It is said that repetition is the mother of all learning. It is also said that insanity is repeating the same mistake and expecting a different result. It is my hope that the result of the former will overwhelm the source of the latter before it is too late.

However, based upon the seemingly continuous flow of decisions from the Tax Court rejecting taxpayers’ characterization of their outlays of funds as indebtedness, it may be a forlorn hope.

What follows is a summary of one especially ill-advised or misguided taxpayer.

Debts and Distributions

Taxpayer was the sole shareholder of S-Corp.[i] The corporation operated a mortgage broker business. It acted as an intermediary between borrowers and lenders; it did not hold any loans itself. https://www.ustaxcourt.gov/USTCInOP/OpinionViewer.aspx?ID=11650

Bad Debts?

In Tax Year, S-Corp. to make a series of advances to Borrower. The advances were made by checks, credit card payments, and wire transfers. Each advance was recorded on S-Corp.’s general ledger as a loan receivable from Borrower.

Borrower did not execute any notes for the advances received during Tax Year. The advances were unsecured, and neither S-Corp. nor Taxpayer made a public filing to record a debt in connection with the advances. Taxpayer did not know the business activities that Borrower conducted.

An adjusting entry in S-Corp.’s general ledger for December 31 of Tax Year reflected that Taxpayer instructed that the loan receivable for the Tax Year advances be written off.

On its return for Tax Year, S-Corp. claimed a large deduction for bad debts; the debt deduction was attributable to a write off for advances made to Borrower.

S-Corp.’s trial balance for the following tax year reflected that it made another loan to Borrower in that year. Taxpayer claimed not to know the purpose for that advance.

“Bad” Distributions?

As S-Corp.’s president and sole shareholder, Taxpayer authorized distributions to himself during the two years in issue. In Tax Year, Taxpayer received total distributions in excess of $1.6 million. In the following year, he received distributions in excess of $2 million.

For the years in issue, S-Corp. reported ordinary business losses, based in part on the bad debt deduction claimed for the advances made to Borrower. Taxpayer claimed S-Corp.’s losses on the Schedules E, Supplemental Income and Loss, Part II, Income or Loss from Partnerships and S Corporations, attached to his Forms 1040, U.S. Individual Income Tax Return. He engaged the same CPA firm to prepare S-Corp.’s returns and his individual returns for the years in issue.

For the years in issue, S-Corp. reported on its returns the distributions to Taxpayer. It issued Schedules K-1, Shareholder’s Share of Income, Deductions, etc., for Taxpayer that reflected the distributions and reported them as “[i]tems affecting shareholder basis”.

Taxpayer did not report any of the distributions that he received from S-Corp. for the years in issue on his individual returns.

The IRS Disagrees

The IRS examined Taxpayer’s income tax returns for the years in issue, and then issued a notice of deficiency in which it: (i) disallowed the full amount of S-Corp.’s claimed bad debt deduction for Tax Year – this adjustment flowed through to Taxpayer and was reflected as an increase to the income reported on his Schedule E; and (ii) determined that Taxpayer had unreported long-term capital gains for the years in issue.

Taxpayer petitioned the U.S. Tax Court.

Bad Debt Deduction

The Code allows a deduction for a taxable year for any debt that becomes wholly worthless within the taxable year. To deduct a business bad debt, the taxpayer must establish the existence of a valid debtor-creditor relationship, that the debt was created or acquired in connection with a trade or business, the amount of the debt, the worthlessness of the debt, and the year that the debt became worthless.

The IRS contended, and the Court agreed, that Taxpayer failed to establish any of these elements as they relate to the advances made by S-Corp. to Borrower during Tax Year.

A bad debt is deductible only for the year in which it becomes worthless. The Court explained that the subjective opinion of the taxpayer that the debt is uncollectible, without more, is not sufficient evidence that the debt is worthless.

The Court observed that Taxpayer failed to present any evidence that the alleged debt was objectively worthless in Tax Year. He testified only as to his subjective belief. Taxpayer did not identify any events during Tax Year which showed that the alleged debt was uncollectible. He testified that Borrower told him early in the following year that he could not repay the Tax Year advances, but he offered no reasoning as to why in that case the alleged debt should be treated as being worthless at the end of Tax Year.

