Posts Tagged ‘S corporation’

Tax Roundup, 1/20/14: If it’s not a scandal, it hurts like one. And: S corporation ESOP play in WSJ.

Monday, January 20th, 2014 by Joe Kristan

The U.S. District Court for the Southern District of Iowa didn’t need my services as a juror this week, so  I will be participating in the Iowa Bar Association webinar this afternoon on new developments for 2014.  It starts at noon.  You can register here and find more information here.   I will join Roger McEowen of the ISU Center for Agricultural Law and Taxation, and Kristie Maitre, IRS Stakeholder Liason for Iowa.


20130419-1If the Tea Party scandal is not a scandal, why would it be so damaging to the IRS?  The TaxProf’s IRS Scandal Roundup for Day 255 has some eye-opening quotes from a high-powered panel from a Pepperdine/Tax Analysts Symposium last week:

Donald Korb (Partner, Sullivan & Cromwell; former IRS Chief Counsel):  I think it is incredibly damaging.  Frankly, I see it as one of the seeds of the next tax shelter era. … And in terms of scandal, I don’t think we really know. We have not been permitted to understand exactly what happened. So, who knows.

George Yin (Edwin S. Cohen Distinguished Professor of Law and Taxation, Virginia; former Chief of Staff, Joint Committee on Taxation):  I think there has been tremendous damage.  Almost without regard to what actually happened.  And I actually despair of finding out what actually happened. …

Donald Tobin (Frank E. and Virginia H. Bazler Designated Professor in Business Law, Ohio State):  I think it is awful. I agree with Don and George.  7 or 8.  I think this is ultimately going to have huge implications. …

Ellen Aprill (John E. Anderson Chair in Tax Law, Loyola-L.A.):  I agree with all of that.  I have myself avoided the word “scandal” because I just don’t know.  And some of the people I know personally.  I don’t think that was their political motivation.  So I’ve used “controversy” and “brouhaha” and everything but tried not to go all the way to scandal. …

Korb: … This is very, very damaging.  Maybe we are at a 9.5

You can already see effects in the reduction of the IRS funding request in the latest budget deal.  While Congress makes the IRS the Swiss Army Knife of tax policy, it continues to cut back its resources.  That can’t end well.  But the GOP sees that the IRS has acted as a tool for its political opponents, and it’s asking a lot for them to fund their opposition.


Robert D. Flach ponders whether the Registered Tax Return Preparer designation could be revived as a voluntary credential.  If any group of preparers can unite behind a voluntary credential with self-administered standards, great.  Just keep the IRS out of it.  It’s a poor use of their resources, and they aren’t to be trusted with that sort of power.


S imageS imageS-SidewalkESOP S corporation strategy.  The Wall Street Journal (Laura Saunders, via the TaxProf) reports on an S corporation that may have found a way to funnel all of its income to a tax-exempt ESOP via restricted stock for the non-ESOP owners.  Paul Neiffer suspects it may be too good to be true.

It would be a hard needle to thread, giving the severe 409(p) excise tax that can apply to allocations of ESOP shares to owners of closely-held S corporation.  If the strategy does win in the courts, I would expect to see legislation to change the result quickly.


Jack Townsend, Eighth Circuit Affirms Offshore Account Related Conviction


Joseph Henchman, What Same-Sex Couples Need to Know This Filing Season  (Tax Policy Blog).  He links to a nice Tax Foundation study that tells how each state is approaching same-sex marriage this filing season.

Roberton Williams, Utah Lets Same-Sex Couples File Joint Tax Returns (TaxVox)

Kay Bell, Girl Scout cookies might be tax deductible.  Unfortunately, only if you don’t eat them.

Russ Fox, The Trouble With Bitcoins: Taxation.  “If you make money with Bitcoins, it is absolutely taxable.”

Jason Dinesen, Issuing 1099s to an Incorporated Veterinarian.  So veterinary services are “medical services.”

So the IRS agrees with Corb Lund.


Tax Justice Blog, Oklahoma Shows How Not to Budget.  “The biggest offender here is one we’ve explained before: the growing trend of funneling general tax revenues toward transportation in order to delay having to enact a long-overdue gas tax increase.”

William Perez, In Honor of Martin Luther King, Jr.  “In 1960, Dr Martin Luther King, Jr., was found not guilty of filing fraudulent state tax returns for the years 1956 and 1958.”  That’s why you don’t want politicized tax enforcement.

TaxGrrrl, Why Justice Matters: The Indictment & Trial Of Dr. Martin Luther King Jr. On Tax Charges   


Annette Nellen, Real revenue sources for tax reform.  “Where can permanent tax increases be generated to offset the desired permanent tax decrease generated from permanent lower rates?”

Good, we need it.  Bloggers = Media for First Amendment Libel Law Purposes (Eugene Volokh).  “To be precise, the Ninth Circuit concludes that all who speak to the public, whether or not they are members of the institutional press, are equally protected by the First Amendment.”

That’s how it should be.

