The Mary And Brad Story

"With respect to petitioner wife’s Federal income tax for 2008, the Internal Revenue Service … determined a deficiency of $106,733 and an accuracy-related penalty of $21,347 under section 6662(a). With respect to petitioners’ joint federal tax for 2010, the IRS determined a deficiency of $100,924 and a section 6662(a) penalty of $20,185.”

Someone went into Tax Court for a quarter of a million dollars. Let’s check it out.

Oh, oh. The issue was whether the taxpayers had a business or nonbusiness bad debt. If they did not, then other tax dominoes would tumble, such as whether a net operating loss existed.

We have Mary Bell. She was single in 2008. She married in 2010. They lived in Texas.

Mary had an MBA, and through 2010 she worked at Blockbuster Corp. You may recall how that turned out, and since 2011 Mary had been a partner with a private equity 

firm.

Her husband also brought some financial chops to the relationship. He was involved with real estate loans, but he lost his job with the 2009 crash. His health thereafter became an issue, but he hoped to get back into the business. His previous clients would eventually have their loans mature, and he wanted to be there when they refinanced.

Our story involves Mary.

Before marrying, Mary dated Brad. Brad was unemployed but full of hope and hype. He was working on a comic strip called “In the Rough,” involving golf.

Mary was making a couple of nickles, and she loaned Brad $75,000. Mary did not go through the due diligence a bank would do, though: investigate his credit rating, request tax returns, obtain other financial information.

She loaned him another $50,000. Brad, being a mature and responsible guy, bought a Hummer with it. He clearly was a keeper.

In all she loaned $430,500 to Brad.

She obtained a written note. It had interest at 5% and matured on December 31, 2007.

How did our tale turn out?

Yep. Our protagonist – the enigmatic, charismatic, problematic Brad – defaulted.

To be fair, he did repay $7,000, so it wasn’t a complete loss.

In 2010 Mary sent an e-mail demanding payment. Brad replied:

"I have no money.”

She continued trying.

In 2011 she filed suit for performance.

In 2012 she received a judgement against Brad.

In 2014 she reasoned that if Brad could get his comic strip syndicated, then he might have enough money to pay her back. She introduced Brad to people. She did not however get any interest, ride or other participation should Brad ever get the comic published.

In 2010 Mary set up an LLC to take-over the note. She then claimed it as a business bad debt on her/their 2010 joint tax return. The note, including interest, was over $600,000 at that time. Not surprisingly, this created a net operating loss, which she carried-back to 2008 for a refund.

We already know that they went to Tax Court.

While there were several issues in the case, we are concerned with only one today 

There are two pieces here:

You made a loan that went south, and

You are in the trade or business of making loans

The IRS quite agreed that Mary made a loan, but they argued that she did not meet the second requirement.

You do not need a building and employees to be in the trade or business of making loans, but you do need to make loans repetitively. That is what “trade or business” means: Jimmy John's does not make one sandwich and call it a day. One loan does not rise to the level of “repetitively.” It also helps to meet the routine requirements that banks and other lenders observe: perform credit checks, obtain financial information, obtain security for the loan, etc.

Mary in turn argued that she worked on content deals all the time at Blockbuster, and Brad’s comic strip was “content” by another name. She was in a “trade or business” because she had done something similar at work.

Not a bad argument, but it had two holes:

Mary did not loan money to Brad in the context of her job at Blockbuster. As a consequence, what she did at Blockbuster was not particularly relevant to the tax outcome of her loan.

Even allowing for that, she did not have an interest, royalty, or other equity participation in the comic strip. She could have demanded it from Brad, but she did not. The only thing she had was a creditor interest, the same as Fifth Third or SunTrust have when they lend money. We are still talking about a loan.

The Court decided that Mary had a nonbusiness bad debt.

The tax difference is huge.

If you have a business bad debt, you can deduct the loan the same way you would deduct your rent, payroll or any other expense. If the sum goes negative, you might have a net operating loss that you can carryback and/or carryforward, offsetting taxable income in other years. If you can carryback, you might even get a refund of taxes previously paid.

