Blog Posts
Tax
When Will the IRS Compromise Tax Liability?
We have all seen the television commercials hawking tax relief with “satisfied clients” shilling for the promoter. But will the IRS really compromise a tax liability? If so, when, how, and why? There are four grounds on which the IRS is authorized to compromise a tax liability: (1) Effective tax administration on grounds of equity or public policy; (2) Effective tax administration on grounds of economic hardship; (3) Doubt as to liability; and (4) Doubt as to collectability. Because the business is the taxpayer, a request to compromise must be made in the name of the business. This means that partners in a partnership cannot compromise an individual’s portion of a partnership tax debt. The partnership must submit its own offer in compromise based upon the partnership’s and the individual partner’s ability to pay. The Internal Revenue Manual (IRM) is the IRS’s internal policies and procedures manual and contains a wealth of information regarding how the IRS evaluates offers in compromise (among many other topics). To see what factors the IRS considers and how it evaluates offers in compromise as set forth in the IRM, click here. Effective Tax Administration on Grounds of Equity or Public Policy This means there is no doubt the tax liability is owed, and that the full amount could be collected. In this case, compelling public policy or equity considerations exist, such that collection of the full liability would undermine public confidence that the tax laws are administered in a fair and equitable manner. Not to say the IRS has never compromised a tax debt on these grounds, but a successful result is almost unprecedented. Effective Tax Administration on Grounds of Economic Hardship Like its sibling, a compromise on grounds of public policy, this exception also means there is no doubt the tax liability is owed and that the full amount could be collected. This ground would apply where full collection would cause severe economic hardship, such as an inability to pay basic, reasonable living expenses. Most efforts to compromise a tax debt under this exception fail because other, more common grounds exist. Doubt as to Liability This means there is a genuine dispute whether the amount of the assessed tax is correct or whether the assessment is correct. Tax protester arguments, i.e., the Income Tax Act is unconstitutional, the income tax is a voluntary tax, wages are not income, the sovereign citizens theory, and a plethora of other arguments do not constitute a genuine dispute. In fact, all these tax protester arguments have been repeatedly characterized as frivolous, which, if made, will subject the person making them to possible sanctions under IRC § 6673(a). For information on tax protester arguments (and the consequences) click here. Doubt as to liability frequently arises in cases involving innocent spouse relief, but may arise in other areas as well. Doubt as to liability can arise in a number of circumstances such as a missed notice from the IRS resulting in the IRS disallowing all deductions, which, assuming the time for correction has not expired, can be proven and credited, mistaken or incorrect reporting such as when a payroll service reports (and pays) employment taxes for one affiliate when it should have been the other affiliate, or the IRS examiner made a mistake in applying the law or in calculating a tax liability. It happens. Doubt as to liability could arise when the IRS seeks to impose a Trust Fund Recovery penalty—the Trust Fund Recovery penalty, or TFR for short, is a 100% penalty— on a corporate official for not making payroll tax deposits and a genuine issue exists whether the person is a “responsible party” for purposes of withholding, collecting, and remitting payroll taxes. In virtually all the litigated tax cases, the issue is doubt as to liability. In each case, the determination of whether there is any doubt as to liability will be made on the totality of the facts and circumstances. To raise the issue of doubt as to liability, several conditions must be met: (1) there cannot be a final court determination regarding the tax liability; (2) there must be a legitimate dispute regarding the tax liability (no tax protester arguments); and (3) you must have supporting documentation. Typically, doubts as to liability are resolved well before the offer in compromise stage; but if not, an offer in compromise on the basis of doubt as to liability is made using Form 656-L. The last category, doubt as to collectability, is the most often used ground for compromising a tax debt. Doubt as to Collectability This means the IRS does not think it can collect the full amount of the tax liability through forced collection, so it would rather have something rather than nothing. Before the Service will consider compromising a tax debt due to doubt as to collectability, it will require the taxpayer to submit Form 433-B, Collection Statement for Businesses (for individuals, there is Form 433-A). Form 433-B requires a business to list extensive financial information. Though it may seem intrusive at first blush, the purpose of Form 433-B is to determine what the IRS can achieve through force collections. After all, the IRS will not compromise a tax debt for doubt as collectability where the full amount can be paid through available assets or income, either in full immediately or through an installment agreement. Though some may be tempted to understate assets and overstate liabilities on Form 433-B, this is a very bad idea. Form 433-B, like all forms submitted to the IRS, is signed under penalty of perjury. Intentionally understating assets or overstating liabilities on a Form 433-B is a 1001 violation (a crime punishable by up to five years imprisonment) just as if the person signing the form had lied to a federal agent. As thorough as Form 433-B is, it is just numbers on a piece of paper. To maximize the chances of getting the IRS to compromise a business tax debt, the business’s story needs to be told, in writing, ideally accompanying Form 433-B. An offer in compromise (OIC) for doubt as to collectability is made on Form 656-B. If the taxpayer can demonstrate that it is unlikely that the IRS will collect the full amount through forced collection and the offer in compromise reflects the taxpayer’s reasonable collection potential (RCP), the IRS will likely accept the offer and compromise the tax debt.
March 11, 2026
Tax
Top Audit Red Flags Businesses Shouldn’t Ignore
My recent blog, So, The IRS Has Selected Your Return for Audit, discussed the four types of IRS audits. What factors may trigger an audit of a business’s income tax return? The presence of multiple red flags in a business’s income significantly raises the likelihood of an audit. Round Numbers While rounding 49 cents up to 50 cents is not problematic—the IRS instructs you to round cents up or down for whole dollar amounts—reporting $10,000 of income from a customer instead of the actual $10,089 or reporting depreciation of $7,500 instead of $7,448 is. The algorithms the IRS uses to select returns for audit are programmed to identify rounding like this because the IRS knows (as we all do) that transactions are rarely in exact round amounts. Claiming Excessive Expenses The IRS compares your deductions against deductions for similarly situated businesses, using figures from returns filed by businesses similar in size and industry sector. The IRS has a bell curve for each category of expense. These figures are tweaked by the Taxpayer Compliance Measurement program. Similarly, your business expenses must be ordinary and necessary. Ordinary means the expense is a type common in your business’s industry sector. Necessary means the expense is helpful for your trade or business. If your business’s figures are excessive as measured against the IRS’s figures or the types of expenses are different than what the IRS routinely sees for businesses of your size or type, the chance of your return being audited increases. The more categories your figures are above the norm or are different from what the IRS usually sees, the greater the chances of an audit. It is also a matter of degree. Being slightly high in several categories is not necessarily an audit flag, but being very high in a few categories is a red flag. It is important to mention business use of automobiles. As a result of changes to the law in the Tax Cut and Jobs Act of 2017, the ability of employees to deduct unreimbursed business expenses was all but eliminated. However, self-employed persons (which includes partners in an entity classified as a partnership for federal income tax purposes) can still deduct business use of automobiles. Claiming 100% business use is a red flag. Likewise, because of accelerated depreciation associated with heavy SUVs and large trucks, the IRS may look twice at purchases near the end of the tax year. So, take advantage of that year-end sale but have the records to substantiate the business purpose and use. Misreporting Income First, beyond rounding cents, don’t round. Second, just because you didn’t receive a 1099 doesn’t mean the payor didn’t file the 1099 with the IRS. If you know you are missing a 1099, call the payor and ask for it otherwise this brings up the next flag. Large Cash or Large Numbers of Cash Transactions Some businesses naturally have large cash transactions or large numbers of cash transactions. If a cash transaction is over $10,000, financial institutions are required to file a currency transaction report (CTR). Breaking a cash transaction into smaller transactions to avoid the CTR threshold is known as structuring and is a crime under federal law. If your business deals in cash, keeping an accurate record of all transactions and documentation is essential in the event of an audit. Real Estate Rental Losses The IRS has strict rules regarding the ability to deduct losses from real estate rental against other income. For those who are not real estate professionals, which means you spend more than 50% of your working hours and more than 750 hours each year materially participating as a developer, landlord, or agent, you must own at least 10% of the value of all interests in the activity (spousal interests are combined for this threshold test) and you must actively participate in the operations of the rental property in the year in which the loss is claimed and in the year in which you seek recognition of the loss. If you meet these requirements, then you may deduct $25,000 of losses from real estate rental activity. This deduction phases out beginning with an adjusted gross income (AGI) of $100,000 and is completely phased out once AGI reaches $150,000. Deducting Hobby Losses Only losses incurred in a trade or business are deductible, which means you are engaging in the activity with the reasonable expectation of making a profit and you conduct the activity in a business-like manner. If your activity three out of every five years (two out of seven years for breeding horses), the IRS presumes that the activity is for profit. If not, whether the activity is for profit depends on the facts and circumstances. If you claim losses year after year, which is common among start-up businesses, your business will likely be audited. As with other areas, substantiation of expenses is imperative. Misclassification of Employees Whether a worker is an independent contractor, in which case your business issues them a 1099 at year end, or an employee, in which case your business issues the worker a W-2, is a hot bed item with the IRS and the U.S. Department of Labor. If a worker is misclassified as an independent contractor, then your business (and potentially you personally) owe employment taxes and withholding, plus interest and penalties. As with other areas, proper documentation (which includes agreements setting forth the worker’s independent contractor status) are essential. If your workers are employees (W-2) consistently filing and paying payroll taxes (941s) will also trigger additional scrutiny that likely will result in an audit. Claiming the R&D Tax Credit The R&D credit is great—if your business qualifies and if your business substantiates the credit. The One Big Beautiful Bill Act (OBBBA) reversed a 2022 law that required businesses to amortize research and development expenses over a five-year period. Businesses are now permitted to expense R&D costs immediately. The OBBBA also provided additional relief for small businesses that applied the new rule retroactively for the 2022 through 2024 tax years. Unscrupulous promoters (for a fee that is a percentage of the R&D credit) offer to analyze a business’s records to see if the business can claim the R&D credit retroactively. Often these promoters try to persuade a business to claim routine expenses as R&D activities to qualify for the R&D credit (which increases the promoter’s fee). Activities that are not eligible for the R&D credit include modifying an existing product, customer-funded research, research after commercial production, or research on a product about which there is no doubt about the expected result (this merely confirms what the company already knows). With proper substantiation costs for these activities still are deductible, just not eligible for the R&D credit. Growing and Selling Mary Jane Despite the current administration’s proposed rescheduling of marijuana, it is still a controlled substance at the federal level. It does not matter to the IRS that marijuana is legal in your state. Because it is illegal, expenses (other than cost of goods sold) incurred in the production, distribution, and sale, even if permitted under state law, are not deductible. Here is the real burn—you must still report and pay taxes on the income generated from your marijuana business. Because marijuana is illegal at the federal level, it also means if you invest in a marijuana business you can’t deduct investment losses. It also means you cannot use your self-directed IRA to invest in marijuana businesses. Bummer man. Home-Office Expense Deduction If you can take the home-office deduction (see Claiming Excessive Expenses above regarding restrictions on the ability to deduct unreimbursed business expenses incurred by employees), to claim the deduction you must use the space exclusively and regularly as your principal place of business. Guest bedroom, bonus room where the kids watch TV or play X-Box? Nope. Exclusive means exclusive. In the IRS’s eyes, returns that claim the home-office deduction is a target rich environment. Don’t paint a bullseye on your back. In the end, avoiding an audit is not about fear—it is about diligence. By keeping accurate records, understanding which expenses truly are allowed, and steering clear of overly aggressive tax positions, businesses can reduce their audit risk significantly. Most importantly, thoughtful documentation and consistent business practices provide the strongest defense should the IRS come knocking.
