Yesterday’s post examined various changes to the taxation of S corporations, partnerships, and their owners.

Today, we will focus on a number of partnership-specific issues that were addressed by the Act.

Profits Interests2017 Tax Act

A partnership may issue a profits (or “carried”) interest in the partnership to a service or management partner in exchange for their performance of services.[1] The right of the profits interest partner to receive a share of the partnership’s future profits and appreciation does not include any right to receive money or other property upon the liquidation of the partnership immediately after the issuance of the profits interest. The right may be subject to various vesting limitations.[2]

In general, the IRS has not treated the receipt of a partnership profits interest for services as a taxable event for the partnership or the partner. However, this favorable tax treatment did not apply if: (1) the profits interest related to a substantially certain and predictable stream of income from partnership assets (i.e., one that could be readily valued); or (2) within two years of receipt, the partner disposed of the profits interest. More recent guidance clarified that this treatment would apply with respect to a substantially unvested profits interest, provided the service partner took into income his share of partnership income (i.e., the service provider is treated as the owner of the interest from the date of its grant), and the partnership did not deduct any amount of the FMV of the interest as compensation, either on grant or on vesting of the profits interest.[3]

By contrast, a partnership capital interest received for services has been includable in the partner’s income if the interest was transferable or was not subject to a substantial risk of forfeiture.[4] A capital interest for this purpose is an interest that would entitle the receiving partner to a share of the proceeds if the partnership’s assets were sold at fair market value (“FMV”) immediately after the issuance of the interest and the proceeds were distributed in liquidation.

Under general partnership tax principles, notwithstanding that a partner’s holding period for his profits interest may not exceed one year, the character of any long-term capital gain recognized by the partnership on the sale or exchange of its assets has been treated as long-term capital gain in the hands of the profits partner to whom such gain was allocated and, thus, eligible for the lower applicable tax rate.

The Act

In order to make it more difficult for some profits interest partners to enjoy capital gain treatment for their share of partnership income, for taxable years beginning after December 31, 2017, the Act provides for a new three-year holding period for certain net long-term capital gain allocated to an applicable partnership interest.

Specifically, the partnership assets sold must have been held by the partnership for at least three years[5] in order for a profits interest partner’s share of such gain to enjoy the lower tax rate applicable to long-term capital gains.

If the assets sold had not been held by the partnership for at least three years, the entire amount of any capital gain allocated to the profits interest would be treated as short-term capital gain, and would be taxed up to a maximum rate of 37% as ordinary income.[6]

An “applicable partnership interest” is any interest in a partnership that is transferred to a partner in connection with the performance of “substantial” services in any applicable trade or business.[7]

In general, an “applicable trade or business” means any activity conducted on a regular, continuous, and substantial basis that consists in whole or in part of: (1) raising or returning capital, and (2) investing in, or disposing of, or developing specified assets.

“Developing” specified assets takes place, for example, if it is represented to investors or lenders that the value, price, or yield of a portfolio business may be enhanced or increased in connection with choices or actions of a service provider or of others acting in concert with the service provider.

“Specified assets” means securities, commodities, real estate held for rental or investment, as well as other enumerated assets.

If a profits interest is not an applicable partnership interest, then its tax treatment should continue to be governed by the guidance previously issued by the IRS.[8]

Adjusting Inside Basis

In general, a partnership does not adjust the basis of partnership property following the transfer of a partnership interest unless the partnership has made an election under Code Sec. 754 to make such basis adjustments, or the partnership has a substantial built-in loss[9] immediately after the transfer.

If an election is in effect, or if the partnership has a substantial built-in loss immediately after the transfer, inside basis adjustments are made only with respect to the transferee partner. These adjustments account for the difference between the transferee partner’s proportionate share of the adjusted basis of the partnership property and the transferee’s basis in its partnership interest. The adjustments are intended to adjust the basis of partnership property to approximate the result of a direct purchase of the property by the transferee partner, and to thereby eliminate any unwarranted advantage (in the case of a downward adjustment) or disadvantage (in the case of an upward adjustment) for the transferee.

For example, without a mandatory reduction in a transferee partner’s share of a partnership’s inside basis for an asset, the transferee may be allocated a tax loss from the partnership without suffering a corresponding economic loss. Under such circumstances, if a Sec. 754 election were not in effect, it is unlikely that the partnership would make the election so as to wipe out the advantage enjoyed by the transferee partner.

The Act

In order to further reduce the potential for abuse, the Act expands the definition of a “substantial built-in loss” such that, in addition to the present-law definition, for transfers of partnership interests made after December 31, 2017, a substantial built-in loss also exists if the transferee would be allocated a loss in excess of $250,000 upon a hypothetical disposition by the partnership of all of its assets in a fully taxable transaction for cash equal to the assets’ FMV, immediately after the transfer of the partnership interest.

Limiting a Partner’s Share of Loss

A partner’s distributive share of partnership loss is allowed only to the extent of the adjusted basis (before reduction by current year’s losses) of the partner’s interest in the partnership at the end of the partnership taxable year in which the loss occurred.

Any disallowed loss is allowable as a deduction at the end of succeeding partnership taxable years, to the extent that the partner’s adjusted basis for its partnership interest at the end of any such year exceeds zero (before reduction by the loss for the year).

In general, a partner’s basis in its partnership interest is decreased (but not below zero) by distributions by the partnership and the partner’s distributive share of partnership losses and expenditures. In the case of a charitable contribution, a partner’s basis is reduced by the partner’s distributive share of the adjusted basis of the contributed property.

In computing its taxable income, no deductions for foreign taxes and charitable contributions are allowed to the partnership – instead, a partner takes into account his distributive share of the foreign taxes paid, and the charitable contributions made, by the partnership for the taxable year.

However, in applying the basis limitation on partner losses, the IRS has not taken into account the partner’s share of partnership charitable contributions and foreign taxes.

By contrast, under the S corporation basis limitation rules (see above), the shareholder’s pro rata share of charitable contributions and foreign taxes are taken into account.

The Act

In order to remedy this inconsistency in treatment between S corporations and partnerships, the Act modifies the basis limitation on partner losses to provide that the limitation takes into account a partner’s distributive share of partnership charitable contributions (to the extent of the partnership’s basis for the contributed property)[10] and foreign taxes. Thus, effective for partnership taxable years beginning after December 31, 2017, the amount of the basis limitation on partner losses is decreased to reflect these items.

What’s Next?

This marks the end of our three-post review of the more significant changes in the taxation of pass-through entities resulting from the Act.

In general, these changes appear to be favorable for the closely held business and its owners, though they do not deliver the promised-for simplification.

Indeed, the new statutory provisions raise a number of questions for which taxpayers and their advisers must await guidance from the IRS and, perhaps, from the Joint Committee (in the form of a “Blue Book”).

However, in light of the administration’s bias against the issuance of new regulations, and given its reduction of the resources available to the IRS, query when such guidance will be forthcoming, and in what form.

Until then, it will behoove practitioners to act cautiously, to keep options open, and to focus on the Act’s legislative history (including the examples contained therein) in ascertaining the intent of certain provisions and in determining an appropriate course of action for clients.

As they used to say on Hill Street Blues, “Let’s be careful out there.”

[Next week, we’ll take a look at the Act’s changes to the estate and gift tax, and how it may impact the owners of a closely held business, as well as the changes to the taxation of C corporations.]

[1]It may be issued in lieu of a management fee that would be taxed as ordinary income.

[2]See Sec. 83 of the Code.

[3]Rev. Proc. 93-27, Rev. Proc. 2001-43.

[4]In general, property is subject to a substantial risk of forfeiture if the recipient’s right to the property is conditioned on the future performance of substantial services, or if the right is subject to a condition other than the performance of services, provided that the condition relates to a purpose of the transfer and there is a substantial possibility that the property will be forfeited if the condition does not occur.

[5]Notwithstanding Code Sec. 83 or any election made by the profits interest holder under Sec. 83(b); for example, even if the interest was vested when issued, or the service provider elected under Sec. 83(b) of the Code to include the FMV of the interest in his gross income upon receipt, thus beginning a holding period for the interest.

[6]Query whether this will have any impact on profits interests that are issued in the context of a PE firm or a real estate venture, where the time frame for a sale of the underlying asset will likely exceed three years.The Act also provides a special rule for transfers by a taxpayer to related persons

[7]A partnership interest will not fail to be treated as transferred in connection with the performance of services merely because the taxpayer also made a capital contribution to the partnership. An applicable partnership interest does not include an interest in a partnership held by a corporation.

[8]Rev. Proc. 93-27, Rev. Proc. 2001-43, Prop. Reg. REG-105346-03.

[9]Prior to the Act, a “substantial built-in loss” existed only if the partnership’s adjusted basis in its property exceeded by more than $250,000 the FMV of the partnership property.

[10]The basis limitation does not apply to the excess of the contributed property’s FMV over its adjusted basis.

Our last post reviewed the “20% deduction” that may now be available to the owners of certain pass-through entities based upon their qualified business income; as we saw, there are many questions that remain unanswered.[1]

Tax Cuts and Jobs Act of 2017

Today’s post is the first of two[2] this week in which we continue our consideration of those income tax provisions of the Tax Cuts and Jobs Act of 2017[3] that most directly relate to pass-through entities – S corporations, partnerships, and sole proprietorships – and their owners.

Excess Business Losses

In determining their taxable income for a taxable year, the shareholders of an S corporation and the partners of a partnership[4] are allocated their share of the pass-through entity’s losses for such year. However, there are a number of rules that limit the ability of these owners to deduct these losses.

As a threshold matter, the aggregate amount of losses taken into account by a shareholder or partner for a taxable year cannot exceed, (i) in the case of an S corporation, the sum of the shareholder’s adjusted basis for his stock, plus his adjusted basis of any corporate indebtedness owed to the shareholder, and, (ii) in the case of a partnership, the adjusted basis of such partner’s interest in the partnership. Any excess for which a deduction is not allowed in a taxable year is carried forward.

Any pass-through loss that is allowed under the above “basis-limitation rule” must also be tested under the “at-risk” and, then, the “passive activity” loss rules before it may be utilized by a shareholder or partner in determining his taxable income. A loss that is disallowed under either of these rules is “suspended” and is carried forward indefinitely to succeeding taxable years until the taxpayer has more amounts at risk, or realizes more passive income, or disposes of his interest in the pass-through entity.

If the loss is not limited by the foregoing rules, it may be applied against the shareholder’s or the partner’s other income.

The Act

The Act imposes another limitation on a non-corporate taxpayer’s ability to utilize a pass-through loss against other income – whether it is realized through a sole proprietorship, S corporation or partnership – which is applied after the basis-limitation, at-risk, and passive loss rules.

Specifically, for taxable years beginning after December 31, 2017 and before January 1, 2026, the excess business losses of a non-corporate taxpayer are not allowed for the taxable year.

A taxpayer’s “excess business loss” for a taxable year is the excess of:

(a) the taxpayer’s aggregate deductions attributable to his trades or businesses for the year, over

(b) the sum of:

(i) the taxpayer’s aggregate gross income or gain for the year attributable to such trades or businesses, plus

(ii) $250,000 (or $500,000 in the case of a joint return).[5]

In the case of a partnership or S corporation, this provision (as in the case of the at-risk and passive activity rules) is applied at the partner or shareholder level. Each partner’s and each S corporation shareholder’s share of the pass-through entity’s items of income, gain, deduction, or loss are taken into account in applying the limitation for the taxable year of the partner or S corporation shareholder.