If you have a nonbusiness bad debt, the most you can do is offset your capital gains plus $3,000. That’s it. The biggest net subtraction you get can on your tax return is $3 grand. And there is no carryback. Mind you, you can carryforward indefinitely, but at $600 grand Mary would be carrying-forward until the cows came home.

Which is why Mary wanted the business bad debt so badly.

But she was not in the business of making loans. The best she could do was the $3,000. 

She owed the tax. She owed the penalty. It was a loser for her all around.

When Hardship Is Not Enough

Let’s talk a bit about hardship distributions from your retirement plan – perhaps your 401(k).

You may know that you are not supposed to touch this money before a certain age. If you do, not only will there be income taxes to pay, but also a 10% early withdrawal penalty. These are two moving pieces here: one is the income tax on the distribution and another for the 10% penalty.

Here is a question for you:

Let’s say you can withdraw money from your plan for hardship reasons. Does that mean that the penalty does not apply?

The answer is no. One would think that the two Code sections move in tandem, but they do not.

Candace Elaine ran into this in a recent Tax Court decision.

Candace lived in California, and in 2012 she withdrew $84,000 from her retirement plan. She had lost her job in 2009, and she was trying to support herself and family.

The tax Code applies two requirements to the income taxation of hardship withdrawals:

·        On account of an immediate and heavy financial need, and

·        Any amount withdrawn is limited to actual need

An “immediate and heavy financial need” would include monies needed for medical expenses or to avoid foreclosure. In addition, one is not allowed to withdraw $20,000 if the need is only $12,000, with the intention of using the excess for other purposes. 

The plan custodian is the watchman for these two requirements. The custodian is to obtain reasonable assurance of need and inquire whether other financial resources exist. This is a role above and beyond routine administration, and consequently many plans simply do not offer hardship withdrawals.

Candace met those requirements and her plan allowed withdrawals. She reported and paid income tax on the $84,000, but she did not pay the 10% penalty.

The IRS bounced her return. Off to Tax Court they went, where Candace represented herself.

Her argument was simple: I received a hardship distribution. There is an exemption for hardship.

The IRS said that there was not. And in the spirit of unemployed taxpayers trying to support their family, the IRS assessed a penalty on top of the 10% chop.

The Court pointed several exceptions to the 10% early withdrawal penalty, including:

·        Separation from service

·        Disability

·        Deductible medical expenses

·        Health insurance premiums while unemployed

·        Higher education

·        First time purchase of a principal residence

There isn’t one for hardship, though.

Meaning that Candace owed the 10% penalty.

The Court did note that the misunderstanding on the 10% is widespread and refused to assess the IRS’ second penalty.

Why did Candace not just borrow the money from her 401(k) and avoid the issue? Because she had been let go, and you have to be employed in order to take a plan loan.

What if she had rolled the money into an IRA?

IRAs are not allowed to make loans, even to you. The only way you can get money out of an IRA is to take a distribution. This is what sets up the ROBs (Roll-Over as Business Start-Up) as a tax issue, for example.

Candace was stuck with the penalty.

Travel Expenses And Your “Tax” Home

I have a friend who used to commute from northern Kentucky to San Francisco.

He has a unique skill set, and the California employer wanted that skill set badly enough to allow him to work a  week there and a week here.

While his employer paid for his commute - and his lodging and meals while in California - let us frame a tax question for more ordinary taxpayers like you and me:

   Can you deduct your expenses while working out of town?

We will use the Collodi decision to walk through this issue.

Mario Collodi lived in northern California - Paradise, California, to be precise. In 2011 he was working for an employer in southern California. He would work a week of 12-16 hour workdays, and then he would return home for a week off. His wife and children lived in Paradise year-round. He was not trying to find work closer to home.

When he filed their 2011 tax return he claimed almost $30 thousand in travel expenses.

The IRS pulled their return and disallowed his travel expenses.

Off to Tax Court they went.

Let's go through Collodi's argument:

• He was a motor hand on an oil rig, meaning that he took care of the motors on the rig.
• The uncertainty of his job made it unreasonable to relocate the family.
• Which meant that he had to travel for work.

He makes a certain amount of sense. 