February 25, 2026
Tax
So, The IRS Has Selected Your Return for Audit
The Internal Revenue Service (“IRS”) audits 1% to 2% of small business income tax returns annually for one of two reasons: (1) something about the return (or information reported on the return) flagged the return for a closer review and the revenue agent reviewing the return decided an audit was appropriate; or (2) (bad) luck of the draw – the return was randomly selected for audit. The first reason – a red flag – is far more common than a random audit. The IRS publishes Audit Technique Guides for use by revenue officers. These guides can be found on the IRS’s website here and provide insight into what the IRS checks for and hopes to discover. Regardless of the reason or type (more on that below), the IRS never emails you and never calls without first sending you correspondence BY MAIL (not email). There are Four Types of Audits There are four types of audits, listed from least to most intrusive. Correspondence Audit The first (and most common) is a correspondence audit, which constitutes about three-quarters of all audits. With correspondence audits, you never meet with a revenue agent face-to-face because everything is done through the mail. In the simplest of audits, the IRS asks for information only regarding certain specific entries on your return. For example, if your return reported sales of stock and the return failed to indicate the basis, the IRS will write and request you to provide them with basis information (how much you paid for the stock you sold). Once you supply the requested information, the audit may be over (assuming the information provided matches the gain or loss reported on the return). Office Audit The second form of audit is an office audit, which takes place at their office, not yours. Office audits arise when a return is too complex for a correspondence audit but does not meet the threshold for a field audit. Often, office audits are over itemized deductions, rental incomes and losses, or Schedule C filers. During an office audit, the examiner will ask you questions in an attempt to find other areas to examine. Often, the examining agent will ask for more information, usually documents, and will give you a reasonable amount of time to gather and supply the requested information. Field Audit The third form of audit is a field audit. This audit takes place at your office, not theirs. During a field audit, the examiner will frequently ask for additional information and expect you to provide it reasonably quickly, after all, they are at your office where (in their mind) the records should reside. Line-By-Line Audit The fourth form of audit is a line-by-line audit, otherwise known as a Taxpayer Compliance Measurement Program (TCMP) audit. In this audit, the IRS reviews the returns of lucky taxpayers, line-by-line. The stated purpose of the audit is to build and refine the data points used to tweak the algorithms that determine whether a return should be selected for audit. Still, it is an audit, nonetheless. No matter the type of audit, the IRS’s starting position is to count all income and deny all deductions. For example, in our correspondence audit example, if you claimed a loss on the sale of stock, unless and until the IRS receives the requested supporting documentation, they will deny the loss, adjust your return accordingly, and send you a tax bill with interest and penalties. Office, field, and TCMP audits are the same way. The IRS wipes out your deductions and makes you build them back, providing reasonable substantiation for each type and amount of deduction. All audits begin the same way regardless of the type: the IRS sends you a letter, often by certified mail, advising you of the audit. The letter always has a response date. Do not ignore this date. If you ignore the date and do not respond, the IRS will either escalate the audit or issue a 30-day letter in which the IRS tells you what changes they propose and how much additional tax, interest, and penalties you will need to pay. If you ignore the 30-day letter, the IRS will issue a Statutory Notice of Deficiency (SNOD), and you will have ninety (90) days to file suit in the United States Tax Court to contest the IRS’s findings. When Do You Need a Tax Lawyer Certainly, for office and field audits. During office and field audits, the audit examiner will be asking you questions. Audits are unpleasant, and many people simply think that if they answer all the examiner’s questions the audit will be over quicker. WRONG. The examiner is asking questions because they are looking for additional areas to audit. Equally important, statements you make to the examiner fall under 18 USC § 1001, more commonly known as a “1001 violation.” 18 USC § 1001 criminalizes knowingly and willfully making materially false, fictitious, or fraudulent statements or representations made to a federal agent. This is the statute under which Martha Stewart was convicted. What she lied about was not a crime, but lying about it to a federal agent was (and still is) a crime under 18 USC § 1001. Whether an incorrect answer is merely the fault of a bad memory or may be considered lying to a federal agent is a question over which reasonable minds can and do differ. Just as I often told baseball teams I coached, never put the calling of a close pitch a ball or strike in the hands of an umpire; you shouldn’t leave the decision whether it was your bad memory or something worse to an IRS agent. A tax lawyer can help keep this from happening. When Should You Call a Tax Lawyer The minute you get the notice in the mail advising you that your return has been selected for audit. An experienced tax controversy lawyer can meet with the audit examiner on your behalf and provide information in a limited, organized manner, which will help limit the scope of the audit. The audit examiner will address questions to your attorney, not you. Tax lawyers’ answers are measured and designed to keep the audit as limited as possible. Even with a correspondence audit, your best solution may be to engage a tax lawyer to respond on your behalf or, at the very least, guide your response. Professional counsel can make a significant difference in the outcome, so leave the DIY to other areas.
February 9, 2026
Business
USPS Postmark Changes Could Impact Tax Filing Deadlines
A couple of years ago, I wrote a blog about the importance of sending any correspondence to the Internal Revenue Service via Registered or Certified Mail or by an approved overnight courier, rather than relying solely on the regular USPS First-Class postmark to determine timely mailing. I like to know the IRS receives what I send. On more than a few occasions, the IRS loses mail, and the only evidence of receipt is the return receipt or proof of delivery. Recently, the USPS announced an upcoming change to its postmark date system, effective December 24, 2025. This change makes it even more critical that taxpayers and their representatives use Registered or Certified mail, or an approved overnight courier, when filing a federal tax return. Here is why this change matters. “Postmarks are generally applied by the Postal Service via automation on machines in originating processing facilities but may also be applied manually by Postal Service personnel at those facilities, or by a Postal Service employee at a retail unit when a customer presents a mailpiece at a retail counter and requests a postmark.” FR Doc. 2025-20740. Under the USPS’s current system, the postmark reflects the date the mail is given to the USPS, i.e., handed to a USPS employee at a USPS counter or placed in an official USPS mailbox. Under IRC § 7502, a return is considered timely filed if it is postmarked on or before the due date of the return. For example, in 2025, the filing deadline for an individual taxpayer who did not request an automatic extension was April 15, 2025. Under the USPS’s current system, if the taxpayer mailed the return on April 15, 2025 by depositing the return, with sufficient postage, in an official USPS mailbox prior to the last mail pickup posted on the USPS mailbox, the return would have been postmarked April 15, 2025. It would be considered timely filed even if the return was not received by the IRS until days or weeks later. However, under the soon to be implemented USPS change, a machine-applied postmark indicates the date of the "first automated processing operation" at a processing facility, which may be later than the date the mail was dropped off, which could happen anytime but particularly during periods of high volume, i.e., April 15 (March 15 for calendar year tax year corporate and partnership taxpayers). With this change, even if the return were deposited into a USPS official mailbox, the return may not be postmarked with the official USPS postmark until after the filing deadline when the return was processed in a processing facility. Still, because most postmarks are applied at processing facilities, the postmark does not represent either the place or date on which the USPS first accepted possession of the mailed return. This means the return would not be considered timely filed, and failure to file penalties and interest would be assessed by the IRS. With this USPS change, an ounce of prevention is worth more than a pound of cure. Mail returns, Register or Certified mail, and get a hand-cancelled receipt, or use an approved overnight courier with an approved level of service. And just in case you were wondering, the postmark on the office postage machine is never sufficient. The views expressed herein are solely those of the author, are not intended as, and do not constitute legal or tax advice.
