Business Strategies Archives - Think Outside the Tax Box

Business Strategies

By Jason Dinesen, CPA

The Tips Deduction and the Self-Employed: Potholes Everywhere

By now, tax professionals and taxpayers are familiar with the fact that the One Big Beautiful Bill (OBBBA) created a new tax deduction for tips received. What we want to look at in this article is — how do self-employed taxpayers handle this deduction?

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The Succession Plan You Keep Meaning to Write

I have a friend who has been retiring “in about two years” for the last five years. He is 67, runs a successful practice with about 400 returns, and specializes in tax planning. He has never had the practice valued. He also has no succession plan in the event he does not come back from his next fishing trip. This is not unusual. This is typical. The 2020 American Institute of Certified Public Accountants (AICPA) firm succession survey found that only 6% of solo and sole practitioners had a practice continuation agreement in place. Nearly half of those surveyed said they knew they needed one and had no idea how to start. That second figure is the one that gets me, because it is not denial. Our colleagues know exactly what is at stake and are stuck. Let us get unstuck.

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Games Industry Lore 101: Basics Tax Practitioners Should Know

When building your book of business, especially small business clients that do the heavy lifting due to their recurring complex tax filings, you might ponder seeking out clients in the video games industry. Salivating at the prospect of capturing just a tiny sliver of that nearly half-trillion market valuation as your social media feeds flood with news and memes from a random indie game you’ve never heard of, you wonder how to attract and retain game developer clients. But there’s several things that tax practitioners should know about how the games industry works, and its innumerable oddities, before diving head-first into taking on game developers as business or individual clients. Ready to press play?

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The NIL Tax Playbook

Regardless of where you stand on the issue, student athletes have been able to tap into a new revenue stream since July 1st, 2021. This is when the National Collegiate Athletic Association (NCAA) began to allow students to profit from their name, image, and likeness (NIL). Which leads to new tax implications for a group of taxpayers who may have never filed a tax return before. As this has unfolded, it reminded me of taxpayers who were on the forefront of making money online. It was something new, so not many taxpayers or even tax practitioners knew how to handle it. It was real money, but was it really a business? I’ve loved seeing it evolve. Now, right off the back of COVID-19, we have student athletes who are able to take advantage of their online presence and also make money. But the income people were making 20 years ago online is pennies compared to what some students can make through NIL deals. In 6 short years, students have gone from not being able to profit monetarily from their likeness while competing as a student to now potentially making millions.

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D&A Planning After the One Big Beautiful Bill Act

After 2021, whether an expenditure was deducted currently or recovered through depreciation often affected timing, but it typically did not create a meaningful advantage from a Section 163(j) perspective. The restoration of depreciation, amortization, and depletion addbacks in the computation of adjusted taxable income (“ATI”) has changed that analysis and created a new opportunity for taxpayers with actual or anticipated interest limitation exposure. As a result, taxpayers should reconsider whether certain expenditures that historically may have been deducted immediately can instead be capitalized into depreciable or amortizable property in order to improve their Section 163(j) profile.

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Tax Research in an AI World

It has never been harder to do quality tax research than at any time in my 43-year career in tax accounting. In the 1980s, when I was part-time in the industry, there was no internet. Since I was part-time, I ordered Publications 1132, 17, and 334. The rest I found at the library. A few hearty souls might even remember when the post office had stacks of tax forms for the public. Once I went full-time for the 1989 tax season I needed more resources. CCH was my tool of choice. I still used IRS publications and the library. My handy reference guide of choice was, and still is, the QuickFinder. I never used TaxBook much, but it is another good resource for general answers. Then came the internet. The promise was that we would have the world at our fingertips. And for the large part we did, only we forgot some things we would rather keep at an arm’s length. The internet slowly allowed us to replace rooms in our office filled with tax guides and forms with online resources. Law offices and accounting firms often wrote tax articles on narrow tax subjects. Research was easier than ever. Then came AI.

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Why Citizenship, Residency, and Domicile Matter

If you spend any time in the world of cross-border taxes, you start to notice a pattern: the hardest problems usually begin with a deceptively simple question—who gets to tax you? And the answer is rarely as simple as “the country where I live.” That’s because tax systems don’t rely on just one concept to decide who belongs in their net. They use citizenship, residency, and domicile. These terms sound similar, and people often use them interchangeably in casual conversation, but in tax law they mean very different things. For globally mobile individuals, understanding the difference matters. You can be a U.S. citizen, a tax resident of another country, and still have your long-term home base tied to a different jurisdiction altogether. Each label can trigger different tax consequences, different filing obligations, and different planning opportunities.

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Client Alert

Sophisticated EMR Software Meets Old-School Skimming: Lessons From The Aryanpure Case

The simplest way to reduce your taxable income from an S corporation is to take some of the gross receipts directly into your personal account without running them through the corporate books. Don’t mention this to your tax preparer and make sure they don’t find out. If you get caught by the IRS, though, hire an expert to explain why it is your preparer’s fault. This plan did not work all that well for a couple, both physicians, who were running two medical family medical clinics through an S Corporation called MedExpress. They ended up being liable for the fraud penalty which has the collateral effect of extending the statute of limitations indefinitely. At 75% the fraud penalty is as bad as it can get without losing your liberty.

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The Follow-Up Framework: How Accountants Can Close More Deals with Less Pressure

Follow-up isn’t nagging. Follow-up is leadership. It’s how we stay relevant, reduce decision friction, and serve prospects who genuinely need help but are overwhelmed, distracted, or uncertain. And if we’re honest, it’s also where a lot of revenue is quietly lost—not because people say “no,” but because they drift. There’s an old saying: the riches are in the follow-up. In public accounting, that’s not hype. It’s math.

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