Business Strategies

“Two men showed up saying they were from the IRS because I hadn’t paid my taxes. It scared me to death. Am I going to jail? Can they do that? I’m scared.” That is what the taxpayer blurted out as soon as I answered my business phone. Now before you say, “Timalyn, no way!” Yes, way! This was February 2020 when the world was still open, and the IRS was wide awake. Revenue officers were still on the phone making calls and showing up to businesses. Since the pandemic, many taxpayers, business owners included, have become lax in taking care of their tax obligations. This is due not only to many small and micro businesses still struggling financially, but also because the IRS has not been as aggressive the past few years. Business owners with employees are in a far more dangerous position if they have not kept up with their taxes. That’s why we’re going to look at one of the worst types of taxes to get behind on, payroll taxes. One of my mentors even refers to them as the “kiss of death” to business owners. The penalties for not paying payroll taxes can bury and put the nail in the coffin of most small businesses. Let me show you how these taxes can be the grim reaper. Let’s start from the top with what payroll taxes are and how the payroll tax penalties work.

Question: I’ve heard other planners talk about using an accountable plan to reduce tax, but how exactly does this save a taxpayer money? Answer: An accountable plan is a type of reimbursement arrangement between an employer and employee that meets certain IRS criteria. It often covers business expenses that an employee incurs while performing their job, such as travel costs, home office expenses, or supplies. The way this plan helps save money on taxes is through the appropriate treatment of reimbursements or allowances under the tax law. Did you know that reimbursements for out-of-pocket expenses are taxable income? Normally, reimbursements for expenses are income, and the employee needs to pay income tax on them. However, if the expenses meet the criteria of an accountable plan, they’re excludable from the employee’s income. This means the employee does not have to pay income tax, Social Security, Medicare, or unemployment taxes on these funds. What about the case of partners in partnerships and shareholders in S-corporations? These individuals often face out-of-pocket expenses that the respective partnership or S-corporation doesn’t reimburse. Is there a way for these individuals to reap tax benefits for these expenditures too? There used to be. Under pre-TCJA rules, employees and owners of partnerships and S-corporations could deduct ordinary and necessary expenses, which were unreimbursed from the business as a Miscellaneous Itemized Deduction subject to the 2 percent floor. To learn how to make sure your S-corporation and partnership out-of-pocket expenses are deductible, and reimbursements are not taxable to the owners, click here to read on.

Section 183, which limits or entirely eliminates deductions attributable to activities not entered into for profit, may be coming in for more attention from an invigorated IRS. Section 183 is commonly referred to, not without reason, as the hobby loss rule. Based on my extensive study of the case law, I believe that practitioners widely misunderstand 183. I have noted cases where taxpayers had not gotten a heads up from their adviser. More commonly there is a misunderstanding of 183(d), a presumption in favor of taxpayers that is rarely relevant at all, but which the agency can never use against them. Most important is the failure to appreciate that it is the objective of making a profit not the expectation that is necessary. With that in mind here are the most recent developments...

Question: I have several long-term clients I’ve advised they didn’t qualify for ERC under the requirements. I’ve discovered over time that all three were sold by an ERC mill and filed amended tax returns to claim credits. What are the risks they will be audited and what are my responsibilities in representing them? Should I release them as clients because they didn’t listen to me? Answer: You know, the Employee Retention Credit (ERC) might sound like a pretty sweet deal, especially if your business took a hit during the pandemic. It's a tax break designed to help you out. But don’t be fooled. It's not as simple as it sounds. You need to know the ins and outs before you jump in. Some new kids on the block, a bunch of specialist firms, are offering to help businesses claim this ERC. Unless you’ve been trapped in a cave (or under a pile of tax files) you’ve probably seen the mail, heard the commercials, clicked the ads. They make it seem so easy, don’t they? Just let us take care of everything and ignore the rules. This is music to the ears of employers – especially if we’ve already told them based on the rules, they don’t qualify. We want our clients to know they gotta be careful. These mills may promise you the moon and the stars, but the reality is, there's a pretty tight rule book on how and when you can claim the ERC. Misunderstanding these rules could mean you lose out on a potential $26,000 tax credit per employee. Worse, you could be tricked into claiming money you're not actually entitled to and end up with a nasty surprise later. And when you factor in the steep fees charged by these fly-by-nights, often up to 30% of promised refunds - there is a real risk of loss should these businesses lose their claims.

Sometimes my mind is not the safest place to be. I mean face it, a few issues ago I wrote on best practices for doing Al Capone’s tax returns. But how did I even get started thinking about the taxability of a business dealing in black market organs? Well, it started when someone on social media (perhaps looking to supplement the income from their tax practice) asked if the gain on selling a kidney was taxable and, if so, what would be the seller’s basis in the organ? Then there was that time I was having dinner and adult beverages with some tax colleagues in Las Vegas, and we started talking about that old urban legend about waking up in a bathtub full of ice missing a kidney. It was a fun night, and we all woke up with all of our kidneys and other organs in place. Nevertheless, I found myself wondering (and continuing to wonder) about the tax consequences of transacting in human body parts—one’s own or those illegally harvested from others. Turns out, there have been some court cases on the topic which means that the discussion is more than merely theoretical.

The story of Scott M. Hoensheid’s charitable planning gone awry as related by Judge Joseph W. Nega of the United States Tax Court is an interesting one. Click here to continue reading…

IRC § 1031 exchanges have the ability to confer substantial financial benefits to taxpayers. Although taxpayers may use § 1031 to place themselves in a superior economic position, taxpayers may not exploit this section in an abusive manner. Taxpayers can use exchanges to give themselves different types of benefits, but one of the primary benefits is the deferral of federal income tax. When conducted correctly, 1031 exchanges are regarded as a form of legitimate tax avoidance. One of the main issues involved with these transactions is determining the boundaries between abusive tax avoidance and non-abusive tax avoidance. In the context of “related party exchanges” – i.e. those transactions which involve subsection 1031(f) – this issue shows up in a relatively complex fashion, because the related party rules are not well understood by most practitioners. Furthermore, determining abusive tax avoidance with related party exchanges is difficult because of the scarcity of case law. Based on the case law which we have, and on the other authoritative references, we can put together a reasonable overview of the risks of related party exchanges. This overview should prove useful when providing expert counsel to taxpayers seeking to conduct this type of transaction. For direct exchanges, the 2-year ownership rule found in 1031(f)(1)(C) should be used as the dominant source of guidance. For “indirect exchanges,” taxpayers must be aware of the higher levels of risk involved, as there is a greater possibility of abusive tax avoidance. To read more click here!

If you were to ask most taxpayers what they worry about when it comes to their tax returns, they might say an unexpectedly high tax liability or even a late penalty. Next to none will worry they are at risk for criminal prosecution. There is a sound reason for this. In the fiscal year ending September 30, 2021, taxpayers filed over 261,000,000 tax returns. During that same period, IRS Criminal Investigation (CI) initiated only 2,581 investigations—a paltry 0.00098% of all tax returns filed. While CI entanglements are not a common experience, there are still lessons to be learned from looking at how things can go awry. So what types of scenarios have resulted in criminal investigations by the IRS, and what can this teach the everyday taxpayer? First of all, working with an expert, such as a Certified Tax Planner, will help you better understand what is permissible by the IRS and reassure you that your returns are fraud-free. For a few tips on what not to do, read the cases below and review our key takeaways for each one.