December 18, 2025
Labor and Employment
In the Know Series - Labor & Employment Law Changes – Federal
Stay Ahead of the Curve with Key Insights from Our L&E Team Now that the first quarter is behind us, employers across the nation must navigate changes in federal labor and employment regulations. Our team has compiled a comprehensive overview of the latest updates at the federal level, providing insights to help you stay compliant and proactive in managing your workforce. While not updates to the law, notable issues are below: With increased scrutiny on the ERC, the Service is starting to send out letters denying the credit. We anticipate it will send letters to employers who deserve the credit. Misdirected payroll tax deposits by payroll companies have increased, particularly where the payroll company handles payroll for related companies. Because they involve payroll taxes, the Service is particularly aggressive in its collection efforts. The quicker the client lets us know, the easier (and quicker) it is to resolve. ACA Issues: companies are receiving deficiency notices for failure to provide MEC. Most notices now are for the 2020 tax year. It is important for employers to understand that Treas. Reg. § 54-4980H-5((e)(2)(ii) does not define whether an offer of coverage is affordable. It simply provides a safe harbor. IRC § 36B(c)(2)(C)(i) determines whether an employer’s offer of coverage is affordable, which means even if coverage does not meet the safe harbor, it still may be affordable, so the employer avoids a penalty. We have obtained penalty abatements for several clients on this issue. Employer-Sponsored Healthcare Plans - The Next ERISA Fiduciary Duty Battlefield: With the issuance of much awaited final regulations, DOL has made clear that ERISA fiduciary duties apply with equal force to health and welfare benefit plans. Plaintiffs’ lawyers are actively looking for plaintiffs who are participants in employer-sponsored plans, particularly following the recent court decision regarding Johnson & Johnson’s healthcare plan. As in many areas, the best offense is a strong defense, which begins with companies implementing a health and welfare benefits committee to take a much more active role in the selection and negotiation of health plan benefits and documenting this process We have guided many clients on how to organize and structure health and welfare benefit committees.
April 15, 2024
Tax
IRS Proposes to Make Monetized Installment Sales a List Transaction
I know. I know. Your reaction is probably, “Huh? Do what? I don’t even know what a monetized installment sale is, why should I care.” As my partnership tax professor, Theodore Seto always says, “To understand the rule, you have to know the game that is being played.” The Problem and the Game: Here’s what a monetized installment sale is and how it works. Peggy Sue has a low basis, high-value asset. For our example, we assume a tax basis of $10,000 and a sales price of $1,010,000 so she has a taxable gain of $1,000,000. If Peggy Sue sells it straight up, unless she has other offsetting losses elsewhere, will have a lot of gain she must recognize and for which she must pay tax. Let’s say instead of selling it for a lump sum, she sells it in an installment sale payable in ten equal annual installments. Under IRC 453 she would allocate and pay tax on the pro rata portion of the gain each payment represents, so she would pay tax on 100k of gain each year over the ten-year period ($1,000,000 gain ÷ 10 years = 100k gain per year). If Peggy Sue has no other income, spreading the gain over 10 years will prevent a bracket run and result in less of a tax bite. The interest component of each payment will be taxable as ordinary income in the year of Peggy Sue’s receipt of each payment. Now here comes the game (greatly simplified for brevity): What if Peggy Sue sells to Elvis and takes back a 30-year, interest-only balloon note? Well, the interest is ordinary income, but Peggy Sue won’t recognize any gain until the balloon payment. This defers gain, but Peggy Sue still doesn’t have her money, only the interest payments. But what if Peggy Sue can find a lender who will lend Peggy Sue say 95% of the sale amount (and coincidentally, the payment terms and interest Peggy Sue pays the lender is the same rate as Elvis’s note to her). In other words, the interest received and interest paid cancel out each other. And because a loan ordinarily is not a taxable event, Peggy now gets 95% of the sales price to invest and grow for 30 years. When Elvis pays her the balloon payment in 30 years she pays the lender. Money for nothing and checks for free. Sweet deal, isn’t it? The Rule (Proposed): Too sweet, actually. So, the IRS has proposed making this and its variants a listed transaction. Being a “listed transaction” means you have to tell the IRS you are doing it, i.e. flag it on your return, so they can decide if it is legit or not (for a very narrow class of assets-farm land-it actually might work, but even then there are limits and restrictions). Also, if the proposed regulation goes into effect anyone who engaged in a monetized installment in a prior year for which the period of assessment is still open (generally three years from the latter of the due date or the date the return was filed) must send the IRS a disclosure of the transaction. Failure to list (“disclose”) the transaction can result in a penalty equal **TO** 75% of the tax savings the transaction produced, together with understatement penalties and interest. And it gets better. If you were required to disclose a listed transaction but didn’t, the period for assessment is extended until one year after the date of disclosure. Now, until the proposed regulation becomes final, this is all somewhat speculative. But if I were a betting man, I would look for a final version of the regulation this fall. Forewarned is forearmed. Scott Tippett is a principal at Offit Kurman PA where he concentrates his practice on tax planning, tax mitigation, and tax controversy in corporate, partnership, executive compensation, and employee benefit matters. He is a member of the firm’s Business Law Transactions and Intellectual Property groups. Offit Kurman PA is a national law firm providing clients with guidance in intellectual property, business, and tax matters. The views expressed herein are solely those of the author, are not intended as, and do not constitute legal or tax advice.
August 11, 2023
Tax
Operating Agreements: The Power of the Partnership Representative
Recently, a colleague asked me to review an operating agreement (not one that my colleague had drafted) from a tax standpoint. The LLC was classified as a partnership for federal income tax purposes. Setting aside the tortured regulatory allocations (it was a service partnership, distributions were pro rata, and there was no 704(c) property (property with a built-in gain or loss at the time the property was contributed to the LLC)), it was fairly straightforward. But therein lies the problem. The often-overlooked section designating a partnership representative needed substantial work. Wait, what!? The Bipartisan Budget Act ("BBA") of 2015 made the centralized partnership audit regime applicable to all partnerships for tax years beginning after December 31, 2017. I frequently encounter many older operating agreements that refer to a "Tax Matters Manager," which came about under the Tax Equity and Fiscal Responsibility Act (TEFRA) of 1982. If your operating agreement is one of these, for the reasons discussed below, it needs to be updated. Under TEFRA, before the effective date of the centralized regime, partnerships could elect the centralized audit regime or have each individual partner audited. Obviously, large partnerships preferred the centralized regime, while smaller ones frequently elected to have an audit at the partner, not the partnership level. The BBA changed all that by taking away the election and making the centralized regime mandatory for partnerships with more than one hundred (100) partners, while partnerships with one hundred (100) or fewer partners can opt out of the centralized audit regime. IRC § 6221(b); Treas. Reg. § 301.6221(b)-1(b). Sadly, I have seen many small partnerships, or, more appropriately, the lawyer drafting the operating agreement, simply copy these provisions from an operating agreement they thought looked good without ever giving a moment's thought to the impact and consequences of these provisions. In fact, the LLC whose operating agreement prompted this particular column had less than ten (10) members. And as Professor Ted Seto, my partnership tax professor, drilled into us, partnership tax is the one area of tax law where the Code and Regs dictate the business deal. The power of the partnership representative is august, cannot be overstated, and definitely should not be overlooked. Under the BBA, the partnership representative is the sole person with authority to act on behalf of the partnership and its partners! Treas. Reg. § 301.6223-2(a). Further, "no partner, or any other person, may participate in an administrative proceeding without the permission of the IRS." Treas. Reg. § 301.6223-2(d). So, even if you wanted to participate, absent the Service's permission, you can't. The partnership representative's decisions are binding on each partner of the partnership. Treas. Reg. § 301.6223-2(a). Disagree with a decision made by the partnership representative in an audit? Tough. You're bound. Can't we limit the power of the partnership representative by including provisions in our operating agreement? As far as the Service goes, no. In fact, any such limits are prohibited by Treas. Reg. § 301.6223-2(c)(1), which states, "[n]o state law, partnership agreement, or other document or agreement may limit the authority of the partnership representative or the designated individual as described in section 6223 and this section." Yikes! The partnership must designate a partnership representative separately for each tax year, and the designation is effective only for the tax year for which it is made. Treas. Reg. § 301.6223-1(c)(1)). The designation is made on the partnership's tax return (IRS Form 1065) and is effective when the return is filed. Treas. Reg. § Regs. Sec. 301.6223-1(c)(2). The partnership representative need not be a partner. Also, the partnership representative does not have to be a person, though if the partnership representative is an entity, it is required to have a "designated individual" so the Service has an actual human being as its point of contact. Clearly, the regs say plenty of things a partnership can't do, which begs the question, what can a partnership do? What you can do is include provisions in your operating agreement that: (1) require the partnership representative to acknowledge it acts in a fiduciary capacity with respect to the partners; (2) requires the partnership representative to provide notice to each partner immediately upon the receipt of any notice (and provide a copy of any such notice) the partnership representative receives from the Service that seeks to make any adjustment or impose any penalty with respect to the partnership or its partners; (3) requires the partnership representative to employ experienced tax counsel to represent the partnership in connection with any audit or investigation of the partnership by the Service and in connection with all subsequent administrative and judicial proceedings arising out of such audit; (4) requires the partnership representative to get approval from the partners before taking any position or action with the Service, including but not limited to any decision: (i) to enter into a settlement agreement which purports to bind the partners other than the partnership representative (which, as noted above any decision will); (ii) to file a petition or request contemplated in Section 6227(a) of the Code; (iii) to enter into an agreement extending the period of limitations as contemplated in Section 6235(b) of the Code. Finally, under the BBA, the partnership can either pay an assessment or penalty at the entity level or pass it down to the partners to be paid pro rata by each partner. This election can be made with respect to each separate assessment or penalty, so to provide the most flexibility, the operating agreement should permit this decision to be made by the partners on a case-by-case basis, then communicated to the Service through the partnership representative. What's in your operating agreement? Scott Tippett is a principal at Offit Kurman, PA, where he concentrates his practice on corporate, partnership, and employee benefit tax matters. He is a member of the firm's Business Law Transactions and Intellectual Property groups. Offit Kurman PA is a national law firm that provides simple, clear solutions to complex business and tax issues. The views expressed herein are solely those of the author, are not intended as, and do not constitute legal or tax advice.
