A Failure To Keep Records

You have to keep records.

Depending upon, this can be easy. Say that you have a job and a money market account – two sources of income. At year-end you receive a W-2 and a 1099-INT. File them with your individual tax return and you have kept records.

Dial this up to business level and the recordkeeping requirement can be more substantial.

Maybe you do not need a bookkeeper or accountant, but you can open a separate business bank account, running all deposit and disbursements through it. You can buy an expanding file – one with a pocket for each month – and keep invoices and receipts throughout the year. That might not be sufficient were you a regional contractor, with equipment and employees and whatnot, but it may be more than enough for what you do.

Why do this?

Because of taxes.

There is a repetitive phrase in tax cases - I have read it a thousand times:

Deductions are a matter of legislative grace, and the taxpayer must prove his or her entitlement to deductions.”

To phrase it another way:

Everything is taxable and nothing is deductible unless we say it is deductible.

One of the things the IRS says is that you must keep records. You can extrapolate what the IRS can do to you concerning deductions if you do not.

“But they can’t eat me, right, CTG?” you ask.

No, but here is what they can do.

Sam Fagenboym was a 50% owner of Alcor Electric, which provided electrical installation for midsize commercial projects. Alcor was a sub to a general contractor. Alcor in turn had suppliers and its own subs.

With the possible exception of the second round of subs, this is pretty routine stuff.

Alcor was an S corporation. It allocated Fagenboym a loss of approximately $110,000 on his 2015 Schedule K-1.

The IRS examined Alcor’s 2015 business return.

Alcor could not document over a quarter million dollars of purchases from a supplier.

Half of that audit adjustment went to Fagenboym, as he was a 50% owner.

The IRS next looked at Fagenboym’s personal return.

So much for the loss he had claimed from Alcor.

Fagenboym went to Tax Court. He went pro se, generally meaning that he was without tax representation.  As we have discussed before, that technically is not correct, as I could represent someone in Tax Court and they would be considered pro se.

Fagenboym argued for Cohan treatment of Alcor’s business expenses.

COMMENT: I would have expected Alcor to fight this issue during its business audit, but here is Fagenboym doing the fighting during his individual audit.    

Cohan is old tax case, going back to 1930 and involving someone who was known for entertaining but not for keeping receipts and records. The Court considered his situation, reasoning there was no doubt that Cohan had incurred expenses. It would be inequitable to disallow all expenses, so the question became: how much to allow?

Cohan has triggered tax changes ever since. It was responsible for the hyper-technical rules concerning meals and entertainment, for example, as well as business use of a vehicle.

Fagenboym wanted some of that Cohan.

I presume there truly were no records. There is no way that I would lead with Cohan if I had any other argument.

Why?

Think about it from the Court’s perspective.

(1) The Court will require a rational basis to estimate the expenses, and

(2)  The Court will consider the taxpayer’s culpability in creating this situation.

Perhaps if there were extenuating circumstances: illness of a key employee, a data loss, a pandemic, something that compromised the taxpayer.  The more one is responsible for causing the mess, the less likely the Court will be to clean-up the mess.

Fagenboym tried. He presented the Court with estimates of job profitability. He then subtracted labor and other known expenses to arrive at what the missing purchases should have been. He submitted four pages of handwritten analysis, but he did not or could not support it with business bank statements or other records, such as an accounts payable history for the supplier in question. Despite how earnest he seemed and how well he understood the business, there were no records backing him up.

Fagenboym could not overcome the two factors above. Even if the Court allowed some leniency on his culpability, it decided it could not independently arrive at a reasonable estimate of the costs involved.

No Cohan. No tax deduction. Bad day in Court for Fagenboym.

Uber Driver Failed To Report Income

I am reading a case concerning an Uber driver who ran afoul of Form 1099 requirements.

The amounts at issue were impressive.

