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Archive for May, 2012

Section 6663 imposes a 75% penalty in the event that any portion of a tax underpayment is attributable to fraud. The problem, of course, is that an allegation of fraud speaks to a taxpayers’ intent, which as you might imagine can be a rather difficult thing to establish. That’s not to say that fraud can’t be proven, however, because like pornography or the infield fly rule, while we may not be able to define it,  we typically know it when we see it.

And the Tax Court certainly saw it today, assessing fraud penalties against a corporation and its sole shareholder. Earlier this week, we warned against using a corporation as an incorporated pocketbook, but this is precisely what Gary Garcia did. When revenue came into his wholly-owned airplane repair company, he redirected many of the funds to pay his personal expenses, including his home mortgage. Making matters worse, the funds were paid out of a bank account that was hidden from his CPA.

Over time, the IRS came calling, and Garcia again neglected to turn over detail of the corporation’s secret account. Unfortunately for Gary, the IRS —  as opposed to your run-of-the-mill CPA – has the power to issue a summons to a bank requesting all of a taxpayer’s data, and the Service did just that, bringing to light Garcia’s shenanigans.

While Garcia eventually conceded to the additions to tax at both the corporate and personal level — for under-reported corporate income and  the assessment of constructive dividend income on his individual return —  he fought the imposition of the fraud penalty.

As part of his argument, Garcia maintained that he did not act fraudulently because he relied in good faith on his accountant to prepare his personal return. This is relevant because prior decisions have established that a taxpayer’s justifiable reliance on an accountant to prepare income tax returns may indicate an absence of fraudulent intent.[i]

There was just one small hole in Garcia’s argument: you cannot rely on the fact that a CPA prepared your returns if you concealed the information necessary for your accountant to prepare an accurate tax return. In fact, the purposeful suppression of relevant tax information works the other way; it is evidence of a taxpayer’s intent to conceal and deceive, one of the major indicia of fraud.

The lesson? Be honest with your tax preparer. Give them all of the information necessary to file a complete return, and if they screw up or do something unethical, while an increased tax liability may be coming your way, at least you won’t be stuck with a 75% fraud penalty, like poor Gary Garcia.


[i] Marinzulich v. Commissioner, 31 T.C. 487 (1958).

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As you may have heard several thousand times over the past few years, President Obama would really like to see the Bush tax cuts expire at the end of the year for America’s wealthiest taxpayers, arbitrarily identified as those with taxable income in excess of $250,000. Should this occur, the top two tax rates for those above the threshold would return from the present-day 33 and 35% to 36 and 39.6%. The current rates for those earning less than $250,000 would remain at 10, 15, 25 and 28%.  

Two weeks ago, House Democratic Leader Nancy Pelosi made news by deviating from the President’s plan, arguing that the Bush tax cuts should be extended for all taxpayers earning less than $1,000,000, a threshold four times larger than Obama’s proposed cutoff.

One would have to think that Pelosi’s proposal is a bit of election-year gamesmanship. Democrats have long maintained that the reticence of their Republican counterparts to allow the Bush cuts to expire has far more to do with protecting the tax rates of the nation’s wealthy than it does a desire to reduce the deficit. By raising the cutoff for the expiration of the reduced rates from $250,000 to $1,000,000, Pelosi likely believes she can back Republicans into a corner: if they still refuse to embrace the cuts at the higher level, Pelosi and other Dems will paint their counterparts as aligning with the nation’s millionaires at the risk of punishing the middle class.  

To the surprise of no one, Pelosi’s plan was largely panned within her own party, with many Democrats claiming her plan would raise far less revenue than the Obama proposal, while also representing a windfall for many households earning $1 million, because they would get the benefit of reduced graduated rates on their income up to $1 million.

Today, the Joint Committee of Taxation got around to putting pencil to paper, and whether or not they validated the concerns of Pelosi’s party-mates depends on your materiality level and how you define “far less” when looking at the deficit. According to the report, which was released by the Center on Budget and Policy Priorities but credited to the Joint Committee, quadrupling the income threshold marking the expiration of the Bush tax cuts from $250,000 to $1,000,000 would raise only $463 billion over 10 years rather than $829 billion.

That sounds like a hefty difference, but then again, to put it in perspective, by merely extending the 2% payroll tax reduction through 2012, Congress was willing to tack $100 billion on to the deficit. So who knows: perhaps those in Congress would view sacrificing $360 million over 10 years in order to avoid the expiration of the Bush tax cuts for all taxpayers as money well spent.