Even accepting Taxpayer’s uncorroborated testimony, Borrower’s statement early in the following year was not enough to establish that the alleged debt to S-Corp. was objectively worthless at the end of Tax Year. Taxpayer did not describe any actions taken to try to collect the alleged debt, and he testified that he did not know whether Borrower was actually insolvent in the following year. Moreover, there was no reasonable explanation for advancing more funds to Borrower the next year if the prior advances were deemed totally unrecoverable.

Bona Fide Debt?

Taxpayer also failed to establish that the advances constituted a bona fide debt – “a valid and enforceable obligation to pay a fixed or determinable sum of money” – and that the parties intended to create a bona fide debtor-creditor relationship. Generally a debtor-creditor relationship exists if the debtor genuinely intends to repay the loan and the creditor genuinely intends to enforce repayment.

Factors indicative of a bona fide debt include: (1) whether the purported debt is evidenced by a note or other instrument; (2) whether any security was requested;

(3) whether interest was charged; (4) whether the parties established a fixed schedule for repayment; (5) whether there was a demand for repayment; (6) whether any repayments were actually made; and (7) whether the parties’ records and conduct reflected the transaction as a loan.

Borrower did not execute any notes, and Taxpayer did not request any collateral or other security for the advances. Taxpayer did not provide any documents reflecting the terms for the purported loan.

Apart from the way that the advances were recorded in S-Corp.’s general ledger, the parties’ conduct did not reflect that the advances were intended as a bona fide loan. S-Corp. made a series of unsecured advances to Borrower, and as the balance of the advances rapidly increased S-Corp. did not receive any offsetting payments or obtain any guaranties of repayment. Taxpayer did not claim that he and Borrower agreed to a schedule for repaying the advances or that he ever demanded repayment. Rather, he contended that he determined that the advances were uncollectible as of the end of Tax Year, only 10 days after the last advance had been made and without making any efforts to collect the amounts allegedly owed. He testified that by early the next year, he believed Borrower would not be able repay the advances, but he continued to direct S-Corp. to advance him more funds.

Taxpayer contended that he had a “good-faith expectation” that Borrower would repay him. He testified about his prior business dealings with Borrower, but the objective evidence and the preponderance of all evidence suggested that Taxpayer had no genuine intention of requiring Borrower to repay the advances. The real purpose of the advances remained unexplained.

The Court was not persuaded that a bona fide debt was created. It held that Taxpayer had failed to establish whether and when the advances became worthless or that the advances should even be considered a bona fide debt for tax purposes. Accordingly, the Court sustained the IRS’s determination to disallow the bad debt deduction in full.

Distributions from S-Corp.

The IRS contended that Taxpayer failed to report capital gains from the distributions that he received from S-Corp., during the years in issue. According to the IRS, the distributions were in excess of Taxpayer’s adjusted basis in S-Corp’s stock.

Under the Code, a shareholder of an S corporation takes into account their pro rata share of the corporation’s items of income, loss, deduction, or credit for the corporation’s taxable year ending with or in the shareholder’s taxable year. The Code also provides that a shareholder’s basis in their stock of the S corporation is increased by items of income passed through to the shareholder, and decreased by passed through items of loss and deduction. A shareholder’s stock basis is also decreased by distributions received from the S corporation that are not includible in the shareholder’s income. A distribution is not included in the gross income of a shareholder to the extent that it does not exceed the shareholder’s adjusted basis for the stock. The portion of a distribution that exceeds this adjusted basis is treated as gain from the sale or exchange of property.

Taxpayer contended that he did not take distributions in excess of basis. He claimed that he was personally liable to S-Corp. for the distributions that he received during the years in issue because he received them in violation of State law. Under State law, Taxpayer claimed, a shareholder who knowingly receives any distribution that exceeds the amount of the corporation’s retained earnings immediately prior to the distribution is liable to the corporation for the amount so received. For each of the years in issue, S-Corp.’s tax return reflected that it had negative retained earnings.

At this point, one might have expected Taxpayer to characterize the erstwhile “distributions” as loans from the corporation; after all, if his description of the result under State law was accurate, the funds had to be returned. However, Taxpayer instead contended that his liability to S-Corp. under State law “increased his debt basis in the corporation.” How this would have been relevant in determining the proper tax treatment of the distributions made to Taxpayer is anyone’s guess.

The Court stated that Taxpayer had misinterpreted the Code in arguing that his purported obligation to repay the distributions created debt basis. The Court then pointed out that even if Taxpayer established that he had basis in some bona fide indebtedness of S-Corp., it would not affect the taxability of the distributions that he received. The Court pointed out that the Code’s S-corporation-distribution provisions do not identify distributions that decrease a shareholder’s stock basis as an item to be applied to a shareholder’s debt basis after the stock basis has been reduced to zero.