May 24, 2023
Labor and Employment
Secure 2.0 Act of 2022
Attorneys Sarah Sawyer and Scott Tippett discuss extensive changes to the 2019 Secure Act, collectively called the Secure 2.0 Act of 2022. The Secure 2.0 Act increases the options for employers and employees regarding retirement plans and outcomes and adds additional compliance considerations for companies. In this informative legal update, Sarah and Scott discuss: Automatic enrollment requirements Increased age for mandatory distributions for IRAs The new inclusion of student loan payments as contributions for matching purposes Tax credit for military spouses Timing considerations for implementing and complying with the Act Sarah and Scott also discuss the importance of understanding the nuances of the Act and being proactive. Listen to learn more!
February 15, 2023
Business
How Long Did You Say I Need to Keep My Tax Records?
I get this question a lot, and not just from non-lawyers. The answer, as with any question you ask a lawyer, is it depends. Several different statutes of limitation apply regarding how much time the IRS has within which to audit your return. The basic period is three years from the due date of the return or the date of its filing, whichever is later. So, if you only recently filed your 2015 return, the three-year clock starts to run on the date your 2015 return was filed. Had you filed your 2015 return early, say on March 1, 2016, the three-year clock started to run on April 15, 2016 (the due date of your 2015 return (for individuals), March 15, 2016 (for businesses)). This means when your 2015 return is selected for audit, you need to be able to produce records that are now seven years old to substantiate any deductions taken. Records get lost and destroyed. Houses and businesses suffer casualty damage, people move, and dogs eat things. The IRS has heard it all and frankly doesn’t care. If the IRS thinks you have understated your income or overstated your basis by more than twenty-five percent (25%), then the Service has six years (computed from the dates like the three-year statute discussed in the preceding paragraph) to audit your return. If the IRS thinks the omission was fraudulent, they have forever. Likewise, if you never file your return, then the statute never starts to run. If you have foreign accounts or have signature authority over foreign accounts and are required to file a FBAR and Form 8938, the IRS deems those tax years open until those forms are filed! So, if you had a foreign account that you should have but forgot to disclose on your 2010 return, the IRS can still go back and audit that return in 2022 because the filing was never completed because all the required forms were not filed, so the return was never filed to start the clock running. The hits just keep on coming. Recently the Tax Court upheld a Notice of Deficiency (NOD) against a taxpayer based on a net operating loss she incurred in 1999 and had been carrying forward every year. Under IRC 172, an individual taxpayer can carry a NOL forward indefinitely until the NOL is completely used. In this case, that’s what the taxpayer did. The taxpayer had a large loss (initially more than $5,000,000.00) from a failed franchise. She first claimed the loss on her 1999 return, which the IRS promptly audited and found no deficiency, i.e., the NOL was proper and fully substantiated. The taxpayer (a CPA) dutifully carried forward and claimed the adjusted NOL each year (she used up a little bit each year), including 2014 and 2015. The Service then challenges the 2014 and 2015 returns and denies the NOL. Yes, this is the same NOL on the previously audited 1999 and 2000 returns that the IRS said passed muster. So, the CPA goes to Tax Court. This is where is really gets good. In Tax Court, the taxpayer introduced the 1999 and 2000 returns to which the Court held-get this-the taxpayer’s “proof to be insufficient to substantiate a taxpayer's entitlement to a loss carryforward.” Amos v. Commissioner, TC Memo. 2022-109. The Court noted, “The prior tax returns show only that [the taxpayers] claimed NOL carryforward deductions. They do not provide evidence that [the taxpayers] are entitled to them.” Amos v. Commissioner. So, even when the IRS audits your return and agrees with your return, if the return is for the first year you are claiming a NOL that will likely be carried forward for years to come, you better hang onto those records that document and establish the NOL. Currently, many of us rely on online banking, online tax payments (property and state income (in states that have a state income tax)), online brokerage activity, and a whole host of other things. Each year, as you prepare your taxes, you should print out and retain copies of any online reports you rely on in determining your federal and state income tax liability. Many service providers purge information after a few years, so it may not necessarily be available should you need it in response to an audit. Retain copies (a personal scanner works great) to scan documents regarding basis information and expense deductions. Setting aside the soundbites coming from both sides of the aisle, the practical reality of increased funding for the Internal Revenue Service is audits will increase. As you may know, a return can be “selected” for audit in one of three ways: (1) the computer flags the return because certain figures or ratios of figures trip its algorithms; (2) the return is randomly selected for audit (nothing triggered the audit, it was just the taxpayer’s unlucky day); and (3) an examiner flags the return (more common in the estate and gift tax area, and other specialized returns, less so, but still possible, for individual returns). Several years ago, the IRS openly announced audits were decreasing because the Service lacked personnel. That will soon change, and with that change comes the need for heightened vigilance by taxpayers regarding record keeping and record retention so that if your return is selected for audit, you have the records to come out of the audit relatively unscathed. Because an audit starts with the IRS denying all deductions you took on the returns, to claim the deductions, you must prove to the revenue officer’s satisfaction that you have kept proper records substantiating the deduction. If you can’t prove it, you can’t take it. This means starting from ground zero, and therein lies the problem with old records. So, depending on your tax situation, you may want to hang onto those records a little longer. Scott Tippett is a principal with Offit Kurman’s Business Law Transactions group. Offit/Kurman PA counsels clients on business and matters, including representing clients before the Internal Revenue Service, Office of Appeals, and United States Tax Court, as well as state and local tax authorities. We counsel clients regarding personal and business tax planning matters and issues and assist with the formation and structuring of entities to maximize tax savings and tax credits. The views expressed herein are solely those of the author, and are not intended as, and do not constitute, legal or tax advice.
January 9, 2023
Business
Forwarding Email to Hotel Front Desk for Printing Waived Privilege!
Normally I write about recent and interesting tax cases in this blog, but every now and then, I come across a case so important I just have to share it here. Fourth Dimension Software v. Der Touristik Deutschland GMBh is such a case with an important cautionary tale. Fourth Dimension Software (“FDS”) is embroiled in a dispute with Der Touristik Deutschland GMBh (“DTD”) regarding DTD’s alleged overuse of a software license for software developed by FDS and licensed to DTD. Prior to the litigation, in preparation for a meeting with DTD in Berlin to discuss the licensing agreement, FDS’s former outside counsel emailed the president of DTD regarding certain issues for the meeting. As people sometimes do, FDS’s president wanted a hard copy of the email for his notes. Having no printer, FDS’s president forwarded the email to info.berlin@hilton.com with a note in the subject line “Please print one copy. I’m waiting at the front desk. Thanks.” How DTD got its hands on a copy of the email was not discussed. What was discussed was the waiver of the attorney-client privilege as a result of FDS’s president forwarding the email to the front desk of the Hilton in Berlin for printing. When the email came to light, FDS sought to exclude it as an attorney-client communication protected by the attorney-client privilege. As a reminder, the attorney-client privilege applies to any communication in which legal advice is sought or communicated, not just communications in the context of litigation. Because the parties were in federal court because they were from different states, and not because the case concerned a question of federal law, California law, not federal law, applied. Under California law, if a client discloses an attorney-client communication to unnecessary third parties, the client manifests an intent to waive the privilege. DTD successfully argued that was exactly what happened here. FDS pointed out that under California law, the privilege is not lost solely because the communication is by electronic means (e-mail) or because persons involved in the delivery, facilitation, or storage of electronic communications may have access to the content of the email. The Court dryly noted, “That statute does help FDS here.” The Court went on to point out the hotel desk clerk was an unnecessary third party to whom FDS’s president knowingly disclosed the communication. Though not mentioned in the court’s order, under the court’s analysis, merely forwarding the email to an unnecessary third party would have resulted in a waiver of the privilege as well. Other states’ laws may not be the same as California, but remember that forum selection clause in that contract you signed that said would only be brought in California? But why risk it? Think twice before forwarding that email to or from your lawyer. Like FDS, you may end up waiving the privilege.