The non-corporate taxpayer’s excess business loss for a taxable year is carried forward and treated as part of the taxpayer’s net operating loss (“NOL”) carryforward in subsequent taxable years.[6]

Thus, consistent with the principle underlying the new rules applicable to NOLs, the excess business loss rule seeks to limit and defer the tax benefit attributable to the “excess” loss.[7]

Accounting Methods

Taxpayers using the cash method of accounting generally recognize items of income when actually or constructively received and items of expense when paid. The cash method is administratively easy and provides the taxpayer flexibility in the timing of income recognition. It is the method used by most individual taxpayers, including sole proprietorships.

Taxpayers using an accrual method generally accrue items of income when “all the events” have occurred that fix the right to receive the income, and the amount of the income can be determined with reasonable accuracy.

Taxpayers using an accrual method of accounting generally may not deduct items of expense prior to when all events have occurred that fix the obligation to pay the liability, the amount of the liability can be determined with reasonable accuracy, and “economic performance” has occurred.

In general, a C corporation, or a partnership that has a C corporation as a partner, may not use the cash method. Prior to the Act, an exception was made to the extent the average annual gross receipts of a C corporation, or of a partnership with a C corporation partner, did not exceed $5 million for all prior years (the “gross receipts test”).

The Act

Under the Act, C corporations and partnerships with C corporation partners may use the cash method of accounting if their annual average gross receipts that do not exceed $25 million for the prior three-taxable-year period (not for all periods, as under prior law), regardless of whether the purchase, production, or sale of merchandise is an income-producing factor.[8]

The Act retains the exceptions from the required use of the accrual method for qualified personal service corporations and for taxpayers other than C corporations. Thus, S corporations, and partnerships without C corporation partners, are allowed to use the cash method without regard to whether they meet the $25 million gross receipts test, so long as the cash method clearly reflects income.

Changes in Accounting Method

Because an S corporation may be able to use the cash method of accounting while an otherwise identical C corporation may be required to use the accrual method, the voluntary or involuntary conversion of an S corporation into a C corporation may cause the corporation to switch its accounting method.[9]

In general, any resulting net adjustments that increase taxable income are generally taken into account by the corporation ratably, over a four-year period beginning with the year of the change.

The Act

Under the Act, any adjustment for an eligible terminated S corporation that is attributable to the revocation of its S corporation election – i.e., a change from the cash method to the accrual method, notwithstanding the new $25 million gross receipts test – is taken into account ratably during the six-taxable-year period beginning with the year of change.

An “eligible terminated S corporation” is any C corporation which (1) was an S corporation the day before the enactment of the Act, (2) during the two-year period beginning on the date of such enactment revokes its S corporation election, and (3) all of the owners of which, on the date the S corporation election is revoked, are the same owners (and in identical proportions) as the owners on the date of enactment.

Post-S-Termination Distributions

Prior to the Act, distributions of cash by a former S corporation to its shareholders during the one-year post-termination transition period (to the extent of the accumulated adjustment account, or “AAA”) were tax-free to the shareholders and reduced the adjusted basis of the stock.

The Act

Under the Act, in the case of a distribution of money by an “eligible terminated S corporation” (see above) after the post-termination transition period, the AAA will be “allocated to such distribution,” and the distribution will be “chargeable to” the corporation’s accumulated earnings and profits, in the same ratio as the amount of the AAA bears to the amount the accumulated earnings and profits.

Thus, some portion of the distribution may be treated as a taxable dividend to the shareholders.

Electing Small Business Trust (“ESBT”)

Only certain types of trusts are eligible to be shareholders of an S corporation. One such trust is the ESBT. Generally, the eligible beneficiaries of an ESBT include individuals, estates, and certain charitable organizations eligible to hold S corporation stock directly. Prior to the Act, a nonresident alien individual could not be a potential current beneficiary[10] of an ESBT.

The Act

Beginning January 1, 2018, a nonresident alien individual may be a potential current beneficiary of an ESBT.

Of course, the S corporation stock held by the ESBT may not, itself, be distributed to the nonresident alien without terminating the S corporation election, though the income therefrom may be.

ESBTs and Charitable Contributions

In addition to its non-separately computed income or loss, an S corporation reports to its shareholders their pro rata share of certain separately stated items of income, loss, deduction, and credit, including charitable contributions made by the S corporation. The treatment of such charitable contributions depends on the tax status of the shareholder.

Generally, a trust is allowed a charitable contribution deduction for amounts of gross income, without limitation, which pursuant to the terms of the governing instrument are paid for a charitable purpose. No carryover of excess contributions is allowed. An individual, by contrast, is allowed a charitable contribution deduction limited to certain percentages of adjusted gross income, generally, with a five-year carryforward of amounts in excess of this limitation.

Prior to the Act, the deduction for charitable contributions applicable to trusts – rather than the deduction applicable to individuals – applied to an ESBT.

The Act

Effective for taxable years beginning after December 31, 2017, the Act provides that the charitable contribution deduction of an ESBT is not determined by the rules generally applicable to trusts but, rather, by the rules applicable to individuals.

Thus, the percentage limitations and carryforward provisions applicable to individuals apply to charitable contributions made by the portion of an ESBT holding S corporation stock.

Technical Termination of Partnerships

Prior to the Act, a partnership was considered “technically terminated” for tax purposes if, within a 12-month period, there was a sale or exchange[11] of fifty percent or more of the total interest in the partnership’s capital or income. Upon a technical termination, the partnership’s taxable year closed, resulting in a short taxable year, partnership-level elections generally ceased to apply, and the partnership’s depreciation recovery periods for its assets started anew.[12]

In other words, a “trap for the unwary” as the saying goes.

However, a technical termination could often prove a “blessing,” as where the sale of a fifty percent interest afforded the terminating partnership an opportunity to make an irrevocable “Section 754 election, thereby generating a beneficial upward inside basis adjustment for the acquiring partner, following which the otherwise irrevocable Section 754 election (and its potential for a downward adjustment on a later transfer), as well as any other “unwanted” elections, would disappear as a result of the termination.

The Act

The Act repeals the technical termination rule, effective for partnership taxable years beginning after December 31, 2017. Thus, the partnership in which a 50% of more interest was sold would be treated as continuing, and its tax elections would remain in effect.[13]

Tomorrow’s Post

Tomorrow, we will continue our discussion regarding the treatment of pass-through entities under the Act, including the revised taxation of profits interests.

[1] For example, when is an employee’s reputation or skill the “principal asset” of a trade or business, such that the trade or business should be treated as a specified service trade or business that does not qualify for the deduction? Should we be looking to the “personal goodwill” line of cases for guidance? For example, would the absence of an employment or non-competition agreement negate the existence of a trade or business “asset?” Or should we wait for the IRS to issue guidance?
[2] The next post will appear tomorrow.
[3] Pub. L. 115-97; the “Act.”
[4] Including a limited liability company that is treated as a partnership for tax purposes.
[5] Indexed for inflation after 2018.
[6] As we will see in a later post, NOL carryovers generally are allowed for a taxable year up to the lesser of (i) the carryover amount or (ii) 80 percent of taxable income determined without regard to the deduction for NOLs. In general, carrybacks are eliminated, and carryovers to other years may be carried forward indefinitely.
[7] Query whether any excess business loss that is carried forward will be allowed in full upon the taxpayer’s disposition of the trade or business to which such loss is attributable.
[8] The $25 million amount is indexed for inflation for taxable years beginning after 2018.
[9] Congress may believe that the reduction in the C corporation tax rate to a flat 21% may cause the shareholders of some S corporations (for example, those that generate ordinary income – as opposed to capital gain – and that do not make dividend distributions) to revoke the S election.
[10] One who is entitled to, or in the discretion of the trustee may, receive a distribution from the principal or income of the trust on a current basis.
[11] A liquidation of an interest was not counted in applying the 50% test, nor was a gift or a bequest.
[12] The terminated partnership retained its EIN.
[13] Of course, if all of the partnership interests were sold to a single person, the partnership would cease to be treated as such for tax purposes under Code Sec. 708(b)(1)(A). See Rev. Rul. 99-6.

In the weeks preceding the introduction of the bill that was just enacted as the Tax Cuts and Jobs Act (the “Act”), my colleagues teased me, “Lou, what are you going to do when Congress simplifies the Code?”

“Simplify?” I responded as I reached for the Merriam-Webster’s Dictionary that I have used since 1980 – it resides next to the HP scientific calculator that I have used since 1987 – change is not always a good thing – “Congress is incapable of simplifying anything.”

Tax Cuts and Jobs Act

“The word ‘simplify’,” I continued, “is defined as follows: to make simple or simpler; to reduce to basic essentials; to diminish in scope or complexity; to make more intelligible.”

After reviewing the final version of the legislation, two thoughts came to mind: first, Congress must not have a dictionary and, second, the most influential lobbying organization in Washington must be comprised entirely of tax professionals.

In order to better appreciate – if not fully understand – the changes wrought by the Act regarding the Federal taxation of trade or business income that is recognized, “directly or indirectly,” by non-corporate taxpayers, the reader should be reminded of the existing rules, and should also be made aware of the policy underlying the changes.

Pre-2018

A business that is conducted by an individual as a sole proprietorship (whether directly or through a single-member LLC that is disregarded for tax purposes) is not treated as an entity separate from its owner. Rather, the owner is taxed directly on the income of the business.

A business that is conducted by two or more individuals as a general partnership, a state law limited partnership, or a state law limited liability company, is treated as a pass-through entity for tax purposes – a partnership. The partnership is not itself taxable on the income of the business. Rather, each partner/member is taxed on their distributive share of the partnership’s business income.

A corporation that is formed under state law to conduct a business is not itself taxable on the income of the business if it is a “small business corporation” and its shareholders elect to treat it as an S corporation. In that case, the corporation is treated as a pass-through entity for tax purposes. In general, it is not taxable on its business income; rather, its shareholders are taxed on their pro rata share of the S corporation’s business income.

In each of the foregoing situations, the business income of an individual owner of a sole proprietorship, a partnership, or an S corporation (each a “Pass-Through Entity” or “PTE”) is treated for tax purposes as though the owner had realized such income directly from the source from which it was realized by the PTE.

In determining the taxable business income generated by a PTE, the Code allows certain deductions that are “related” to the production of such income, including a deduction for the ordinary and necessary expenses that are paid or incurred by the PTE in carrying on the business.

Because business income is treated as ordinary income (as opposed to capital gain) for tax purposes, the taxable business income of the PTE is taxed to its individual owner(s) at the regular income tax rates.[1]

What’s Behind the Change?

The vast majority of closely-held businesses are organized as PTEs, and the vast majority of newly-formed closely-held businesses are organized as limited liability companies that are treated as partnerships or that are disregarded for tax purposes.[2]

In light of this reality, Congress sought to bestow some unique economic benefit or incentive upon the non-corporate owners of PTEs in the form of a new deduction, and reduced taxes.[3]

However, Congress restricted this benefit or incentive in several ways that reflect a bias in favor of businesses that invest in machinery, equipment, and other tangible assets:[4]

  • in general, it is limited to PTEs that do not involve only the performance of services;
  • it benefits only the net business income of the PTE that flows through to the taxpayer; it does not apply to any amount paid by the PTE to the taxpayer in respect of any services rendered by the taxpayer to the PTE;
  • it does not apply to the PTE’s investment income; it is limited to the PTE’s business income; and
  • the benefit is capped, based upon how much the PTE pays in wages or invests in machinery, equipment, and other tangible property.

Beginning in 2018: New Sec. 199A of the Code

For taxable years beginning after December 31, 2017 and before January 1, 2026, an individual taxpayer[5] (a “Taxpayer”) who owns an equity interest in a PTE that is engaged in a qualified trade or business may deduct up to 20% of the qualified business income allocated to him from the PTE.