The Court agreed with the IRS that the distributions had to be reported as income and treated as capital gain to the extent that they exceeded Taxpayer’s basis in S-Corp.’s stock. Taxpayer did not dispute the IRS’s calculations of his stock basis for the years in issue. Thus, the Court sustained the determination that Taxpayer had unreported capital gain for the years in issue.

Another One Bites the Dust

Taxpayer did not fare well, but he received his “just deserts.” He totally failed to establish that the advances to Borrower were real debts. The disallowance of the bad debt deduction claimed by Taxpayer resulted in an increase of his “flow-through” S corporation income and, thereby, an increase in his basis for his S-Corp. stock.

The interplay of the disallowed bad debt deduction for Tax Year, and the tax treatment of the distribution made to Taxpayer that year, affords us an opportunity to consider the order in which stock basis is increased or decreased under the Code, and the importance thereof.

The taxability of a distribution and the deductibility of a loss are both dependent on stock basis; for this reason, there is an ordering rule in computing stock basis. Under this rule – which favors tax-free distributions over currently deductible losses – stock basis is adjusted annually, as of the last day of the S corporation’s tax year, in the following order:

  1. Increased for income items;
  2. Decreased for distributions;
  3. Decreased for non-deductible, non-capital expenses; and
  4. Decreased for items of loss and deduction.

When determining the taxability of a distribution, the shareholder looks solely to their stock basis; debt basis is not considered, as Taxpayer learned.

Thus, there was a “silver lining” in the denial of Taxpayer’s loss deduction in that his stock basis was increased, thereby sheltering some of the distribution from S-Corp. – small comfort, though, because he recognized more ordinary income in exchange for less capital gain. Oh well.

 

[i] The corporation was always treated as an S corporation for tax purposes, and had no earnings and profits accumulated from the operations of any C corporation tax years.

Some lessons need to be repeated until learned. It’s a basic rule of life. Don’t tug on Superman’s cape; don’t spit into the wind; don’t pull the mask off that old Lone Ranger; and if you are going to make a loan, give it the indicia of a loan and treat it as a loan.

The last of these lessons appears to be an especially difficult one for many owners of closely held businesses, at least based upon the steady flow of Tax Court cases in which the principal issue for decision is whether an owner’s transfer of funds to his business is a loan or a capital contribution.

The resolution of this question can have significant tax and economic consequences, as was illustrated by a recent decision.

Throwing Good after Bad

Corp had an unusual capital structure. It had about 70 common shareholders, including key employees and some of Taxpayer’s family members, but common stock formed a very small portion of its capital structure. Indeed, although Taxpayer was Corp’s driving force, he owned no common stock. Corp’s primary funding came in the form of cash advances from Taxpayer.

Over several years, Taxpayer made 39 separate cash advances to Corp totaling millions of dollars. For each advance, Corp executed a convertible promissory note, bearing market-rate interest that Corp paid when due.

Taxpayer subsequently advanced a few more millions, of which only a small portion was covered by promissory notes, Corp recorded all these advances as loans on its books, and it continued to accrue interest, though no interest was paid on any of this purported indebtedness.

After a few years, the entirety of this purported indebtedness was converted to preferred stock (the “Conversion”), representing 78% of Corp’s capital structure.

Taxpayer then made additional cash advances to Corp which were Corp’s sole source of funding during this period. Taxpayer generally made these advances monthly or semi-monthly in amounts sufficient to cover Corp’s budgeted operating expenses for the ensuing period.

Corp executed no promissory notes for these advances and furnished no collateral. As before, it recorded these advances on its books as loans and accrued interest, but it never paid interest on any of this purported indebtedness. These advances, coupled with Taxpayer’s preferred stock, constituted roughly 92% of Corp’s capital structure.

Corp incurred substantial losses during most years of its existence. This fact, coupled with Corp’s inability to attract other investors or joint venture suitors, caused Taxpayer to question the collectability of his advances. He obtained an independent evaluation of Corp’s financial condition, and was informed that Corp’s condition was precarious: Its revenue was 98% below target, and it had massive NOLs. Without Taxpayer’s continued cash infusions, he was told, the company would have to fold.