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On Tuesday, the IRS issued proposed regulations that would clarify some key points under I.R.C. § 83 that could affect many taxpayers. As we like to do around here, we’ve summarized the proposed regulations in the ever-popular Q&A format:

Q: What’s the point of I.R.C. § 83?

A: We’ve discussed I.R.C. § 83 before, but allow me to provide a refresher:

If you provide services for someone and get paid in cash, that’s taxable income upon receipt, agreed?

But what if you were paid in property instead, like stock? That should also be taxable to the extent of the value of the property, since it remains remuneration for services, correct?

Continuing along that line of thinking, what if you’re paid in property, but you might have to give that property back in the future if you don’t continue to provide additional services or meet some other condition AND  you can’t transfer the property to someone else? In that case, it would seem rather unfair to tax you on the value of the property since it may not remain yours and you can’t even get rid of it.

This is precisely the purpose of I.R.C. § 83, to make sure that when someone who has provided services in the past, or will do so currently or in the future, but is paid in property rather than cash recognizes taxable income on the property received when the time is right.

Q: OK, so when is the time right?

A: With a few exceptions here and there, any property received by a service provider for the provision of past, current, or future services is taxable when EITHER of the following conditions are met:[i]

1. the property is not subject to a substantial risk of forfeiture, or

2. the property is freely transferable.

This is a concept that confuses many tax advisers. Property must be subject to BOTH conditions in order for the recipient to defer the recognition of taxable income. The moment the property either becomes transferable or no longer subject to a substantial risk of forfeiture, the recipient must recognize taxable income.

Q: What is the amount and character of the income?

A: In the year that the property first becomes EITHER freely transferable or no longer subject to a substantial risk of forfeiture, the recipient must recognize taxable income equal to the excess of the FMV of the property at that time over any amount paid by the recipient for the property. The excess is taxed as compensation, resulting in ordinary income to the recipient.

Ex: A provides services to X Co. X Co. gives A stock worth $200 in year 1, but the stock is not freely transferable by A, and A must continue to work for X Co. until year 3 in order to retain the stock. In year 3, when A “vests” in the stock, it is worth $400. A must recognize $400 of ordinary income in year 3. [ii]

Q: Alright, that makes sense…but when is property subject to a substantial risk of forfeiture?

A: That’s where the proposed regulations come in. There had been some confusion as to what types of restrictions created a “substantial risk of forfeiture” worthy of deferring income recognition.

In general, the regulations had provided that a substantial risk of forfeiture exists where the recipient’s rights to the property were conditioned  upon the future performance (or refraining from performance) of substantial services, or the occurrence of a condition related to a purpose of the transfer, such as the issuer of the property maintaining certain income or revenue levels.

The IRS found that taxpayers were looking to other conditions not contained in the preceding paragraphs as justification for deferral; as a result, the proposed regulations clarify that a substantial risk of forfeiture exists ONLY where there is a service condition present, or another condition related to the purpose of the transfer.

Q: You lost me on the “condition related to the purpose of the transfer” part. Can you explain?

A: Say your employer hires you and gives you stock. The stock is nontransferable, and in order to keep it, the employer’s revenue must remain at 90% of what it was prior to the issuance for the next three years. This type of restriction may qualify as a substantial risk of forfeiture.

Before that determination can be made, however, the proposed regulations clarify that consideration must be given to how likely it is that the condition would not be met. If in the example above, the employer was an established seller of a product and there was no reason to believe revenues would dip, the IRS takes the position that the unlikelihood of having to surrender the stock must be taken into consideration, and thus the condition should not constitute a substantial risk of forfeiture. As a result, the stock would be taxable upon issuance.

Q: OK, I’ve got the “substantial risk of forfeiture part” down. What about transferability restrictions?

A: The proposed regs will clarify a common misconception: transfer restrictions do NOT create a substantial risk of forfeiture. Why is that important? Because of property is not transferable but has no other elements of a substantial risk of forfeiture, then both factors necessary for deferral are not present, and the recipient must recognize income upon issuance, even though the property is not transferable.

Q: What about stock that is not transferable under SEC law, like Rule 144 or Section 16(b)?

A: Great question. Section 83(c) and Rev. Ruling 2005-48 have made clear that the only provision of the securities law that would delay taxation under I.R.C. § 83 is section 16(b) of the SEC law. See Treas. Reg. §1.83-3(j) for more.

