Feature Article

In Matt Metras’ excellent article on tax reporting for clients who receive settlements from the Celsius bankruptcy, he says “It’s unclear if this section could apply to digital asset bankruptcies for a variety of reasons outside the scope of this article.” Matt provides an example of the IRS’ preferred method of accounting for settlement proceeds as published on the Taxpayer Advocate’s website. Matt also notes that the TAS tax tip lacks any citations to substantial authority. It may or may not be taxpayer friendly. The articles published by many cryptocurrency exchanges are also citation free and, after a cursory review, seem geared in a larger sense toward helping exchange users account for the settlement accurately on the exchange itself. In this article, I would like to look at the forest of tax law principles that the Celsius bankruptcy settlement puts into play rather than any specific tax reporting tree. Welcome to the jungle.

Why is the freezing point of water 32 degrees? It was a fairly arbitrary decision made by inventor Daniel Gabriel Fahrenheit in 1724 and demonstrates that Americans will do just about anything to avoid using the metric system. But this isn’t a story about Fahrenheit, it’s about Celsius. Celsius was a major cryptocurrency exchange founded in 2017, which at its peak had over $12 billion in assets under management. Celsius declared Chapter 11 bankruptcy on July 13, 2022. Celsius found itself caught up in the major crypto collapse of 2022...

Creativity on a tax return is a natural tendency. Many strategies and behaviors we know are wrong, e.g. not reporting all income. However, is it ever okay to disregard some deductions and pay more tax? At first glance, it would seem that the IRS should like the idea of more reported income and a higher tax liability attached to the additional income. The IRS does not.

Misinformation, misinterpretations, and catastrophizing – much has been written these past few months about BOI (Beneficial Ownership Information), all coming from a range of voices, from tax professionals to politicians. There have been dire predictions of small business owners being ushered to jail for failing to file and fears of tax professionals rounded up for the unauthorized practice of law (UPL). Then there are those who mistakenly say BOI has been ruled unconstitutional and who reject any need to worry about it. That is profoundly wrong. Let’s look at the facts and put an end to all of this fearmongering.

A really neat thing happens when you turn 70 and ½. Your IRAs essentially turn into donor advised funds if you don’t need all the money in them to make ends meet. Rather than withdraw money from your IRA to make charitable contributions, you can make them out of the IRA. So instead of an itemized deduction, you get an exclusion from adjusted gross income. For some people this might be a wash, but for most it probably isn’t. Besides the possibility of not being over the standard deduction threshold, there are a host of computations and thresholds that involve AGI. There are some things you need to watch out for, but first let’s go over the basics.

The concept of cost segregation began in the 1960s, when taxpayers argued specific components of real estate had a shorter life than the depreciation tables allowed (39 years for commercial property and 27.5 years for residential real estate). After decades of legal cases, the IRS provided rules and safe harbors in 1996 and 2002. Taxpayers now can use cost segregation and remain compliant with IRS regulations. The real question now is: Does a cost segregation study really reduce a taxpayer’s liability? And if so, by how much?

In the labyrinth of tax planning and business structure, the path to protecting your client’s multiple business strategy from the ever-watchful eye of the IRS can be as intricate as a well-played game of chess. However, while the strategic moves might be complex, the rules of the game are quite clear. Today, let’s dissect these rules with a blend of cautionary tales and cheeky wisdom, ensuring your business maneuvers stay sharp and IRS-compliant. Ever heard of the tax strategy to just “create a new C corporation” and shift income by paying management fees from your main company? Well, so has the IRS, and they are highly skeptical when they see it in the field. The Aspro, Inc. v. Commissioner case serves as a stark reminder for taxpayers about the importance of meticulous documentation and the strict adherence to IRS guidelines for deducting management fees. Aspro, an Iowa-based C corporation in the asphalt-paving business, faced scrutiny over its practice of paying "management fees" to its shareholders, which the IRS and subsequent court rulings reclassified as non-deductible disguised dividends.

The IRS has spent the past several months crowing about the relative ease of filing season 2023 and improvements the service has made on behalf of American taxpayers. Filing season 2024 opened on Monday, January 29 with Commissioner Danny Werfel thanking the tax professional and assuring us that “your efforts make a difference, not just for your clients, but for the IRS and the entire nation.” Despite Werfel’s rose-colored press releases, there’s still plenty of room for improvement, especially on the tax-professional-facing side of the service.