Qualified Trade or Business

Taxpayer’s qualified business income (“QBI”) is determined by each qualified trade or business (“QTB”) in which Taxpayer is an owner.[6] A QTB includes any trade or business conducted by a PTE other than a specified service trade or business.[7]

A “specified service trade or business” means any trade or business involving the performance of services in the fields of health, law, accounting, consulting, financial services, brokerage services, or any trade or business where the principal asset of such trade or business is the reputation or skill of one or more of its employees, or which involves the performance of services that consist of investing and investment management, or trading or dealing in securities.[8] However, a trade or business that involves the performance of engineering or architectural services is not a “specified service.”

Qualified Business Income

Taxpayer’s QBI from a QTB for a taxable year means Taxpayer’s share of the net amount of qualified items of income, gain, deduction, and loss that are taken into account in determining the taxable income of the QTB for that year.[9]

Items of income, gain, deduction, and loss are “qualified items” only to the extent they are effectively connected with the PTE’s conduct of a QTB within the U.S.[10]

“Qualified items” do not include specified investment-related income, gain, deductions, or loss; for example, items of gain taken into account in determining net long-term capital gain, dividends, and interest income (other than that which is properly allocable to a trade or business) are not included[11]; nor are items of deduction or loss allocable to such income.

Taxpayer’s QBI also does not include any amount paid to Taxpayer by an S corporation that is treated as reasonable compensation for services rendered by Taxpayer. Similarly, Taxpayer’s QBI does not include any “guaranteed payment” made by a partnership to Taxpayer for services rendered by Taxpayer.[12]

The Deduction

In general, Taxpayer is allowed a deduction for any taxable year of an amount equal to the lesser of:

(a) Taxpayer’s “combined QBI amount” for the taxable year, or

(b) an amount equal to 20% of the excess (if any) of

(i) Taxpayer’s taxable income for the taxable year, over

(ii) any net capital gain for the taxable year.

The combined QBI amount for the taxable year is equal to the sum of the “deductible amounts” determined for each QTB “carried on” by Taxpayer through a PTE.[13]

Taxpayer’s deductible amount for each QTB is the lesser of:

(a) 20% of the Taxpayer’s share of QBI with respect to the QTB, or

(b) the greater of:

(i) 50% of the “W-2 wages” with respect to the QTB, or

(ii) the sum of:

(A) 25% of the W-2 wages with respect to the QTB, plus

(B) 2.5% of the unadjusted basis, immediately after acquisition, of all “qualified property”.[14]

In general, the W-2 wages with respect to a QTB for a taxable year are the total wages subject to wage withholding, plus any elective deferrals, plus any deferred compensation paid by the QTB with respect to the employment of its employees during the calendar year ending during the taxable year of Taxpayer.[15]

“Qualified property” means, with respect to any QTB for a taxable year, tangible property of a character subject to depreciation that is held by, and available for use in, the QTB at the close of the taxable year, which is used at any point during the taxable year in the production of QBI, and for which the depreciable period[16] has not ended before the close of the taxable year.

Example

The taxpayer is single. She is a member of an LLC (“Company”) that is treated as a partnership for tax purposes (a PTE). The company is engaged in a QTB that is not a specified service trade or business.

Taxpayer’s taxable income for 2018 is $500,000 (i.e., gross income of $520,000 less itemized deductions of $20,000), which includes a guaranteed payment from Company of $120,000, for services rendered to Company during 2018, and her allocable share of QBI from Company for 2018 of $400,000. She has no investment income for 2018.

Her allocable share of W-2 wages with respect to Company’s business for 2018 is $300,000.

During 2018, Company purchases machinery and immediately places it into service in its QTB (the machinery is “qualified property”). Taxpayer’s allocable share of the purchase price is $750,000.

The taxpayer is allowed a deduction for the taxable year of an amount equal to the lesser of:

(a) her “combined QBI amount” for the taxable year (the guaranteed payment of $120,000 is not included in QBI), or

(b) 20% of her taxable income of $500,000 for the taxable year, or $100,000.

Taxpayer’s combined QBI amount for 2018 is equal to her “deductible amount” with respect to Company. The deductible amount is the lesser of:

(a) 20% of Taxpayer’s QBI (20% of $400,000 = $80,000), or

(b) the greater of:

(i) 50% of the W-2 wages with respect to the QTB (50% of $300,000 = $150,000), or

(ii) the sum of: 25% of the W-2 wages with respect to the QTB ($75,000), plus (B) 2.5% of the unadjusted basis, immediately after acquisition, of all qualified property (2.5% of $750,000 = $18,750): $75,000 + $18,750 = $93,750.

Thus, Taxpayer’s deductible amount is $80,000. Because this amount is less than $100,000 (20% of her taxable income of $500,000 for the taxable year), Taxpayer will be allowed to deduct $80,000 in determining her taxable income for 2018.

Looking Ahead

It remains to be seen whether the “20% deduction” based upon the QBI of a PTE will be a “game changer” for the individual owners of the PTE.

After all, the deduction is subject to several limitations that may dampen its effect. For example, QBI does not include the amount paid by the PTE to Taxpayer in respect of services rendered by Taxpayer. In addition, the losses realized in one QTB may offset the income realized in another, thereby reducing the amount of the deduction. Finally, the deduction is subject to limits based upon the wages paid and the capital investments made by the QTB.

Maximizing the Deduction?

Might an S corporation shareholder or a partner in a partnership reduce the amount paid to them by the entity for their services so as to increase the amount of their QBI and, so the amount of the deduction? In the case of an S corporation, this may result in the IRS’s questioning the reasonableness (i.e., insufficiency) of the compensation paid to the shareholder-employee.[17]

Or might a PTE decide to invest in more tangible property than it otherwise would have in order to set a greater cap on the deduction?

In any case, the business must first be guided by what makes the most sense from a business perspective.

Becoming a Pass-Through?

What if a business is already organized as a C corporation? Should the QBI-based deduction tip the scales toward PTE status?

Before taking any action with respect to changing its status for tax purposes, a C corporation will have to consider much more than the effect of the deduction for PTEs.

For example, does it even qualify as a small business corporation? If not, what must it do to qualify? Must it redeem the stock owned by an ineligible shareholder, or must it recapitalize so as to eliminate the second class of stock? Either option may prove to be economically expensive for the corporation and the remaining shareholders.

If the corporation does qualify, what assurances are there that all of its shareholders will elect to treat the corporation as an S corporation? Even if the election is made, will the presence of earnings and profits from “C” taxable years implicate the “excess passive income” rules?

In any case, a C corporation that is not otherwise contemplating a change in its tax status, should probably not become an S corporation solely because of the PTE-related changes under the Act, especially if the corporation does not contemplate a sale of its business in the foreseeable future.

Wait and See?

The deduction based on the QBI of a PTE will expire at the end of 2025 unless it is extended before then. It is also possible that it may be eliminated by Congress after 2020.

An existing PTE and its owners should continue to operate in accordance with good business practice while they and their tax advisers determine the economic effect resulting from the application of the new deduction to the PTE.

They should also await the release of additional guidance from the IRS regarding “abusive” situations, tiered entities, and other items.[18]

*This post is the first of several that will be dedicated to those portions of the Tax Cuts and Jobs Act of 2017 (H.R. 1) that are most relevant to the closely-held business and it owners.

[1] The Act reduces the highest income tax rate applicable to the individual owner of a PTE to 37% (from 39.6%) for taxable years beginning after December 31, 2017 and before January 1, 2026. Note that the 3.8% surtax continues to apply to the distributive or pro rata share of an individual partnership or shareholder who does not materially participate in the trade or business conducted by the PTE.

[2] Though occasionally, the owner(s) will elect to treat the LLC as a corporation for tax purposes; for example, to reduce employment taxes.

[3] The Act includes a number of business-related benefits that are applicable to both corporate and non-corporate taxpayers. It also includes some that are unique to corporations, such as the reduction of the corporate income tax rate from a maximum of 35% to a flat 21%.

[4] As we will see in the coming weeks, that Act contains a number of such provisions.

[5] More accurately, the benefit is available to non-corporate owners; basically, individual taxpayers, though trusts and estates are also eligible for the deduction.

[6] A PTE may conduct more than one QTB – different lines of business – or Taxpayer may own equity is more than one PTE.

[7] Also excluded is the trade or business of being an employee.

[8] The exclusion from the definition of a qualified business for specified service trades or businesses is phased in for a taxpayer with taxable income in excess of a “threshold amount” of $157,500 ($315,000 in the case of a joint return). The exclusion is fully phased in for a taxpayer with taxable income at least equal to the threshold amount plus $50,000 ($100,000 in the case of a joint return).

[9] If the net amount of the QBI is a loss (negative), it is treated as a loss from a QTB in the succeeding taxable year.

[10] Generally, when a person engages in a trade or business in the U.S., all income from sources within the U.S. connected with the conduct of that trade or business is considered to be effectively connected income.

[11] Qualified items should include the gain recognized on the sale of business assets.

[12] The IRS is authorized to issue regulations that would exclude any amount paid or incurred by the partnership to Taxpayer for services provided by Taxpayer to the partnership other than in his capacity as a partner.

[13] Taxpayer does not need to be active in the business in order to qualify for the deduction.

[14] This “wage limit” is phased in for a taxpayer with taxable income in excess of the threshold amount. The limit is fully applicable for a taxpayer with taxable income equal to the threshold amount plus $50,000 ($100,000 in the case of a joint return).

[15] In the case of a partnership or S corporation, the provision applies at the partner or shareholder level. Each partner or shareholder, as the case may be, takes into account his allocable or pro rata share of each qualified item of income, gain, deduction, and loss, and is treated as having W-2 wages and unadjusted basis for the taxable year equal to his allocable or pro rata share of the W-2 wages and unadjusted basis of the partnership or S corporation, as the case may be.

[16] The “depreciable period” is the period beginning with the date the qualified property is first placed in service and ending on the later of the date that is 10 years after such date, or the last day of the last full year in the applicable recovery period for the property.

[17] State and local taxes also need to be considered; for example, NYC’s unincorporated business income tax and its general corporation tax.

[18] “What we do in haste, we regret at leisure?”

Worlds Collide?

I like to tell my partners that there are Codes (upper case “C”), and there are codes (lower case “c”). The former include the Ten Commandments, the Code of Hammurabi, the Code of Justinian, and the Internal Revenue Code. The latter include the Pirate’s Code – which, as Captain Barbossa tells us in the movie Pirates of the Caribbean, “is more what you’d call ‘guidelines’ than actual rules” – and the Bankruptcy code.[1]

Notwithstanding the great divide that normally separates these two sets of coda, the space-time continuum is sometimes warped in such a way that they overlap, as they did in a recent decision of the bankruptcy court that considered whether a debtor-corporation’s status as an “S corporation” for tax purposes should be considered “property” for the purposes of the Bankruptcy code (the “BC”).

“S” Election as “Property”?

Debtor was a privately-held company. As a result of a large settlement and the resulting adverse effects on its business, Debtor’s relationship with its secured lender became severely strained. Debtor eventually defaulted under its loan facilities. In response, the lender discontinued debtor’s borrowing ability and cut off its access to its existing accounts. With no ability to access its cash and with no alternative sources of financing immediately available, Debtor was forced to file for protection under Chapter 11 (“reorganization”) of the BC, following which the U.S. Trustee appointed a committee of unsecured creditors.

However, prior to filing its voluntary petition, and with the consent of a majority of its shareholders, Debtor revoked its election to be treated as an S corporation for tax purposes, though it continued to satisfy the criteria for such status.[2]

Pre-Petition

During the period that Debtor was classified as an S corporation, each shareholder – and not Debtor – reported, and paid tax on, his share of Debtor’s taxable income as reflected on the Sch. K-1 issued by Debtor to the shareholder.