Q: You’ve done a thorough and all-around excellent job. One last question: When are these proposed regs effective?

A: You’re too kind. The regulations are proposed to apply as of January 1, 2013, and will apply to property transferred after that date.


[i] Treas. Reg. §1.83-3(b).

[ii] Barring a I.R.C. § 83(b) election.

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Any tax adviser who has ever been saddled with the unenviable task of reporting a client’s charitable contribution of real estate knows that it’s a colossal pain in the ass. The rules of I.R.C. § 170 and the related regulations contain numerous substantiation requirements for contributions of property with value in excess of $5,000, including the need for a qualified appraisal that must be attached to the return containing the contribution. The “qualified appraisal,” in turn, comes with its own lengthy set of requirements, ranging from who can be considered a “qualified appraiser” to a laundry list of information that must be contained within the report. These onerous substantiation requirements have left some tax advisers pondering whether the IRS is actually trying to discourage charitable giving.

Expect that sentiment to reach well beyond the tax world when word leaks out about the Tax Court’s decision today in Mohamed v. Commissioner, T.C. Memo 2012-152. In Mohamed, a prominent California entrepreneur and philanthropist who everyone seems to concede contributed over $18,000,000 in real estate to qualified charities, received zero charitable contribution deduction because of his failure to comply with the substantiation requirements of Treas. Reg. §1.170-13.

Joseph Mohamed made his millions in real estate; as a broker and certified appraiser, he amassed a fortune in real property. Mohamed and his wife wanted to share their considerable wealth, so they established a charitable remainder unitrust  — or CRUT — to facilitate the transfer of some of their properties to charitable organizations.

During 2003 and 2004, Mohamed donated six properties to his CRUT, claiming $4.2 million in charitable contribution deductions, with another $15 million limited by AGI and carried forward to future years.

Mohamed is a bright guy with one fatal flaw: he ventured to prepare his own tax return. In doing so, he filled out Form 8283 — Noncash Charitable Contributions — without reading the instructions, because it “seemed so clear that he didn’t think he needed to.” This would prove to be a costly mistake.

Before we go any further, a quick primer on the specific substantiation requirements for property contributions in excess of $5,000 is in order. These requirements are found in Treas. Reg. §1.170-13.

  • A qualified appraisal must be made not more than 60 days before the gift and no later than the due date of the return;
  • It must be signed by a qualified appraiser, who cannot be the donor or taxpayer claiming the deduction or the donee of the property.
  • The qualified appraisal must contain scores of information required by the regulations, including a description of the property, the basis of the property, and the appraised FMV of the property.

Having read neither the regulations nor the form instructions, Mohammed knew not of these requirements. Instead, he took a rational approach when completing Form 8283: he was a real estate appraiser, he knew the value of the contributed properties, so he filled out the form with the information as he saw it. As a result, Mohamed failed to comply with the regulations in the following ways:

  • He didn’t obtain an independent appraisal. Instead, he appraised the properties himself, a direct violation of the regulations;
  • He did not sign the Declaration of Appraiser (because Form 8283 indicated he could not since he was the donor, which should have tipped him off to larger problems);
  • He attached statements to the return that failed to contain much of  the required information concerning the properties, including basis of the contributed properties and their manner of acquisition.

The IRS began auditing Mohamed in 2005, and sought to strike down the full amount of his charitable contribution deductions . To combat the IRS scrutiny, Mohamed obtained an independent appraisal in 2005, which verified that the values actually exceeded the amounts claimed on the return. Undeterred, the IRS then  shifted its attack to the substantiation requirements, arguing that since Mohamed failed to satisfy the rules of Treas. Reg. §1.170-13, the deductions must be denied in full.

In his defense, Mohamed posed three argument:

1. That the I.R.C. § 170 regulations were invalid,

2. That he substantially complied with the substantiation requirements, or

3. That Form 8283 was not adequate in advising taxpayers of the substantiation requirements.

The Tax Court quickly dismissed arguments 1 and 3, holding that the regulations were indeed valid, and that while Form 8823 may be confusing, the ultimate sources of law are the statute, regulations, and judicial decisions and not the form instructions.

As a result, the Tax Court was left to decide whether Mohamed substantially complied with the substantiation regulations; in other words, did he do enough to justify a deduction even in the absence of meeting the formal requirements of Treas. Reg. §1.170-13?

