Guest Article

A case currently before the Supreme Court, Charles Moore, G. Moore et ux. v. United States , has the court looking at some of the fundamentals of the Constitution’s treatment of taxation. Advocates of various views are hoping for an earthshaking result. Also, many “tax protester” arguments base themselves on misreading of Supreme Court decisions from around the time of the 16th Amendment. Knowing a fuller version of what surrounds the snippets they feed you probably won’t help you bring them around if they have drunk deep of the tax protester Kool-Aid, but it will help you maintain your own sanity. Let’s start with what the Moore case is about.

Time flies when you’re dealing with taxes. For instance, eight years must have seemed like an epoch when Washington passed the Tax Cuts and Jobs Act of 2017 (TCJA), the biggest federal tax reform in decades and one that altered tax brackets, deductions, and estate planning, to name just a few. Best of all, lawmakers probably thought back then, we won’t have to worry about some of these provisions changing until all the way off in 2026! Except suddenly, we now have less than 26 months to get ready for the end of nearly two dozen TCJA provisions that will happen without action from Congress. That’s barely enough time for some of the planning before what could be one of the biggest groundswell tax years of recent memory.

When I started my business, referrals and testimonials were not on my mind. Like most entrepreneurs, my crucial motivator was to have freedom of time for my family, to expand my skill set, and to remove the cap on my earnings potential. When I got my first client as a side hustle, my referral source was a board member who knew my skills very well and recommended me to the non-profit he served as treasurer. In December 2018, a prospect asked me for referrals, and I had no idea what to say. There was only a little besides my resume and employer as a reference. Then I thought, hey, I have my non-profit client, and I asked my client whether they would speak with this prospect and answer any questions they had, and they agreed. That’s when I realized the power of referrals and testimonials.

Considering how soon Halloween comes after October 15, the extended due date for individual returns, having a tax horror story seems really appropriate. The horror story came out on October 24, with the Eleventh Circuit decision in the case of Lee v U.S. Dr. Wayne Lee seemed to have done everything right to be in compliance. His estimates overpaid his taxes every year, and he would let the refund ride into the next year. He hired a CPA to prepare his returns and dutifully signed and sent the CPA Form 8879 IRS e-file Signature Authorization. He did this for his 2014, 2015, 2016, and 2017 returns. Then disaster struck.

Regulatory tsunamis come in batches. By now, for example, most of you have heard about the tax-reporting requirement slated to kick in next year, where the IRS would've learned about the income of individual taxpayers who made just $600 on the likes of eBay. That sounded like a looming nightmare -- until the IRS suddenly put it off a year two days before Thanksgiving. (Sometimes removing tax regulations without warning creates as much confusion as adding them.) Small businesses aren’t off the regulatory hook that easily for 2024. Come January 1, a new ownership-reporting requirement begins for millions of American companies. Now’s the time to prepare yourself and your company.

Joseph Michael Balint had some really hard luck. He was in prison in Florida from December 17, 2013, through January 6, 2015. Fearful of forfeiting assets, he transferred everything to his wife, Jacqueline, and gave her power of attorney early in his prison term. What he had not planned on was her emptying the retirement accounts and leaving him with the tax tab. His luck turned a bit in Tax Court, as we shall see.

Coming up on the end of the year, year end planning is kind of a ritual for me. I take my first pass in early November and will do it again no later than December. It is pretty boring. I thought it would be worthwhile to do a survey of a variety of year end tips articles. What is going on here is something like Ahab’s hunt for the great white whale. I am looking for something to help out HENRY. HENRY stands for High Earnings Not Rich Yet. I wrote about the quest in 2019. I found nothing much for HENRY then, and this year’s batch of advice articles really does not offer much. The articles do not all say exactly the same thing, but there is a lot of commonality. Due to the sophisticated nature of the readership of TOTTB, I will just allude to the tips, not explain them in detail, because I am going someplace else with this. There is nothing dramatic for HENRY coming from conventional advisers, which accounts for HENRY’s vulnerability to sketchy tax shelters. I will share a bit about what I have seen in that department and reflect a bit.

The federal government is there to reduce taxpayer confusion. That, at least, was one point of the reasoning for the recent IRS decision to again postpone a $600 tax-reporting threshold for people paid via third-party settlement networks. Those who made that amount on the likes of eBay and other online sales sites and who received payment via such platforms as PayPal and Venmo will not have that money reported to the IRS for another year. Does this really let taxpayers off the hook? What strategies should you adapt for when the IRS does mandate this reporting?