Guest Article Archives - Page 10 of 53 - Think Outside the Tax Box
By Timalyn Bowens, EA

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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IRS And Courts Have Wisdom to Offer Startup Businesses

There is a wealth of business wisdom in a fairly unlikely area. All the businesses involved lost money, sometimes enormous sums. The source is the litigation and regulation around Code Section 183 of the Internal Revenue Code – Activities not engaged in for profit. In order to deduct those losses against other income, taxpayers need to convince the IRS or the court that they had an honest objective of making a profit. The determination of whether an activity is carried on for profit is made by reference to objective standards. Is it possible that following those standards might contribute to you being profitable? It’s worth thinking about.

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TAX COURT ROUNDUP – October 2025

There are new insights and old unresolved questions in this month's instalment. There's always the old and new.

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You Don’t Need a Bigger Stack — You Need a Better Portfolio

In every tax Facebook group or conference session, there's always that one pro excitedly talking about the latest app they've added to their "tech stack." But here's the dirty little secret: most of us aren't running integrated tech stacks. We're juggling a mix of disconnected tools that may or may not play nicely together. Let's stop pretending we're all building perfectly integrated ecosystems. What we really need is a tech portfolio—a curated collection of tools that serve our actual needs, reflect how we really work, and support the kind of client experience we want to deliver. A portfolio recognizes reality: tools don’t have to talk to each other perfectly. They just need to work for you. So let’s explore how to build a smart, efficient, and secure tech portfolio that helps you thrive whether you’re a solo professional or managing a growing team.

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Tracking and Measuring Your Business Development Efforts: KPIs for CPAs

As CPAs, we were trained to work with precision, accuracy, and strategy in everything we do. However, business development has not been part of our standard training; therefore, many accounting professionals not only struggle with business development tactics but also shy away from tracking and measuring the impact of their efforts. But here's the truth: Just as we track and measure other financial data, it is essential to measure business development efforts in order to improve. You can unlock significant growth in your firm by understanding which key performance indicators (KPIs) to track, how you manage your practice, how you acquire new clients, and how to increase your revenue.

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Are There Tax Consequences of The GENIUS Act? It Depends!

The Guiding and Establishing National Innovation for U.S. Stablecoins Act became Law on July 18, 2025. It “establishes a regulatory framework for payment stablecoins,” which are defined in the legislation as “digital assets which an issuer must redeem for a fixed value.”

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Client Alert

Vibe Preparing: Ignoring Partnership Agreement Impacts on K1s

Nothing derails a busy season schedule like being forwarded emails from client’s investors asking “are you sure the loss is allocated correctly?” It can expose a weakness in technical expertise – especially when it’s a partnership K1. Whether the operating agreement includes Safe Harbor or Target Capital allocations is one of the most important places to start for a preparer. And knowing these basics can be the difference between a confident reply or a lost week.

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Deducting Gambling Losses: Part 2: Sessions Method

Recently I polled my peers on a social media platform dedicated to tax professionals. My hope was to find a resource for tax rules on a state level for handling gambling sessions. I knew it would be an uphill battle to get the information needed for a comprehensive guide state-by-state. What surprised me was the response. A large percentage of tax professionals were either unaware of gambling sessions or were unclear on how gambling sessions were handled in their state. Since gambling sessions might be the best way to reduce taxes on gambling wins, a lot of money might be left on the table with clients paying the price. Even if the state a tax professional prepares most tax returns for does not have gambling, the likelihood a client travels to a state that does, gambles, and wins is high.

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TAX COURT ROUNDUP – September 2025

If reviewing Tax Court opinions teaches one thing, it's that tax legislation is too important to leave to legislators. Tax Court Judges are hyper-qualified; they need to be, to deal with what this month shows.

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