Ultimately, while conceding that the ruling was extremely harsh, the Tax Court disallowed all of Mohamed’s charitable contribution deductions, holding that he failed to substantially comply with the regulations, as he made the following fatal mistakes:

  • He failed to comply with the “essential requirement” of obtaining a qualified appraisal,
  • He failed to qualify as a qualified appraiser, since he was both the donor and donee;
  • His attachments to Form 8283 lacked detailed information to put the IRS on notice of the nature of the donation;  
  • He didn’t sign his statements or indicate the method for computing the valuations;
  • The appraisals by the independent appraiser were performed more than a year and a half after the required due dates, and thus could not be “qualified appraisals.”

There are two lessons of note here: First and foremost, this is a cruel reminder that good intentions do not guarantee tax deductions. You must comply with any substantiation requirements, onerous and unnecessary as they may seem. The IRS and Tax Court both conceded that Mohamed made a deduction of eligible property to a qualified organization, and in fact may have understated the properties’ values, but failure to follow the substantiation rules doomed his entire deduction.

Secondly, no matter how smart you fancy yourself, hire a tax preparer. I’ve met some bad preparers in my day, but there’s nary a one who would claim a $19 million charitable deduction without making sure the required i’s were dotted and t’s crossed. The tax rules are too complicated for those outside the industry to fully grasp; do yourself a favor and get some professional help.

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Late last week, the IRS announced that it will be publishing Revenue Ruling 2012-14, which will provide guidance for determining the amount of a partnership’s nonrecourse liabilities a partner is permitted to include in his measurement of insolvency for purposes of applying the exception to cancellation of indebtedness income found at I.R.C. § 108(a)(1)(B).

That’s quite the mouthful, so let’s break it down into more easily digestible parts so we can understand why Revenue Ruling 2012-14 may be important:

  • Section 61(a)(12) provides that gross income includes income from the discharge of indebtedness. This is a natural and logical result, because being forgiven of a debt is an accession to wealth; if someone loans you $100 and you don’t pay it back, you’re $100 richer and should therefore recognize taxable income. As the economy and real estate values have tanked in the past few years, many taxpayers have been unable to service their loans or mortgages, bringing the COD rules to the forefront of the tax law.
  • Section 108(a)(1)(B) provides an exclusion to the general rule found in I.R.C. § 61, generally excluding discharged indebtedness from a taxpayer’s gross income if the discharge occurs when the taxpayer is insolvent. Section 108(a)(3) limits the amount of income excluded by reason of I.R.C. § 108(a)(1)(B) to the amount by which the taxpayer is insolvent.

What’s the point of the insolvency exclusion? Believe it or not, Congress can, at times, be rational. If a taxpayer cannot service his debt, it seems rather silly to tack on a tax bill for the amount of any forgiven loans. A taxpayer who owes more than they own should be given the opportunity to receive a “fresh start;” one that wouldn’t be possible if the forgiven debt was included in taxable income. Of course, that only makes sense if the taxpayer is insolvent at the time of the debt discharge. If the taxpayer is solvent, they presumably would have the ability to pay the tax associated with the debt discharge.

  • Section 108(d)(3) of the Code defines “insolvent” as the excess of liabilities over the fair market value of assets. That section further provides that whether a taxpayer is insolvent, and the amount by which the taxpayer is insolvent, is determined on the basis of the taxpayer’s assets and liabilities immediately before the discharge.
  • Unfortunately, nowhere does I.R.C. § 108 actually define the term “liabilities,” causing a bit of confusion when trying to determine whether a taxpayer who has benefitted from the cancellation of indebtedness is in fact insolvent.
  • Confusing matters even more, while C and S corporations must determine insolvency at the entity level, forgiven partnership debt doesn’t work that way. Instead, the partnership recognizes the COD, and any exclusion, including the insolvency exclusion, must be determined at the partner level. This means that the determination of insolvency must also be determined at the partners level when partnership debt is forgiven.

Combine all of these bullets, and a natural question arises: how does a partner in a partnership account for the partnership’s liabilities in determining whether their individual liabilities exceed the FMV of their assets, making them insolvent?

Keep in mind, a partnership can have two types of liabilities, recourse and nonrecourse. Recourse liabilities are those that one or more partners is personally liable for, and the responsible partner should certainly include his share of the partnership’s recourse liabilities in the computation of his insolvency in the event a partnership debt is forgiven.