October 14, 2022
Tax
Virtual Currency and Virtual Transactions – Real Tax Issues in Real Dollars
Recently the IRS released a draft form of Form 1040 for the upcoming tax year. The biggest change is a more detailed question about virtual currency transactions. The new draft form asks, “At any time during 2022, did you: (a) receive (as a reward, award, or compensation); or (b) sell, exchange, gift, or otherwise dispose of a digital asset (or a financial interest in a digital asset),” followed by a “Yes” or “No” box. You can see a copy of the draft form here. Although not as bad as some expected (Line A-How much did you make last year? Line B-How much do you have left? Line C-Send Line B.), this change shows the Service is increasing its scrutiny of virtual currency transactions and, not coincidentally, subjecting taxpayers to false statement penalties if they are not truthful in their answer. Although the question asking about virtual currency did not appear on the 1040 until 2020, as seen here, the Service began issuing guidance on virtual currency and transactions as early as 2014, as seen in Notice 2014-21. Five years later, in Rev. Rul. 2019-24, the Service issued further guidance to address “hard forks” and “airdrops.” So, what are the rules? First, despite the moniker, virtual currency or cryptocurrency, the Service considers virtual currency (Bitcoin, Dogecoin, Ethereum, as well as all other cryptocurrencies) to be personal property, not currency. Setting aside currency arbitrage transactions, the basis of currency is the face value of the currency. If I receive a $100.00 bill, my basis in that Benjamin is always $100.00 (I can’t depreciate it), and when I dispose of it (use it to buy, say $100.00 of Dogecoin), I have no gain or loss on the disposition of that bill. Now, because Dogecoin is treated as property and not currency if my $100.00 of Dogecoin grows to $300.00 and I use it to buy something else for $300.00, I have taxable gain, in this case, $200.00. Because my Dogecoin is considered property, not currency, the gain will be taxed either as ordinary income or as a capital gain. Whether the gain is taxed as a capital gain depends on whether the Dogecoin is a capital asset in my hands. See Q &A No. 7, Notice 2014-21. If I do not hold the Dogecoin in inventory for sale to others but hold it as an investment, much like stocks, bonds, and other investments, it should be treated as a capital asset and taxed at capital gains rates. If I satisfy the long-term capital holding period (more than one year, i.e., a year and a day), then I get the favorable long-term capital gain rates, which generally are lower than short-term capital gain rates. Let’s take the flip side. What if someone pays me in virtual currency? What is my basis in the virtual currency with which I was paid? My basis is the fair market value of the virtual currency on the date of receipt. See Q & A No. 4, Notice 2014-21. Transactions using virtual currency must be reported in U.S. dollars for U.S. tax purposes. If the virtual currency is traded on an exchange, the value can be determined simply by looking at the exchange rate on the date of receipt or payment. Where the virtual currency is not traded on an exchange, the taxpayer still must determine the fair market value based on all the facts and circumstances. What if I receive virtual currency in payment for services? If I am an independent contractor (I receive a 1099), the receipt of virtual currency is considered self-employment income, which means it is subject to self-employment tax. This also means that payment to an independent contractor using a virtual currency is subject to information reporting, i.e., reporting to the IRS payments of $600 or more in the same tax year to the same person, and the attendant penalties for not filing information returns. If I am an employee (I receive a W-2 from my employer), the payment of wages in virtual currency is subject to federal income tax withholding and, if I am the employer, to the employer’s share of employment taxes. If I am an employer, I must pay the taxes withheld and the employer’s share of employment taxes in U.S. currency, not Dogecoin or any other virtual currency. What if I “mine” virtual currency? If I mine virtual currency, the fair market value of the virtual currency as of the date of my receipt of it is included in gross income. What if I “mine” virtual currency as a trade or business? If I mine virtual currency for my own trade or business or as an independent contractor, the net earnings from that activity constitute self-employment income, but I am entitled to deduct my ordinary and necessary business expenses in determining my net income. You said something about hard forks and airdrops; tell me more. (For those unfamiliar with soft forks and hard forks, click here to read an Investopedia article containing a brief explanation). Typically, and grossly general terms, a hard fork results in the creation of a new cryptocurrency. After a hard fork, transactions involving the new cryptocurrency are recorded on a new distributed ledger, while transactions involving the old or legacy virtual currency continue to be recorded on the old legacy ledger. An airdrop is a way of distributing units of virtual currency to the distributed ledger addresses of multiple taxpayers. Hard forks are often, but not always, followed by airdrops. Generally, a virtual currency is received from an airdrop on and at the date and time it is recorded on the distributed ledger. For U.S. tax purposes, whether the taxpayer received the virtual currency on and at that date and time is determined by the dominion and control test. If the taxpayer has dominion and control over the virtual currency on the date and at the time it was airdropped, then the taxpayer, if on the cash basis of accounting, has gross income under IRC § 61(a)(3) on and at the date and time of receipt. On the other hand, if the hard-forked virtual currency is airdropped into a wallet managed by an exchange that does not support the newly created (hard forked) virtual currency, which means the taxpayer cannot transfer, sell, exchange, or otherwise dispose of it, then the taxpayer does not have dominion and control over the new hard fork airdropped virtual currency, and it would not be included in the taxpayer’s gross income unless and until the taxpayer later acquired dominion and control over it. The use of virtual currencies and transactions using virtual currencies can create real tax issues. If these tax issues result in federal tax liability, those liabilities must be paid with the U.S., not virtual, currency. If in doubt regarding the tax consequences of buying, selling, using, or mining virtual currency, taxpayers should consult their tax advisor regarding the implications of buying, selling, and using virtual currencies. Offit/Kurman PA counsels clients on intellectual property matters such as virtual currency and NFTs, including the tax aspects and effects of those matters. The views expressed herein are solely those of the author, are not intended as, and do not constitute, legal or tax advice.
August 24, 2022
Tax
Harvesting Tax Credits Is Legitimate Business for Tax Purposes
If the sole purpose of a partnership is to harvest tax credits, is that a legitimate business for tax purposes? According to the Tax Court and the D.C. Circuit Court of Appeals, yes. In Refined Coal, LLC. V. Commissioner, No. 20-1015, (D.C. Cir. August 5, 2022), the answer is a resounding yes. But first, some background. In 2004, to stimulate the production of refined coal, which produces fewer emissions when burned, Congress created a tax credit for the production and sale of refined coal. But there was a catch – a producer could only receive the credit if it sold refined coal for 50% more than the market value of unrefined coal. Well, surprise, surprise, this went nowhere, so in 2008 Congress removed the 50% restriction and lo-and-behold, it worked. To take advantage of this change (and resulting tax credit), AJG Coal, Inc. launched a coal-refining facility at a power plant on Santee Cooper in South Carolina. Under the agreement, AJG, through a subsidiary, signed a lease that allowed it to build a coal refining facility inside the power plant. Next, the subsidiary entered into an agreement with the power plant to buy unrefined coal from the power plant, refine it, and sell it back to the power plant at $.75 less per ton. Finally, the sub entered an agreement with its parent to license the coal-refining technology. Wait a minute; they are reselling refined coal to the company from which they bought it for less money!? How could this ever make good business sense? The answer? Tax credits. The only possible way this was only profitable was through the application of the tax credit for refined coal. And we are not talking peanuts here. AJG projected that the sub would realize a $140 million after-tax profit over a ten-year period. Sadly, profits were much less than projected. In fact, the project had several lengthy shutdowns. Finally, in 2012, Santee shut down the coal-refining operation because of insufficient demand for local power, which caused two of the partners to suffer $ 2.9 million and $700,000 after-tax losses, which they wrote off on their respective federal income tax returns. Not so fast, the IRS said. To be a legitimate business, i.e., to write off expenses and losses, you must have a profit motive, and operating a business solely to harvest tax credits do not count, so the partnership was not a bona fide partnership; therefore, the losses are not deductible. Au contraire mon frère said the Tax Court. Yes, harvesting tax credits is a legitimate business purpose, and if the business would not be profitable, but for the tax credits, that is okay. It is still a legitimate business. Not content with the Tax Court, the Service appealed to the D.C. Circuit Court. The D.C. Circuit Court noted that due to special benefits the tax code affords partnerships, there is the ever-present temptation for an entity to appear as a partnership, even if it is not. The Court noted there are two requirements to be a partnership. The first requirement is the partners must intend to carry-on business as a partnership, i.e., the business must be undertaken for profit or other legitimate nontax purposes. Factors examined include the duration of the partnership and the business rationale for forming a partnership. The Court observed, “Taxpayers that structure their dealing to receive tax benefits afforded by statute are entitled to those benefits, no matter their subjective motivations.” The second requirement is the partners must intend to share in the profits or losses or both; that is, the partners’ interests must have the prevailing character of equity. If a partner is insulated from the upside and downside risks of the business, that partner looks more like a secured creditor, not a true partner. Applying these factors, the D.C. Circuit Court found the partnership was a true partnership and dismissed the Service’s objection that the partnership had no pre-tax profit motive and, therefore, was not a true partnership. The Court noted a partnership’s pursuit of after-tax profit, even one only made possible by tax credits, is a legitimate business activity. Finally, the Court held that even transactions that are only profitable on a post-tax basis can still have a nontax business purpose. The decision by the D.C. Circuit Court was unanimous. So, where does that leave us? Consider for a minute all the tax credits provided by the tax code. The Refined Coal decision confirms and affirms that a partnership organized solely to harvest tax credits is a legitimate business for tax purposes. The question is, what tax credits can your business harvest? Offit/Kurman PA counsels clients on business matters, including the formation and structuring of entities to maximize tax savings and tax credits. The views expressed herein are solely those of the author, are not intended as, and do not constitute, legal or tax advice.