The IRS fired back with the following:

• The Code allows a taxpayer to deduct ordinary and necessary expenses, including traveling expenses while away from home.
• Which means that one has to determine the location of the taxpayer's home.
• Which is not what you would immediately think. The Code considers your tax home to be where you work, not where you live. For most of us, that is one and the same, but that was not the case for Collodi. He lived in northern California but worked in southern California.

COMMENT: It is odd to think of one's tax home that way, but it makes more sense if you consider that the term "home" is being used in an income-tax context. If one's purpose to tax your income, then it makes sense that “home” would be redefined to where you earn that income.

• Collodi immediately had a problem, as his work-home was in southern - not northern - California. He cannot be away from home under this definition.
• But there is an exception: if you can expect to start and end that out-of-town job in a year or less, the IRS will consider you to be temporarily away from your home, now defined to mean where your wife and kids are. That would cover, for example, the consultant constantly on the road.
• The flip side is that - if you expect to be there more than a year - then you are hosed. You are considered "indefinitely" away from home, meaning your tax home moved with you and there are no travel deductions.

It all came down to this: how long was Collodi in southern California?

He started in 2010, worked all through 2011 and ended in October, 2012.

More than a year, way more than a year. He was not "temporary." He was "indefinite" and did not qualify for any travel deduction.

At least the Court did not pop them for penalties, reasoning that they relied on a tax professional to prepare the return.

OBSERVATION: The professional should have known better, though. While not said, I wonder whether he/she drew a preparer penalty.

Circling back to my commuting friend, he would not have been able to deduct his northern Kentucky - California travel expenses as he worked there for well over a year. He would have been deemed "indefinite," meaning his tax home moved with him when he traveled to San Francisco.

Why did he not move?

His wife refused.

How did the story turn out?

He changed jobs eventually. The commute and hassle wasn't worth it.

Tax Break For Wealthy (Federal Government) People

Let's talk about a tax break; some may even call it a gimmick. It will never affect your or me, unless we go into the federal government.

Here is Code section 1043:

Sale of property to comply with conflict-of-interest requirements 

(a) Nonrecognition of gain

If an eligible person sells any property pursuant to a certificate of divestiture, at the election of the taxpayer, gain from such sale shall be recognized only to the extent that the amount realized on such sale exceeds the cost (to the extent not previously taken into account under this subsection) of any permitted property purchased by the taxpayer during the 60-day period beginning on the date of such sale.

(b) Definitions

For purposes of this section -

(1) Eligible person

The term "eligible person" means -

(A) an officer or employee of the executive branch, or a judicial officer, of the Federal Government, but does not mean a special Government employee as defined in section 202 of title 18, United States Code, and

(B) any spouse or minor or dependent child whose ownership of any property is attributable under statute, regulation, rule, judicial canon, or executive order referred to in paragraph (2) t a person referred to in subparagraph (A).

Let's say that you are pulling down several million dollars a year from your day job. You have the opportunity to head-up the EPA or the National Park Service. It is almost certain that your paycheck will shrink, and the Congressional committee investigating you may request you sell certain investments or other holdings to avoid conflict of interest concerns.

Folks, this is an uber-elite tax problem.

To ease your decision, the tax Code will allow you to sell your investments without paying any tax. To do so you are required to buy replacement securities within 60 days, and the non-taxed gain will reduce your basis in the new securities.

OBFUSCATION ALERT: To say it differently, your "basis" in the old securities sold will carry-over as your basis in the new securities.

By way, it is not necessary to have Congress to tell you to unload your investments. There is a more lenient "reasonably necessary" standard that might work for you. I am reasonably certain I could come up with some necessary argument so I would not pay tax.

While sweet, Section 1043 is not a complete escape clause. If you think about it, all you have done is delay the taxable gain until you sell the new securities. I suppose an escape clause is to die without selling, but I generally do not consider dying to be a viable tax strategy.

The numbers can add-up, though. It is estimated that Paul O'Neill, a former Treasury Secretary, sold approximately $100 million of Alcoa stock when he took the position. I do not know what the gain would have been (as we do not know the cost), but the tax he deferred must have been eye-opening.

By the way, you can get the same break by drawing a judicial appointment.

I do have a question: do you wonder why the politicos never mention Section 1043 whenever they rail against "tax breaks" used by wealthy people?