In accordance with Debtor’s Shareholders’ Agreement, Debtor made distributions to its shareholders to reimburse them for Debtor’s pass-through tax liability. Debtor also made direct payments of tax to the IRS on behalf of its shareholders.

As a result of revoking its “S” election, Debtor became subject to corporate-level tax as a “C” corporation, and its shareholders – to whom distributions from Debtor would likely have ceased after the filing of its petition – were no longer required to report its income on their personal returns.

C vs S Corps

Under the Code, a corporation’s “default” status is as a “C corporation,” the net income of which is subject to two levels of taxation: once at the corporate level, and then to the shareholders when distributed to them as dividends.[3]

In contrast to C corporation status, S corporation status confers “pass-through taxation.” S corporations pass corporate income, gains, losses, deductions, and credits to their shareholders, who must report their respective shares of the income and losses of the S corporation on their personal income tax returns.

Sale of Assets

A couple of months following Debtor’s petition, the Court entered an order which authorized the sale of substantially all of Debtors’ operating assets to Buyer, and the sale occurred shortly thereafter. The Court then confirmed Debtor’s Plan of Liquidation, pursuant to which the Liquidating Trust was formed as the successor to Debtor and to the unsecured creditors committee.

The Liquidating Trustee filed a complaint against the IRS and Debtor’s shareholders, seeking to avoid the revocation of Debtor’s S corporation status as a fraudulent transfer of property under the BC.[4]

The U.S. filed a motion to dismiss the complaint because, it stated, “a debtor’s tax status is not ‘property’.”

Other Courts

The Court noted that only a handful of courts have considered this issue in the context of fraudulent transfers. Of these courts, only the Third Circuit concluded that S corporation status did not constitute a property right in bankruptcy; all of the others found S corporation status to be a property right in bankruptcy.

Some of the courts that found a property right defined “property” under the BC as something that a person has rights over in order to use, enjoy, and dispose of. These courts reasoned that a debtor corporation did have a property interest in its S corporation status on the date that the status was allegedly “transferred” because the Code “guarantees and protects an S corporation’s right to dispose of [the S corporation] status at will.” Until such disposition, the corporation had the “guaranteed right to use, enjoy, and dispose” of the right to revoke its S corporation status. Consequently, these courts held that the right to make or revoke S corporation status constituted “property” or “an interest of the debtor in property.”

In contrast, the Third Circuit, reviewing a post-petition revocation, concluded that S corporation status did not constitute an interest of a debtor corporation in “property” in a bankruptcy case.

Court’s Analysis

The issue before the Court was whether Debtor’s S corporation status was an interest in “property” that was subject to transfer. If it was not, then the “S” election was not subject to the fraudulent transfer provisions of the BC.

The Court explained that the issue whether S corporation status is “property” for the purposes of the BC was a question of law. The fraudulent transfer provision allows a trustee to avoid obligations voidable under state law. The fraudulent transfer provision allows a trustee to avoid certain transfers that occurred two years prior to the petition date.

The Court acknowledged that the property of the bankruptcy estate is composed of “all legal or equitable interests of the debtor in property as of the commencement of the case.” Congressional intent, it stated, indicates that “property” under the BC is a sweeping term and includes both intangible and tangible property.

Defining “Property”

However, it continued, no BC provision “answers the threshold questions of whether a debtor has an interest in a particular item of property and, if so, what the nature of that interest is.” Property interests are created and defined by state law, unless some countervailing federal interest requires a different result.

Normally, the “federal [tax] statute ‘creates no property rights but merely attaches consequences, federally defined, to rights created under state law.'” Once “‘it has been determined that state law creates sufficient interests in the [taxpayer] to satisfy the requirements of [the statute], state law is inoperative,’ and the tax consequences thenceforth are dictated by federal law.”

In this case, the Court stated, federal tax law governed any purported property right at issue. There was clearly a countervailing federal interest because S corporation status is a creature of federal tax law. State law created “sufficient interests” in the taxpaying entity by affording it the requisite corporate and shareholder attributes to qualify for S corporation status; at that point, “‘state law [became] inoperative,’ and the tax consequences [were] dictated by federal law.” Federal tax law, which was dependent on certain state law conclusions, dictated whether S corporation status was a property right for purposes of the BC.

The Court recognized that certain interests constitute “property” for federal tax purposes when they embody “essential property rights,” which include (1) the right to use; (2) the right to receive income produced by the purported property interest; (3) the right to exclude others; (4) the breadth of the control the taxpayer can exercise over the purported property; (5) whether the purported property right is valuable; and (6) whether the purported right is transferable. A reviewing court must weigh those factors, it stated, in order to determine whether the interest in S corporation status constitutes “property” for federal tax purposes.

Applying these “essential property rights” factors, the Court observed that only one of the factors leaned in favor of classifying S corporation status as property; specifically, Debtor’s ability to use the S corporation tax status to pass its tax liability through to its shareholders. However, according to the Court, the “right to use” factor was the weakest of the “essential property rights.” Without the rights of control and disposition, the right to use was “devoid of any meaningful property interest,” the Court stated. While Debtor may have had the right to use the S corporation status, it lacked the ability to control the use of its tax classification. The right to use the classification existed only until termination.

The second factor, that the tax classification was valuable, did not lean in favor of finding that S corporation status qualified as a property right. The Liquidating Trustee hoped to generate value through avoidance of the “transferred” S corporation revocation, thus retroactively reclassifying Debtor as an S corporation during that taxable year. The Liquidating Trustee believed that by doing so, Debtor’s losses would pass through to its shareholders (to the extent of their basis in Debtor stock), offsetting other income on their personal returns, and thereby generating refunds that the Liquidating Trustee intended to demand from the shareholders for the benefit of the Liquidating Trust and the creditors.[5]

In response to this “plan,” the Court pointed out that, though something may confer value to the estate, it does not necessarily create a property right in it.

Similarly, the Court continued, a corporation cannot claim a property interest to a valuable benefit that another party has the power to legally revoke at any time.

The Court explained that the “S” election removes a layer of taxation on distributed corporate earnings by permitting the corporation to pass its income through to the corporation’s shareholders. The benefit is to the shareholders — it allows them to avoid double taxation. To the extent there is value inherent in the S election, it is value Congress intended for the corporation’s shareholders and not for the corporation.

The remaining factors, the Court continued, also leaned in favor of finding that S corporation status did not constitute a property right under federal tax law. Most importantly, a corporation has very little control over its S corporation status, yet the right to exercise dominion and control over an interest is an essential characteristic defining property.

Shareholders have the overwhelming ability to control the tax status of their corporation. Election of S corporation status may be achieved by one method—unanimous shareholder consent; the corporation does not elect S corporation status. Thus, any interest in electing S corporation status belongs to the shareholders.

The Court stated that an S corporation does not have a vested interest in its tax status after the election has been made. Rather, termination of S corporation status – including by the consent of majority of shareholders – is contingent on shareholder action; the corporation has no unilateral control over the revocation of its S corporation status.

For example, the sale by a shareholder of one share of stock to a partnership would automatically terminate a corporation’s S corporation status. As the S corporation election could be terminated voluntarily by the actions of any one shareholder, it is impossible to state that a corporation has complete control over its S corporation status. Unilateral shareholder action could extinguish S corporation tax status without the corporation taking any action.

The Court observed that S corporation status is not reflected as an asset on a corporation’s balance sheet; it is not something of value that can be transferred by the corporation to an acquiring company; it does not produce income. Rather, S corporation status is a statutory privilege that qualifying shareholders can elect in order to determine how income otherwise generated is to be taxed.

The Court ended its analysis by noting that neither the BC nor the Code allow for a trustee to choose the tax status of the entity. Rather, the BC requires that a trustee furnish returns for any year where a return was not filed as required. Similarly, the Code requires that a trustee “make the return of income for such corporation in the same manner and form as corporations are required to make such returns.” In this case, Debtor was a C corporation for tax purposes. Debtor was required to file as such. The Liquidating Trustee could no use the fraudulent transfer provisions of the BC to maneuver around that requirement.

After weighing all the factors, the Court held that S corporation status was not property under the Code. Although a corporation and its shareholders could elect to use S corporation status in order to avoid double taxation, that factor alone was not enough to outweigh all the remaining characteristics essential to qualify tax status as a property right.

Accordingly, Debtor’s S corporation status could not be considered “property” for the purposes of the BC, and there was no transfer of Debtor’s interest in property that was subject to avoidance under of the BC.

Takeaway?

A financially distressed S corporation make be forced to sell properties in order to generate liquidity with which to pay creditors, or it may negotiate for the cancellation of certain indebtedness owing to such creditors.

These transactions may generate gain or income[1] that will flow through, and be taxable, to the corporation’s shareholders. Moreover, it is likely that the corporation’s creditors will not permit it to make cash distributions to its shareholders to enable them to pay the tax on the flow-through income or gain.

On the other hand, a distressed S corporation has likely generated substantial losses, having lost not only its undistributed income and its shareholders’ capital contributions, but also the funds acquired via loans from third parties and from shareholders.

Some of these losses may have been “suspended,” and remain unused by the shareholders, because the shareholders have exhausted their basis for their shares of stock and for their loans to the corporation.

The flow-through of income or gain to the shareholders would increase their debt and stock bases (in that order), thereby allowing them to utilize some, though perhaps not all, of their suspended losses. It is also possible that the income or gain will exceed the available losses, thus resulting in a net cash outlay by the shareholders for taxes owing.

Of course, if the “S” election were revoked prior to the corporation’s filing its petition, the foregoing issues may be averted, though the corporation’s creditors may object (as the Liquidating Trustee did in the decision discussed above) because any gain or income, and the related tax liability, resulting from the sale or debt cancellation would be captured at the level of the corporate debtor.

At the end of the day, it will behoove the debtor S corporation to consult its tax and bankruptcy advisers well before approaching its creditors, and to thoroughly analyze the foregoing issues and options before deciding to revoke its tax status.

[1] With apologies to the Title 11 Bar? Nah.

[2] Fewer than 100 individual shareholders, one class of stock, etc.

[3] The Tax Cuts and Jobs Act (H.R. 1), on which the House and Senate will be voting this week, would reduce the corporate income tax rate to 21%, effective January 1, 2018. If enacted, we will cover this legislation in later posts.

[4] For example, the trustee may avoid any transfer of a debtor’s interest in property: that was made within 2 years before the date of the filing of the petition if the debtor made such transfer with intent to hinder, delay, or defraud any entity to which the debtor was or became, on or after the date that such transfer was made, indebted; or for which it received less than a reasonably equivalent value in exchange for such transfer; or was insolvent on the date that such transfer was made, or became insolvent as a result of such transfer.

[5] The Trustee’s plan was a bit more convoluted than this. You can’t make this stuff up.

[6] The application of the Code’s bankruptcy and insolvency exceptions to COD income is made at the level of the S corporation.

Some shareholders are content with being wholly passive investors in a corporation. Others desire some degree of participation in the day-to-day management of the corporation’s business. Still others are willing to abstain from any involvement in the operation of the business, but insist upon having a say with respect to certain “significant” matters (so-called “sacred rights”). Then there are those who, as a result of unforeseen circumstances, are thrust into positions of authority.

Many of these taxpayers fail to appreciate that any shareholder, director, officer, or employee of a corporation who has a “duty to act” for the corporation in complying with the NY sales tax law, may be held personally liable for the sales tax collected or required to be collected by the corporation, even if the circumstances that ultimately led to the imposition of personal liability were not of the responsible person’s doing, as illustrated by a recent decision of NY’s Division of Tax Appeals.

Tale of Two Brothers

Taxpayer was an officer and shareholder of Corp, which was a subcontractor for general contractors on numerous projects in the NY metro area.