August 19, 2022
Tax
Pass-Through Entities in Bankruptcy-Beware of Phantom Income
Recently I discussed the tax issues created by the inadvertent inclusion of partnership tax provisions in an operating agreement for a LLC taxed as an S-corp. Today we have a different problem – not following what the operating says regarding dissolution and the potentially serious adverse tax consequences that can create. This is a bankruptcy case with important income tax lessons for members of pass-through entities. LeClairRyan PLLC was a law firm in Virginia that was taxed as an S-corporation for federal and state income tax purposes. In 2019 LeClairRyan filed bankruptcy (initially Chapter 11 (reorganization) but converted to Chapter 7 (liquidation). On July 29, 2019, the firm voted to dissolve. On July 31, 2019, Mr. LeClair terminated his employment with the firm. Three years later, he was in bankruptcy court, asking the court to order the bankruptcy trustee to remove his name from the list of equity security holders (members of the law firm) on the ground he had terminated his interest. Under Virginia’s LLC act, an LLC “is bound by its operating agreement, which regulates the conduct of its business and the relations of its members.” Most, if not all, state LLC acts contain similar provisions. Here, the law firm’s operating agreement provided that a member’s interest terminated on the date the member’s employment with the firm ceased. For Mr. LeClair, this was July 31, 2019. But the firm’s operating agreement also provided that as long as a member-owned shares (instead of a membership interest, the law firm used common and preferred shares), no member could withdraw prior to dissolution and winding up of the [law firm]. Because the law firm voted to dissolve on July 29, 2019, two days before Mr. LeClair attempted to terminate his employment, the bankruptcy court ruled Mr. LeClair’s termination was ineffective based on this provision of the operating agreement. Had it been the other way around, that is, had Mr. LeClair terminated his employment before the firm voted to dissolve, then he would not have been a member as of the date of dissolution. So why was Mr. LeClair trying to do this, and what difference does all this really make? The reason: Taxes. The difference it makes: Potentially a big one, and here’s why. Under the Bankruptcy Code, when an individual files bankruptcy, the bankruptcy estate is its own tax entity, meaning it, not the debtor (the individual who filed bankruptcy), is responsible for paying any taxes associated with the income from the bankruptcy estate. See IRC § 1398. However, this rule does not apply to corporations or partnerships. IRC § 1399. In the case of a C-corporation, this is no big deal because C-corporations are separate tax-paying entities anyway. But…where a pass-through entity (PTE) is involved (entity taxed as an S-corporation or partnership)…it can be a big (taxable) problem for the partners/shareholders/members. Recall, with PTEs, items of profit and loss flow through to and are taxed at the shareholder/member/partner level. In bankruptcy, if the PTE has assets that continue to produce income, the bankruptcy estate–not the shareholders/members/partners–gets the income, but and this is a BIG BUT because the income flows through to the individual shareholders/members/partners, they, not the PTE, must pay the taxes associate with that income. Ouch!! So, coming back to Mr. LeClair’s case, that meant that as the bankruptcy trustee collected the law firm’s receivables (which are income), the bankruptcy trustee got to keep the money to pay the firm’s creditors, but for tax purposes, the income was allocated to the members of the now bankrupt firm who had to pay income taxes on money they never received. I know what some of you are thinking. Would the result have been different if the firm had made an election to pay tax at the entity level instead of at the shareholder/member/partner level? After all, Virginia has adopted pass-through entity tax (PTET) as a SALT workaround. Highly doubtful. PTET legislation, at least in Virginia as well as most states, does not create or define a property interest (IRS looks to state law to determine whether a taxpayer has a property interest, then federal law governs how that interest is taxed). Maybe a closer call in Connecticut, where PTET is mandatory but still doubtful, in my opinion. Let this be a cautionary tale that if you are a shareholder/member/partner of a PTE that is contemplating bankruptcy, you should seek not only competent bankruptcy counsel but competent tax counsel as well, lest you wind up with phantom income for which you, not your now defunct PTE, will have to pay income taxes. Offit/Kurman PA counsels clients on bankruptcy and insolvency matters, including the tax aspects and effects of those matters. The views expressed herein are solely those of the author, are not intended as, and do not constitute, legal or tax advice.
August 16, 2022
Tax
Self-Employed and Deducting Car Expenses? – Document or Else!
An internet search of “Schedule C filers” will yield a bevy of sites warning of the increased audit risk and audit red flags for Schedule C filers. As a reminder, Schedule C of Form 1040 is used by sole proprietors, and LLCs taxed as disregarded entities. The recent Tax Court case of Eze v. Commissioner, T.C. Memo. 2022-083 (Aug. 4, 2022) serves as a potent reminder of the need for taxpayers not only to document their business expenses but, when it comes to cars and trucks, to make sure the strict substantiation requirements of IRC § 274(d) and Temp. Treas. Reg. § 1.274-5T(c) are satisfied. Plain English, please. This means keeping records of car and truck expenses, i.e., where you go, the purpose of the trip, miles traveled, who you saw, etc… and make those records close in time to when the expenses were incurred. In Eze, the taxpayer, who’s return was selected for audit (this means the automated system flagged it because his expenses were so high), created his records months, if not years after the fact, created and used a calendar solely for the purpose of the IRS examination, offered no clear explanation when he made the entries, and could not explain how he could have remembered the minute details months and years after the fact. Other things the Tax Court had trouble believing: (1) the taxpayer made the same trip to the same client on the same day of each year; (2) recorded mileage was inconsistent (some trips from his home to New York he recorded as 354 to 362 miles, others he recorded as 448 to 450). There may have well been good reason for that. If I travel to our home office in Baltimore, my mileage each way, will range from 329 to 383, depending on the route. Like most others, I map the route when I am leaving and take the one that suits me the best. But if the taxpayer did that here, he did not offer a plausible explanation why. With the other issues involving his auto expenses records, the Court found the taxpayer’s testimony was not credible. Other things the Tax Court had trouble believing: (1) he took four round trips to Buffalo, New York, and three round trips to Charleston, South Carolina (the taxpayer lived in or around Baltimore, Maryland), all in one month, but could not explain why he needed to visit the same client that many times in one month; and (2) In 2015 the taxpayer showed some personal mileage, but none in 2016. Consistency matters! So, if you are entitled to deduct business mileage, keep accurate records. At a minimum, this should include: (1) miles driven; (2) date; (3) place; and (4) business purpose. These records should be made close in time to when the miles were driven. Have trouble remembering to do that? There’s an app (actually several) for that. Just remember to do period downloads or printouts so if your return is selected for audit, you can substantiate your business mileage deduction. Offit/Kurman PA counsels clients in business and corporate matters, including tax planning and advocacy. The views expressed herein are solely those of the author, are not intended as, and do not constitute legal or tax advice.
August 11, 2022
Tax
Legal Fees – Deductible as Ordinary Business Expenses or Capitalized?