Peter Reilly, Soldier To Tax Accountant – Rachel Millios EA   


News from the Profession.  CPA Exam Pass Rates Basically Went Right Off the Cliff at the End of 2013 (Going Concern).  


Tax Roundup, 8/15/2013: Turning on the revenue cameras honestly. And mink cashmere capes!

Thursday, August 15th, 2013 by Joe Kristan

But I thought it was about safety, not money.  
 The Des Moines Register reports:

The Clive City Council today is likely to reactivate its dormant red-light camera program, but only through June 30, 2014.

In his email, Weaver said it was necessary to reactivate the cameras to ensure the city’s financial health. But tonight’s vote, he wrote, will also set in motion the dismantling next year of the camera contract and of the city ordinance authorizing the use of red-light cameras in Clive.

Give them credit for being honest, at least, rather than insulting our intelligence by saying it’s about safety.


Chicago Congressmen’s wife gets 12 months on tax charges.  At the same hearing where her husband, former Congressman Jesse Jackson Jr., received a 30-month prison term for using $750,000 in campaign funds to live the good life, Sandri Jackson received a 12-month sentence on related tax charges.  Huffington Post reports:

Jackson’s wife, Sandra, was also sentenced Wednesday. She will serve one year in prison and was ordered to pay $22,000 in restitution, after pleading guilty to a related charge of filing false tax returns. U.S. District Court Judge Amy Berman Jackson, who is not related to the Jacksons, allowed the couple to stagger their sentences so their children would have at least one parent at all times. Jackson Jr. will go to prison first, followed by Sandra.

Jackson Jr. pleaded guilty in February to using campaign funds to purchase an array of personal items, including Bruce Lee memorabilia, a $43,000 Rolex watch and a mink cashmere cape.

A mink cashmere cape?  Considering that the Congressman was elected as a Democrat in a district that hasn’t elected a Republican since the last mastodons moved out, I suppose he had to do something with the money.  I’m glad he used it to build a modest and dignified wardrobe.

TaxGrrrl has more.


Missed your S corporation deadline?  The IRS has issued a new Revenue Procedure that S-Sidewalkcombines in one place relief late or missed elections related to S corporation status.  From Revenue Procedure 2013-30, which takes effect September 30:

This revenue procedure expands and consolidates relief provisions included in prior revenue procedures that provide a simplified method for taxpayers to request relief for late S corporation elections, ESBT elections, QSST elections, QSub elections, and corporate classification elections intended to be effective on the same date as the S corporation election for the entity.

These relief provisions, which require no user fee, are a great friend to the taxpayer and the practitioner.  Still, it unfortunately continues the “reasonable cause” requirement, usually requiring some advisor to take one for the team.  Fortunately the IRS doesn’t seem to look at the reasonable cause disclosures very closely.


Speaking of S corporations:  S Election For Cash Basis C Corporation Fraught With Peril  (Peter Reilly).  The accumulated accrual-to-cash benefit is a built-in gain, taxable to the coproration.  From Peter’s post:

The only scenario I have been able to think of that might make it worthwhile to organize a professional practice as a C corporation is a sole practitioner who has the need to make very large out-of-pocket medical payments – a special school for a disabled child for example.  That would make a medical reimbursement plan worthwhile. 

And as Peter’s post illustrates, C corporations can be like lobster traps: easy to get into, difficult to live in, and painful to get out of. (apologies to Bittker and Eustice).


#Tax Justice Blog,  ITEP to Legislators: Business Tax Breaks Don’t Live Up to the Hype.  Of course they don’t.  They only exist to allow politicians to call a press conference or cut a ribbon.  From the post:

Among the reasons ITEP urged lawmakers to be skeptical of these special breaks:

  • Tax incentives often reward companies for hiring decisions or investments they would have made anyway. These “windfall” benefits significantly reduce the cost-effectiveness of every tax incentive.
  • State economies are closely interconnected, so the taxpayer dollars given to companies through incentive programs never remain in-state for very long.
  • Tax incentives require picking winners and losers. Incentive-fueled growth at one business usually comes at the expense of losses at other businesses – including businesses located in the same state.
  • Tax incentives must be paid for somehow, and state economies are likely to suffer if that means skimping on public services like education and infrastructure that are fundamental to a strong economy.

Exactly right.  It’s like taking your wife’s purse to the bar for money to pick up girls.  It’s not a great use of the money, the girls aren’t impressed, and any you get that way aren’t likely to be prizes.

Christopher Bergin, 15 Years of IRS Reform (Tax Analysts Blog):

Certainly, the IRS needs reforming, and has done some pretty bad stuff. That reform can come from within the agency or from lawmakers, but it needs to come from another place as well: a good place, a place of positive change not negative political expedience.

It’s hard to elicit “positive” thoughts for the IRS from legislators when it is clear that the agency was harassing their allies.


Kay Bell,  Unemployed? You still could face tax issues.  Unemployment comp is still taxable income.