Nah, there is no wonder at all.

Do You Have To Register To Be Considered A College Student?

I cannot believe this case made it to the Tax Court.

Granted, it is a "pro se" decision, which means that the taxpayer represented himself/herself. It sometimes is the professional wrestling of tax literature.

I will give you the facts, and you can tell me how the case was decided.

Through 2012 Brittany was a student at Saddleback College (Saddleback) in Mission Viejo, California. Our story takes place in the spring, when Brittany registered for a five-hour physiology course.  She also attended (for eight weeks, at least) a contemporary health course, although she never registered or enrolled in the course.

She filed her 2012 tax return and claimed a $2,500 American Opportunity tax credit. This is the credit for the first four years of college.

The IRS bounced the return. It pointed out the following from Code section 25A:

(B) Credit allowed for year only if individual is at least 1/2 time student for portion of year

The Hope Scholarship Credit under subsection (a)(1) shall not be allowed for a taxable year with respect to the qualifies tuition and related expenses of an individual unless such individual is an eligible student for at least one academic period which begins during such year.

The term "eligible student" in turn is defined as one carrying at least half the normal full-time workload at school.

The IRS saw a five-hour load and did not see an eligible student.

Brittany did not see it that way. She saw a five-hour load and her sitting-in on a three-hour course. That added up to eight hours, which was more than half-time.

What did the Tax Court decide?

We do not need Apple's tax department for this one.

The Regulations require that a student enroll at the school. And the course. Each course.

Five hours was not enough to be half-time. She did not qualify for the credit.

Benefitting Too Much From A Charity

I suspect that many of us know more about public charities and foundations than we cared to know a couple of years ago.

What sets up the temptation is that someone is not paying taxes, or paying extraordinarily low taxes. For example, obtain that coveted 501(c)(3) status and you will pay no taxes, barring extreme circumstances. If one cannot meet the "publicly supported" test of a (c)(3), the fallback is a private foundation - which only pays a 2% tax rate (and that can be reduced to 1%, with the right facts).

We should all be so lucky.

Let's discuss the issues of charities and private benefit and private inurement.

These rules exist because of the following language in Section 501(c):

No part of the earnings [of the exempt organization] inures to the benefit of any private shareholder or individual….”

In practice the Code distinguishes inurement depending upon who is being benefitted.

If that someone is an “insider,” then the issue is private inurement. An insider is someone who has enough influence or sway to affect the decision and actions of the organization.

A common enough example of private inurement is excessive compensation to a founder or officer.  The common safeguard is to empower an independent compensation committee, with authority to review and decide compensation packages. While not failsafe, it is a formidable defense.

If that someone is an “outsider,” then the term is private benefit.

Here is a question: say that someone sets up a foundation to assist with the expenses of breast cancer diagnosis and treatment. Several years later a family member is so diagnosed. Have we wandered into the realm of private inurement or benefit?

The Code will allow one to receive benefits from the charity – if that individual is also a member of a charitable class. In our example, that class is breast cancer patients. If one becomes a member of that class, one should sidestep the inurement or benefit issue.

The “should” is because the Code will not accept too small a charitable class. Say – for example - that the charitable class is restricted to the families of Cincinnati tax CPAs who went to school in Florida and Missouri, have in-laws overseas and who would entertain an offer to play in the NFL. While I have no problem with that charitable class, it is very unlikely the IRS would approve.

By the way, the cost of failing can be steep. There may be penalties on the charity and/or the insider. Push it too far and the organization's exempt status may be revoked altogether.

Or you may never be exempt to begin with. Let’s look at a recent IRS review of an application for exempt status.

A family member has a rare disease. You establish a foundation to "assist adolescent children and families in coping with undiagnosed and/or debilitating diseases."

The Code allows you to operate for a while and retroactively apply for exemption, which you do.

Sounds good so far.

You and your spouse are the incorporators.

This is common. You can still establish an independent Board.

Your organizing paperwork does not have a "dissolution" clause.

Big oversight. The dissolution clause means that - upon dissolution - all remaining assets go to another charity. To say it differently, remaining assets cannot return to you or your spouse.

The charity is named after your son, who suffers from an unidentified illness.

Not an issue. I suspect many foundations begin this way.