This is the question currently on appeal from the Tax Court to the Third Circuit. In Myland, Inc. v. Commissioner of Internal Revenue (Case No. 22-1193, 1194 & 1195) the IRS appealed the Tax Court’s ruling that Mylan (the taxpayer) was entitled to deduct, as an ordinary business expense under IRC § 162(a), approximately $50 million in legal expenses it incurred to defend patent infringement actions in connection with its manufacture of generic drugs. The Service contended Mylan’s $50 million in legal expenses should be capitalized under IRC § 263(a) because, in its mind, the expenses were related to the acquisition of a capital asset. Okay, so what difference does this make? A big one. If Mylan establishes the legal fees were ordinary business expenses, it gets to deduct those fees as they are incurred (which they did on their timely filed tax returns for the years at issue). If not, Mylan must recover its legal fees over a fifteen-year period, through amortization and depreciation deductions (Ouch!). Because Mylan deducted the fees currently as an ordinary business expense, if the Service ultimately prevails and those deductions are denied, Mylan will also incur interest and penalties (salt in the wound). What is it, an ordinary business deduction or a capital expense? The answer all depends on whether the expense either: (1) creates or enhances a separate and distinct asset; or (2) otherwise generates significant benefits for the taxpayer extending beyond the current taxable year. Yep. About as clear as mud. To provide clarity the Service promulgated Treas. Reg. § 1.263 to provide additional guidance. Without getting too deep into the weeds, if a taxpayer incurs expenses (including legal fees) to create or improve an intangible asset, which includes “rights obtained from a governmental agency,” i.e., trademark, trade name, copyright, license, permit, franchise, or similar right granted by that governmental agency,” those expenses are capital expenses that may only be recovered over the useful life of the asset through amortization and depreciation deductions. Treas. Reg. § 1.263(a)-4(d)(9)(l). Although most businesses do not have patents, many do have other intangibles such as trademarks, trade names, and copyrights, to name a few. The deductibility of legal expenses depends on the nature of the underlying claim for which the legal expenses were incurred, so businesses must look to the substance of the claim or transaction that gave rise to the legal fees to determine whether the expenses are ordinary business expenses (and, therefore currently deductible) or a capital expenditure, recoverable over the useful life of the asset. With intellectual property becoming ever more important and valuable to businesses of all types and sizes, business owners need to be mindful of how and when legal fees (and other expenses) incurred to create or defend rights in intellectual property are treated for federal income tax purposes-deductible currently as an ordinary business expense or capitalized over the life of the asset. As for how the Third Circuit will rule? My money is on Mylan. Offit Kurman PA counsels clients on creating, enhancing, and protecting intellectual property, including the tax aspects and effects of those transactions. The views expressed herein are solely those of the author, are not intended as, and do not constitute legal or tax advice.
August 5, 2022
Tax
Operating Agreements – One Size Does Not Fit All
A recent private letter ruling highlights the danger of using a form or template blindly. PLR 202219005 involved a limited liability company (the “Company”) that sought, but failed, to be taxed as an S-corporation. On the effective date of the Company’s organization, the Company duly adopted a written operating agreement. The problem was the written operating agreement contained provisions appropriate for partnerships but not S-corporations. Specifically, one provision of the operating provided, “the proceeds from liquidation will be allocated to members with positive balances in their respective capital accounts, pro-rata, in proportion to the positive balances in those capital accounts.” Provisions like this one are seen routinely in operating agreements for entities taxed as partnerships for federal income tax purposes but are wholly inappropriate for entities taxed as S-corporations. Recall an S-corporation may have only one class of stock. While an S-corporation can have voting and non-voting shares, all shares must have identical rights to distribution and liquidation proceeds. The problem is partnership allocation provisions, such as the one at issue here, do not confer identical rights to distribution and liquidation proceeds. More of a problem among the DIY community who grab forms off the internet; this also can happen with attorneys who create limited liability companies (and operating agreements for those LLCs) without understanding what the agreements actually say and do. The allocation and distribution provisions of an operating agreement are the meat of the agreement because these provisions determine how members get money (or don’t get it) (distributions) and how they are taxed on money (or not taxed) (allocations). You don’t go to your dentist for heart surgery, and you don’t go to your cardiologist to fill a tooth. Lawyers are the same. When setting up a new company, turn to a lawyer well-versed in business and tax matters. The PLR does not discuss how the operating agreement came to contain partnership tax allocation provisions, only that it did. This PLR serves as a cautionary tale – do not use forms blindly. With operating agreements, one size DOES NOT fit all. Each operating agreement should be tailored to the facts and circumstances of the particular transaction and the parties’ intended tax treatment. In the case the Company was fortunate, the Service granted relief. Still, the need for (and cost of) a PLR easily could have been avoided had the taxpayer carefully reviewed the operating agreement. Scott Tippett is a member of Offit Kurman, where he focuses his practice on business and tax planning. Offit Kurman counsels business owners on strategic business, tax, and risk management techniques. The views expressed herein are solely those of the author’s and do not constitute and are not intended as legal or tax advice.
June 22, 2022
Tax
North Carolina Enacts Pass – Through Entity Tax
Recently the North Carolina General Assembly changed the law to permit pass-through entities (partnerships and s-corporations) to pay entity-level tax, thereby joining a majority of states (29 at last count) in doing so. The change is effective for tax years beginning January 1, 2022. As with most states, paying tax at the entity level is optional (mandatory in Connecticut). If a partnership pays tax at the entity level, the tax paid is a separately allocable item to the individual partners, so the net effect is the same, which begs the question, then why pay tax at the entity level. Originally pass-through entity tax (PTET) laws came about as a workaround for the state and local tax (SALT) limitations imposed by the Tax Cut and Jobs Act of 2017 (TCJA). Recall the TCJA limits deductions of state and local taxes to ten thousand ($10,000) annually, but taxes paid y an entity are business expenses, not subject to the 10K cap. There are two potential drawbacks of PTET. First, not all states give their residents credit for PTET paid in other states. Second, in some states, PTET is paid at a state’s top marginal rate (or more), so the advantage may be illusory at best. But let me suggest an additional aspect of PTET – asset protection. In the traditional model, a partnership would, at a minimum, make distributions to its partners to cover the taxes for the income allocated to each partner. Within the partnership, and here we are talking about a limited liability company taxed as a partnership, not a true general partnership, assets held within the LLC are beyond the reach of an individual partner’s creditors. However, when a tax distribution is made, the funds out of the LLC and into the individual partners’ bank accounts where the funds then become subject to set-off by the bank, garnishment by a judgment-creditor, withdrawal by a joint account holder, not to mention subject to the joint account holder’s judgment creditors, or, in extreme cases, prejudgment attachment. Depending on the amount of income allocated to a partner, the tax distribution could be substantial. Imagine the disgruntled, secretly planning to separate spouse who waits until the tax deposit is made to drain the joint bank account, leaving the partner/member without immediate liquid assets with which to pay tax liabilities. On the other hand, if the entity elects PTET, then the funds never leave the entity and are paid by the entity directly to the relevant tax authorities and the tax paid is allocated to the individual members/partners as though the tax distribution had been made to them and they, in turn, paid their respective tax obligations. No doubt, neither the North Carolina General Assembly nor any other state legislative body that enacted a PTET did it for asset protection purposes, but every now and then, life has its little bonuses. Scott Tippett is a member of Offit Kurman, where he focuses his practice on business and tax planning. Offit Kurman counsels business owners on strategic business, tax, and risk management techniques. The views expressed herein are solely those of the author’s and do not constitute and are not intended as legal or tax advice.
June 16, 2022
Tax
Excess Compensation and Disguised Dividends – Take Care and Beware!
Yesterday I wrote about a case involving constructive dividends. Today it is disguised dividends. The issue in Clary Hood, Inc. v. Comm.,T.C. Memo. 2022-15, was whether the salary and bonus paid to the company’s president (Mr. Hood) was excessive under IRC 162(a)(1) and was therefore a disguised dividend. Recall that compensation, if reasonable and not excessive, is a deductible business expense for the company, but dividends are not. In this case the company was a C-corporation, which, because of the double layer of taxation (first at the corporate level, then again at the shareholder and employee level), had every incentive to characterize the payment as compensation, not as a dividend. The company’s story is the great American success story, and the opinion is well worth the read for this story alone. Starting with little money and used equipment in 1980, the company, largely through the efforts of Mr. Hood, who, together with his wife owned all the stock and were the only directors of the company, became a multimillion-dollar company by 2016 with revenues in excess of 60 million dollars. Along the way Mr. Hood did what many small business owners do when starting out – he often did not draw a salary, so the business had enough money to pay its other employees and creditors. When things finally began to turn around, Mr. Hood and his wife, as the company’s directors, decided to pay a bonus to Mr. Hood in the company’s 2015 and 2016 fiscal years. For the 2015 bonus, the company engaged its outside accountants to perform a salary survey. Based on the accountants’ recommendations, the company paid Mr. Hood a bonus of 5 million dollars in 2015. The company paid Mr. Hood the same bonus in 2016 but did so without engaging the company’s accountants to perform another salary survey. Without going through the math, the difference in the Hoods’ pocket between the company declaring and paying a dividend to the Hoods for 5 million (not deductible by the company) or paying the Hoods a 5 million bonus (deductible by the company) was about one million dollars. The substantial increase on Line 12 of the company’s return caught the watchful eye of the Service. Audits and notices of deficiencies promptly followed, including accuracy related penalties under 6662 for substantial understatement of income. The company put on several experts to demonstrate Mr. Hood’s bonus was calculated reasonably and the Service put on one expert. Based on deficiencies in their reports, the Tax Court placed little value in the company’s experts. On the other hand, the Service’s expert’s report did not have the same deficiencies and the Tax Court found that expert (who concluded Mr. Hood’s bonus was excessive) credible. The Tax Court determined reasonable compensation for Mr. Hood was $3,681,269 for tax year 2015 and $1,362,831 for tax year 2016. Further the Tax Court abated the substantial understatement penalty for 2015, based on the company’s engagement of and reliance upon its outside accountants, but did not waive the penalty for 2016 because the company essentially relied on the 2015 accountant report and performed no new study. Among the issues the Tax Court considered in ruling the bonus was excessive and therefore a disguised dividend, were the following: (1) Mr. Hood had no employment contract with his company; (2) other company executives did not receive bonuses comparable to Mr. Hood’s bonus and the company had no policy in place for setting non-shareholder employee compensation; (3) Mr. and Mrs. Hood were the sole shareholders and sole directors of the company, who, as such, had sole authority to review and approve the bonus amount; and (4) in its entire history, the company had never paid a dividend to its shareholders. Although every tax case is highly fact specific, things the company and Mr. Hood could have done differently that might have affected the outcome include: (1) had a written employment agreement with Mr. Hood specifying how salary and bonuses would be determined; (2) had a written compensation and bonus eligibility policy for all employees (and followed it); (3) had outside directors and perhaps even an independent compensation committee that reported to the board; (4) had a history of paying some dividends as approved by the board of directors. For practitioners, this case has an excellent discussion of the “independent investor” test versus the “multi-factor” test for excessive compensation. It also provides a detailed road map for what expert reports should include to be deemed credible. Offit Kurman counsels business owners on strategic business, tax, and risk management techniques, including the design and implementation of executive compensation packages. The views expressed herein are solely those of the author’s and do not constitute and are not intended as legal or tax advice.