Taxpayer discussed with his accountant the possibility of claiming a bad debt loss deduction for some or all of his advances. Taxpayer took the position that all of his advances were debt and that the advances should be written off individually under a “first-in, first-out” approach.

Taxpayer’s attorney prepared a promissory note to consolidate the still-outstanding advances that Taxpayer did not plan to write off. While these documents were being prepared, Taxpayer made additional monthly advances to Corp. Taxpayer and Corp executed a debt restructuring agreement, a consolidated promissory note, and a certificate of debt forgiveness, all of which were backdated to a date after the Conversion.

Corp continued to operate with Taxpayer continuing to advance millions which, again, were not evidenced by promissory notes.

Taxpayer filed his Federal income tax return on which he reported a business bad debt loss reflecting the write-down of his advances to Corp. According to Taxpayer, this loss corresponded to advances he had made after the Conversion. Taxpayer claimed this loss as a deduction against ordinary income.

Business Bad Debt

The IRS disallowed the business bad debt deduction, and issued a notice of deficiency. Taxpayer petitioned the Tax Court.

The Code allows as an ordinary loss deduction for any “bona fide” business debt that became worthless within the taxable year. A business debt is “a debt created or acquired in connection with a trade or business of the taxpayer” or “a debt the loss from the worthlessness of which is incurred in the taxpayer’s trade or business.” To be eligible to deduct a business bad debt, an individual taxpayer must show that he was engaged in a trade or business, and that the debt was proximately related to that trade or business.

A bona fide debt is one that arises from “a debtor-creditor relationship based upon a valid and enforceable obligation to pay a fixed or determinable sum of money.” Whether a purported loan is a bona fide debt for tax purposes is determined from the facts and circumstances of each case, including the purported creditor’s reasonable expectation that the amount will be repaid.

Advances made by an investor to a closely held or controlled corporation may properly be characterized, not as a bona fide loan, but as a capital contribution. In general, advances made to an insolvent debtor are not debts for tax purposes, but are characterized as capital contributions.

The principal issue for decision was whether Taxpayer’s advances to Corp constituted debt or equity.

Bona Fide Debt

Taxpayer asserted that all of his advances to Corp constituted bona fide debt, whereas the IRS contended that Taxpayer made capital investments in his capacity as an investor. In determining whether an advance of funds constitutes bona fide debt, the Court stated, “economic reality provides the touchstone.”

The Court began by noting that, if an outside lender would not have lent funds to the corporation on the same terms as did the insider, an inference arises that the advance was a not a bona fide loan, even if “all the formal indicia of an obligation were meticulously made to appear.”

In general, the focus of the debt-vs.-equity inquiry is whether the taxpayer intended to create a debt with a reasonable expectation of repayment and, if so, whether that intent comports with creating a debtor-creditor relationship. The key to this determination is generally the taxpayer’s actual intent.

The Court identified the following nonexclusive factors to examine in determining whether an advance of funds gives rise to bona fide debt as opposed to an equity investment:

Labels on the Documents

If a corporation issues a debt instrument, such as a promissory note, that labeling supports the debt characterization.

Corp issued promissory notes for some of the cash advances Taxpayer made before the Conversion, those notes were converted to preferred stock and were not before the Court. The amount that was before the Court was advanced after the Conversion, and Corp did not issue a single promissory note to cover any of those advances. Rather, Taxpayer advanced cash on open account.

It was only in connection with the write-down that Corp issued a promissory note to Taxpayer to consolidate the portion of his advances that he chose not to write off, backdated to an earlier time. The Court found that this document was a self-serving document created in connection with Taxpayer’s year-end tax planning.

Fixed Maturity Date

A fixed maturity date is indicative of an obligation to repay, which supports characterizing an advance of funds as debt. Conversely, the absence of a fixed maturity date indicates that repayment depends on the borrower’s success, which in turn supports characterization as equity.

Because Corp issued no promissory notes for any of the advances at issue, there was of necessity no fixed maturity date.

Source of Payments

Where repayments depend on future corporate success, an equity investment may be indicated. And where prospects for repayment are questionable because of persistent corporate losses, an equity investment may be indicated.

Corp had substantial losses, its expenses vastly exceeded its revenue for all relevant years, and no payments of principal or interest had been made on Taxpayer’s still-outstanding advances. Corp was kept afloat only because Taxpayer continued to provide regular cash infusions keyed to Corp’s expected cash needs for the ensuing period. Thus, the most likely source of repayment of Taxpayer’s advances would be further cash infusions from Taxpayer himself.