David Shakow, The Taxation of Cloud Computing and Digital Content.   (Tax Analysts, via The TaxProf.  The rise of software-as-a-service creates a lot of challenges for the tax man.

TaxProf, The IRS Scandal, Day 98.

Cara Griffith, California’s Aggressive Position on Passive Income (Tax Analysts Blog)


Jason Dinesen,  Baseball and “Games Behind in the Loss Column”  For us Cubs fans, it’s an exercise in large numbers.


TaxGrrrl,  ‘Real Housewives’ Stars Plead Not Guilty As Bethenny Claims: I Don’t Feel Sorry For Them.   In case that matters.

The Critical Question. What’s Getting a PhD in Accounting Really All About? (Going Concern).  As far as I can tell, it’s about learning statistical techniques and writing things nobody will read over a long-enough time that you will forget any useful information you might have imparted to students from your pre-Ph.D career.  More importantly, it’s about restricting the pool of tenure-eligible candidates to maintain the salaries of the guild members.

News you can use.  E- Filing makes tax fraud easier (



Tax Court: even if you lose money, your S corporation needs to pay “reasonable” compensation.

Thursday, August 8th, 2013 by Joe Kristan

20120801-2One thing I like about S corporations is that while corporation income is taxed on shareholder’s 1040s, income on the K-1 isn’t subject to payroll or self-employment tax.

Except when it is.

Mr. Blodgett had an S corporation called Glass Blocks Unlimited, which “sold and distributed ‘glass blocks’ for the real estate market in North America.”  He was the sole shareholder and president of the company.

The Tax Court lays out some key facts (my emphasis, footnotes omitted):

 He worked full time for petitioner, which had no other full-time employees. He was responsible for all operational and financial decisions of the company, and he performed nearly all of the work necessary to run the business. Petitioner additionally used an unspecified number of day laborers, whom it paid totals of $39,733 and $41,453 in 2007 and 2008, respectively.

Petitioner did not on its 2007 and 2008 Forms 1120S report paying Mr. Blodgett a salary or wages. It did, however, distribute money to him as cash was available and he asked for it. Petitioner distributed not less than $30,844 to Mr. Blodgett over the course of 2007. During 2008, petitioner made distributions to Mr. Blodgett totaling not less than $31,644.

The IRS treated the distributions as taxable wages to the taxpayer and assessed FICA and Medicare taxes.  The taxpayer disagreed, saying that the his “reasonable” compensation was lower than that assessed by the IRS.  The judge sided with the IRS:

As president of the company, Mr. Blodgett was petitioner’s only officer. Mr. Blodgett was also petitioner’s sole full-time worker in 2007 and 2008. He performed substantially all of the work necessary to operate the business, including processing orders, collecting payments, arranging shipment of goods, managing inventory, and handling customer relations. His services generated all of petitioner’s income.

     Because Mr. Blodgett was petitioner’s employee for the periods at issue and performed substantial services for it yet it did not pay him a salary, its distributions to him are deemed wages and thus are subject to Federal employment taxes.

The taxpayer also said some of the distributions were repayment of loans to the company.  Here the taxpayer was the victim of informal bookkeeping:

There were no written agreements or promissory notes supporting Mr. Blodgett’s testimony that the transfers were loans. While it is true that a portion of the transfers was reported as loans from shareholders on petitioner’s Forms 1120S, that entry is of little value without the support of other objective criteria. Indeed, petitioner did not even report the $10,000 transfer as a shareholder loan on its 2008 return. The absence of notes or other instruments, plus petitioner’s failure to treat the $10,000 transfer as a loan at all, indicates that the transfers were not loans.

To make things worse, the court upheld late payment penalties on the payroll taxes.

I think the taxpayer gets a raw deal here.  The IRS imposed $30,844 of wages on the taxpayer in 2007, even though the corporation’s net taxable income for the year was only $877, not counting the “wages.”  It hit him with another $31,644 if wages for 2008, when pre-wage income was only $8,950.  In other words, the Tax Court expected the corporation to incur a taxable loss just to generate some payroll taxes for the IRS.  That’s ridiculous, and a worse result than the same taxpayer would have had running the business on a Schedule C.

Furthermore, the Tax Court was too cavalier in disregarding the loans and repayments.  It’s wrong to expect a one-man corporation to generate prissy paperwork when the shareholder advances funds.   Yet because he didn’t have pieces of paper with the magic words, he got stuck with payroll taxes — and penalties.

The Moral?  When advancing and withdrawing funds from an S corporation, be sure to generate the appropriate prissy paperwork.  And if a wholly-owned S corporation generates enough cash to distribute to an owner working in the business, set a salary and pay the payroll taxes on at least a “reasonable” amount, or the IRS might impose payroll taxes on all of it.  You have to protect yourself from an unreasonable IRS assessment, because it looks like the Tax Court won’t.

Cite: Glass Blocks Unlimited, T.C. Memo. 2013-180



How much K-1 loss can I deduct? Start with your basis.