But what about nonrecourse debt? Nonrecourse debt, as opposed to recourse debt, is a partnership liability for which no partner is personally liable. In other words, if the partnership fails to pay the debt, tough luck for the lender. Nonrecourse debt is most commonly seen as a mortgage: the lender retains the right only to foreclose on the mortgaged property; they cannot pursue the partnership for any deficiency in the event the FMV of the nonrecourse debt plummets below the principal balance of the debt.

So if a partnership has nonrecourse debt forgiven, are the partners entitled to include any portion of the nonrecourse debt in their individual computations of insolvency?

The answer, according to Revenue Ruling 2012-14, is yes. Building on the principles established in Rev. Ruling. 92-53, the IRS held that a partner may include two pieces of a partnership nonrecourse debt in their individual computation of insolvency:

1) the amount of the debt equal to the FMV of the property (meaning it’s a wash from an insolvency standpoint), and

2) any debt in excess of the FMV of the property, but only to the extent it is forgiven, and the income resulting from the forgiveness is allocated to that partner.

The specific fact pattern in the ruling is as follows:

X and Holdco, a corporation, are equal partners in PRS, a partnership. In Year 1, PRS borrows $1,000,000 from Bank and signs a note payable to Bank for $1,000,000 that bears interest at a fixed market rate payable annually. The note is secured by real estate valued in excess of $1,000,000 that PRS acquires from Seller, in part with the proceeds of the note. The note is a nonrecourse liability within the meaning of § 1.752-1(a)(2) of the Income Tax Regulations. Neither PRS nor its partners (X and Holdco) are personally liable on the note. 

In Year 2, when the value of the real estate is $800,000 and the outstanding principal on the note is $1,000,000, Bank agrees to modify the terms of the note by reducing the note’s principal amount to $825,000. The PRS partnership agreement provides for income to be allocated equally to X and Holdco under § 704(b) and the regulations thereunder. X and Holdco share PRS nonrecourse liabilities equally under § 1.752-3. At the time of the modification of the note, X and Holdco have no assets or liabilities other than their partnership interests in PRS. PRS’s sole asset is the real estate subject to the note, and PRS’s sole liability is the note.

The IRS held that of the $1,000,000 note, X and Holdco may each consider the following portion of the liability as part of their liabilities for purposes of measuring insolvency:

 1. 50% of the $800,000 balance of the note equal to the FMV of the asset, or $400,000 each, and

2. The portion of the debt in excess of FMV that was forgiven, but only to the extent the COD income was allocated to X and Holdco, or 50% * $175,000 = $87,500 

Thus, for both X and Holdco, in computing each partner’s insolvency, they may include $487,500 of partnership liabilities, and $400,000 of FMV from the partnership (each partner’s share of the asset.)

As a result, both X and Holdco are insolvent to the extent of $87,500, and each may exclude the $87,500 of COD allocated to them from PRS under I.R.C. § 108(a)(1)(B).

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A few things you may have missed over the three (four?) day weekend:

Now that most of America is suing Mark Zuckerberg, Robert Wood at Forbes discusses the resulting tax implications — specifically, capital gain versus ordinary income — of any settlement or judgment proceeds should the plaintiffs’ win.

Kelly Erb Phillips has the solution to that whole  “illegal aliens claiming billions in illegitimate tax refunds” problem. Spoiler: it does not involve a giant electrified fence on the southern border of Texas and Arizona.

House Democtratic leader Nancy Pelosi wants the Bush tax cuts to disappear, but only for taxpayers earning more than $1,000,000.

Former Eagle, Giant William James earned $9.2 million over 5 years, but failed to file tax returns. If he’s smart, he’ll hop on the current sympathy train and claim concussion-like symptoms caused his annual tax filing to slip his mind.

Finally: Best. Catch. Ever.

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As tax advisers, one of the more difficult hurdles we face is convincing clients not to turn their closely-held corporations into incorporated pocketbooks. The temptation is strong for shareholders to use their corporations to pay all expenses, whether they be legitimate expenses of the business or — as is often the case — their own personal expenses.

We face an uphill battle communicating the perils of such a philosophy for one simple reason: because the odds of an audit are so remote, many corporations get away with paying the personal expenses of its owner. The owners of these corporations then invariably head off to the gym or golf course or strip club and brag to other business owners about their “tax deductible personal expenses,” which in turn causes those business owners — our clients — to pick up the phone and ask us why they aren’t getting the same tax benefits.