Taxpayer testified that he hoped to secure ultimate repayment upon sale of Corp to a third party or a third-party investment in Corp. But this, the Court countered, is the hope entertained by the most speculative types of equity investors. Taxpayer was a “classic capital investor hoping to make a profit, not a creditor expecting to be repaid regardless of the company’s success or failure.”

Right to Enforce Payment of Principal and Interest

A definite obligation to repay, backed by the lender’s rights to enforce payment, supports a debt characterization. A lack of security for repayment may support equity characterization.

Although Taxpayer’s advances were shown as loans on Corp’s books, there was no written evidence of indebtedness fixing Corp’s obligation to repay at any particular time. None of Taxpayer’s advances was secured by any collateral. And even if Taxpayer were thought to have a “right to enforce repayment,” that right was nugatory because his continued cash infusions were the only thing keeping Corp afloat. Had he enforced repayment, he would simply have had to make a larger capital infusion the following month.

Participation in Management

Increased management rights, in the form of greater voting rights or a larger share of the company’s equity, support equity characterization.

Although Taxpayer had de facto control, he literally owned no common stock. But through his cash advances and preferred stock he held about 92% of Corp’s capital. Taxpayer contended that none of his advances gave him increased voting rights or a larger equity share. This was literally true, but it meant little because he already had complete control of the company by virtue of his status as its sole funder.

Status Relative to Regular Creditors

If Taxpayer had subordinated his right to repayment to that of other creditors, that would have supported an equity characterization.

However, Taxpayer was the only supplier of cash to Corp, which borrowed no money from banks and had no “regular creditors.” Taxpayer had, in absolute terms, none of the rights that a “regular creditor” would have; there was no promissory note, no maturity date, no collateral, no protective covenant, no personal guaranty, and no payment of interest. No “regular creditor” would have lent funds to a loss-ridden company like Corp on such terms.

Parties’ Intent

The Court examined whether Taxpayer and Corp intended the advance to be debt or equity. The aim is to determine whether the taxpayer intended to create a “definite obligation, repayable in any event.”

Taxpayer’s actions suggested that he intended the advances to be equity. He did not execute promissory notes for any of the advances at issue. He received no interest on his advances and made no effort to collect interest or enforce repayment of principal. Although Corp recorded the advances as loans and accrued interest on them, Taxpayer’s control over the company gave him ultimate discretion to decide whether and how repayment would be made. In fact, he expected to be repaid, as a venture capitalist typically expects to be repaid, upon sale of Corp to a third party or a third-party investment in Corp.

Inadequate Capitalization

A company’s capitalization is relevant to determining the level of risk associated with repayment. Advances to a business may be characterized as equity if the business is so thinly capitalized as to make repayment unlikely.

Taxpayer urged that, after the Conversion, the bulk of Corp’s capital structure consisted of preferred stock. He accordingly insisted that Corp was adequately capitalized at the time he made later advances.

The Court disagreed with Taxpayer’s assessment of the situation, observing that he made dozens of cash advances totaling many millions of dollars, and did not receive promissory notes until he decided to write off a portion of the purported debt.

Moreover, the Court continued, while Corp’s capitalization may have been adequate, that fact was not compelling. Normally, a large “equity cushion” is important to creditors because it affords them protection if the company encounters financial stress: The creditors will not be at risk unless the common and preferred shareholders are first wiped out. But because Taxpayer himself supplied almost 100% of Corp’s “equity cushion,” he would not derive much comfort from the latter prospect.

Identity of Interest between Creditor and Sole Shareholder

Taxpayer was not Corp’s sole shareholder, but he controlled the company and during the relevant period owned between most of Corp’s capital structure. There was thus a considerable identity of interest between Taxpayer in his capacities as owner and alleged lender. Under these circumstances, there was not a “disproportionate ratio between * * * [the] stockholder’s ownership percentage and the corporation’s debt to that stockholder.”

Payment of Interest

If no interest is paid, that fact supports equity characterization. Corp made no interest payments on any of the advances that Taxpayer made after the Conversion.

Ability to Obtain Loans From Outside Lending Institutions

Evidence that the business could not have obtained similar funding from outside sources supports characterization of an insider’s advances as equity. Although lenders in related-party contexts may offer more flexible terms than could be obtained from a bank, the primary inquiry is whether the terms of the purported debt were a “patent distortion of what would normally have been available” to the debtor in an arm’s-length transaction.