Wednesday, April 10th, 2013 by Joe Kristan

20130410-1If search statistics for the Tax Update are any indication, one of the most pressing issues for people who end up here is “why can’t I deduct my K-1 loss?”

There are three main reasons why your S corporation or partnership loss might be non-deductible:

1. You can’t deduct losses in excess of your basis.
2. Even if you have basis to deduct losses, the basis has to be “at-risk,” and
3. Even if the basis is “at-risk,” losses that are “passive” might be limited.

So how do you know your basis?



– Your basis starts with your initial investment in your ownership interest.

-It is increased by taxable income and deductible expenses, as reported in lines 1-12 of the 1120-S K-1, or lines 1-13 of the 1065 K-1.

-It is increased by tax-exempt income (like municipal bond income) and reduced by permanently non-deductible expenses (like the 50% non-deductible portion of meals and entertainment expenses); these are reported on line 16 of the 1120S K-1 and line 18 of the 1065 K-1.  If you have a business that generates depletion deductions, your “excess depletion” from 1120S K-1 line 15c, or line 20 of your partnership K-1, also reduces your basis.

– It is increased by capital contributions, which appear nowhere on the 1120S K-1 and on Part I, line L of the 1065 K-1.

– It is reduced by distributions, which are on line 16 of the 1120-S K-1 and Line 19 of the 1065 K-1.

If your losses exceed your basis, your losses are limited to your basis.   If you have multiple deduction items, you have to prorate them to fit your basis.


Lets say you have an S corporation interest that starts 2010 with $3,000 in basis.  You have a K-1 line 1 loss of 9,000, line 4 interest income of $2,000, and a charitable contribution passing through on line 12 (code A) of $1,000.

You have $5,000 in basis to deduct your $10,000 in in expenses – the opening $3,000 in basis plus the positive $2,000 interest income.  You pro-rate the $10,000 expenses — you can (potentially) deduct $4,500 of line 1 loss and $500 of charitable contributions.  The remaining deductions carry forward until you increase your basis via contributions, loans, or future income.

Even if you have basis, that just gets you past one hurdle.  Your basis still has to be “at-risk,” and you can’t deduct a loss that’s “passive.”  More on that later this week.

This is, of course, a simple example.  It gets more complicated if there are distributions during the year (they count first), and if there are non-deductible expenses, like meals and entertainment.   Shareholders can count direct loans they make to an S corporation in basis — but not borrowings by the S corporation from anybody else, and not guarantees of S corporation debt.  You can learn more about S corporation basis at the IRS web site.

Come back for more 2013 filing season tips through April 15!


Bad records help stick struggling S corporation owner with extra salary

Thursday, December 27th, 2012 by Joe Kristan

S corporation K-1 income isn’t subject to self-employment or payroll taxes.  This tempts S corporation owners to take minimal salary and take earnings out as S corporation distributions instead.   Former vice-presidential nominee and model husband John Edwards famously used an S corporation to minimize his payroll taxes.

20121227-1The IRS has had success in imposing additional payroll taxes when owners of profitable S corporations take little or no salary.  Yesterday the Tax Court also imposed payroll taxes on the owner of a struggling S corporation.

The owner of a small Twin Cities courier business reported wages of $24,452 to $28,452 in 2004-2006.  He took only $2,400 in salary in 2007.  The IRS found that $55,000 was transferred from the S corporation to the owner’s bank accounts in 2007 and imposed payroll taxes on that amount of salary.

How do we know the business struggled?  The Tax Court explains:

During petitioners’ operation of H&H up to some point in 2009, H&H either lost money every year or earned little income. In 2009 petitioners finally closed the business down, after losing their home on  account of losses incurred in the business and their inability to make payments on a home equity loan obtained in 2004 to finance their purchase of the business.

This wasn’t like the CPA who earned around $200,000 from his busienss and reported salary of only $24,000.  Yet the IRS didn’t let the taxpayer’s financial ruin stand in the way of an assessment of additonal payroll taxes.  The Tax Court upheld part of the assesment:

     We believe and accept petitioner’s testimony that he in fact paid significant H&H expenses with cash using funds received from H&H. For example, petitioner credibly testified that after finishing deliveries, truck drivers often would assist with repairs on the trucks and that he would pay the drivers cash for their assistance. No evidence indicates any unusual personal use by petitioners of the funds in question received from H&H.

     In spite of the limited evidence before us, we believe it improper and excessive to charge petitioner with receipt from H&H in 2007 of $52,600 in additional wages. However, we also believe petitioner’s reported H&H wages of $2,400 are unreasonably low.

Unfortunately, as you might have guessed from this, the taxpayer’s records were a mess.  The Tax Court used a very rough estimate:

To estimate what portion of the funds petitioner received from H&H in 2007 is to be treated as wages, we believe it appropriate to average petitioner’s wages for 2002 through 2006 and to use the average wage amount as the total for petitioner’s 2007 H&H wages subject to employment taxes — namely, $30,445.