The reason, of course, is an obvious one. Just because an expense is incurred in a separate legal entity — like a corporation or partnership — doesn’t make it a de facto “business expense.”  For example, expenses incurred by a business for a car, plane or rent that would be personal in nature if paid by an individual don’t suddenly become business expenses when the underlying asset or expense is dumped inside a corporation.

But don’t take my word for it. If you need to scare a client straight, just show them D’Errico v. Commissioner, T.C. Memo 2012-149.

In D’Errico, Joseph D’Errico was the sole shareholder of TPM, a C corporation that provided management services to D’Errico’s wholly-owned tax preparation firms.  D’Errico ran just about every expense he could through the corporation, inviting scrutiny from the IRS that ultimately resulted in the assessment of some heavy tax deficiencies.

What follows is a discussion of just two of the many expenses denied by the Tax Court as personal, highlighted here because they are common areas of abuse.

Rent

TPM entered into a lease with D’Errico’s father for the use of his personal residence. In turn, TPM subleased a portion of the residence to D’Errico for his personal use. Neither the lease nor the sublease identified what portion of the property would be used by TPM for business purposes or what portion would be used by D’Errico’ personally. TPM deducted the rent expense paid to D’Errico’s father on its corporate tax return.

The IRS argued that TPM did not use the residence for business purposes. The Tax Court agreed, holding that TPM failed to prove its entitlement to deductions for the rent expenses:

Although TPM admits part of the Barton Drive home was used for Mr. D’Errico’s personal purposes, it contends that a larger portion of the home was used for business purposes. TPM failed to produce records of any business activity it performed at the property. We also note that the Barton Drive home was approximately 400 miles from Mr. D’Errico’s primary places of employment in southern California during those tax years. Considering the evidence presented, we find TPM has failed to establish that it conducted business-related activities at the Barton Drive home, and we sustain respondent’s determination disallowing deduction of the rent expenses by TPM.

 Airplane

TPM also purchased a Cessna airplane.  D’Errico had a pilot’s license and several years of flight training at the time TPM purchased the airplane, and he testified that TPM purchased the airplane in order for him to travel quickly between TPM’s purported office in Nevada and his two active tax preparation corporations which were in southern California (a commute of approximately 400 miles).

TPM also entered into a lease agreement whereby it would rent the plane for up to 75 hours a month. The purpose of the arrangement, according to the lease, was to allow TPM to generate revenue to offset some of the plane’s costs.

On its corporate tax return, TPM deducted  airplane operating expenses and depreciation. Again, the IRS argued that the airplane was not used for business purposes, and thus the related expenses were not ordinary and necessary business expenses deductible under I.R.C. § 162. And again, the Tax Court agreed:

…At the time TPM purchased the airplane, D’Errico knew that he was going to be selling [the tax preparation firms.] The only business-related use of the airplane shown by petitioners was Mr. D’Errico’s use of the airplane to travel to southern California in December 2004 to speak with the parties buying D’Errico & McCollor and D’Errico & Wedge. TPM has produced no evidence that the airplane was used in TPM’s tax management business after 2004.

D’Errico also testified that TPM entered “the business of renting * * * [the airplane] out”. To determine whether a taxpayer is conducting a trade or business requires an examination of the facts of each case. For a taxpayer to be engaged in a trade or business, the primary purpose for engaging in the activity must be for income or profit. However, a mere hope that an activity will generate profits, in the absence of any specific plan to generate a profit, is inconsistent with an allegation that the belief is in good faith. TPM has not proven that it entered into the lease agreement with Flying Start Aero with the primary purpose of making a profit. Indeed, the lease agreement itself stated that TPM was entering the agreement “with the intention of generating some revenue for the purpose of offsetting a portion of the aircraft operating costs”. The Court of Appeals for the Ninth Circuit (to which this case is appealable) has held that a profit motive does not exist where “activities represented mere attempts torecoup some of * * * [the taxpayers’] costs.” We therefore find that TPM was not engaged in the trade or business of renting out the airplane.

To make matters worse, when a shareholder’s personal expenses are paid by a corporation, the tax hit is doubly painful. Not only are the expenses disallowed at the corporate level — as they were to TPM — but the expenses are typicallly treated as constructive distributions to the shareholders, which they were in D’Errico’s case. When these constructive dividends are deemed made by a C corporation, they result in dividend income to the shareholder to the extent of any corporate earnings and profits. .

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[Ed note: I'm aware that we planned to publish a video blog every Friday morning, but since we don't expect many people to be working tomorrow, we've moved it up a day.]