The evidence was clear that no third party operating at arm’s length would have lent millions to Corp without insisting (at a minimum) on promissory notes, regular interest payments, collateral to secure the advances, and a personal guaranty from Taxpayer. Especially is that so where the purported debtor was losing millions a year and could not fund its operations without Taxpayer’s monthly cash infusions.

Corp’s financial condition was extremely precarious in every year since its inception. The IRS determined that Corp had an extremely high risk of bankruptcy and that, without Taxpayer’s continued advances, it would surely have ceased operations. Under these circumstances, no third-party lender would have lent to Corp on the terms Taxpayer did.

In addition, Taxpayer continued to advance funds to Corp even after he concluded that its financial condition was dire enough to justify writing off some of his advances. An unrelated lender would not have acted in this manner.

After evaluating these factors as a whole, the Court found that Taxpayer’s advances were equity investments and not debt. Thus, it disallowed the Taxpayer’s business bad debt deduction.

Lesson

The proper characterization of a transfer of funds is more than a metaphysical exercise enjoyed by tax professionals. It has real economic consequences. In the Taxpayer’s case, it meant the loss of a deduction against ordinary income. Whether out of ignorance, laziness, or negligence, many business owners continue to act somewhat cavalierly toward the characterization and tax treatment of fund transfers to their business.

This behavior begs the question: “Why?” Why, indeed, when the owner can dictate the result by following a simple lesson: a promissory note, consistent bookkeeping, accrual and regular payment of interest at the AFR. C’mon guys.

What Was Intended?

Over the last thirty years, I have reviewed the income tax returns of many closely held corporations and partnerships. Quite often, on Schedule L (the balance sheet), I will see an entry for “other assets” or “other liabilities,” which are described on the attached explanatory statement as loans to or from affiliates, as the case may be. I then ask a series of questions: did the board of directors or managers of the entities approve the loan; how was the loan documented; is there a note with repayment terms; is the debt secured; does the loan provide for interest; has interest or principal been paid; has there ever been a default and, if so, has the lender taken action to collect on the loan?

Bona Fide DebtThe proper characterization of a transfer of funds to a business entity from a related entity may determine a number of tax consequences arising from the transfer, including, for example, the following: the imputation of interest income to the lender; the ability of the lender to claim a bad debt deduction; the payment of a constructive dividend to the lender’s owner where the “loan” is really a capital contribution.

If a transfer of funds to a closely held business is intended to be treated as a loan, there are a number of factors that are indicative of bona fide debt of which both the purported lender and the borrower should be aware: evidence of indebtedness (such as a promissory note); adequate security for the indebtedness; a repayment schedule, a fixed repayment date, or a provision for demanding repayment; business records (including tax returns) reflecting the transaction as a loan; actual payments in accordance with the terms of the loan; adequate interest charges; and enforcement of the loan terms.

The big question is whether there was “a genuine intention to create a debt, with a reasonable expectation of repayment, and did that intention comport with the economic reality of creating a debtor-creditor relationship?” A transaction will come under special scrutiny where the borrowing entity is related to the lender. In that case, especially, can it be shown that there was a realistic expectation of repayment? Would a third party lender have made the loan on similar terms?

A recent Tax Court opinion considered these questions at some length.

An “Investment Company”?

Taxpayer was the sole owner of Corp, an S corporation that advanced funds to start-up companies and to established companies that had an opportunity for a new product or line of business. Inexplicably, Taxpayer rarely reviewed formal written projections. obtained any third-party audits, or requested any financial statements for the companies that Corp invested in. As a matter of course, Corp did not finance any company if that company had other means to borrow, such as traditional banking. Taxpayer acknowledged that Corp provided “high-risk capital” and that it was engaged in “an investment business.”

In “return” for the money that Corp advanced, Taxpayer would acquire an equity interest in the borrower-company. Taxpayer would also acquire financial control over of the company by becoming a director, a bank account signatory, and the CFO.

According to Taxpayer, repayment of amounts advanced by Corp to a company to fund a start-up or other new “project” were not anticipated until the project had been “completed.”

Corp invested in three Companies that were relevant to the tax year at issue. Corp advanced significant amounts to each Company, some of which were advanced after the year at issue. In each case, Taxpayer acquired a significant equity interest in the Company; he was appointed a director, the CFO, the bookkeeper, and the paymaster of the Company; and he was made a signatory of its accounts. Taxpayer never received a salary from the Companies, and he stipulated that his goal for his investment in the Companies was to profit from his ownership interest.