Corp was a family-owned business, and was originally owned by Taxpayer’s parents. Taxpayer, who was an attorney, joined Corp as its counsel. Over time, Taxpayer’s brother (“Brother”) became president of Corp, and Taxpayer became its CFO. In addition, the brothers eventually became shareholders, with Taxpayer owning 22% of Corp’s issued and outstanding shares, and Brother owning 28%; their parents continued to own the remaining 50%.

Corp entered into a contract with a general contractor (“GC”) to perform work on a construction project in NYC that was more than double the size of any previous project undertaken by Corp (the “Project”). Brother negotiated the contract on behalf of Corp.

Not long afterward, Brother resigned as president of Corp because he had significantly underestimated Project’s cost in making Corp’s bid, thereby causing significant financial hardship for Corp. Upon Brother’s departure, Taxpayer assumed control of Corp and, along with it, responsibility for all phases of its work on Project.

Despite the financial difficulties, Corp continued to work on Project under Taxpayer’s direction. However, according to Taxpayer, GC began to renege on payments to Corp required under the contract. Further, Taxpayer maintained that he was forced by GC to replace several of Corp’s own employees with those of an unrelated Company, on “a time and material basis.” According to Taxpayer, Company overcharged for the work it performed and abused its overtime allowance, further hampering Corp. In addition, Taxpayer claimed that GC paid Company directly from funds allocated for Corp under their contract, rather than simultaneously paying Corp. These efforts, according to Taxpayer, were made to force Corp to fail to complete Project and allow GC to collect on an insurance bond that would have provided GC with a windfall.

As a result of the difficulties arising from Project, Corp filed a voluntary petition for relief under Chapter 11 of the Bankruptcy Code. Corp continued to operate as debtor-in-possession while in bankruptcy.

Corp also brought adversary proceedings, in the course of its bankruptcy, against both GC and Company, seeking redress for fraud, breach of contract, and other similar causes of action.

The Responsible Person

In general, the sales tax is a transaction tax, with the liability for the tax arising at the time of the transaction. It is also a “consumer tax” in that the person required to collect tax – the “vendor” (Corp, in this case) – must collect it from the buyer when collecting the sales price for the transaction to which the tax applies.

The vendor collects the tax as trustee for and on account of the State, then holds it in trust for the State until the vendor remits the tax to the State.

NY imposes personal responsibility for payment of sales tax on certain owners, officers, directors, or employees (“responsible persons”) of a corporate vendor.  This means that a responsible person’s personal assets may be taken by the State to satisfy the sales tax liability of the corporation’s business.

Personal liability may attach even where the “responsible” individual’s failure to take responsibility for collecting and/or remitting the sales tax was not willful.

Corporations

Every individual who is under a duty to act for a corporation in complying with the sales tax law is a responsible person required to collect, truthfully account for, and pay over the sales tax.  Whether an individual is a responsible person is to be determined in every case on the particular facts involved. Generally, a person is under a duty to act for a corporation if he is authorized to sign a corporation’s tax returns, is responsible for maintaining the corporation’s books, or is responsible for the corporation’s management.

It is important to note that the personal liability of a responsible person (like a corporate officer) for sales taxes is separate and distinct from that of the business – it extends beyond the business.   For example, a corporate bankruptcy does not affect the officer’s liability for the tax, since the latter involves a separate claim than one that is asserted in the corporate bankruptcy proceeding.

An officer-shareholder may not be held responsible where his role was essentially that of a minority investor who was precluded from taking action with regard to the financial and management activities of the corporation.

Bankruptcy Court’s Findings

Several examiner’s reports regarding Corp were prepared pursuant to an order of the bankruptcy court. One of these reports addressed potential avoidance actions against Corp’s insiders, and reported that disbursements from Corp were made, through the date that the bankruptcy petition was filed, to or for the benefit of Taxpayer, his father, and Brother.

Additionally, the examiner reported that during the two-year period ending with Corp’s petition, Taxpayer deposited funds into Corp’s account, but also withdrew funds from Corp that he deposited into his personal account. The net effect of these withdrawals and deposits was a deposit of $1.5 million into Corp’s account, which was treated by Corp as a loan from Taxpayer.

Another of the examiner’s reports stated that after the filing of the petition, two of Corp’s stockholders received compensation from Corp, and that Corp paid rent to an entity owned by Taxpayer’s father.

Thus, notwithstanding its financial challenges, it appeared that Corp may have had funds available with which to pay the sales tax owing, but chose, instead, to pay other obligations.

The DTA’s Analysis

The State issued notices of deficiency to Taxpayer that asserted sales tax penalties against him as a responsible person of Corp for the periods beginning after Brother’s resignation, noting that each of the sales tax returns for the periods in issue were signed by Taxpayer as president of Corp.

According to NY’s sales tax law, every person required to collect the tax shall be personally liable for the tax imposed, collected or required to be collected.

The law, in turn, defines a “person required to collect” the sales tax to include, in the case of a corporate taxpayer, any officer, director or employee of the corporation (including of a dissolved corporation), who as such officer, director or employee is under a duty to act for such corporation in complying with the sales tax law.

Whether a person is a “responsible person” must be determined based upon the particular facts of each case, including whether the person was authorized to sign the corporate tax return, was responsible for managing or maintaining the corporate books, or was permitted to generally manage the corporation.

The Court explained that the question to be resolved in any particular case is whether the individual had, or could have had, sufficient authority and control over the affairs of the corporation to be considered a responsible officer or employee. The case law, it continued, identified a variety of factors as indicia of responsibility: the individual’s status as an officer, director, or shareholder; authorization to write checks on behalf of the corporation; the individual’s knowledge of and control over the financial affairs of the corporation; authorization to hire and fire employees; whether the individual signed tax returns for the corporation; the individual’s economic interest in the corporation.

Once sales tax liability has been asserted against an individual taxpayer as a “responsible person,” the taxpayer has the burden of establishing the extent of his responsibilities and authority with respect to tax law compliance.

The Court observed that Taxpayer signed all the sales tax returns as president of Corp.

The Court also noted that Taxpayer did not testify to explain why he was not a person responsible for the collection and remittance of sales tax. Instead, Taxpayer’s case rested entirely upon the financial difficulties that Corp found itself in as a result of Project.

The Court pointed out that these financial difficulties did not absolve an otherwise responsible person from liability arising from nonpayment of sales tax. Consequently, the Court affirmed the notices of deficiency and Taxpayer’s personal liability.

Decisions, Decisions

An individual shareholder has to weigh his desire to have some control over his investment in a corporation against the personal exposure for trust fund taxes (like the sales tax) that such control may bring.

In the case of a family-owned business, a family member/shareholder may find himself having to “step up to the plate” because of the family relationship.

In either case, if an individual is to be involved in the corporation’s business and in its management, he must be prepared to subordinate his own economic and personal interests in order to ensure that the corporation’s tax liabilities are satisfied.

He must also be prepared to shut down the business where it cannot satisfy its responsibility for trust fund taxes owing to the government, instead of continuing its operation and further increasing its tax liabilities, in the hope of one day “turning the corner.” After all, the government is not in the business of making loans to a failing business.

Ah, December

As we near the end of the taxable year ending December 31, 2017, the thoughts of most people turn to holidays and family gatherings, feasting and celebrations, and reflecting, perhaps, on another year gone-by.

Not so for tax professionals.

Instead of “visions of sugar plums” dancing in their heads, these poor folk dream of proposed legislation, obsess over the effective dates of regulations, struggle to close year-end transactions and to implement last-minute tax planning, and prepare for the upcoming tax filing season.

Speaking of tax filings, there is a new filing obligation that should be of interest to U.S. tax professionals who advise foreigners with U.S. investments or U.S. business interests. This filing requirement went into effect for taxable years beginning on or after January 1st of 2017; thus, the first returns to be filed under the new requirement will be due in early 2018.

Specifically, if a domestic LLC is wholly-owned by one foreign person, and it is otherwise treated as a disregarded entity for tax purposes, then the LLC must comply with certain reporting and record maintenance requirements that were previously limited to foreign-owned U.S. corporations.

Entity Classification

In general, a business entity with two or more members is treated, for tax purposes, as either a corporation or a partnership, and a business entity with a single owner is treated as either a corporation or an entity disregarded as separate from its owner (“disregarded entity”).

Certain domestic business entities, such as LLCs, are classified by default as partnerships (if they have more than one owner) or as disregarded entities (if they have only one owner), but are eligible to elect for federal tax purposes to be classified as corporations.

Some disregarded entities are not obligated to file a return or to obtain an employer identification number. According to the IRS, the absence of a return filing obligation (and the associated record maintenance requirements), made it difficult for the IRS to implement and enforce the tax laws applicable to foreigners that invest, or operate a business, in the U.S. through as disregarded entity.

Information Reporting

Under the Code, a domestic corporation that is at least 25% foreign-owned (a “reporting corporation”) is subject to specific information reporting and record maintenance requirements.

A reporting corporation is required to file an annual return on IRS Form 5472, Information Return of a 25% Foreign-Owned U.S. Corporation or a Foreign Corporation Engaged in a U.S. Trade or Business, with respect to each “related party” (including, among others, the 25%-foreign shareholder) with which the reporting corporation has had any “reportable transactions” including, for example, sales, leases, services, rentals, licenses, and loans.

The Form 5472 for a tax year must be attached to the reporting corporation’s income tax return for such year by the due date (including extensions) of the return. A separate Form 5472 must be filed for each foreign or domestic related party with which the reporting corporation had a reportable transaction during the tax year.

The reporting corporation must also keep books and records that are sufficient to establish the accuracy of the federal income tax return of the corporation, including information, documents, or records to the extent they may be relevant to determine the correct U.S. tax treatment of its transactions with related parties.

An Issue for the IRS

When a foreign-owned entity, such as an LLC, was classified as a corporation or a partnership for tax purposes, general ownership and accounting information was available to the IRS through the return filing and EIN application requirements.

Before 2017, however, when a single-member, foreign-owned, domestic LLC was treated as a disregarded entity for tax purposes, it was generally not subject to a separate income or information return filing requirement. Its owner was treated as owning directly the entity’s assets and liabilities, and the information available with respect to the disregarded entity depended on the foreign owner’s own return filings, if any were required.

Thus, if the LLC was wholly-owned by a foreign corporation, foreign partnership, or nonresident alien individual, generally no U.S. income or information return would have been required if neither the disregarded LLC nor its owner received any U.S. source income or was engaged in a U.S. trade or business.

Moreover, if the disregarded entity only received certain types of U.S. source income, such as portfolio interest or U.S. source income that was fully withheld upon at source, its foreign owner would not have had a U.S. return filing requirement.

The IRS found that even in cases when the disregarded entity had an EIN, as well as in cases when income earned through a disregarded entity had to be reported on its owner’s return (for example, income from a U.S. trade or business), it could be difficult for the IRS to associate the income with the disregarded entity based solely on the owner’s return.

The absence of specific return filing, and associated recordkeeping, requirements for foreign-owned, single-member domestic entities, and the resulting lack of ready access to information on ownership of, and transactions involving, these entities, made it difficult for the IRS to ascertain whether the entity or its owner was liable for any federal tax.

New Reporting Obligation

Thus, at the end of 2016, the IRS adopted a new regulation under which a domestic LLC, that is wholly-owned (directly, or indirectly through one or more other disregarded entities) by one foreign person, is treated as a domestic corporation (i.e., as an entity that is separate from its owner) for the limited purposes of the reporting and record maintenance requirements (including the associated procedural compliance requirements) described above. Importantly, it does not alter the framework of the existing entity classification regulations, including the treatment of certain LLCs as disregarded for income tax purposes.

