All Articles - Think Outside the Tax Box

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By Matt Metras, EA

Lessons Learned from the Tax Court: The Root of the Issue

When is a business really a business? As Supreme Court Justice Potter Stewart said in 1964, “I know it when I see it.” The US Tax Court, however, maintains a slightly less subjective standard. The Roots were pretty sure they were running a bona fide business; the IRS, however, didn’t share the sentiment. And since we’re reading about them in a segment called “Lessons Learned,” one should assume it did not go the way the Roots would have liked.

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What You Need to Know About the Proposed Trump Savings Accounts

Tucked inside the narrowly passed “One Big Beautiful Bill Act,” President Trump’s sweeping tax and spending package, is a provision that’s drawing media attention: the creation of a new tax-deferred investment account called a Trump Account. A proposed $1,000 “baby bonus” tied to the account only adds to the intrigue. While the reconciliation bill primarily focuses on extending the 2017 tax cuts and reshuffling federal spending priorities, this unexpected addition could offer new planning opportunities for taxpayers.

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Freelancer Deductions: What You Might Be Missing and What You Need to Remember

Even savvy freelancers often miss deductions that could significantly reduce tax liability. The IRS offers legitimate ways for freelancers to deduct business-related costs, but it’s not always obvious which expenses qualify and which ones cross the line into nondeductible territory. This confusion is made worse when we see some of the terrible advice from so-called “experts” on social media. In this article, we’ll explore the most commonly missed deductions for freelancers, highlight real-world examples, and review what tax professionals need to keep in mind when advising these clients.

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Client Alert

How to Help Your Clients Maximize College Financial Aid

College tuition continues to climb, and for many families, financial aid can make or break their ability to afford their child’s higher education dreams. What most don’t realize is that their tax return — filed long before students even begin applying for college — plays a major role in determining how much financial aid they’ll receive. This is where you come in. Tax professionals and financial planners are uniquely positioned to help clients qualify for more college financial aid. But only if you know what to look for.

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The Rise of Post-Cognitive Tax Accounting: Embracing a New Frontier in 2027 (or Sooner!)

The year is 2027, and the landscape of tax accounting has undergone a dramatic transformation. Artificial Intelligence (AI) has automated many traditional tasks once considered the bedrock of the profession. Yet, contrary to fears of widespread job losses among tax preparers, this technological revolution has ushered in a new era – Post-Cognitive Tax Accounting. This paradigm shift is redefining the role of tax professionals, opening opportunities to explore uncharted territories that leverage human intuition, creativity, and strategic insight.

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TAX COURT ROUNDUP – May 2025

Once again, Tax Court provides slices of life as well as hyper-technical drilldowns into convoluted legal conundrums. To any who say that tax law is dull, I refer them to the annals of 400 Second Street, NW, where anything goes.

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2025 Summer Education Series Event Calendar

We are thrilled to bring you the 2025 Summer Education Series, sponsored by Vistia! All summer long we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax. Each webinar will feature our usual blend of high-quality education and entertainment and include continuing education credits for those who qualify. All of this is included in your regular subscription! Continue reading to see what we have in store...

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2025 Spring Fling Webinar Event

As we prepared our 4th Annual Summer Education Series, our friends at Sandy Bay challenged us to go bigger and do even more live events than we originally planned. So, we did! We are proud to present Think Outside the Tax Box's first ever “Spring Fling” live webinar event. As a monthly or annual subscriber, this webinar is 100% exclusive, and free to you! Every webinar comes with free continuing education credits for those who qualify! Keep reading for more details...

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Just How “Hot” Should IRC Section 751 Be?

Tax rules are generally designed with a purpose in mind. Most rules serve to define the tax base and tax rates. Many others serve a behavioral purpose to encourage or discourage certain activities. The focus of this article stems from tax rules that are a combination of favoring certain activity such as generation of capital gains, and a limitation on such gains for certain taxpayers, such as the so-called “hot assets” rule for partners under IRC Section 751, Unrealized Receivables and Inventory Items. While Section 751 has been in the tax law for decades, a new application of it was raised by both the IRS and California FTB. This article summarizes Rawat, TC Memo 2023-14, rev’d, No. 23-1142 (DC Cir., 2024), and FTB Legal Ruling 2022-02, and offers observations on their relevance to tax research and practice.

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