Your fundraising materials specifically request donations to help your son.

You are stepping a bit close to the third rail with this one.

Since inception, the only individual to receive funds is your son. Granted, you have said you intend to make future distributions to other individuals and unrelated nonprofits with a similar mission statement. Those individuals and organizations will have to apply, and a committee will review their application. It just hasn’t happened yet.

Problem.

The IRS looked at your application for exemption and bounced it. There were two main reasons:

First, the problem with the paperwork, specifically the dissolution clause. The IRS would likely have allowed you the opportunity to correct this matter, except that ...

Secondly, there were operational issues. It does not matter how flowery that mission statement is. The IRS reserves the right to look at what you are actually doing, and in this case what you were actually doing was making your son's medical expenses tax-deductible by introducing a (c)(3). Granted, there was language allowing for other children and other organizations, but the reality is that your son was the only beneficiary of the charity's largesse. The rest was just words.

The IRS denied the request. All the benefits of the organization went to your family, and the promise of future beneficiaries was too dim and distant to sway the answer. You had too small a charitable class (that is, a class of one), and that constitutes private inurement.

And you still have a tax problem. You have an entity that has collected money and made disbursements. The intent was for it to be a charity, but that intent was dashed. The entity has to file a tax return, but it will have to file as a taxpaying entity.

Are the monies received taxable income? Are the medical expenses even deductible? You have a mess.

The upside is that you would only be filing tax returns for a year or two, as you would shut down the entity immediately.

Worst. Tax. Advice. Ever.

Dad owned a tool and die company. Son-in-law worked there. The company was facing severe foreign competition, and - sure enough - in time the company closed. For a couple of years the son-in-law was considerably underpaid, and dad wanted to make it up to him.

The company's accountant had dad infuse capital into the business. The accountant even recommended that the money be kept in a separate bank account. Son-in-law was allowed to tap into that account near-weekly to supplement his W-2. The accountant reasoned that - since the money came from dad - the transaction represented a gift from dad to son-in-law.

Let's go through the tax give-and-take on this.

In general, corporations do not make gifts. Now, do not misunderstand me: corporations can make donations but almost never a gift. Gifts are different from donations. Donations are deductible (within limits) by the payor and can be tax-free to the payee, if the payee has obtained that coveted 501(c)(3) status. Donations stay within the income tax system.

Gifts leave the income tax system, although they may be subject to a separate gift tax. Corporations, by the way, do not pay gift taxes, so the idea of a gift by a corporation does not make tax sense.

The classic gift case is Duberstein, where the Supreme Court decided that a gift must be made under a "detached and disinterested generosity" or "out of affection, respect, admiration, charity or like impulses." The key factor the Court was looking for is intent.

And it has been generally held that corporations do not have that "detached and disinterested" intent that Duberstein wants.  Albeit comprised of individuals, corporations are separate legal entities, created and existing under state law for a profit-seeking purpose. Within that context, it becomes quite difficult to argue that corporations can be "detached and disinterested."

It similarly is the reason - for example - that almost every job-related benefit will be taxable to an employee - unless the benefit can fit under narrow exceptions for nontaxable fringes or awards. If I give an employee a $50 Christmas debit card, I must include it in his/her W-2. The IRS sees an employer, an employee and very little chance that a $50 debit card would be for any reason other than that employment relationship.   

What did the accountant advise?

Make a cash payment to the son-in-law from corporate funds.

But the monies came from dad, you say.

It does not matter. The money lost its "dad-stamp" when it went into the business.

What about the separate bank account?

You mean that separate account titled in the company's name?

It certainly did not help that the son-in-law was undercompensated. The tax Code already wants to say that all payments to employees are a reward for past service or an incentive for future effort. Throw in an undercompensated employee and there is no hope.

The case is Hajek and the taxpayer lost. The son-in-law had compensation, although I suppose the corporation would have an offsetting tax deduction. However, remember that compensation requires FICA and income tax withholding - and no withholdings on the separate funds were remitted to the IRS - and you can see this story quickly going south. Payroll penalties are some of the worst in the tax Code.

What should the advisor have done?

Simple: have dad write the check to son-in-law. Leave the company out of it.