           Tax                          $193,784

           Penalties                  $ 85,354

Robert Nurumbi drove for Uber in 2015. He ran the business through a single-member LLC and used two bank accounts. Business was doing well. He bought multiple cars which he rented out to family and friends who drove for Uber through him. The twist to the tale is that all Uber payments were paid to the LLC’s bank account - meaning Nurumbi’s bank account, as he was the LLC - and he in turn would pay his family and friends.

Sounds like he established a small business, with employees and all.

Except that he treated his drivers as independent contractors, not employees. I get it: Uber is gig economy.

Every week Uber would pay Nurumbi. He would transfer the family-and-friends portion to a second bank account. He would sometimes pay them by electronic transfer; at other times he paid in cash. He did not keep documentation on these payments, and he further muddied the waters by also paying nondriver expenses from the second bank account.

He filed his 2015 personal tax return showing wages of approximately $19 grand.

Uber meanwhile issued him two 1099s totaling approximately $543 thousand.

The IRS saw a case of unreported income.

It is not clear to me how Nurumbi prepared his tax return, as a self-employed does not receive a W-2 from himself. He should have filed a Schedule C with his return, as Schedule C reports self-employed business activity. I would have expected his C to report gross receipts of approximately $543 grand, with a bunch of expenses reducing the net to approximately $19 thousand. The IRS would have matched Uber’s 1099 to the gross receipts on the Schedule C and spared us the drama.

However, Nurumbi did not prepare his taxes this way.

Dumb, I am thinking, but not necessarily fatal. Nurumbi would submit a Schedule C (or a facsimile thereof) and argue his point.

But the damage had been done. Nurumbi had spotted the IRS gross income of $543 grand. He next had to show expenses bringing his net income down to $19 thousand. This gave the IRS the chance to say: prove it.

Which is why we keep records: invoices, bank statements, cancelled checks, QuickBooks files and so forth.  

Nurumbi had a problem. He kept next to no records. He had not issued 1099s. His records in many cases were inadequate to even calculate a 1099.

Nurumbi played a wild card.

There is a court-created exception to the customary documentation requirements. It is called the Cohan rule, and it refers to the person and case that prompted the exception decades ago. The rule has two key requirements:

(1)  One must prove that the expenditure occurred, and

(2)  One must prove that the expenditure relates to and was incurred in one’s trade or business.

Even then, the exception will probably not yield the same result as keeping records. The Court may spot you something, but that something is likely to be much less than what you actually incurred.

Nurumbi’s records were so feckless that it would have been unsurprising if the Court allowed nothing.

Except …

Remember that he sometimes paid his drivers electronically from the second bank account.

The Court spotted him a deduction of approximately $157 grand for those payments.

What about the cash payments to his drivers?

No dice.

Let’s summarize the damage.

The IRS increased his 2015 income from $18 to $543 thousand.

The Court allowed a deduction of approximately $157 thousand.

There was another significant deduction that we did not discuss: the fee paid to Uber itself. That was approximately $163 thousand.

That still leaves a bump to income of almost $205 grand.

I believe that Nurumbi paid the money to his family and friends.

But there was no tax deduction.

To be fair, he is the one who decided to keep the payments under-the-table. While not stated, I suspect this … flexibility … was a key factor in the Court’s decision.

Our case this time was Nurumbi v Commissioner, TC Memo 2021-79.

You Sell Your Lottery Winnings

I was looking at a case where someone won the New York State Lottery.

I could have worse issues, methinks.

But there was a tax issue that is worth talking about.

Let’s say you won $17.5 million in the lottery.

You elect to receive it 26 years.

          QUESTION: How is this going to be taxed?

Easy enough: the tax Code considers lottery proceeds to be the same as gambling income. It will be taxed the same as a W-2 or an IRA distribution. You will pay ordinary tax rates. You will probably be maxing the tax rates, truthfully.

Let’s say you collected for three years and then sold the remaining amounts-to-be-received for $7.1 million.

          QUESTION: How is this going to be taxed?

I see what you are doing. You are hoping to get that $7.1 million taxed at a capital gains rate.