Although Corp’s records included journal entries labeling some of its advances to the Companies as “loans,” neither Taxpayer nor Corp executed any notes, agreements, or other documents evidencing any loans to the Companies.

The IRS Steps In

On its tax return, on Form 1120S, for the tax year at issue, Corp deducted approximately $10 million as bad debt that was attributed to the advances made to the Companies. According to Taxpayer, he believed the possibility that the Companies would become profitable was remote. The bad debt deduction resulted in Corp’s reporting a net loss for the year; this loss flowed through to the Taxpayer’s personal income tax return.

The IRS examined Corp’s tax return for the tax year at issue and concluded that the bad debt deduction was erroneous. The IRS issued a notice of deficiency that disallowed Corp’s bad debt deduction, attributed the resulting income to the Taxpayer, and determined the resulting deficiency in tax.

The Tax Court asked Taxpayer to offer into evidence financial information regarding the Companies to show that they could not pay the debts to Corp. Taxpayer was unable to do so. Taxpayer did not provide any evidence that Corp ever held any of the Companies in default, and he admitted that Corp neither demanded repayment of these advances from the Companies, nor did it take legal action against them. There was no documentary evidence that Corp wrote off any portion of the alleged debts of the Companies on its books for the tax year at issue. Indeed, after the year at issue, the Companies were still operating and in good standing.

Taxpayer asserted that because he was an insider wearing several hats, no formal demands were necessary. He also claimed that Corp did not take legal action against the Companies because of his status as a shareholder of the Companies.

Bona Fide Debt

A taxpayer is entitled to a deduction in a tax year for any bona fide debt that becomes worthless within the tax year.

To be able to deduct the reported bad debt for the tax year at issue, Taxpayer had to show: (1) that the advances made to the Companies were debt (not equity); (2) that the debt became worthless in the year at issue; and (3) that the debt was incurred not as an investment, but in connection with a trade or business (i.e., the business of promoting, organizing, and financing or selling corporations). (If a taxpayer makes advances as an investor, and not in the course of a trade or business, then its loans may yield nonbusiness bad debt, which may be deducted as such only when they become worthless, and then only as short-term capital losses.)

According to the Court, a bona fide debt arises from “a debtor-creditor relationship based on a valid and enforceable obligation to pay a fixed or determinable sum of money.” By definition, a capital contribution is not a debt. The question before the Court was whether Taxpayer proved that Corp’s advances to the Companies were loans or, instead, were equity investments.

The Code authorizes the IRS to prescribe regulations setting forth factors to be taken into account in resolving the issue of whether an interest in a corporation is debt or equity, and it provides five factors that “the regulations may include”, the first of which is “a written unconditional promise to pay on demand or on a specified date a sum certain in money in return for an adequate consideration in money or money’s worth, and to pay a fixed rate of interest.” The other factors are: whether there is subordination to or preference over any indebtedness of the corporation; the ratio of debt to equity of the corporation; whether there is convertibility into the stock of the corporation; and the relationship between holdings of stock in the corporation and holdings of the interest in question.

Many courts have expanded upon these factors, and have relied upon the following criteria by which to judge the true nature of an investment which is in form a debt:
(1) the intent of the parties; (2) the identity between creditors and shareholders; (3) the extent of participation in management by the holder of the instrument; (4) the ability of the corporation to obtain funds from outside sources; (5) the “thinness” of the capital structure in relation to debt; (6) the risk involved; (7) the formal indicia of the arrangement; (8) the relative position of the obligees as to other creditors regarding the payment of interest and principal; (9) the voting power of the holder of the instrument; (10) the provision of a fixed rate of interest; (11) a contingency on the obligation to repay; (12) the source of the interest payments; (13) the presence or absence of a fixed maturity date; (14) a provision for redemption by the corporation; (15) a provision for redemption at the option of the holder; and (16) the timing of the advance with reference to the organization of the corporation.

However, the courts have also cautioned that, in such an analysis, no single criterion or group of criteria is conclusive. Moreover, the enumerated factors should be used only as aids in analyzing the economic reality of the transaction; that is, whether there is actually a contribution to capital or a true loan for income tax purposes.