I think the result would have been better if the taxpayer had kept better records.  If the taxpayer had kept personal and company spending separate and could account for all expenses, the Tax Court might have left him alone.

Still, I think the IRS and the Tax Court did the taxpayer a disservice.  Lee Iacocca famously took a $1 salary when he was in charge of struggling Chrysler.  If Warren Buffett can hold his salary to $100,000 in a fabulously profitable company, it’s plain mean to stick a struggling owner with additional salary just to collect more payroll taxes.

Fortunately this is a “summary opinion,” which isn’t supposed to serve as precedent.  A better-represented and better-organized taxpayer might well do better.

Cite:  Herbert, T.C. Summary Opinion 2012-124



Tax Roundup, 9/21/2012: Area S corp owner knocks on Supreme Court door. And breaking! Businesses aggressively cut costs!

Friday, September 21st, 2012 by Joe Kristan

West Des Moines CPA asks Supreme Court to overturn employment tax assessment on S corporation income.  The taxpayer has filed a petition asking the U.S. Supreme Court to overturn the Eighth Circuit decision imposing employment tax on his share of S corporation income.  The taxpayer had around @200,000 of income from his accounting S corporation but only called $24,000 of it compensation, treating the remainder as K-1 income not subject to FICA and Medicare tax.  The courts raised his “salary” to about $90,000.

The petition says that the Eighth Circuit decision (Watson, 668 F.3d 1008 (8th Cir. 2012)) conflicts with a Seventh Circuit decision treating a C-Corporation CPA firm as paying disguised dividends through management companies.  While I know and admire the attorneys on the Watson petition, the Seventh Circuit case (Mulcahy, Puritsch, Salvador & Co) doesn’t really cover the same ground as Watson.

The Supreme Court only hears a small fraction of cases it is asked to hear, so the chances for a Supreme Court decision on this issue are poor.

Related: Eighth Circuit upholds ‘Watson’ decision requiring increased comp for CPA S corporation shareholder; When professional C corporations go bad

Link: Tax Analysts subscriber link to Watson petition.


Janet Novack, Senate Report Details HP & Microsoft Offshore Tax Ploys:

A new report from the Senate Permanent Subcommittee On Investigations asserts Microsoft  Corp. and Hewlett-Packard have used “aggressive” offshore ploys to save or defer billions in U.S. corporate tax.

For any expense other than tax, nobody would question the wisdom, let alone the patriotism, of “aggressive” cost-cutting.  Related: Transfer Pricing and Common Sense, Martin Sullivan,


West Des Moines Patch, Metro Developer Walters Pleads Guilty to One Count of Bank Fraud:

Metro area developer Randal L. Walters pleaded guilty Thursday to one count of bank fraud in connection with a loan to develop a Des Moines area condominium project, announced federal court officials in a news release.

During the plea proceeding in federal court, Walters, 55, of Polk County, admitted to diverting money borrowed from First Bank of West Des Moines for a Des Moines area condominium project know as the Meadow Cove project, the release said.

The story said prosecutors are recommending against prison time.


Jim Maule, Subsidies and Tax Breaks:

When a special interest or specific industry gets a tax break, it causes one or the other, or a combination, of two things to happen. First, if nothing else is adjusted, the reduction in tax revenues causes an increase in the federal deficit, which in turn adversely affects everyone. Second, if revenue is maintained, it means other taxpayers must pay more in taxes to make up for the reduction in taxes for the special interest or specific industry, and that clearly affects everyone.

It’s just as true on the state level.


Jaywalker hunting on the moors: US tax net closes on Americans living in Britain. (Financial Times via Tax Break)

Richard Morrison,Context and Background on the Nonpayers Debate (Tax Policy Blog)

TaxProf, Fleischer: Are Whistleblowers the New IRS Business Model?  Paul Caron links to a New York Times piece by Victor Fleisher on the role of snitches in tax administration.

Anthony Nitti, Is Now a Good Time to Convert Your S Corporation to An LLC?

Jason Dinesen, “Consumer Reports” Highlights Identity Theft

TaxGrrrl, Millions More Taxpayers Subject to Health Care Penalty Tax

Kay Bell, 6 million Americans expected to face Obamacare’s uninsured penalty, er, tax

Jack Townsend, Sentencing Enhancement for Defendant Perjury at Trial

Trish McIntire, e-Services and TIGTA



Have a great weekend!



IRS: you aren’t allowed to escape our trap!

Tuesday, June 19th, 2012 by Joe Kristan

Flickr image courtesy Woodswalker under Creative Commons license

A bunch of McDonalds franchisees in Utah were run in a multy-entity structure: the restaurants were operated in one corporation, while a management company provided payroll, training and benefits services to the restaurants to the operating company.  In 2002 they began working with a consultant who advised them to make an S election for the management company and start an ESOP in it.  The management company also began a non-qualified deferred comp plan for the highly-compensated employees of the managmeent company.

