All Articles - Think Outside the Tax Box


By Jeff Stimpson

How to Deal with Huge Tax Debt

The only thing scarier than owing Uncle Sam a lot in taxes is being unable to pay the bill. Luckily, the Internal Revenue Service has ways for you to whittle what you owe. Just make sure which method works for you, depending on such factors as the size of your tax debt and what you can afford to pay and when. Don’t panic. Here’s how individual taxpayers can proceed – and what to watch out for.


Client Retention Strategies for Accountants: Building Long-Term Relationships

Client acquisition is crucial for business growth in the fast-paced accounting world. However, retaining existing clients is equally important, if not more so. Servicing long-term client relationships is a testament to your firm’s reliability and is critical to sustained success. My first client is still with me, now more than seven years. Our relationship has grown and changed over time but has also strengthened. Loyalty and commitment are two of my core values. I’m always looking to provide value to my prospects and clients to attract and retain them long-term. However, some clients do not fit those values, and I have decided to forgo working with them. I believe that attracting and retaining the right clients starts with your mission, vision, and core values. However, it is also essential to have effective client retention strategies to ensure clients remain loyal and satisfied for the long haul.

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Health Savings Accounts vs Flexible Spending Accounts

With the rising cost of healthcare, our clients are looking to save money where they can, especially if they can save money on their healthcare costs and taxes at the same time. As their trusted advisor, you can offer them a basic understanding of what savings tools are available to your clients. Some of the tools available will come in handy if there is a minor unexpected tax bill this spring. That is why today we’re going to look at the triple tax advantaged health savings account (HSA) and the health flexible spending account (FSA). We’ll look at what they are, who is eligible to open one, and how they can save your clients money each year.

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Sometimes it is Clear There are Lessons, But Not Clear What They Are

A recent opinion in the ongoing litigation in the case of Clair R. Couturier makes a really important point about the distinction between a penalty and a tax. We will get to that, but I would also like to discuss the larger story of the case as I struggle with what the lesson is. I thought this case might be a good illustration of Reilly’s Second Law of Tax Planning – Sometimes it’s better to just pay the taxes – but I’m not 100 percent sure, so I will let you be the judge.

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Tax Court concludes tax season this year with a webinar on Practical Perspectives on Discovery, chaired by Judge Greaves, on April 16, 11:00 a.m. Eastern. With all the discovery jousting accompanying conservation easements and other high-dollar litigation, this is a must for all practitioners, so I'm headlining it. Information and registration on the Tax Court website.

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Tax Considerations of Turning Your Hobby Into a Business

For many, owning a small business is the American dream. However, the tax situation incurred by turning your hobby into that business can be a real American headache. Still, who can resist the allure of a job that’s loved and makes the hours fly? You don’t have to resist it. Just be sure of what you’re getting into with Uncle Sam.

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How to Differentiate Yourself as an Accountant

In a highly competitive business landscape, even we accountants face the challenge of setting ourselves apart from our peers. The accounting profession has changed significantly in recent years, with technological advancements, changing regulations, and shifting client expectations. To thrive in this environment, as accountants, we must possess strong technical skills and differentiate ourselves by offering unique value to our clients. The hardest part of establishing our unique value is objectively looking at our accounting journey and pinpointing our most significant achievements.

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A ChatGPT Plus User’s Guide to Effortlessly Creating Custom GPT Apps with GPT Builder

In an astonishing breakthrough that’s flipping the tax world on its head, certified tax planners now have the power to craft their very own AI-powered tax genie, thanks to the revolutionary GPT Builder. Gone are the days of sifting through stacks of tax codes and legislation. With a few clicks and a sprinkle of AI magic, these financial wizards are conjuring up custom tax strategies that promise to save fortunes. Dive into the future of tax planning where technology meets savvy to create the ultimate tax-saving ally. This isn’t just a game changer; it’s a wealth transformation phenomenon!

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An S Corporation Basis Decision That You Need to Know About

The Estate of Thomas H. Fry v. Commissioner is an opinion that anybody who deals with S corporations needs to know about. You may have read about it as a taxpayer win and it is. Another reading is that it is a cautionary tale to not do what Thomas H. Fry and his team did with his S corporations, Crown Disposal Inc (CD) and CR Maintenance Services Inc (CRM). Think of the win part of this opinion as a life jacket that might come in handy if you run your ship into the rocks. Better you should pay attention to the rocks and avoid them.

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