March 11, 2022
Tax
S-Elections Gone Wrong
The IRS just released four separate Private Letter Rulings (“PLRs”) addressing the inadvertent termination of a taxpayer’s S-election. It is often said the devil is in the details, which is demonstrated aptly by these four PLRs. Fortunately for the taxpayer, in each case the Service found that the terminations were inadvertent, which means the taxpayer was allowed to correct the issues and be treated as though the S-election was never terminated, likely saving the taxpayer untold thousands of dollars in taxes, penalties, and interest. Although PLRs may be relied upon only by the taxpayer who obtained the PLR and may not be cited by other taxpayers in similar positions, PLRs reveal how the IRS approaches certain issues, in this case inadvertent termination of S-elections. Recall, a small business entity (100 or fewer equity owners) may elect to have the entity taxed as a S-corporation, rather than the default classification of partnership, corporation (meaning C-corporation), or disregarded entity). Depending on the revenue flow, it is often advantageous for a limited liability company (“LLC”) that would otherwise be taxed as a partnership or disregarded entity to elect to be taxed a S-corporation. This would permit the entity to receive the asset benefits of being structured as a LLC, and receive the tax benefits of being taxed as a S-corporation. Similarly, small businesses that are set up as corporations may wish to be taxed as S-corporations, not C-corporations, which is the default classification assigned by the Service (C-corporations have two layers of tax-one at the corporate level and one at the shareholder level, while S-corporations have just one level of tax-the shareholder level). In either case, the taxpayer and the taxpayer’s owners must qualify and make an affirmative election by filing certain forms in a timely manner with the Service. In PLR 2022090001 the taxpayer was a corporation that converted to a LLC, but failed to read or did not understand the operating agreement it adopted. This happens with some regularity, typically with DIY entities or when done by an advisor who simply relies on “a form” operating agreement without reading or understanding the tax provisions contained in the operating agreement. In this case the taxpayer’s operating agreement was one designed for a LLC taxed as a partnership, the provisions of which created interests with different rights, which violated the single class of stock rule applicable to all entities taxed as S-corporations (a S-corporation may only have one class of stock so every owner has the same dividend and liquidation rights. Non-voting shares are permitted if the non-voting shares have the same dividend and liquidation rights). The Service noted the operating agreement “included provisions in contemplation of Company being treated as a partnership for federal income tax purposes (inclusion of capital account rules under Treas. Reg. § 1.704(1)(b))(analysis supplied); however, the applicability of those provisions was not limited to such a situation…,” meaning that even though the entity was not seeking to be taxed as a partnership, it could under its operating agreement. In this case the taxpayer failed to make sure the operating agreement was drafted correctly for an entity to be taxed as a S-corporation (failure to remove the capital account provisions among other things). PLRs 202209003 and 202209005 each concerned trusts as owners of S-corporation stock that failed to make appropriate and timely elections. Only certain types of trusts may be S-corporation shareholders, and one of the steps a trust must take to be an eligible shareholder include making the affirmative election to be an electing small business trust (ESBT) under the requirements set forth in IRC § 1361(e). In PLR 2022090003, the trust at issue failed to do that. Similarly, in PLR 2022090005, the trust qualified as an ESBT within the meaning of § 1361(e), but the trustee failed to make an election under § 1361(e)(3) to treat the trust as an ESBT. In other words, make sure you dot your “I” and cross your “T.” Finally, PLR 2022090010, which also involved a LLC that sought to be taxed as a S-corporation, the entity’s owner (there was only one) failed to sign the required consent to be taxed as a S-corporation. As noted above, to be taxed as a S-corporation the entity and its owners must make an affirmative election to be taxed as a S-corporation. Here it appears the entity signed and timely submitted the requisite consent to the Service, but the entity’s owner failed to sign the consent. Although PLRs never mention specific dates actions were taken, it is possible that the S-election was submitted near the end of the allotted time for making the election so by the time the taxpayer became aware of the oversight the time for electing S-corporation treatment for that tax year had passed. PLRs are highly fact specific, and there is no assurance the Service would come to a taxpayer friendly resolution in a different case. To avoid making similar mistakes, business owners should make sure their business advisors understand the tax ramifications of the business documents being used, and are aware of the steps that must be taken and the time for taking those steps for the entity to make a valid S-election. Offit Kurman counsels business owners on strategic business, tax, and risk management techniques, including the design and implementation of executive compensation packages. The views expressed herein are solely those of the author’s and do not constitute and are not intended as legal or tax advice.
March 10, 2022
Tax
Ipads, iPhones, and Barter Transactions
From the hardly noticed case of Sherwin Community Painters, Inc. v. Commissioner, T.C. Memo. 2022-19, come some interesting tidbits. First, just the facts. Sherwin Community Painters, Inc. is a C-corporation with a single shareholder. As its name implies, Sherwin was a painting contractor. The case arose from the Service’s disallowance of certain business deductions claimed by Sherwin and the Service’s attempt to characterize the disallowed deductions as a constructive dividend. The Service also asserted accuracy related penalties against both taxpayers under IRC 6662(a) and a late filing penalty against the shareholder under IRC 6651(a)(1). All issues were limited to the taypayers’ 2016 tax year and returns for that year. Among the deductions Sherwin claimed were deductions for office equipment (iPads, iPhones, a speaker, accessories, and service contacts), office supplies, gas, entertainment (remember this was 2016 and entertainment expenses were deductible back then), and a business deduction for a coding course the company paid for that was taken by the shareholder’s soon to be son-in-law. After the coding course the soon to be son-in-law, using the skills acquired in the course, updated Sherwin’s website and made numerous changes to the website. PSA No.1 – File a timely request for an extension. The shareholder’s 2016 return was filed on October 12, 2017, three days before the automatic extension deadline of October 15, 2017 (actually four days because that year October 15th fell on a Sunday). Had the taxpayer timely filed an extension for the 2016 return, with the extension the return would have been timely filed and no late filing penalty would have been asserted. PSA No.2 – iPads, iPhones, speakers, and accessories are deductible provided they are ordinary and necessary under IRC 162(a). The Tax Court wasted little time in allowing this deduction noting the taxpayer properly substantiated the deduction. PSA No. 3 – Document your barter transactions! Sherwin argued that its tuition payment to the educational institution for the coding course was essentially a barter transaction in exchange for website design services. The Tax Court did not dispute Sherwin’s assertion that the soon to be son-in-law performed web design services, but did take issue with the lack of any documentation. The Court noted the soon to be son-in-law was not an employee of Sherwin and there was no agreement that the web design services were in consideration of payment of the tuition. It seems Sherwin was arguing an after-the-fact quid pro quo. Had Sherwin documented (in writing) the arrangement contemporaneously, that deduction would probably have been allowed. Finally, the Service attempted to argue the disallowed deductions were constructive dividends to the shareholder, which if true, would have been includible in the shareholder’s gross income under IRC 61(a)(7). Apparently the Service thought Sherwin made a loan to the shareholder and this was the basis for its constructive dividend claim. The records showed just the reverse-a loan from the shareholder to Sherwin. Refusing to give up the constructive dividend claim, the Service then argued the disallowed business expenses were a constructive dividend. You can almost see the Court scratching its head looking at counsel for the Service and saying “REALLY!?” Noting “Respondent [IRS] refuses to concede his error and instead argues on brief that the disallowed business expenses should be treated as a constructive dividend,” the Court held there was no relation between disallowed business expenses and a constructive dividend. All taxpayers should make sure they file an extension request in a timely manner to avoid a late filing penalty. All business owners should make sure expenses they deduct are ordinary and necessary, and are properly substantiated in case those expenses are later challenged. Finally, in the gig economy barter transactions have become more prevalent. To make sure businesses can deduct these expenses, businesses need to be sure to document such arrangements in writing, contemporaneously. Offit Kurman counsels business owners on strategic business, tax, and risk management techniques, including the design and implementation of executive compensation packages. The views expressed herein are solely those of the author’s and do not constitute and are not intended as legal or tax advice.
March 10, 2022