You googled the definition of a capital asset and find the following:

            § 1221 Capital asset defined.

(a)  In general.

For purposes of this subtitle, the term "capital asset" means property held by the taxpayer (whether or not connected with his trade or business), but does not include-

(1)  stock in trade of the taxpayer or other property of a kind which would properly be included in the inventory of the taxpayer if on hand at the close of the taxable year, or property held by the taxpayer primarily for sale to customers in the ordinary course of his trade or business;

(2) property, used in his trade or business, of a character which is subject to the allowance for depreciation provided in section 167 , or real property used in his trade or business;

(3) a patent, invention, model or design (whether or not patented), a secret formula or process, a copyright, a literary, musical, or artistic composition, a letter or memorandum, or similar property, held by-

(A)  a taxpayer whose personal efforts created such property,

(B)  in the case of a letter, memorandum, or similar property, a taxpayer for whom such property was prepared or produced, or

(C)  a taxpayer in whose hands the basis of such property is determined, for purposes of determining gain from a sale or exchange, in whole or part by reference to the basis of such property in the hands of a taxpayer described in subparagraph (A) or (B) ;

(4) accounts or notes receivable acquired in the ordinary course of trade or business for services rendered or from the sale of property described in paragraph (1) ;

(5) a publication of the United States Government (including the Congressional Record) which is received from the United States Government or any agency thereof, other than by purchase at the price at which it is offered for sale to the public, and which is held by-

(A)  a taxpayer who so received such publication, or

(B)  a taxpayer in whose hands the basis of such publication is determined, for purposes of determining gain from a sale or exchange, in whole or in part by reference to the basis of such publication in the hands of a taxpayer described in subparagraph (A) ;

(6) any commodities derivative financial instrument held by a commodities derivatives dealer, unless-

(A)  it is established to the satisfaction of the Secretary that such instrument has no connection to the activities of such dealer as a dealer, and

(B)  such instrument is clearly identified in such dealer's records as being described in subparagraph (A) before the close of the day on which it was acquired, originated, or entered into (or such other time as the Secretary may by regulations prescribe);

(7) any hedging transaction which is clearly identified as such before the close of the day on which it was acquired, originated, or entered into (or such other time as the Secretary may by regulations prescribe); or

(8) supplies of a type regularly used or consumed by the taxpayer in the ordinary course of a trade or business of the taxpayer.

Did you notice how this Code section is worded: a capital asset is property that is not …?

You don’t see anything there that looks like your lottery, and you are thinking maybe you have a capital asset. The sale of a capital asset gets one to capital gains tax, right?

You call me with your tax insight and planning.

If tax practice were only that easy.

You see, over the years the Courts have developed doctrines to fill-in the gaps in statutory Code language.

We have spoken of several doctrines before. One was the Cohan rule, named after George Cohan, who showed up at a tax audit long on deductions and short on supporting documentation.  The Court nonetheless allowed estimates for many of his expenses, reasoning that the Court knew he had incurred expenses and it would be unreasonable to allow nothing because of inadequate paperwork.

Congress felt that the Cohan rule could lead to abuses when it came to certain expenses such as meals, entertainment and travel. That is how Code section 274(d) came to be: as the anti-Cohan rule for selected expense types. No documentation means no deduction under Sec 274(d).

Back to our capital gains.

Look at the following language:

We do not see here any conversion of a capital investment. The lump sum consideration seems essentially a substitute for what would otherwise be received at a future time as ordinary income."

The substance of what was assigned was the right to receive future income. The substance of what was received was the present value of income which the recipient would otherwise obtain in the future. In short, consideration was paid for the right to receive future income, not for an increase in the value of the income-producing property."

This is from the Commissioner v PG Lake case in 1958.

The Court is describing what has come to be referred to as the “substitute for ordinary income” doctrine.

The easiest example is when you receive money right now for a future payment or series of future payments that would be treated as ordinary income when received.

Like a series of future lottery payments.