Last week our video blog (or “vlog,” as one of my hip co-workers clarified the lexicon for me) focused on Situation 1 of Revenue Ruling 99-6, which provides the tax consequences upon the conversion of a multi-member partnership into a single member LLC disregarded as separate from its owner. Specifically, Situation 1 dealt with a fact pattern where one partner purchased the interests from the remaining partners, converting the partnership into a SMLLC. 

Today we take on Situation 2 of Revenue Ruling 99-6, which again deals with the conversion of a multi-member partnership into a SMLLC, but this time addresses a fact pattern where an outside buyer purchases all the partnership interests from the current members.

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Dimiter Hristov operated his medical practice thorough a wholly owned S corporation. Tired of handing over 45% of his income to the IRS each year, he began searching for tax saving alternatives. Because Hristov regular tax preparer was an enrolled agent who — admittedly — did not have the sophistication to conjure up such tax solutions, he eventually sought the help of a snake-oil salesman named William Alexander.

Alexander pitched pension plans and Section 419 plans for a living, and he pitched them hard. Fraudulently holding himself out as an enrolled agent, Alexander claimed to have “learned from 8-10 of the sharpest and most aggressive CPAs in the country” about how to take advantage of retirement plans and defend them on audit. To hear Alexander tell it, Hristov could lower his tax liability with large retirement contributions, yet still have access to the cash to make additional income-producing investments.

 And if Hristov’s regular accountant didn’t agree, well…she just didn’t know any better:

 What do most accountants and tax attorneys say about all of this? Most would never advise you to put these plans together and do what I do because they don’t understand and know about what I do. Why? By nature, it seems like U.S. accountants are conservative and backward people that are not creative. It’s really easier for them just to have you pay a lot of tax. You have a lady accountant now, who is conservative and backward, but if she does what I tell her to do, you can keep her; otherwise, use one of my accountants * * *.

Though skeptical at times, Hristov signed on, allowing Alexander to establish retirement plans for the S corporation. Each year from 2004 through 2006, Hristov would make a cash payment to the retirement account,  Alexander would take his cut, and the rest would be “loaned” back to Hristov, never to be repaid; a rather large violation of the qualified plan rules. But that didn’t concern Alexander:

 If I put $400K into the pension plans, you would have no tax, but obviously, you would have to borrow a lot of money from the pension plans, which my clients do as I promote this. Assets in the money purchase plan can be invested anywhere while I use fixed and variable annuities for the 419 plan, you really are not supposed to borrow money from the 419, but I’m aggressive so I have my clients do this * * *.

As if that weren’t egregious enough, Alexander encouraged Hristov to amend his 2002 return by reclassifying large expenses paid for assets to retirement plan contributions, resulting in a $100,000 refund request, from which Hristov took his 10% cut.

Throughout the process, Alexander continued to assuage Hristov’s fears with letters such as this:

 “I also think this amendment will move through easily without IRS even asking for copies of the checks because we are amending a K-1, but if I am wrong, and IRS asks for checks, we can come up with check[s]…we are just asking for a refund so the worse thing that could happen is to be denied, but typically I get the refund although sometimes it takes a while”.

To be fair, with the smooth delivery and impeccable grammar evidenced in that communication, who wouldn’t have their nerves calmed?  

 The IRS, however, predictably began auditing Hristov, resulting in a full disallowance of all the pension plan contributions and leaving Hristov on the hook for over $400,000 in back taxes. And despite Alexander’s previous assurances to Hristov that he was an acclaimed audit negotiator,  he cut and run, refusing to provide documentation to the IRS before eventually having an order of injunction filed against him, prohibiting him from promoting his pension plan scam.

But here’s the real lesson of the Hristov case: despite being rooked by Alexander, Hristov was not able to use the “reasonable cause” defense of I.R.C. § 6664 to avoid understatement penalties.

In general, the most common taxpayer appeal for reasonable cause comes in the form of “reliance upon the advice of a tax professional.” In determining whether a taxpayer’s reliance on a professional is reasonable, the courts tend to look at three factors:

 1. Was the adviser a competent professional who had sufficient expertise to justify reliance?

 2.Did the taxpayer provide necessary and accurate information to the adviser; and

 3. Did the taxpayer actually rely in good faith on the adviser’s judgment?

Hristov, the Tax Court concluded, was not reasonable in relying on Alexander for two reasons: First, there was an obvious conflict of interest: Alexander only got paid to the extent Hristov made contributions to the retirement plan pitched and managed by Alexander. Furthermore, reliance on the professional advice of a tax shelter promoter is unreasonable when the advice would seem to a reasonable person to be “too good to be true.” Because Hristov was made aware by Alexander that he would both 1) get a tax deduction for the funds contributed to the retirement plans, and 2) have access to the cash, he should have sought independent confirmation from a reliable and disinterested adviser familiar with retirement plans.

