Capital Gain Strategies

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!

Many tax professionals cringe at the thought of a client coming to them with cryptocurrency transactions. However, a May 2021 NASDAQ survey shows that 17 percent of American adults own crypto, making it harder for tax pros to avoid. It may soon be inevitable that practitioners will need to process cryptocurrency transactions. IRS Circular 230 requires practitioners to “possess the necessary competence” and to “exercise due diligence” in the return they prepare. Failure to meet these provisions could result in the taxpayer unnecessarily overpaying tax. What exactly does that require? Read on to find out!

The headlines have said it all. “Biden Wants up to 43 percent of Your Retirement Gains!” or “Americans Can’t Afford Biden Inflation Tax!” Also recently seen, “Biden Doubles Capital Gains Rate,” and “Biden Tax Rule Would Rip Billions From Big Fortunes at Death!” The hysteria presented in the media as we anxiously await proposed changes in tax law through the pending budget proposal has many investors debating whether or not to lock in low capital gains before anticipated tax hikes. Wealthy investors like Jeff Bezos and Warren Buffet have reportedly been selling large numbers of stock market shares rumored as a response to news of an impending capital gains tax increase, many people are left wondering what moves, if any, should they take now to avoid higher taxes. Given that we know to anticipate higher taxes, here’s what you should do now to lock in taxes while they are on sale.