Helping Out A Family Member’s Business

Let’s say that you have a profitable business. You have a family member who has an unprofitable business. You want to help out the family member. You meet with your tax advisor to determine if there is tax angle to consider.

Here is your quiz question and it will account for 100% of your grade:

What should you to maximize the chances of a tax deduction?

Let’s discuss Espaillat and Lizardo v Commissioner.

Mr. Jose Espaillat was married to Ms. Mirian Lizardo. Jose owned a successful landscaping business in Phoenix for a number of years. In 2006 his brother (Leoncio Espaillat) opened a scrap metal business (Rocky Scrap Metal) in Texas. Rocky Scrap organized as a corporation with the Texas secretary of state and filed federal corporate tax returns for 2008 and 2009.

Being a good brother, Jose traveled regularly to help out Leoncio with the business. Regular travel reached the point where Jose purchased a home in Texas, as he was spending so much time there.

Rocky Scrap needed a big loan. The bank wanted to charge big interest, so Jose stepped in. He lent money; he also made direct purchases on behalf of Rocky Scrap. In 2007 and 2008 he contributed at least $285,000 to Rocky Scrap. Jose did not charge interest; he just wanted to be paid back.

Jose and Mirian met with their accountant to prepare their 2008 individual income tax return. Jose’s landscaping business was a Schedule C proprietorship/sole member LLC, and their accountant recommended they claim the Rocky Scrap monies on a second Schedule C. They would report Rocky Scrap the same way as they reported the landscaping business, which answer made sense to Jose and Mirian. Inexplicably, the $285,000 somehow became $359,000 when it got on their tax return.

In 2009 Rocky Scrap filed for bankruptcy. I doubt you would be surprised if I told you that Jose paid for the attorney. At least the bankruptcy listed Jose as a creditor.

In 2010 Jose entered into a stock purchase agreement with Leoncio. He was to receive 50% of the Rocky Scrap stock in exchange for the aforementioned $285,000 – plus another $50,000 Jose was to put in.

In 2011 Jose received $6,000 under the bankruptcy plan. It appears that the business did not improve all that much.

In 2011 Miriam and their son (Eduan) moved to Texas to work and help at Rocky Scrap. Jose stayed behind in Phoenix taking care of the landscaping business.

Then the family relationship deteriorated. In 2013 a judge entered a temporary restraining order prohibiting Jose, Miriam and Eduan from managing or otherwise directing the business operations of Rocky Scrap.  

Jose, Miriam and Eduan walked away. I presume they sold the Texas house, as they did not need it anymore.

The IRS looked at Jose and Mirian’s 2008 and 2009 individual tax returns.  There were several issues with the landscaping business and with their itemized deductions, but the big issue was the $359,000 Schedule C loss.

The IRS disallowed the whole thing.

On to Tax Court they went. Jose and Mirian’s petition asserted that they were involved in a business called “Second Hand Metal” and that the loss was $285,000. What happened to the earlier number of $359,000? Who knows.

What was the IRS’ argument?

Easy: there was no trade or business to put on a Schedule C. There was a corporation organized in Texas, and its name was Rocky Scrap Metals. It filed its own tax return.  The loss belonged to it. Jose and Mirian may have loaned it money, they may have worked there, they may have provided consulting expertise, but at no time were Jose and Mirian the same thing as Rocky Scrap Metal.

Jose and Mirian countered that they intended all along to be owners of Rocky Scrap. In fact, they thought that they were. They would not have bought a house in Texas otherwise. At a minimum, they were in partnership or joint venture with Rocky Scrap if they were not in fact owners of Rocky Scrap.

Unfortunately thinking and wanting are not the same as having and doing. It did not help that Leoncio represented himself as the sole owner when filing the federal corporate tax returns or the bankruptcy paperwork. The Court pointed out the obvious: they were not shareholders in 2008 and 2009. In fact, they were never shareholders.

OBSERVATION: Also keep in mind that Rocky Scrap filed its own corporate tax returns. That meant that it was a “C” corporation, and Jose and Mirian would not have been entitled to a share of its loss in any event. What Jose and Mirian may have hoped for was an “S” corporation, where the company passes-through its income or loss to its shareholders, who in turn report said income or loss on their individual tax return. 

 

The Court had two more options to consider.