Failure to do so cost him dearly.

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[Ed note: this post is nothing more than me asking questions based on what I know about tax…and what I DON'T know about SEC law. If I'm charging down an incorrect path -- or if you happen to be an SEC attorney -- please let me know.]

As Facebook grew during its formative years, to avoid reaching a shareholder limit that would have forced them to report their financial statements as if they were a public company, the tech giant switched from issuing stock options to Restricted Stock Units (RSUs) to compensate its employees. As of December 2011, Facebook had 378,772,184 shares of RSUs outstanding.

The granting of restricted stock units — as opposed to the granting of restricted stock — does NOT involve the issuance of actual shares of stock at the time of grant. Rather, after the recipient employee reaches certain pre-determined vesting bogeys, either shares of company stock or cash can be used to “settle” the employee’s right to receive the value of the RSUs. For the remainder of this post, let’s assume all Facebook RSUs will indeed be settled with Facebook stock.

This much I’m certain of: under I.R.C. § 83, when the employee vests in the underlying RSUs and actual shares are issued, the employee recognizes ordinary income equal to the value of the shares less any amounts paid by the employee for the RSUs. In order for an employee to vest in the RSU, the Facebook S-1 provides:

Pre-2011 RSUs granted under our 2005 Stock Plan vest upon the satisfaction of both a service condition and a liquidity condition. The service condition for the majority of these awards is satisfied over four years. The liquidity condition is satisfied upon the occurrence of a qualifying event, defined as a change of control transaction or six months following the completion of our initial public offering.

Assuming most employees have met the service condition (and the S-1 seems to indicate they have), all employees who received pre-2011 RSUs will vest and receive their Facebook stock six months after the IPO date of Friday, May 18th.  Each employee will recognize compensation income at that time equal to the FMV of the shares less any amount paid for the stock.

Here’s where my SEC knowledge may be leading me astray.

Under  Rule 144, once Facebook has been subject to public company reporting requirements for at least 90 days, any person who is not deemed to have been an “affiliate” for purposes of SEC law at any time during the 90 days preceding a sale and who has beneficially owned the shares proposed to be sold for at least six months, is free to sell those shares. The Facebook S-1 further provides:  

The shares of common stock that were not offered and sold in our initial public offering as well as shares underlying outstanding RSUs will be upon issuance, “restricted securities,” as that term is defined in Rule 144 under the Securities Act. These restricted securities are eligible for public sale only if they are registered under the Securities Act or if they qualify for an exemption from registration under Rule 144 or Rule 701 under the Securities Act, which are summarized below.

Putting this all together, does this mean that the RSUs issued to employees upon vesting six months after the IPO date cannot be sold for another six months?

This is an important question, because based on my understanding of the relevant case law and underlying congressional reports, the Rule 144 restriction is not considered a restriction on transferability worthy of postponing the recognition of income under Section 83. As a result, the employees would be required to recognize compensation income upon receipt of the stock on November 18, 2012, even though they cannot sell it pursuant to Rule 144 for an additional six months. This would lead to two problems:

 1. The employees would not be able to sell the stock in order to pay the tax on the compensation income recognized upon vesting. It appears this concern is being mitigated by Facebook’s decision to net-settle the RSUs, selling enough stock to cover the employee’s tax burden and only issuing the “net” shares to the employee.

2. There is a risk that the value of the stock on the vesting date will exceed the value six months later, when the shares can be freely traded. If that is the case, the employees will have recognized ordinary income to the extent of the higher value, with an offsetting capital loss which may provide no immediate tax benefit — or only a 15% benefit by offsetting long-term capital gains.

Understand, I don’t think this is what’s going to happen, but I can’t be certain. It appears based on discussions on the Internet — and when have anonymous web comments ever led us astray?  — that the vested RSUs will be free to be sold immediately upon vesting in November, so the issues I identified may be completely moot. It’s completely dependent on the application of Rule 144, which is where my comfort level dissipates.

So please, if you can add some clarity to the topic, do so in the comments.

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