Mind you, there are limits on this doctrine. For example, one could argue that the value of a common stock is equal to its expected stream of future cash payments, whether as dividends or in liquidation. When looked at in such light, does that mean that the sale of stock today would be ordinary and not capital gain income?

The tax nerds would argue that it is not the same. You do not have the right to those future dividends until the company declares them, for example. Contrast that to a lottery that someone has already begun collecting. There is nothing left to do in that case but to wait for the mailman to come with your check.

I get the difference.

In our example the taxpayer got to pay ordinary tax rates on her $7.1 million. The Court relied on the “substitute for ordinary income” doctrine and a case from before many of us were born.

Our case this time was Prebola v Commissioner, TC Memo 2006-240.

A CPA Goes Into Personal Audit

Folks, if you wind up before the Tax Court, please do not say the following:

… petitioner testified that allocating some of the expenses between his personal and business use required more time than he was willing to spend on the activity.”

Our protagonist this time is Ivan Levine, a retired CPA who was trying to get a financial service as well as a marketing business going. He worked from home. He used personal credit cards and bank accounts, as well as a family cellular plan. He also drove two vehicles – a Porsche 911 and a Chevrolet Suburban – for both personal and business reasons. All pretty standard stuff.

The IRS came down like a sack of bricks on his 2011 return. They challenged the following:

(1) Advertising

(2) Vehicle expenses

(3) Depreciation, including the vehicles

(4) Insurance (other than health)

(5) Professional fees

(6) Office expenses

(7) Supplies

(8) Utilities

(9) Cell phone

(10)       Office-in-home

Whoa! It seems to me that some of these expenses are straight-forward – advertising, for example. You show a check, hopefully an invoice and you are done. Same for professional fees, office expenses and supplies. How hard can it be?

It turns out that he was deducting the same expense in two categories. He was also confusing tax years – currently deducting payments made in the preceding year.

The office-in-home brings some strict requirements. One of them is that an office-in-home deduction cannot cause or increase an operating loss. If that happens, the offending deductions carryover to the subsequent year. It happens a lot.

It happened to Mr. Irvine. He had a carryover from 2010 to 2011, the year under audit. The IRS requested a copy of Form 8829 (that is, the office-in-home form) from 2010. They also requested documentation for the 2010 expenses.

COMMENT: Why would the IRS request a copy of a form? They have your complete tax return already, right? This occurs because the IRS machinery is awkward and cumbersome and it is easier for the revenue agent to get a copy from you.

Mr. Irvine refused to do either. The decision does not state why, but I suspect he thought the carryover was safe, as the IRS was auditing 2011 and not 2010. That is not so. Since the carryover is “live” in 2011, the IRS can lookback to the year the carryover was created. Dig in your heels and the IRS will disallow the carryover altogether.

The vehicles introduce a different tax technicality. There are certain expenses that Congress felt were too easily subject to abuse. For those, Congress required a certain level of documentation before allowing any deduction. Meals and entertainment are one of those, as are vehicle expenses.

Trust me on this, go into audit without backup for vehicle expenses and the IRS will just goose-egg you. You do not need to keep a meticulous log, but you need something. I have gotten the IRS to allow vehicle expenses when the taxpayer drives a repeating route; all we had to do was document one route. I have gotten the IRS to accept reconstructions from Outlook or Google calendar. The calendar itself is “contemporaneous,” a requirement for this type of deduction.

BTW the tricky thing about using Outlook this way is remembering to back-up Outlook at year-end. I am just saying.

You know Mr. Irvine did not do any of this.

Why?

Because it would have required “… more time than he was willing to spend on the activity.”

This from a CPA?

Being a CPA does not mean that one practices tax, or practices it extensively. I work tax exclusively, but down the hall is a CPA who has careered in auditing. He can exclaim about myriad issues surrounding financial statements, but do not ask him to do a tax return. There are also nouveau practice niches, such as forensic accountants or valuation specialists. One is still within the CPA tent, but likely far away from its tax corner.