By treating an affected LLC as a foreign-owned domestic corporation, the LLC becomes a “reporting corporation.” Consequently, it is required to file a Form 5472 information return with respect to any “reportable transactions” between the LLC and its foreign owner or other foreign “related parties” (transactions that would have been regarded under general U.S. tax principles if the entity had been, in fact, a corporation for U.S. tax purposes) including, for example, sales, leases, services, rentals, licenses, and loans. It is also required to maintain records sufficient to establish the accuracy of the information return and the correct U.S. tax treatment of such transactions. In addition, because the foreign-owned LLC has a filing obligation, it is required to obtain an EIN.

To ensure that a wholly-owned LLC reports all of its transactions with its foreign owner and other related parties, even if its foreign owner already has an obligation to report the income resulting from those transactions (for example, transactions resulting in income effectively connected with the conduct of a U.S. trade or business), the regulations specify, as an additional reportable category of transaction, any transaction to the extent not already covered by another reportable category. Thus, for example, contributions and distributions (both current and liquidating) are considered reportable transactions with respect to a “reporting LLC.”

Accordingly, any transaction between such an LLC and its foreign owner (or another disregarded entity of the same owner) would be considered a reportable transaction for purposes of the reporting and record maintenance requirements, even though, because the transaction involves a disregarded entity, it generally would not be considered a transaction for other tax purposes.

In order to facilitate the implementation of this reporting requirement, the reporting LLC is treated as having the same taxable year as its foreign owner, if the foreign owner has a U.S. return filing obligation. If the foreign owner has no U.S. return filing obligation, then the LLC is treated as having the calendar year as its taxable year.

Penalties

The penalty provisions associated with the failure to file the Form 5472 and the failure to maintain records will apply to reporting LLCs. For example, a penalty of $10,000 will be assessed against any reporting LLC that fails to file Form 5472 when due. The penalty also applies for a failure to maintain records as required. If the failure continues for more than 90 days after notification by the IRS, additional penalties will apply.

What Does It Mean?

Ah, the beginning of a new taxable year, and of a new era of transparency for many foreign-owned LLCs. What is one to do?

For starters, the U.S. professionals who advise these entities and their owners should alert them of the new reporting requirements, if they haven’t already done so. They should also be on the lookout for new Form 5472 instructions.

If a reporting LLC does not already have one, it must obtain an EIN as soon as possible. In connection therewith, the LLC will have to identify its “responsible party” (basically, the individual who controls the disposition of the LLC’s funds and assets), which means that the responsible party will itself have to obtain its own U.S. identification number (for example, an ITIN).

In addition, the LLC, its foreign owner, and their U.S. advisers will have to make certain that they have properly documented their 2017 reportable transactions, have maintained sufficient records to substantiate the accuracy of the information return to be filed by the LLC, and have implemented the appropriate internal procedures to ensure future compliance with the new reporting requirement.

Old Dog, New Tricks?

It’s a concern for every new investor in a closely held business: will the founding owners continue to operate the business as they always have, or will they recognize that they now have new co-owners to whom they owe a fiduciary duty, and on whom they made be dependent for funding or services, and will this recognition inform their actions with respect to the business and guide their relationship with the new investors?

Because of this concern, the new investor will insist that the owners enter into a shareholders’ or partnership agreement that includes various provisions that seek to protect the new owners’ rights, and to limit the original owners’ ability to ignore those rights and thereby compromise the economic benefits sought by the new investors.

Unfortunately, at least from the perspective of the new investor, it is not unusual for the founder, notwithstanding any shareholders’ or partnership agreement, to “forget” that he has others to whom he has to report. While such “forgetfulness” will strain the relationship among the owners of any business entity, it can be especially stress-inducing in the context of a pass-through entity like a partnership or an S corporation, the income of which is taxed to its owners without regard to any owner’s ability to influence or control the entity’s activities.

Yet Another Example

In a recent case before the Tax Court, the taxpayer tried to convince the Court that she should not be required to include her share of S corporation income in her gross income because the controlling shareholder had effectively prevented her from enjoying the beneficial ownership of her shares.

Corp was created by Founder to operate a diagnostic laboratory. Founder approached Taxpayer – who worked with Merchant Bank (“MB”) – to ask whether she would consider getting involved in Corp. Taxpayer and Founder discussed certain issues that Corp was facing, including its lack of a solid financial infrastructure.

Corp eventually entered into a consulting agreement with MB, under which MB would assist Corp with settling existing liabilities, diversifying the business, and implementing a financial infrastructure. In consideration for these services, Corp would pay MB a fixed monthly fee.

As part of this arrangement, Founder’s ownership of Corp was reduced to 50%, and members of MB or their designees (MB shareholders, including Taxpayer) acquired ownership of the other 50%.

Shareholders’ Agreement

The shareholders of Corp executed a Shareholders’ Agreement. The Agreement named various individuals, including Founder and Taxpayer, as officers of Corp. The board of directors of Corp consisted of its officers, including Taxpayer. The Shareholders’ Agreement stated that “[a]ll matters relating to the management of [Corp’s] business and operations of any kind or nature whatsoever shall be approved by a majority vote of [Corp’s] Board of Directors.” The board of directors, however, met only once after executing the Shareholders’ Agreement.

The Shareholders’ Agreement further stated:

The timing and amount of any distributions of net profits or cash flow from [Corp’s] operations or otherwise (the “Distributions”) to be made by [Corp] to the Shareholders hereunder shall be approved by the Board of Directors . . . . All Distributions shall be made by [Corp] to the Shareholders pari passu in accordance with their proportionate Share ownership hereunder.

In addition, the Agreement implemented a new payment approval procedure for Corp, stating:

The authorizing resolution to be delivered to the bank or other depository of funds of [Corp] shall provide that any officer signing singly may execute all checks or drafts of [Corp] in an amount up to $100,000.00, and two (2) persons consisting of [Founder] and one (1) member of the MB shareholders, shall be authorized as joint signatories in respect of all checks or drafts on behalf of the [Corp] in excess of $100,000.00.

Nevertheless, Corp frequently made payments in excess of $100,000 that were not authorized in conformity with the Shareholders’ Agreement.

Finally, the Agreement gave the shareholders the right to inspect and copy all books and records of Corp. At the beginning of MB’s relationship with Corp, Corp’s CFO distributed copies of monthly financial statements to representatives of the MB shareholders.

The Loan

One concern raised by Corp’s financial statements involved a loan from Founder to Corp close to the time of its organization. General ledgers made available to the MB shareholders, and reviewed as part of MB’s due diligence, showed a loan balance in excess of $7 million. Money paid by Corp on Founder’s behalf, including personal expenses, was charged against this loan, reducing the loan balance, and interest on the loan was paid to Founder monthly.

An audit of Corp’s financial statements found that payments made from Corp to Founder were recorded on the loan payable’s general ledger account, and the loan appeared as a “Note Payable” on the audited financial statements, and appeared as “Liabilities” on Corp’s Federal income tax returns. However, no “Loan from Shareholder” was reflected on the Schedules L of Corp’s Federal income tax returns on Form 1120S.

As Founder’s relationship with MB and the MB shareholders began to deteriorate, Taxpayer approached Founder concerning certain Corp expenses that Taxpayer believed were personal and unrelated to Corp’s business.

At that point, Founder no longer permitted MB and the MB shareholders to enter Corp’s premises, and he instructed Corp’s employees to stop providing financial information to them. Corp also stopped paying MB for its consulting services.

Unbeknownst to the MB shareholders, Founder also filed a complaint seeking judgment against Corp for the loans he claimed to have made to Corp over the course of many years. Founder served the complaint on the comptroller of Corp, Corp did not defend the lawsuit, and a default judgment was entered against Corp.

MB sued Founder for breach of the consulting agreement and failure to pay consulting fees. In reaction to this lawsuit, Founder filed for chapter 11 bankruptcy.

The bankruptcy court appointed a forensic accountant to investigate Corp’s business operations. The accountant’s report determined that the transfers of funds to Founder disputed by MB and the MB shareholders were recorded on the books by Corp as loan repayments. The report also described the default judgment that Founder had obtained against Corp.

As a result of the above findings, the bankruptcy court appointed a trustee as a financial overseer of Founder’s activities at Corp. The trustee was responsible for evaluating the financial status of Corp, taking financial control, and reporting his findings to the bankruptcy court. During the trustee’s time with Corp, payments of expenses or transfers of funds could not be accomplished without his approval. Additionally, the trustee provided Corp’s shareholders with monthly financial reports.

The Tax Returns

When Taxpayer filed her Forms 1040, U.S. Individual Income Tax Return, for the taxable years at issue, she attached to the return a Form 8082, Notice of Inconsistent Treatment or Administrative Adjustment Request. The Form 8082 included the following statement pertaining to Taxpayer’s ownership interest in Corp:

[Corp] has initiated litigation against the [T]axpayer retroactively contesting [T]axpayer’s ownership interest. The entity and certain shareholders have prevented [T]axpayer from exercising [her] shareholder rights including: sale of shares, voting on business matters, exercising dominion and control of the ownership interest, or enjoying any economic benefits or other ownership rights. The referenced Schedule K-1 is inconsistent with the entity’s contention that [T]axpayer is not entitled to any ownership interest. Therefore until legal ownership is resolved by the court, it was improper for the controlling shareholders to issue a Schedule K-1 to [T]axpayer, and those amounts are not reported in this return.

The issue for decision before the Tax Court was whether Taxpayer was a shareholder of Corp during the years in issue and was, therefore, liable for tax on her pro rata share of Corp’s income for the taxable years at issue.

Court’s Analysis

The Code provides that the shareholders of an S corporation are required to take into account their pro rata shares of the S corporation’s income, loss, deductions, and credits for the S corporation’s taxable year ending with or within the shareholders’ taxable year. An S corporation’s shareholders must take into account the corporation’s income regardless of whether any income is distributed to the shareholder.

The Court stated that, in determining stock ownership for Federal income tax purposes, it must look to the beneficial ownership of shares, not to mere legal title. Cases concluding that a shareholder did not have beneficial ownership, the Court continued, have considered both agreements between shareholders that effectively eliminated ownership, and provisions in the corporation’s governing articles affecting ownership rights.

Mere interference, the Court observed, with a “shareholder’s participation in the corporation as a result of a poor relationship between the shareholders * * * does not amount to a deprivation of the economic benefit of the shares.”

Taxpayer contended that while she was issued Corp shares, the removal of her power to exercise shareholder rights, as well as the actions of Founder, “removed” the beneficial ownership of her shares; therefore, Taxpayer asserted, she was not required to include in gross income her “pro rata share” of Corp’s income.

The Court noted, however, that Taxpayer identified no agreement, nor any provisions in Corp’s governing articles, removing her beneficial ownership.

Moreover, Taxpayer identified no authority supporting her position that a violation of a shareholders’ agreement could deprive shareholders of the beneficial ownership of their shares.

Further, Taxpayer cited no authority that allowed a shareholder to exclude her share of an S corporation’s income because of poor relationships with other shareholders.

In the absence of an agreement passing Taxpayer’s rights to her stock to another shareholder, a poor relationship between shareholders did not deprive Taxpayer of the economic benefit of her shares. Indeed, the Court pointed out, Taxpayer ultimately sold her shares for valuable consideration.

The Court held that because Taxpayer remained a shareholder of Corp for the taxable years at issue, she had to include in gross income her pro rata share of Corp’s income for those years.

Takeaway

The Taxpayer was hardly the first to argue that she was not liable for the tax on her share of S corporation income because she was improperly denied the beneficial ownership of shares in the corporation, notwithstanding her record ownership.

As in other cases, the Tax Court rejected Taxpayer’s position, noting that when a controlling shareholder merely interferes with another shareholder’s participation in the corporation, such interference does not amount to a deprivation of the economic benefit of the shares. Thus, the shareholder is not relieved from reporting her share of the S corporation’s income on her tax return.