The ink had barely dried on the new structure when the IRS issued new regulations that pretty much wrecked it all.  New rules on S corporation ESOPs, combined with the deferred comp plan, changed everything, as the Tax Court explains (my emphasis):

 On July 21, 2003, the Commissioner issued temporary regulations under which, for the first time, the definition of synthetic equity under section 409(p)(6)(C) included employee balances under nonqualified deferred compensation plans such as the NQDCP which petitioners had established within the management company…

Where the deemed-stock ownership tests of section 409(p) are violated, there are significant consequences to the disqualified persons, to the S corporation, and to the ESOP. Prohibited allocations in favor of disqualified persons are treated as currently taxable to the disqualified persons, sec. 409(p)(2)(A), and excise taxes equal to 50% of the total prohibited allocations are imposed on the S corporation, sec. 4979A. Further, the ESOP will not satisfy the requirements of section 4975(e)(7) and will cease to qualify as an ESOP.

But other than immediate tax, a 50% penalty tax, and ESOP termination, the structure would work just fine.  So the franchisees went back to the drawing board.  They bought the management company stock back from the ESOP. paid out the deferred comp balances of about $3 million, and terminated the ESOP under their own terms.  The taxpayers pretty much undid their plan and went back to their old setup.  But the IRS had another surprise:

On audit respondent determined that petitioners’ July 12, 2004, purchase and acquisition from the ESOP of the stock in the management company occurred for the principal purpose of avoiding or evading taxes by obtaining a loss deduction to which petitioners would not otherwise have been entitled, and respondent disallowed under section 269 the approximate loss deduction of $2,969,000 petitioners claimed.

They weren’t even joking.  Now Sec. 269 is a very obscure and rarely used tool in the IRS terror kit.  In the rare cases when it is used, it usually involves C corporations trying to buy net operating losses or tax credits.  I have never heard of it used on an S corporation, and the Tax Court seemed surprised too:

Respondent acknowledges that because S corporations are passthrough entities for Federal income tax purposes and do not keep their own deductions and losses (i.e., S corporation deductions and losses automatically pass through to the shareholders), it is extremely rare that the Commissioner would seek to make a section 269 adjustment in the context of a taxpayer’s acquisition of an S corporation.

The Tax Court sensibly saw things the taxpayers way.  The judge pointed out that the taxpayers would have been stuck with a bad tax structure caused by IRS rules adopted after they had already set it up (citations omitted):

The above transactions and steps clearly were related and planned as part of an effort to avoid problems created for petitioners by the Commissioner’s temporary regulations, to restructure the management company, and to terminate the ESOP; but they represent valid and real transactions with economic effect that require our recognition as legitimate business transactions.

It’s disturbing to see the IRS try to use Sec. 269 here.  Every ownership structure is tax-motivated in one way or another.  To challenge  a taxpayer’s entity structure is an improperly tax-motivated transaction, absent some weird result like a windfall tax loss or credit, is grossly improper.  This kind of position would result in penalties if taken by a taxpayer.  Taxpayers should be able to collect a similar penalty from the IRS when the agency litigates abusively like this.

Cite: Love, T.C. Memo 2012-166


Tax Court: you can use distributions from one S corporation to restore basis in another.

Thursday, June 7th, 2012 by Joe Kristan

An important Tax Court decision issued yesterday validates a traditional S corporation planning tactic from an overreaching attack by the IRS.  Incidentally, it validates some old Tax Update advice.

S corporations, as longtime readers know, don’t generally pay their own tax.  Instead corporation income and loss passes through to the shareholders’ 1040s.  The ability to deduct corporation losses is a popular feature of S corporations, but it is limited.  Shareholders can only deduct S corporation losses to the extent they have basis in either their stock of the S corporation or loans they have made directly to the corporation.

S corporation basis starts with your investment in the company.  Income passed through to shareholders increases their basis, as do capital contributions.  Basis is reduced by losses and distributions.  Distributions of funds earned as an S corporation are generally a tax-free recovery of basis.

Taxpayers with more than one S corporation often find their basis is in the wrong place.  They may have plenty of basis in a profitable corporation, but they need more basis in a sister corporation that is losing money to deduct the losses.  The logical answer is distribute funds from the profitable business and contribute it to the loser.  That was the strategy used by a Kentucky auto dealer S corporation, Auto Acceptance, and a sister finance company, CNAC.  The Tax Court explains how the business worked:

Auto Acceptance is a car dealership, and CNAC is a finance company that deals exclusively with Auto Acceptance’s customers. Auto Acceptance is primarily engaged in the purchase of used vehicles at auction and the resale of those vehicles. CNAC purchases retail installment notes related to the vehicles that Auto Acceptance sells.

From 2004 through 2006 Auto Acceptance was losing money, while CNAC was making money.  Their accounting firm advised the common owners of the companies to make distributions from profitable CNAC and contribute them to money-losing Auto Acceptance so they could deduct the Auto Acceptance losses.  Unfortunately, CNAC’s cash was tied up in receivables, so instead CNAC distributed the receivables to shareholders, who then contributed them to the capital of Auto Acceptance. 

