Guest Article Archives - Page 11 of 50 - Think Outside the Tax Box
By Peter J Reilly CPA

When Debts Go Bad: The Challenges of Deducting Delinquent Debts

It is painful when you finally realize that the money you expected to be repaid is never coming back. The tiny silver lining in that cloud might be the tax benefit of “writing off” the debt. Unfortunately, that silver lining may well be eclipsed by an even bigger cloud. Writing bad debt off is not that easy, and there’s probably no silver lining to that cloud. Ironically, you might find that the mistakes that caused you to be holding a bad debt might be what prevents you from getting a usable deduction.

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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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1099 K(ickstarter): Crowdfunding and Taxes

Astronomical expenses crop up more than ever in our economy. From medical bills, business startups, a long-cherished artistic project, it feels like things are harder to afford now than ever. But the internet has also helped create a revolutionary way to raise large amounts of money for some of these causes: crowdfunding. But what does that mean for when the Tax Man comes calling?

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Client Alert

Dave Ramsey And His Critics

Somehow I got through the last thirty years without ever hearing of Dave Ramsey. Now when I go on YouTube, which I do way too often, there is usually a Dave Ramsey video or a video by one of his critics in my feed, sometimes several. I have also looked at a few of his books. I was once told that because I am an Aquarian I want everybody to get along. So I am going to try to reconcile Ramsey’s recommendations and the significant criticism of them.

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Effective Sales Strategies for CPAs: Converting Prospects into Clients

As a Certified Public Accountant (CPA), you possess the technical knowledge and expertise to assist businesses and individuals with their financial needs. However, in today's competitive marketplace, more than possessing technical skills is needed to grow your client base. To succeed, CPAs must also master effective sales strategies to convert prospects into paying clients. In this article, I will explore critical techniques I had to learn to enhance my sales efforts and achieve my business goals, and I hope they help you reach yours!

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IRS and DOJ Enforcement Against Tax Professionals: Trends, Cases, and Lessons

In recent years, the IRS Criminal Investigation (CI) division and the Department of Justice (DOJ) have aggressively pursued tax professionals involved in fraud or other tax-related crimes. Certified tax planners, preparers, accountants, and attorneys who engage in misconduct are facing serious legal consequences. This article reviews notable prosecutions from roughly the past five years, highlighting enforcement trends and the types of fraud authorities have targeted. We then distill 10 key lessons from these cases – each supported by real-world examples and case citations – demonstrating how broad enforcement has impacted tax professionals. Finally, we conclude with a comprehensive list of dos and don'ts to help tax practitioners stay on the right side of the law and avoid the pitfalls that landed others in trouble.

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How to Overcome the Fear of Delivering Bad News to Clients

We’ve all been there. Breaking bad news is one of the hardest parts of being a tax professional. But avoiding these conversations only makes things worse. The good news? There are ways to make this process easier. With the right approach, you can turn these tough conversations into opportunities to build trust, strengthen your reputation, and reinforce your expertise.

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Selling a Piece of Real Estate? You Don’t Have to Pay Taxes, Even if You Don’t Use Section 1031

Overpaying on taxes puts a damper on anyone’s mood. You should be paying precisely what you owe—no less, and no more. When it comes to selling your real estate, you really don’t have to pay taxes on that sale right away. One way to avoid the taxes is by using a Section 1031 exchange, but you actually have other options. This article will show you how to take advantage of them.

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Client Alert
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