First, perhaps Jose made a capital investment. If that investment had become worthless, then perhaps … 

Problem is that Rocky Scrap continued on. In fact, in 2013 it obtained a restraining order against Jose, Miriam and Eduan, so it must have still been in existence.  Granted, it filed for bankruptcy in 2009. While bankruptcy is a factor in evaluating worthlessness, it is not the only factor and it was offset by Rocky Metal continuing in business.  If Rocky Scrap became worthless, it did not happen in 2009.

Second, what if Jose made a loan that went uncollectible?

The Court went through the same reasoning as above, with the same conclusion.

OBSERVATION: In both cases, Jose would have netted only a $3,000 per year capital loss. This would have been small solace against the $285,000 the IRS disallowed.

The Court decided there was no $285,000 loss.

Then the IRS – as is its recent unattractive wont – wanted a $12,000 penalty on top of the $60-plus-thousand-dollar tax adjustment it just won. Obviously if the IRS can find a different answer in 74,000+ pages of tax Code, one must be a tax scofflaw and deserving of whatever fine the IRS deems appropriate.

The Court decided the IRS had gone too far on the penalty.

Here is the Court:

He [Jose] is familiar with running a business and keeping records but has a limited knowledge of the tax code. In sum, Mr. Espaillat is an experienced small business owner but not a sophisticated taxpayer.”

Jose and Mirian relied on their tax advisor, which is an allowable defense to the accuracy-related penalty. Granted, the tax advisor got it wrong, but that is not the same as Jose and Mirian getting it wrong. The point of seeing a dentist is not doing the dentistry yourself.

What should the tax advisor done way back when, when meeting with Jose and Mirian to prepare their 2008 tax return?

First, he should have known the long-standing doctrine that a taxpayer devoting time and energy to the affairs of a corporation is not engaged in his own trade or business. The taxpayer is an employee and is furthering the business of the corporation.

Granted Jose and Mirian put-in $285,000, but any tax advantage from a loan was extremely limited – unless they had massive unrealized capital gains somewhere. Otherwise that capital loss was releasing a tax deduction at the rate of $3,000 per year. One should live so long.

The advisor should have alerted them that they needed to be owners. Retroactively. They also needed Rocky Scrap to be an S corporation.  Retroactively. It would also have been money well-spent to have an attorney draw up corporate minutes and update any necessary paperwork.

That is also the answer to our quiz question: to maximize your chance of a tax deduction you and the business should become one-and-the-same. This means a passthrough entity: a proprietorship, a partnership, an LLC or an S corporation. You do not want that business filing its own tax return.  The best you could do then is have a worthless investment or uncollectible loan, with very limited tax benefits.

The IRS Did Not Like This Bonus

Let’s say that you own 100% of a company. Let’s say your company is quite profitable, and that you take out massive bonuses at year-end. The bonuses serve two purposes: first: why not? You took risk, borrowed money and worked hard. If the thing folded, you would have sunk with it. If it succeeds, why shouldn’t you succeed with it? After all, no politician built it for you. Second, bonuses help reduce taxes the company has to pay. Granted, they increase the taxes the shareholder has to pay, but that is a conversation for another day.

Let’s say the IRS questions the bonus.  They think your bonus is unreasonable.

Let’s discuss the Midwest Eye Center case.

Dr. Afzal Ahmad was the sole shareholder of Midwest Eye Center (Midwest), a multi-location ophthalmology and eye care center in Chicagoland. This is a pretty large practice, with approximately 50 employees, five surgeons, three optometrists and so on. Dr. Ahmad was doing well, receiving a salary of $30,000 every two weeks. At the end of the year he would also draw a sizeable bonus, which coincidently reduced corporate taxable income to zero. In 2007 he took a bonus of $2,000,000.   

Dr. Afzal Ahmad

There were reasons for the bonus. One of his busier surgeons quit unexpectedly in June, 2007. That surgeon was generating approximately $750,000 in revenues, and Dr. Ahmad took over the additional patients. Then there was another doctor who was reducing her workload as she established her own practice. Dr Ahmad starting absorbing some of these patients too.

Busy year for the doctor.

One more fact: Midwest filed taxes as a C corporation, which means it paid its own taxes.

The IRS came in and disallowed $1,000,000 of the bonus. Why $1,000,000 exactly? Who knows, except that (1) it is an impressive amount, and (2) it is close enough for government work.

As Midwest was a professional services corporation, its tax rate was the maximum, so there immediately was additional tax of $340,000.  The IRS also assessed penalties of over $62,000.

