

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A Compendium Of Year End Tax Tips

As summer turns to fall, the leaves turn and houses start being decorated, the air becomes crisper and the internet fills with year-end tax tip pieces. I call them tip sheets. I just love reading tip sheets, but I’m retired from active practice. Somebody who doesn’t have time on their hands might look at two or three and figure they have seen it all and didn’t learn anything they didn’t know already. I’m here to tell you that if you keep hunting, you might find some gems. But better than that, I will share what I have found in the event you don’t have the time or inclination to look at another twenty or thirty tip sheets.

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Advising Clients About Prenups

To have and to hold and happily ever after is a nice dream, but into every married life a little reality about money must fall. Enter the prenuptial agreement, aka the prenup. This contract between prospective spouses clarifies the rights and obligations of the parties during their marriage – and during the sometimes-ugly aftermath should they separate, divorce, annul the marriage, or die. Prenups can help couples set financial expectations for the marriage, including whether they’ll have a joint bank account and file taxes together, among many other matters. Given the sensitive nature of these conversations, it’s important to know how to advise on such an important document. What do your clients need to know?

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Dodging the IRS Penalty Flag: Avoiding the Accuracy-Related Penalty

A penalty specifically for taxpayers who have made a mistake on their return. That's how I explain the accuracy related penalty to taxpayers. This penalty carries a punch as well, with 20% of the tax the IRS didn't receive due to the taxpayer making a mistake. This seems harsh out of context. The reason for this harshness is because the IRS considers these "mistakes" to be intentional due to taxpayer negligence. This is one of the reasons at my firm that we encourage our clients to take their time when filling out the intake form and gathering their documents. Omitting an income document can be costly in the end to both you and your client. The IRS will hit your client with penalties that they could have avoided, and you may compromise the integrity of your firm.

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Talking Taxes and Money With New Graduates

Clients who recently graduated college brim with enthusiasm for adult life. If they’re like most other adults, they’re less enthusiastic about tax strategies and probably don’t know much about grown ups’ taxes. Some might not even know filing deadlines and may never have filed a 1040. Withholding, deductions and dependency, saving for retirement and lowering taxable income: It’s always difficult to realize all that others don’t know about taxes, and here’s how to continue these young clients’ education.

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Navigating IRS Penalty Relief and Forgiveness

Yes, the IRS does forgive some tax penalties. The IRS refers to this forgiveness as penalty abatement. Abatement is the act or process of reducing or removing something. In this case it is removing or reducing a penalty. But penalty forgiveness is not a blanket offer that everyone qualifies for the way the radio ads make it seem. There is a process that the IRS has for requesting and granting abatement. It is up to the taxpayer to prove that they qualify for abatement. That’s where you come in.

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Don’t Let the IRS Put Your Client in The Penalty Box

There’s only one thing worse than your client overpaying their taxes when you could have helped them – them not paying enough in taxes and having to deal with penalties as well. It's like adding insult to injury. There is only so much that we can do to help our clients avoid penalties. Educating ourselves, so we can educate our clients, is a big part of that. Penalties are inevitable, but that doesn't mean that the client must max out their penalties. But it also doesn't mean that we should not do our due diligence to avoid penalties where possible.

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Gone Phishing: Don’t Get Scammers Catch You!

Today’s criminals are using more than hooks and lines (more like huge trawling nets), and they are looking for small as well as really big fish. If you think your tax practice is too small to be a target, you’re wrong. And you probably know that. You are probably well aware of the phishing and smishing (using SMS/text messaging) attempts that try to gain access to your firm’s computers and/or computer network.

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How to Fight Tax-Related ID Theft

Every tax season brings out the crooks and scammers trying to steal money and sensitive information using tax-related schemes, and even though we’re still a few months out from the beginning of filing season, it’s important to always be aware of threats out there and how you can combat them. Tax authorities like the IRS have countered these scams with electronic defenses that offer protection for both clients and tax preparers. Here’s a look at a few.

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