Along comes the IRS, saying that the distributions and contributions never took place.  The taxpayers had paperwork that convinced the court that IRS was wrong.  The IRS raised an uglier argument: that there was no substance to the transaction.

Respondent also argues that no economic outlay was made, because the resolutions and adjusting journal entries made to the books of the related companies were devoid of any economic reality and did not alter the economic positions of the parties.

This argument is similar to that made regarding “circular loans” among S corporations.  The IRS has successfully disallowed basis increases when one S corporation “loans” money to shareholders, who then “loan” the money to another S corporation, which then loans the money back to the corporation where it started.  The Tax Court said this case is different (my emphasis, footnotes omitted):

Respondent also argues that no economic outlay was made, because the resolutions and adjusting journal entries made to the books of the related companies were devoid of any economic reality and did not alter the economic positions of the parties. We find that the distributions and contributions did have real consequences that altered the positions of petitioners individually and those of their businesses. As petitioners point out, the distributions and contributions created actual economic consequences for the parties, because the accounts receivable had real value in that they were legitimate debts that Auto Acceptance owed to CNAC and thus were legitimate assets of CNAC. Petitioners’ contribution of the accounts receivable resulted in their being poorer in a material sense in that the accounts receivable were no longer collectible by them individually.

When petitioners received the accounts receivable from CNAC, as they had every right to do, and contributed them to Auto Acceptance, that transaction reduced the liabilities of Auto Acceptance; made Auto Acceptance solvent in terms of its assets exceeding its liabilities; and increased the net worth of Auto Acceptance, exposing a greater amount of its assets to its general creditors. At the same time, petitioners’ bases in CNAC were reduced by the amounts of the accounts receivable that CNAC had distributed to them, thereby reducing their ability to receive future tax-free distributions from CNAC. See sec. 1368.

The fact that the CNAC accounts receivable were distributed to petitioners and then contributed to a related entity does not require a finding that there was no economic outlay.

This supports thoughts I posted in 2004 regarding the owner of the Dart Trucking business, a Mr. Oren, who lost his deductions when the IRS disallowed basis increases from circular loans:

If Dart had instead made a cash S corporation distribution to Mr. Oren, and if Mr. Oren had then contributed the cash to the loss corporations, Mr. Oren would probably have gotten his losses. If the loss corporations then had loaned the contributed funds right back to Dart, the transaction might have still failed, but the IRS would have had a tougher argument. If the funds were left in the loss corporations, it’s hard to see where the IRS would have been able to challenge the losses.

The Moral?  The tax law allows S corporation holding companies now.  If you have commonly-owned S corporations, you can combine their basis by contributing them to an S corporation holding company and making “Q-Sub” elections.  That way you don’t have to worry about shifting basis before year-end.  If for some reason you can’t form an S corporation holding company, or really don’t want to, you should use distributions from the profitable corporation — not loans — to restore basis in the loss corporation.  You shouldn’t then stash the cash back in the starting corporation. 

Also, in this case the shareholders carefully documented their transactions; the paperwork was critical to winning the case.  So remember, paperwork really matters.

Anthony Nitti has more.

Cite: Maguire, T.C. Memo. 2012-160



Tax pro’s airplane deduction misses the runway.

Tuesday, May 29th, 2012 by Joe Kristan

A man who operated tax prep businesses in California and Nevada probably felt that he knew how to arrange things to stay out of tax trouble.  The Tax Court decided otherwise last week in the case of Joseph Anthony D’Errico v. Commissioner

TPM was a C corporation set up by the taxpayer to provide management services to S corporations that he owned in the tax prep business.  It’s possible that he used the C corporation for the “bracket racket,” diverting enough income from the S corporations to fully use the 15% corporate bracket, but the case doesn’t say so.  The taxpayer sold his S corporation businesses in 2005, which would leave the taxpayer with a management C corporation with nothing to manage. A few weeks before the January 1, 2005 sale of his businesses, the corporation got another asset:

 In December 2004 TPM purchased a Cessna airplane (airplane) for $137,500. Mr. D’Errico  had a pilot’s license and several years of flight training at the time TPM purchased the airplane. Mr. D’Errico testified that TPM purchased the airplane in order for him to travel quickly between TPM’s purported office at the Barton Drive home in Stateline, Nevada, and his two active tax preparation corporations

So what does a mangement company with nothing to manage do with its airplane?

On December 29, 2004, TPM entered into an “Aircraft Leaseback Agreement” (leaseback agreement) which allowed the flight training company Flying Start Aero to make the airplane “available to the public for rental” for no more than 75 hours per month. The leaseback agreement stated that TPM was entering into the agreement “with the intention of generating some revenue for the purpose of offsetting a portion of the aircraft operating costs”. Even though the airplane was leased to Flying Start Aero, TPM was still responsible for airplane expenses such as insurance and maintenance. The lease was canceled by Flying Start Aero in early 2006 upon TPM’s failure to pay such expenses.