The Court’s Analysis

The Court grouped the above factors into three categories: (1) the intent of the parties; (2) the form of the instrument; and (3) the objective economic reality of the transaction as it relates to the risks taken by investors.

Form
The Court noted that, unlike most “debt vs. equity” controversies, which involve investments in the form of a debt, Corp’s investment in the Companies had little or no form. There was no loan agreement providing for repayment of Corp’s advances; there was no written agreement of any sort.

According to the Court, the absence of an unconditional right to demand payment was practically conclusive that an advance was an equity investment rather than a loan for which an advancing taxpayer might be entitled to claim a deduction for a bad debt loss.

The salient fact of this case, the Court continued, was the lack of written evidence demonstrating that there was a valid and enforceable obligation to repay on the part of any of the Companies at issue that received advances from Corp. There was no written evidence of an enforceable obligation between Corp and any of the Companies, much less a provision for a fixed maturity date or a fixed rate of interest.

The Court observed that Taxpayer was not a financially unsophisticated person unaccustomed to having written agreements, yet the loans allegedly made by Corp were undocumented. Taxpayer’s uncorroborated oral testimony was insufficient to satisfy his burden in an equity-versus-debt determination. The absence of any type of formality typically associated with loans supported the conclusion that the advances were contributions to capital.

Intent
Taxpayer testified that the intent of both sides was that this was a loan and that there would be no profit-sharing, that interest would be paid and only interest would be paid, and that principal and only principal would be repaid. There was, Taxpayer said, an understanding between the parties that the borrower would post the advances as borrowed money and the lender would post them as money loaned out; and consistent with that, Taxpayer offered Corp’s journal entries that labeled some advances as loans.

In the absence of direct evidence of intent, the Court stated, the nature of the transaction may be inferred from its objective characteristics. In this case, the Court continued, no loans were documented. Such objective characteristics may include the presence of “debt instruments, collateral, interest provisions, repayment schedules or deadlines, book entries recording loan balances or interest payments, actual repayments, and any other attributes indicative of an enforceable obligation to repay the sums advanced.”

Economic Reality
The Court then turned to the economic reality of the advances. “A court may ascertain the true nature of an asserted loan transaction by measuring the transaction against the ‘economic reality of the marketplace’ to determine whether a third-party lender would extend credit under similar circumstances.”

If an outside lender would not have loaned funds to a corporation on the same terms as did an insider, an inference arises that the advance is not a bona fide loan; in other words, would an unrelated outside party have advanced funds under like circumstances?

Taxpayer stated that the Companies he chose to finance were start-up ventures that could not obtain financing from unrelated banks. As a matter of Corp policy, if a start-up company had other sources or means to borrow, Corp would not advance money to it. The Court concluded that the Companies were objectively risky debtors, and an unrelated prospective lender would probably have concluded that they would likely be unable to repay any proposed loan.

When Taxpayer decided to write off the advance to the Companies, it was because he believed the possibility they would be profitable was remote. And yet Corp continued to provide financing to the Companies after the tax year for which the bad debt deduction was claimed. No prudent lender would have continued to advance money to any of the Companies under such circumstances. The amounts advanced to the Companies were, as a matter of economic reality, placed at the risk of the businesses and more closely resembled venture capital than loans.

Also at odds with a conclusion that this was a genuine loan transaction was Taxpayer’s failure to obtain third-party audits, financial statements, or credit reports for the Companies that Corp had chosen to invest in.

The Court believed that no reasonable third-party lender would have extended money to these Companies when none of the objective attributes which denote a bona fide loan were present, including a written promise of repayment, a repayment schedule, and security for the loan.

The transfers simply did not give rise to a reasonable expectation or enforceable obligation of repayment. For these reasons, the Court found that the relationship between Taxpayer and Corp on the one hand and the three Companies on the other was not that of creditor and debtor, and the Court concluded that Corp’s advances of funds were in substance equity, and that the IRS properly disallowed the deduction.

The Lesson

The factors discussed by the Court, above, provide helpful guidance for structuring a loan between related companies. If these factors are considered, and the parties to the loan transaction document it on a contemporaneous basis, they will have objectively determinable proof of their intent, as reflected in the form and economic reality of the transaction. Of course, they will also have to act consistently with what the transaction purports to be – they will have to act as any unrelated party would under the circumstances.
There are many other situations in which the proper characterization of a transfer of funds between related entities can have significant income tax consequences. The bottom line in each case can be stated simply: decide early on what is intended, then act accordingly