Capital Gain Strategies

One of the IRS’ favorite ways to entertain itself is to release new and important guidance at 5 pm on a Friday. They self-award bonus points if it is the Friday before a holiday. They hit “publish” and immediately shut down the office before anyone can react. When it comes to digital asset guidance, I speculate they also have access to my vacation calendar to release it at the most inconvenient time possible. Last summer, they released the temporary regulations on 1099 crypto reporting while I was on vacation in South Africa. This year, at 4:45 pm on the Friday before the 4th of July, they released the final regulations. I then had to spend the rest of the summer dodging my editors at TOTTB because this article was really harshing on my vacation plans.

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...

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.

The inherent optimism of entrepreneurs makes thinking about things that mitigate the effect of failure not that unpleasant. In a career in accounting, you are likely to see many deals that don’t work out, so it’s best to remember anything that will lessen the pain. Section 1244 is such a provision. Section 1244 allows what would otherwise be a capital loss to be treated as ordinary. Its significance has been somewhat diminished, but every little bit helps.

The price of a forever stamp increased from $0.58 to $0.63 on January 1, 2023. A tax pro posted this fact as a public service announcement on Facebook. Of course, tax pros being tax pros, someone chimed in, “Do I have to recognize a capital gain upon disposition of my forever stamp?” And of course, someone (me) felt obliged to answer, “It depends.” A direct message followed this bit of tax drollery on Twitter that says, “In theory, if I’m holding stamps as an investment, they would be a capital asset.” And so it begins…

When an individual sells a stock for a loss, it is a capital loss, and Congress makes it difficult for individuals to use their capital losses. The tax law only allows capital losses to the extent of capital gains. If capital losses exceed capital gains, the individual can only use up to $3,000 per year against ordinary income ($1,500 if married filing separately). However, there is a way around this rule: Losses on Section 1244 stock are ordinary losses, and claiming this valuable tax benefit allows an individual to save thousands of dollars in tax in the year of sale compared to the standard capital loss treatment. Let’s review what qualifies as Section 1244 stock, what benefits a taxpayer can get from Section 1244 stock, and how to claim those benefits on a tax return.

Practically overnight, cryptocurrency has gone mainstream, with more and more investors funneling money into Bitcoin, Dogecoin, and other cryptocurrencies. The IRS has responded with increased interest and scrutiny, demonstrated by the addition of the cryptocurrency question on the front page of 1040. Whether you have invested in cryptocurrency or not, you are required to answer this tax return question. Many investors choose to take the most conservative position to avoid future correspondence from the IRS but trying to avoid a letter is no reason to pay more tax than necessary. Keep reading to learn more!