This was a nice audit for the IRS: limited issues and big bucks.

So how did the tax advisor defend Midwest?

There is standard text that any tax practitioner (at least, one who follows tax cases) has read a thousand times:

“Deductions are a matter of legislative grace and are allowed only as specifically provided by statute.”

Basically the tax Code says that everything is taxable and nothing is deductible – unless the Code says otherwise.  IRC Section 162 allows us to deduct “reasonable and necessary expenses.” So far, so good. Salaries have to be deductible, right? Hold up. The Code says that a “reasonable allowance for salaries or other compensation” is deductible.

We have to show the “reasonableness” of the salary.

The first way is to show that an “independent investor” would have paid the salary. Midwest decided not to use this line of defense, as no dividends were paid and no profits were left in the company. You have to leave some crumbs on the plate so the investor does not starve. Granted, Warren Buffett does not pay dividends, but he always leaves profit in Berkshire Hathaway.

OBSERVATION: The lack of dividends does not have to be fatal, but it does complicate the argument. For example, if I owned an NFL team, I might be willing to operate it at a loss. The value of my team (if I were to sell it) would likely be increasing more than enough to offset that operating loss.

The next way is by comparison to other businesses. Think professional athletes. If a team is willing to pay the salary, the player must then be worth it. Therefore if someone somewhere with your job duties has a similar salary, there is a prima facie argument that your salary is reasonable. This is more difficult to do with closely-helds than publicly-tradeds, as closely-helds do not tend to publish profitability data.  

A third way involves profit-sharing and other incentive plans, hopefully written down and providing formulas should certain thresholds be met. It is important to establish the plan ahead of time and to be certain there is some rhyme or reason to the calculations. Examples include: 

1.  Documenting the doctor’s activities over the years, putting a value to it and keeping a running tally of how compensation is still due. This can be done to “reimburse” the shareholder for those start-up years when the money was not there to properly compensate the shareholder, for example.
2. Setting up a bonus formula and following it from year-to-year. If there isn’t enough cash to pay out the amount generated by the formula, then the business would accrue it as “compensation payable.” It is not deductible until paid, but it does indicate that there is a compensation plan in place.
3. Having an independent Board of Directors, who in turn decide the amount of compensation. This can be done on an annual basis, preferably earlier rather than later in the year. This technique is not often seen in practice. 
4. Valuing the company on a regular basis (perhaps as frequently as annually). The intent is to attribute the increase in the value of the business to the shareholder’s efforts. The business would then share some of that increase via a bonus.

So what did Midwest do?

They did nothing, that’s what they did.

And I am at a loss. Midwest had a professional tax preparer, but when push came to shove the preparer provided the Court … nothing.

On to the penalty. The IRS will reverse a penalty if the taxpayer can show that he/she relied upon professional advice. The insurance companies go apoplectic, but it is common (enough) practice for a CPA to fall on the sword to get the client out of a penalty. 

But Midwest’s tax preparer was nowhere to be found.

The IRS won on all fronts.

My thoughts?

My corporate clients have overwhelmingly shifted to S corporations over the years. S corporations have their own tax issues, but reasonable compensation is not one of them. It is rare for a tax practitioner to recommend a C corporation nowadays, unless that practitioner works with Fortune 500 companies.

Midwest is an example why. It is a second pocketbook for the IRS to pick.

Do You HAVE To Cash That Bonus Check (To Get A Tax Deduction)?

For (very) closely-held service companies, it is common to “bonus” enough profit to bring taxable income down to zero (or very close). There are two reasons for this:

(1)  The company is a personal services company (PSC), meaning that it will face a maximum corporate tax rate on whatever profit is left in the company. This is a tremendous impetus to not leave profit in the company.

(2)   There is one owner (or very few owners) and the majority of the money is going to him/her/them anyway.

In many cases the company is also cash-basis taxpayer, and the accountant normally pays very close attention to cash in-and-out during the last few days of the tax year. With electronic bank transfers becoming more commonplace, I have seen carefully-monitored tax planning destabilized by sizeable electronic customer transfers on the last day or two. It happens, as the customer may be doing cash-basis planning themselves, and payment to my client is a tax deduction to them.

