Guest Article Archives - Page 31 of 46 - Think Outside the Tax Box

Guest Article

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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DeFi Games as a § 162 Activity

In our recent issue, we discussed the exponentially growing universe (or metaverse if you will) of DeFi or blockchain based gaming. In that article, I shared how dedicated players support their livelihood, especially in places with a low cost of living, by playing the games. In this issue we will explore the concept of a “Trade or Business” as defined by § 162, and how specifically how blockchain gaming meet this threshold. For a quick refresher of what constitutes a § 162 activity, see our article “Pros and Cons of Cryptocurrency Mining as a Trade or Business. Why become a trade or business? Meeting these requirements can make a difference between video games being treated as a hobby and becoming a tax benefit. Click here to keep reading.

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US V Harry Stonehill – America’s Jarndyce v Jarndyce

1962. It was the only year in which JFK was president for the whole entire year. World events impinged on my family. My older brother served onboard an aircraft carrier chasing Soviet submarines and when not recovering Mercury astronauts, had his four-year enlistment extended to five. Somehow the bright fourth grader that I was, I missed the story of the dramatic raid by the Philippines National Bureau of Investigation on March 3, 1962. According to reporter, Amando Doronila, who covered the raid, 200 agents seized 35 truckloads of documents from 27 offices and corporations controlled by American expatriate Harry Stonehill. Why should we care? Believe it or not, the implications of that March 3, 1962, raid are still being litigated in the United States. Read on to learn more!

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TAX PLANNING FOR CLERGY

“The hardest thing to understand in the world is the income tax” – Albert Einstein You may have spoken to clergy members about many things, but I’ll bet you never spoke with them about their tax issues. Did you ever wonder whether and how clergy are taxed and how they pay taxes? Clergy taxation has some surprising twists and turns. Are they employees or self-employed? Is their income taxable or exempt from income tax? Can they deduct their business expenses? If these were multiple-choice questions, you might need an “all of the above” option. Or, as is often the case with tax-related questions, an “it depends” option. Tax compliance pitfalls and tax planning opportunities abound. Read on for more.

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Tax Planning for DeFi Based Games

As cryptocurrency continues to become more popular, its reach into areas not normally associated with crypto has expanded dramatically. One of the largest areas of growth is the DeFi Gaming sector. DeFi games function like regular video games with one major difference: They are either built on or rely on a blockchain to record activity. This can allow in-game assets to be NFTs that can be bought, sold, or even used in different gaming platforms. While this is a highly desirable ability for the player, it also carries with it tax consequences that gamers have previously not had to consider. With careful planning however, these tax consequences can be mitigated. Continue reading to learn more!

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Enjoy Decades of Tax-Free Growth With a 529A

If you’re disabled or support someone who is, a 529A plan can be a powerful way to save for the future. Potential earnings grow tax-free, and you won’t have to pay taxes when you withdraw, as long as the withdrawals meet qualifications. Also known as Qualified ABLE (Achieving a Better Life Experience) programs, these will not only assist you next time you are playing Tax Code Jeopardy but help you create a tax advantaged savings account. One reason you may not hear much about these tax vehicles is that there really is no way I can discern that advisers can make money on them. But since you and I are members of the same club as tax practitioners, I’m confident you will tell your clients about things that can help regardless of whether there is any profit in it. As my first managing partner the late Herb Cohan used to say, “The world is longer than a day.” To learn more about future tax-free money, keep reading.

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Just Good Business – Review Your Insurance Policies

Regular readers of this column may know that I came involuntarily to the tax business. I inherited it from my mother in 2010. Less well known is that the tax business was Mom’s side hustle. Mom’s main business was as an independent insurance agent. The insurance side of the business closed in 2017, but during the time I was administering that side of the business (I was never a licensed agent), I learned a lot about insurance. One of the most important lessons I learned was that the longer you hold a policy, the more the rates increase and that it pays to make the effort to review (and shop) your various insurance policies regularly. Another important lesson was that all coverage is not equal and, just as when looking for a tax professional, price should be a consideration but not the consideration. The third important lesson was to know your coverage before you need the insurance. Many times we had to remind a customer they had refused uninsured motorist coverage to save a few dollars after an uninsured motorist totaled the client’s vehicle or to explain the limits of flood coverage after a building flooded. Regularly reviewing your insurance policies for coverage and value provides peace of mind and is just good business. Click here to learn the ins and outs of getting a great deal.

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Avoiding Underpayment of Estimated Tax Penalties – Non-Traditional Strategies for Individuals

Paying your income taxes is a fact of life for most taxpayers. The annual dance of gathering, reconciling, and reporting income/deductions/payments/credits (a.k.a. filing a tax return) keeps taxpayers and tax professionals hopping during each annual filing season and beyond. If you’re a W-2 employee, your employer takes care of your tax compliance by withholding and remitting federal, state, local, Social Security, and Medicare taxes from your salary. You may also have taxes withheld from pensions, unemployment compensation, gambling winnings, and other income. It may feel as if you’re not paying taxes because all you see is your net pay after taxes. Often it’s a direct deposit, and your payslips may be available only online. If you’re self-employed or have other income not subject to withholding, you prepay your taxes by making estimated tax payments. The traditional schedule for estimated tax payments is quarterly (4/15, 6/15, 9/15, 1/15). If not followed, steep penalties can exist, even if you pay them all by April 15. But some folks have trouble with the quarterly payment schedule, cash can be tight and that estimated tax payment money you’ve set aside might really come in handy. Happily, there are strategies to keep in compliance in a way that meets your budget and cash flow needs; and there are ways to avoid those late payment penalties. Want to know how? Keep reading to learn more.

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Pros and Cons of Cryptocurrency Mining as a Trade or Business

As cryptocurrency grows in popularity, more people are turning to what is known as mining as a way to bring in some extra income. However, not all mining activities are equal; small differences in the facts and circumstances can have substantial impact on the tax consequences. Much of the nuance hinges on whether the activity is a trade or business under Section 162, which, in many circumstances, may not be a simple thing to determine. If you choose to treat your mining as a business, earned bitcoin is reported on a Form 1040 Schedule C. The benefit of this is the ability to deduct mining expenses as deductions for your crypto business. Along with direct costs to mine the digital currency, treating the work as a business opens the door to additional tax reduction strategies. To learn how to maximize your crypto mining activity, keep reading.

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