Although a CPA, Mr. Irvine could have used a good tax practitioner. 

Credit Card Debt And Yankee Doodle Dandy

There is a tax doctrine known as the Cohan rule. It is named after the American composer and playwright George M. Cohan, the subject of the movie Yankee Doodle Dandy. While a renown musician, composer and playwright, he was not much of a recordkeeper, and he found himself in front of the Court defending his business expenses against challenge by the IRS. The Court took an extremely friendly stance and allowed him to estimate his deductions.

While the Cohan rule still exists (in some capacity) today, it should be noted that the tax Code has been changed to disallow the next George Cohan any tax deduction for estimated meals, travel and entertainment. Those particular deductions have to be substantiated or no deduction will be allowed, with or without a friendly judge.

I just read a case where (I believe) a variation on the Cohan rule came up.

The case has to do with cancellation of indebtedness income.

Did you know you could be taxed if a credit card company forgives your balance?

The reason is that the tax Code considers an "accession to wealth" to be "income" (with exceptions, of course). Take the conventional definition of wealth as 

... assets owned less debts owed ...

and you can see that the definition has two moving parts. The asset part is easy - your paycheck increases your bank account, if only fleetingly. The liability part in turn is the reason you can borrow money and not have it considered income (assets and liabilities increase by the same amount, so the difference is zero). Have the bank forgive the debt, however, and the difference is no longer zero.

Newman did something odd. He wrote a check on his Wells Fargo account and opened a new account at Bank of America. He withdrew money from the new account. Meanwhile the check on Wells Fargo bounced.

Bank of America wanted its money back. Newman did not have it anymore.

Impasse.

You may know that a bank will issue a Form 1099 (Form 1099-C, specifically) when it cancels a debt. That 1099 informs the IRS about the forgiveness, and it is a heads-up to them to check for that income on your tax return.

            Question: when does the the bank issue the 1099?

In general it will be after 36 months of inactivity. Newman bounced the check in 2008 and received the 1099 in 2011.

Newman left the 1099 off his tax return. The IRS put it back on.

The Court decided Newman had - potentially - income in 2011.

Newman fired back: he did not have income because he was insolvent in 2011, and the tax Code allows one to avoid debt income to the extent one is insolvent.

You and I use another word for "insolvent" in our day-to-day conversation:  bankrupt.

Bankrupt means that you owe more than you are worth. The tax Code has an exception to debt income for bankruptcy, but it only applies if one is in Bankruptcy Court. But what if you are trying to work something out without going to Bankruptcy Court? The Code recognizes this scenario and refers to it as "insolvency."

So Newman had to persuade the Court that he was insolvent.

One would expect him to bring in a banker's box of bank statements, credit card bills, car loan balances and so forth to substantiate his argument.

The Court looked and said:

At trial petitioner provided credible testimony that his assets and liabilities were what he claimed they were."

"Testimony?"

What about that banker's box?

Newman ran a Hail Mary play with time expiring on the game clock. While a low-probability play, he connected for a touchdown and the win.

To a tax advisor, however, Newman was decided differently from Shepherd, another Tax Court case from 2012 where the taxpayer needed much more than his testimony to substantiate his insolvency.

Why the difference between the two Court decisions?

With that question you have an insight into the headaches of professional tax practice.

IRS Fires Revenue Agent Who Lost Own Case in Tax Court

Would you be aggressive on your taxes if your job was on the line?

I am reading Agbaniyaka v Commissioner. Benjamin Agbaniyaka (Ben) started with the IRS in 1986. He received excellent evaluations, several promotions and a Master’s Degree in taxation from Long Island University. Between the years 1988 and 2006 Ben engaged in a side business selling African arts and crafts.  Here are the business results for selected years;

            2001    no sales and a loss of $5,661

            2002    sales of $3,216 and a loss of $15,232

            2003    sales of $1,372 and a loss of $7,624

            2004    sales of $200 and a loss of $6,383

He also claimed itemized deductions, including annual expenses for “Union Dues” and “Accounting Journals.”