A minority owner in any pass-through entity must appreciate the risk that she may be denied the opportunity to participate in the business in any meaningful way, that she may be denied any opportunity for gainful employment in the business, and that she may not receive any distributions from the entity.

The minority owner must also recognize that even when she is fortunate to be party to an agreement with the other owners that provides for mandatory tax distributions and for super-majority voting for certain decisions, such an agreement is meaningless in the face of a majority’s disregard of its terms unless the minority owner actually seeks to enforce the agreement.

In the face of a stubborn or determined founder, a minority owner must be prepared to act fairly quickly to protect herself, or “accept” the economic and tax consequences of having to report her share of the entity’s net income on her tax return. In that case, the minority owner must look to her other assets to provide the cash necessary to satisfy the resulting tax liabilities.  This can turn into an expensive proposition.

A post earlier this year considered the basis-limitation that restricts the ability of S corporation shareholders to deduct their pro rata share of the corporation’s losses. It was observed that, over the years, shareholders have employed many different approaches and arguments to increase the basis for their shares of stock or for the corporation’s indebtedness, in order to support their ability to claim their share of S corporation losses.

Many of these arguments have been made in situations in which the shareholder did not make an economic outlay, either as a capital contribution or as a loan to the S corporation.

In a recent decision, however, the Tax Court considered a shareholder who did, in fact, make a significant economic outlay, but who also utilized a form of transaction – albeit for a bona fide business purpose – that the IRS found troublesome. In defending its right to claim a loss deduction, the shareholder proffered a number of interesting arguments.

The Transaction

Taxpayer owned Parent, which was taxed as an S corporation.

Parent acquired 100% of the issued and outstanding stock of Target from Seller through a reverse triangular merger: Parent formed a new subsidiary corporation (“Merger-Sub”), which was then merged with and into Target, with Target surviving. As a result of the merger, Target became a wholly-owned subsidiary of Parent, and the Seller received cash plus a Merger-Sub promissory note; Target became the obligor on the note after the merger.

Immediately after the merger, Target made an election to be treated as a qualified subchapter S subsidiary (“QSub”).

The cash portion of the merger consideration was funded in part by a loan (the “Loan”) from Lender, which was senior to the promissory note held by Seller.

After the merger, Taxpayer decided to acquire the Loan from Lender. However, Taxpayer believed that (i) if he loaned funds directly to QSub to acquire the Loan, or (ii) if he contributed funds to Parent, intending that they be loaned to QSub to repay the Loan in full, his loan would not be senior to the QSub note held by Seller without obtaining Seller’s consent.

In order to make QSub’s repayment of the Loan to Newco senior to QSub’s repayment of the note to Seller, Taxpayer organized another S corporation, Newco, to acquire the Loan from Lender. Taxpayer transferred funds to Newco, which Newco used to purchase the Loan, following which Newco became the holder of the Loan.

Thus, the indebtedness of QSub was held, not directly by Taxpayer, but indirectly through Newco.

During the Tax Year, Parent had ordinary business losses that were passed through to Taxpayer.

The Tax Return

In preparing his return for Tax Year, Taxpayer used his adjusted basis in the Parent stock, and also claimed adjusted basis in what he believed was QSub’s indebtedness to Taxpayer, to claim deductions for the losses passed through to Taxpayer from Parent for the Tax Year.

The IRS reduced the losses Taxpayer could take into account for the Tax Year, thereby increasing Taxpayer’s taxable income by that amount. Taxpayer petitioned the Tax Court.

Taxpayer argued that Newco should be disregarded for tax purposes, and that the Loan should be deemed an indebtedness of Parent (through its disregarded QSub) to Taxpayer. This would allow Taxpayer to count Newco’s adjusted basis in the Loan in calculating the amount of Parent’s flow-through losses that he could deduct for the Tax Year.

The IRS urged the Court to respect Newco’s separate corporate existence, and not to treat the Loan as indebtedness of Parent to Taxpayer.

S Corp. Losses

The Code generally provides that an S corporation’s shareholder takes into account, for his taxable year in which the corporation’s taxable year ends, his pro rata share of the corporation’s items of income, loss, deduction, or credit.

However, the aggregate amount of losses and deductions taken into account by the shareholder is limited: It may not exceed the sum of the adjusted basis of the shareholder’s stock in the S corporation plus the shareholder’s adjusted basis of any indebtedness of the S corporation to the shareholder (the “loss-limitation rule”).

The Code does not define the term “indebtedness of the S corporation to the shareholder” as used in the loss-limitation rule.

QSub

A QSub is a domestic corporation which is wholly-owned by an S corporation, and that elects to be treated as a QSub. In general, a QSub is not treated as a separate corporation, and all of its assets, liabilities, and items of income, deduction, and credit are treated those of the S corporation. Thus, for purposes of the loss-limitation rule, a QSub’s indebtedness to its parent S corporation’s shareholder is treated as the parent’s indebtedness for purposes of determining the amount of loss that may flow through to the parent’s shareholder.

Acquisition of Basis in Indebtedness of Parent

The IRS argued that a shareholder can acquire basis in an S corporation either by contributing capital, or by directly lending funds, to the corporation. The loan must be direct, the IRS maintained; no basis is created where funds are loaned by a separate entity that is related to the shareholder.

The IRS emphasized that the Loan ran to QSub from Newco, not from Taxpayer; thus, the Loan could not be considered in computing the basis of any indebtedness of Parent to Taxpayer.

Taxpayer conceded that the courts have interpreted the loss-limitation rule generally to require that the indebtedness of an S corporation be owed directly to its shareholder. However, the Taxpayer asserted, “form is but one-half of the inquiry, and the transaction’s substance also needs to be considered.”

The IRS asserted that Taxpayer ought to be bound by the form of the transaction chosen, and should not, “in hindsight, recast the transaction as one that they might have made in order to obtain tax advantages.”

Moreover, the IRS pointed out, where the entities involved in transactions are wholly-owned by a taxpayer, the taxpayer bears “a heavy burden of demonstrating that the substance of the transactions differs from their form.”

Taxpayer posited that an intermediary, such as Newco, could be disregarded for tax purposes where it (1) acted as a taxpayer’s incorporated pocketbook, (2) was a mere conduit or agent of the taxpayer, or (3) failed to make an actual economic outlay to the loss S corporation that made the intermediary poorer in a material sense as a result of the loan.

Incorporated Pocketbook

Taxpayer urged the Court to find that Newco acted as the Taxpayer’s incorporated pocketbook in purchasing the Loan from the Lender and holding it thereafter.

Taxpayer emphasized that Newco had no business activities other than holding the Loan and acting as a conduit for payments made by QSub.

The Court observed that the term “incorporated pocketbook” refers to a taxpayer’s habitual practice of having his wholly-owned corporation pay money to third parties on his behalf.

The Court, however, stated that the “incorporated pocketbook” rationale was limited to cases where taxpayers sought to regularly direct funds from one of their entities through themselves, and then on to an S corporation. Here, the Court found, Taxpayer did not use Newco to habitually to pay QSub’s, or his own personal, expenses. “Frequent and habitual payments,” the Court stated, are “key to a finding that a corporation served as an incorporated pocketbook.” Newco did not make frequent and habitual payments on behalf of Taxpayer.

Conduit or Agent

Taxpayer also argued that Newco served as Taxpayer’s agent in purchasing the Loan from Lender and, as such, could be ignored for tax purposes.

Taxpayer pointed out that the Court had previously suggested that, in a true conduit situation, a loan running through a corporate intermediary could instead be considered to run directly from the shareholder for purposes of the loss-limitation rule.

Taxpayer emphasized that Newco had no business activity besides the Loan acquisition, and no assets besides the Loan; all the funds necessary to purchase the Loan came from Taxpayer; thus, Newco served effectively as a conduit for payments from Parent and QSub.

The IRS reminded the Court that, in other cases, it had been reluctant to apply the agency exception to the rule that indebtedness must run directly from the S corporation to its shareholder.

Moreover, the IRS argued, Parent, QSub, Newco and Taxpayer were sophisticated parties who consulted with their advisers before purchasing the Loan from Lender. They consciously chose the form of the transaction to maintain the Loan’s seniority with respect to QSub’s obligations under the notes.

The IRS also asserted that the record was devoid of any indication of an agency relationship.

The Court agreed with the IRS that Newco did not act as Taxpayer’s agent. It set forth several factors that are considered when evaluating whether a corporation is another’s agent, including:

  • whether it operates in the name, and for the account, of the principal,
  • whether its receipt of income is attributable to the services of the principal or to assets belonging to the principal,
  • whether its relations with the principal depend upon the principal’s ownership of it,
  • whether there was an agreement setting forth that the corporation was acting as agent for its shareholder with respect to a particular asset,
  • whether it functioned as agent, and not principal, with respect to the asset for all purposes, and
  • whether it was held out as agent, and not principal, in all dealings with third parties relating to the asset.

The Court reviewed each of these indicia, and concluded that no agency relationship existed between Newco and Taxpayer.

 Actual Economic Outlay

Taxpayer argued that: (i) Newco made no economic outlay to purchase the Loan, (ii) it was he who provided the funds used by Newco to purchase the Loan, (iii) he owned and controlled Newco, (iv) Newco was a shell corporation with no business or other activity besides holding the Loan, and (v) Newco’s net worth both before and after the Loan’s acquisition was the amount of Taxpayer’s capital contribution.

The IRS noted that the amounts contributed by Taxpayer to Newco were first classified by Newco’s bookkeeper as shareholder loans and then as paid-in capital, which increased Taxpayer’s basis in the Newco stock; accordingly, Taxpayer’s capital contributions to Newco, which increased his stock basis in that corporation, could not be used to increase his debt basis in Parent.

The IRS also disputed Taxpayer’s characterization of Newco as a shell corporation, arguing that Taxpayer had a significant business purpose in structuring the transaction as he did: the maintenance of the Loan’s seniority to Seller’s promissory note.

The Court agreed that Taxpayer did make actual economic outlays, and that these outlays were to Newco, a corporation with its own separate existence. It was not simply a shell corporation, but a distinct entity with at least one substantial asset, the Loan, and a significant business purpose. Taxpayer’s capital contributions, combined with Newco’s other indicia of actual corporate existence, were compelling evidence of economic outlay.

The Court also noted that taxpayers generally are bound to the form of the transaction they have chosen. Taxpayer failed to establish that he should not be held to the form of the transaction he deliberately chose. Therefore, any economic outlays by Taxpayer were fairly considered to have been made to Newco, a distinct corporate entity, which in turn made its own economic outlay.

Step Transaction Doctrine (?)

Finally, Taxpayer argued that the Court should apply the step transaction doctrine (really “substance over form”) to hold that Taxpayer, and not Newco, became the holders of the Loan after its purchase from Lender.

The IRS disputed Taxpayer’s application of the step transaction doctrine, arguing that Taxpayer intentionally chose the form of the transaction and should not be able to argue against his own form to achieve a more favorable tax result. The IRS added that because Newco was not an agent of or a mere conduit for Taxpayer, the form and the substance of the Loan acquisition were the same, and the step transaction doctrine should not apply.

Again, the Court agreed with the IRS, stating that Taxpayer’s “step transaction” argument was just another permutation of his other theories, which were also rejected by the Court.

Taxpayers, the Court continued, are bound by the form of their transaction and may not argue that the substance triggers different tax consequences. It explained that they have “the benefit of forethought and strategic planning in structuring their transactions, whereas the Government can only retrospectively enforce its revenue laws.”

Accordingly, the Court found that Taxpayer did not become the holder of the Loan after its acquisition from Lender.