There are limitations on how far this can be pushed, though. It is not acceptable to delay depositing customer checks, for example, in order to avoid income recognition. In addition, one has to be careful about writing so many checks that it creates a bank overdraft. A common way to plan around an overdraft is to have a line of credit available. The bank would then sweep funds from the line as necessary to cover any overdraft. One might also run an overdraft if he/she knows that a deposit will arrive early the following month, as that deposit would occur during the float period of any outstanding checks.  A business owner might “know” that check is coming because said check is already in the owner’s desk drawer, but we will not speak further of such absurd examples. It is not as though I have ever seen such a thing, of course.

Let’s talk about Vanney Associates, Inc. Robert Vanney is an architect with perilously close to 40 years experience. The firm has about 25 employees, and Robert is the sole shareholder. He is – without question – the key man. His wife, Karen, is a CPA with a retired license, and she takes care of the books and records.

In 2008 Mr. Vanney received $240,000 in monthly payroll. At the end of the year, he determined and paid employee bonuses, taking as a personal bonus whatever was left over. The leftover was $815,000. The withholdings on the leftover were approximately $350,000, leaving approximately $464,000 payable to Mr. Vanney.

Problem: there was only $389 thousand in the bank.

There was enough money to pay the withholding taxes, but there wasn’t enough to also pay Mr. Vanney. What to do? The Vanney’s did not need the money, so they decided not to borrow from the bank. Mr. Vanney instead endorsed the check back to the company, and that was the end of the matter.

But it wasn’t. The IRS looked at the business tax return and decided to disallow the $815,000 bonus and almost $12,000 in related employer payroll taxes.

Why? The government got their taxes, so why should they care? 

There is a legal concept when paying with a check. A check is referred to as a “conditional payment,” because writing the check is subject to a condition subsequent. That subsequent condition is the check clearing the bank. We take it for granted, of course, so we overlook that technically there are two steps. When the check clears, the two steps unify and become as one. This is why you can send a check to a charity on December 31 and claim the deduction in the same tax year. There is no chance that the charity is receiving that check and depositing it by December 31. Still, if it clears in the normal course of business, all parties – including the IRS – consider the check as having been written on December 31.

That is not what happened here. The check never cleared the bank.

Which is unfortunate, as the IRS now could argue that the check remained conditional. Being conditional there was never payment in 2008. This was fatal, as Vanney Associates was a cash-basis taxpayer.  

And the Court agreed.

Think about this for a moment. The corporation was disallowed a 2008 deduction for the $815,000. Whereas the Court did not address this point, that bonus was included on Mr. Vanney’s 2008 Form W-2. He would have reported that W-2 on his 2008 individual tax return.

There is something seriously wrong with this picture.

I suppose Vanney Associates could amend its 2008 payroll tax returns. It could reverse that bonus, as well as the related withholding taxes. It would get a refund, but it would be amending multiple federal and state (and possibly local) payroll returns.

Mr. Vanney would then amend his personal 2008 tax return.

But that is assuming we are within the statute of limitations to amend all those returns.

When then would Vanney Associates get its $815,000 bonus deduction?

Your first response might be the following year: in 2009. I believe you would be wrong. Why? Because Mr. Vanney did not cash his check in 2009. The check remained a conditional payment in 2009. Same answer for 2010, 2011, 2012 and 2013. This case was decided September, 2014. Seems to me the first time Mr. Vanney could “cash” his check is this year – 2014.

Let me ask you another question: why didn’t the Court allow the (approximately) $350,000 in withholdings as a tax deduction? That check cashed, right?

I think I know. If the company did not “pay” the $815,000 in 2008, then there is no “bonus” for that withholding to attach to. From a tax perspective, the company overpaid its withholding taxes in 2008. The tax problem is that the overpayment is not a "deduction," as no payroll taxes were actually due. Payroll taxes attach to payroll, and there was no payroll. It was a "prepayment," waiting on Vanney to request a refund.

What is our takeaway?

Over the years I have heard more than one practitioner declare a tax outcome as “making no sense.” An unfortunate consequence is that the practitioner may not pursue a line of reasoning to conclusion. There are reasons for this, of course. First, an accountant has probably been exposed somewhere to generally accepted accounting principles. GAAP is a financial statement concept (think auditors, not tax accountants) and GAAP generally has some symmetry to it. The practitioner forgets that the IRS not bound by GAAP. The purpose of the IRS is to collect and enforce, and it does not consider itself bound by any symmetry should GAAP get in its way. The second is human: we respond to an absurd result by assuming we must have made a mistake in our reasoning. Many times we are right. In Vanney’s case, we were not.

What could Vanney have done?