He gets audited for 2001.

Let’s go over what the IRS expects when it sees that Schedule C on your return. It expects you to maintain records so that you can compile a tax return at the end of the year. Records can be as simple as a checkbook with a year-sheet recapping everything by category. The IRS also wants you to keep invoices and receipts, to allow a third party to trace a check to something. There are some expenses where Congress itself tells the IRS what documentation to review. Meals and car expenses are two of the most common examples. With those two, the IRS is somewhat limited in its flexibility because Congress called the tune.

Then we have the hobby loss rules. The idea here is that a business activity is expected to show a profit every so often. If the activity has always shown losses, it is difficult to buy-into the argument that it is a business. An actual business would eventually shut down and not throw good money after bad. There are exceptions, of course, but it is a good starting point.

The third point is that a revenue agent is going to be held to a higher standard. There is the education and training involved, as well as that whole working for the IRS thing.

The IRS audits 2001. It finds the following:

(1)   Ben deducted expenses for a course on trust and estates. He cannot provide any documentation, however. He also has other unsubstantiated education expenses, including his journals.

(2)   Ben claimed a deduction for union expenses. He cannot present any proof he paid the union.

(3)   Ben is hard-pressed to persuade the IRS that there was any profit intent to his arts and crafts activity. The problem is that Ben never reported a profit – ever. The IRS simply disallowed the loss.

(4)   The IRS is now miffed at Ben, especially since Ben is one of their own. They argue that the Ben’s failure to make any reasonable attempt to comply with the tax code is negligence. In fact, failure to keep records shows not only negligence but also Ben’s intentional disregard of the regulations. The IRS slapped Ben with a substantial understatement penalty.

The IRS expands the audit to 2002, 2003 and 2004, with similar results.

Can this get worse? You bet. The 1998 IRS Restructuring and Reform Act requires termination of an IRS employee found to have willfully understated his federal tax liability, unless such understatement is due to reasonable cause and not willful neglect.

Let’s go back to the substantial understatement penalty. One of the exceptions to the penalty is reasonable cause. Ben goes to Tax Court. He pretty much has to. He has to win, at least on the penalty issue. If he can get the court to see reasonable cause, he might be able to save his job.  

The Tax Court is unimpressed. Here are some comments:

We found Mr. Agbaniyaka’s testimony to be general, vague, conclusory, uncorroborated, self-serving and/or questionable in all material respects.”

During the years at issue, Mr [] was a trained revenue agent and was fully aware of the requirements imposed by …. Nonetheless, petitioners failed to maintain sufficient records for each of their taxable years 2001 through 2004 to establish their position with respect to any of the issues presented.”

On the record before us, we find that petitioners have failed to carry their burden of showing that they were not negligent and did not disregard rules and regulations, or otherwise did what a reasonable person would do, with respect to the underpayment for each of the years at issue.”

After the Tax Court’s decision, the IRS ended Ben’s employment effective April 15, 2008.

Ben appeals to the Federal Court of Appeals. That too fell on deaf ears:

“… he was undoubtedly aware that he had to substantiate his efforts to conduct a business in 2001 and beyond. Being an experienced and knowledgeable Agency employee, he had to have been aware that he could not substantiate his alleged business activities. By claiming deductions on Schedule C, he knowingly and willfully submitted tax filings to which he was not entitled.”

Ben next tried other channels. In the end, he lost and stayed fired.

How much money are we talking about? The court does not come out and specifically give a dollar amount, but there is enough to approximate the taxes as little more than $10,000.

I question the lack of documentation for some of these claimed expenses. The bank can provide cancelled checks for the subscriptions or seminars, and the union will provide a letter of membership and dues activity.  The court doesn’t elaborate, but it is clear that Ben wasn’t trying too hard.

Would you gamble your job for $10,000? Ben did.

I wouldn’t.