The airplane was not used in TPM’s tax management related business during 2005 or 2006. Petitioner claimed in his testimony that he used the airplane on business related trips in both January and April 2007. However, Mr. D’Errico did not introduce a log of his airplane use during 2007 into evidence. The only 2007 airplane records summarized expenses one Matthew Laughlin incurred in a trip to Los Angeles. Mr. Laughlin had been Mr. D’Errico’s certified flight instructor since Mr. D’Errico began to fly in 2001. Mr. D’Errico testified that Mr. Laughlin “came out from Denver to talk to me about multiple uses for the airplane. He thought it would be a good idea for us to start our own flight school, in which he would have a flight school and I would rent the airplane to his flight school.”

Perhaps it was an excellent idea, though nothing apparently came out of it.  Deducting the airplane expenses in the corporation also seemed like a good idea:

On its TYE April 30, 2006, tax return TPM reported income from the airplane rental of $21,869, airplane expenses of $17,042, and airplane depreciation of $11,408. On its TYE April 30, 2007, tax return TPM reported no airplane rental income,7 airplane expenses of $19,351, and total depreciation of $7,324.

The corporation also deducted expenses for a Chevy Tahoe that the taxpayer testified was “exclusively for business use,” according to the opinion.  The corporation also deducted phone expenses, “supplies,” and meals.  The corporation paid “rent” to the taxpayer for an office in his home.  Also:

TPM deducted utility expenses for the Barton Drive home of $2,695 and $2,491 for its TYE April 30, 2006 and 2007, respectively. These expenses included cable television, Internet, gas, electric, and certain repairs.

Well, the corporation didn’t have a business to manage.  Maybe having cable and Internet gave it something to do. 

The Tax Court didn’t like the deductions.  It had this to say about the airplane:

TPM argues that the airplane was necessary for its tax management business because Mr. D’Errico had to travel between Nevada and southern California to fulfill TPM’s business obligations to [his tax preparation S corporations sold in 2005]. However, at the time TPM purchased the airplane, Mr. D’Errico knew that he was going to be selling… TPM has produced no evidence that the airplane was used in TPM’s tax management business after 2004.

The Tax Court didn’t just disallow the deductions (my emphasis):

As discussed above, TPM failed to establish that it conducted business-related activities at the Barton Drive home, with the result that the rent payments made to Anthony D’Errico are not deductible by TPM. Further, Mr. D’Errico failed to introduce evidence to support his claim that he used only a portion of the Barton Drive home as his personal living area. Neither the lease between TPM and Anthony D’Errico nor the sublease between Mr. D’Errico and TPM identifies certain areas of the Barton Drive home reserved for TPM’s business use. We find that Mr. D’Errico derived a personal benefit from his use of the entire Barton Drive home and received constructive dividend income as a result of the rent payments made by TPM.

Petitioners have also failed to prove TPM’s entitlement to deductions for the airplane expenses. Further, petitioners have failed to introduce evidence to show that Mr. D’Errico did not benefit from TPM’s purchase of the airplane or TPM’s paying for rental of another airplane for Mr. D’Errico to fly. Mr. D’Errico admitted that he “enjoy[ed] flying and everything” and that he used the rented airplane to continue his flight training. Mr. D’Errico also discussed using TPM’s airplane to start a flight training school with his certified flight instructor, Mr. Laughlin. Finally, petitioners failed to substantiate any amount of business travel or lack of Mr. D’Errico’s personal use of the airplane during the years at issue. We find that Mr. D’Errico derived a personal benefit from the airplane expenses paid by TPM and received constructive dividend income as a result.

When an expense of a C corporation is changed to a “constructive dividend” in an audit, the taxpayer loses twice: the corporation loses a deduction, but the taxpayer gets extra dividend income. 

The Moral? Sometimes when taxpayers sell their business, they think it might be a good idea to keep the business around “in case they need it.”  That’s fine, if pointless, but when you don’t have a business any more, you no longer have a reason to claim business expense deductions.  If the corporation pays arguably personal expenses, you run the risk of losing the corporation deduction while boosting your personal tax bill.   That’s true no matter how much you know about taxes.

Cite: D’Errico, T.C. Memo 2012-149.



So is Newt really vindicated?

Thursday, March 1st, 2012 by Joe Kristan

While his presidential campaign seems to be fading, Peter Reilly at Forbes says that at least Newt’s tax return filings are looking better after last week’s decision on S corporation compensation by the Eighth Circuit in the Watson case:

I think Newt is being more than generous to Medicare compared to what the IRS has let Mr. Watson get away with. Of course, the other side of the argument is that the IRS made Mr. Watson pay payroll tax on almost half his total compensation while Newt is at less than 10%. So it depends on whether you want to focus on the percentage or the absolute number.

I don’t think you can focus on either exclusively. You have to look at comparable employees in the business, if any, and what they are paid, as well as the role of capital in the business.
Prior coverage: Eighth Circuit upholds ‘Watson’ decision requiring increased comp for CPA S corporation shareholder