Simple.

He could have had a line of credit in place. He could have cashed that check.

BTW I almost invariably recommend my cash-basis clients have a line of credit, even if they have no intention of using it. This costs them money, as the bank may charge a flat fee (say $100 or $250) annually for keeping the line of credit available. In addition, many a bank will require at least one draw over a month-end annually in order to keep the line open. This means there will be some interest expense.

Why do I recommend it? It is cheap insurance against nightmares like this.

What Does It Take To Claim a Business Bad Debt Deduction?

Do you know what it takes to support a bad debt deduction?

I am not talking about a business sale to a customer on open account, which account the customer is later unable or unwilling to pay. No, what I am talking about is loaning money.

Then the loan goes south, other partially or in full.

And I –as the CPA - find out about it, sometimes years after the fact. The client assures me this is deductible because he/she had a business purpose – being repaid is surely a business purpose, right?

Unless you are Wells Fargo or Fifth Third Bank, the IRS will not automatically assume that you are in the business of making loans. It wants to see that you have a valid debt with all its attributes: repayment schedule, required interest payments, collateral and so forth. The more of these you have, the better your case. The fewer, the weaker your case. What makes this tax issue frustrating is that the tax advisor is frequently uninformed of a loan until later – much later – when it is too late to implement any tax planning.

Ronald Dickinson (Dickinson) and Terry DuPont (DuPont) worked together in Indianapolis. DuPont moved to Illinois to be closer to his children. DuPont was having financial issues, including obligations to his former wife and support for his children.

Dickinson started up a new business, and he reached out to DuPont. Knowing his financial issues, Dickinson agreed to help:

Anyway, I want to reiterate again my commitment to you financially, and what I would expect from you in paying me back. I am not going to prepare a note, or any form of contract, because I trust you to be honest about this matter, just like all of the other people I have loaned money.

Anyway, I agree you loan you money to get settled in over here, and help you out financially as long as I see our new company is working, and you are going to work as hard as you did for me the last time we worked together.”

Sounds like Dickinson was a nice guy.

Between 1998 and 2002, Dickinson wrote checks to DuPont totaling approximately $27,000.

DuPont acquired a debit card on a couple of business bank accounts, and he helped himself to additional monies. He was eventually found out, and it appears that he was not supposed to have had a debit card. By 2003 the business relationship ended.

Dickinson filed a lawsuit in 2004. He wanted DuPont to pay him back approximately $33,000. The suit went back and forth, and in 2009 the Court dismissed the lawsuit.

Dickinson, apparently seeing the writing on the wall, filed his 2007 tax return showing the (approximately) $33,000 as a bad debt. He included a long and detailed explanation 0f the DuPont debacle with his return, thereby explaining his (likely largest) business deduction to the IRS.

The IRS disallowed the bad deduction and wanted another $15,000-plus from him in taxes. But - hey – thanks for the memo.

Dickinson took the matter pro se to Tax Court.

And there began the tax lesson:

(1)   Only a bona fide debt qualifies for purposes of the bad debt deduction.

(2)   For a debt to be bona fide, at the time of the loan the following should exist:

a.      An unconditional obligation to repay

b.      And unconditional intention to repay

c.       A debt instrument

d.      Collateral securing the loan

e.      Interest accruing on the loan

f.        Ability of the borrower to repay the alleged loan

Let’s be honest: Dickinson was not able to show any of the items from (a) to (f). The Court noted this.

But Dickinson had one last card. Remember the wording in his letter:

            … just like all of the other people I have loaned money.”

Dickinson needed to trot out other people he had made loans to, and had received repayment from, under circumstances similar to DuPont. While not dispositive, it would go a long way to showing the Court that he had a repetitive activity – that of loaning money – and, while unconventional, had worked out satisfactorily for him in the past. Would this convince the Court? Who knows, because…

… Dickinson did not trot out anybody.

Why not? I have no idea. Without presenting witnesses, the Court considered the testimony to be self-serving and dismissed it.

Dickinson lost his case. He took so many strikes at the plate the Court did not believe him when he said that he made a loan with the expectation of being repaid. The Court simply had to point out that, whatever Dickinson meant to do, the transaction was so removed from the routine trappings of a business loan that the Court had to assume it was something else.

Is there a lesson here? If you want the IRS to buy-in to a business bad debt deduction, you must follow at least some standard business practices in making the loan.

Otherwise it’s not business.