Conclusion

Thus, the Court held that Taxpayer did not carried his burden of establishing that his basis in Parent’s (i.e., QSub’s) indebtedness to Taxpayer was other than as determined by the IRS.

Was it Equitable?

I suspect that some of you may believe that the Court’s reasoning was too formulaic. I disagree.

Both taxpayers and the IRS need some certainty in the application of the Code, so as to assure taxpayers of the consequences of transactions, to avoid abuses of discretion, and to facilitate administration of the tax system, among other reasons.

Of course equitable principles play an important role in the application and interpretation of the Code, but as to the Taxpayer, well, he was fully aware of the applicable loss-limitation rule, chose to secure a business advantage instead (a senior loan position) by not complying with the rule, which in turn caused him to resort to some very creative justifications for his “entitlement” to the losses claimed.

So, was the Court’s decision equitable? Yep.

Some Days Are Stones[1]

It’s not always easy to find a topic about which to write a weekly blog post. I usually look for a ruling or decision that illustrates one of the recurring themes of the tax law, and then develop a lesson or message around it. Sometimes I’ll use a project on which I’m working.

Some weeks are more fruitful than others. This week was a relatively lean one.

That being said, I did come across a recent letter ruling issued by the IRS that was short on facts and legal analysis, and the outcome of which would be obvious to most, but which I thought might serve my purpose.

The taxpayer to which the ruling was issued asked the IRS to consider whether the conversion of a State law limited liability company (“LLC”) into a State law limited partnership would cause the LLC or its members to recognize taxable income or gain.

Now, some of you may say, “big whoop.” (I did say the result was obvious.)

Nevertheless, the ruling does offer an opportunity for some fruitful discussion based upon the significance of the factual representations on which the ruling was based.

Basic Facts

LLC-1 was classified as a partnership for federal tax purposes. It had two managing members:

  • Corp-1 was a state law limited liability company that was classified as a corporation for tax purposes;
  • LLC-2 was a limited liability company that was disregarded as an entity separate from its owner for tax purposes;
    • Corp-2 was classified as a corporation for tax purposes, and was the sole member of LLC-2; thus, Corp-2 was treated as the second member of LLC-1 for tax purposes.

The other membership interests in LLC-1 were non-managing member interests owned either indirectly by Corp-2 (including through subsidiaries of LLC-2), or by other investors.

LLC-1 planned to convert to a limited partnership in accordance with State law (the “Conversion”), after which it would continue to carry on the business operations it previously conducted as a limited liability company before the Conversion.

Creation of Disregarded Entities

Before the Conversion, Corp-1, LLC-2, and one of LLC-2’s wholly-owned subsidiaries (we are not told whether this subsidiary was itself a disregarded entity – i.e., a limited liability company – or a corporation) would each form a single-member limited liability company (three in all) that would be disregarded as an entity separate from its respective owner for federal tax purposes (the “Disregarded Entities”).

In connection with the Conversion, LLC-2 and LLC-2’s subsidiary would each contribute all of its interest in LLC-1 (including its managing-member interest) to its respective Disregarded Entity. Corp-1 would contribute a portion of its interest in LLC-1 to its Disregarded Entity.

As part of the Conversion, the three Disregarded Entities would become the State law general partners of LLC-1; for tax purposes, their “regarded” owners (Corp-1, LLC-2 and LLC-2’s subsidiary) would be treated as the general partners of post-Conversion LLC-1 (as compared to the two State law managing members of pre-Conversion LLC-1).

(The ruling did not give the business reason for the Disregarded Entities. There are several possibilities, including planning for creditors upon the conversion of the managing member interests into general partner interests.)

The Representations

According to LLC-1, the limited partnership agreement that would replace its operating agreement would be substantively identical to the operating agreement; in other words, the economic arrangement among the members/partners, including the allocation of income, gain, loss, deduction, and credit among them would not be changed by virtue of the Conversion.

Consistent therewith, it was represented in the ruling that:

  • the balances in each partner’s (formerly member’s) capital account immediately after the Conversion would be the same as they were immediately before the Conversion
  • each partner’s total percentage interest in X’s profits, losses, and capital after the Conversion will be the same as that partner’s percentage interest in X’s profits, losses and capital before the Conversion, and the allocation of tax items will also remain unchanged
    • there would be no change in how they shared these tax items after the Conversion;
  • each partner’s share of liabilities of LLC-1 immediately after the Conversion would be the same as it was immediately before the Conversion
    • there would be no deemed distribution or deemed contribution of cash to any partner, or any deemed sale of partnership interests between any partners; there would be no change in any partner’s share of value, gain, or loss associated with the partnership’s unrealized receivables or inventory items in connection with the Conversion
    • thus, no partner would be treated as having exchanged an interest in so-called “hot assets” for a greater interest in other assets of the partnership, or vice versa, which could result in income or gain to such partner; and
  • LLC-1 would retain the same method of accounting and accounting period.

Interestingly, LLC-1 represented to the IRS that it had not issued any profits interest in the two years preceding the date of the Conversion. You may recall that a person’s receipt of a profits interest in a partnership will generally not be treated as a taxable event; this result will not follow, however, if the partner disposes of the profits interest within two years of receipt.

LLC-1 also represented that the “Sec. 704(b) book basis” of its property (the fair market value of the property at the time of its contribution to LLC-1, adjusted for subsequent book depreciation) that secured nonrecourse debt exceeded the amount of such debt; in other words, there was no “partnership minimum gain” – the gain that the partnership would realize if it disposed of the property for no consideration other than full satisfaction of the liability.

The IRS’s “Analysis”

According to the Code, an existing partnership is considered as continuing if it is not terminated. A partnership is considered as terminated only if: (1) no part of any business, financial operation, or venture of the partnership continues to be carried on by any of its partners in a partnership; or (2) within a 12-month period, there is a sale or exchange of 50 percent or more of the total interest in partnership capital and profits (a “technical termination”).

The IRS has, on several occasions, published rulings in which it examined the federal income tax consequences of a conversion of one form of partnership interest into another form of partnership interest in the same partnership. In general, provided each partner’s total percentage interest in the partnership’s profits, losses, and capital would remain the same after the conversion, and the partnership’s business would continue, no gain or loss would be recognized by the partners as a result of their exchanging their interests in the partnership.

Similarly, the IRS has previously ruled that the conversion of a domestic partnership into a domestic limited liability company classified as a partnership for tax purposes is treated as a partnership-to-partnership conversion that is subject to the same principles as an exchange of interests within the same partnership. It has also stated that the same holdings would apply if the conversion had been of an interest in a domestic limited liability company that is classified as a partnership for tax purposes into an interest in a domestic partnership.

IRS regulations provide that a business entity that is not classified as a corporation per se (a so-called “eligible entity”) can elect its classification for federal tax purposes. An eligible entity with at least two members can elect to be classified as either an association or a partnership, and an eligible entity with a single owner can elect to be classified as an association or to be disregarded as an entity separate from its owner. The regulations also provide that unless the entity elects otherwise, a domestic eligible entity will be treated as a partnership if it has two or more members.

Without further discussion, the IRS concluded that the Conversion would not cause a “technical termination” of LLC-1’s status as a partnership for tax purposes, and that neither LLC-1 nor its members would recognize taxable income, gain, or loss upon the Conversion.

Although not stated in the ruling, the IRS could have added that: the taxable year of the pre-Conversion limited liability company did not close as a result of the Conversion, the post-Conversion partnership would continue to use the EIN of the converted limited liability company, the tax elections made by the converted limited liability company would remain in effect as would its depreciation methods, and the members’ bases in their membership interests would carry over to their partnership interests.

So What? Is That It?

Pretty much.

The point is that there is a lot of thought and planning that goes into securing a “duh” ruling. The ruling becomes a foregone conclusion only because of the analysis, structuring and drafting that preceded it.

In the case of the ruling described herein, the failure of any of the representations set forth above may have resulted in a taxable event to one or more of the partners.

For that reason, it would behoove anyone who advises taxpayers and their business entities to become familiar with the kinds of representations that are made in connection with a “successful” ruling on a specific kind of transaction.

These representations highlight many of the issues that others have encountered in similar transactions over the years, and on which the IRS may be focusing. As such, they may provide a good starting point for an adviser’s consideration of, and planning for, his or her own client’s transaction.

 

[1] From “Some Days Are Diamonds” by Dick Feller, sung by John Denver.

Skirting Employment Tax?

The Code imposes the self-employment tax on the net earnings from self-employment derived by an individual during any taxable year.

In general, the term “net earnings from self-employment” means the net income derived by an individual from any trade or business carried on by such individual, plus his distributive share (whether or not distributed) of net income from any trade or business carried on by a partnership of which he is a member.

The shareholders of an S corporation are not subject to self-employment taxes on their distributive share of the corporation’s net income, though they and the corporation are subject to employment taxes on any wages paid to them by the corporation.

Over the years, many taxpayers have sought to reduce the exposure of their business income to employment tax.

Many taxpayers, for example, have organized their business as an S corporation, rather than as a partnership: they avoid entity-level tax; the corporation pays them a salary that is subject to employment tax but that may be considered low relative to the value of the services rendered; because the shareholders’ distributive share of S corporation income (after being reduced by their salary) is not subject to employment tax (in contrast to a partner’s share of partnership income), the shareholders are able to reduce their employment tax liability.

Of course, the IRS seeks to compel S corporations to pay their shareholder-employees a reasonable salary for services rendered to the corporation, so as to prevent the “conversion” of taxable income into investment income that is not subject to employment tax.

There are other items of income that are excluded from the reach of the employment tax, and which may be “manipulated” by some taxpayers in a manner similar to the payment of wages by some S corporations.

Among these exclusions is the rental income from real estate.

In contrast to wages, however, where the IRS’s concern is that the S corporation-employer may be paying an unreasonably low salary for the services rendered, thereby leaving the shareholder-employee with more “distributive share income” that is exempt from employment taxes, the concern as to rental payments is that a taxpayer-owner’s business may be paying an unreasonably large amount for the use of the owner’s separately-owned property, thereby reducing the taxpayer-owner’s net earnings from self-employment and the resulting employment tax.

The Tax Court recently considered a variation on the rental situation. The question presented was whether rent payments received by Taxpayer were subject to self-employment tax.

Well Life on a Farm is Kinda Laid-Back?

Taxpayer owned a farm, and performed the farm’s bookkeeping, other management services, and a portion of the physical labor.

During the years at issue, Taxpayer entered into an agreement (“Agreement’) with an unrelated party (“Chicken-Co”) pursuant to which Chicken-Co would deliver poultry to Taxpayer to be cared for in accordance with detailed instructions. Taxpayer was allowed to hire additional laborers or employees; however, Taxpayer’s discretion ended there.

Shortly thereafter, Taxpayer organized Corp as an S corporation. Using a recent appraisal which analyzed the cost of “performing” the Agreement purely as an investment (and not as an active business), Taxpayer entered into an employment agreement with Corp, and set his salary accordingly. Taxpayer agreed to provide bookkeeping services to Corp and, along with any hired laborers or employees, would provide the requisite labor and management services.

Chicken-Co approved Taxpayer’s assignment of the Agreement to Corp; nothing in the Agreement required Taxpayer to personally perform the duties required thereunder.

Taxpayer entered into a lease agreement with Corp by which Corp would rent the farm and various structures and equipment from Taxpayer. Corp agreed to pay rent to Taxpayer; Corp was required to remit each rent payment regardless of whether it had fulfilled its requirements under the Agreement or had received sufficient income. The rental amount represented fair market rent.

Corp fulfilled its duties under the lease, making all of the necessary rent payments to Taxpayer. At no point during the years in issue did Taxpayer believe that he was obligated to render farm-related services as a condition to Corp’s obligation pursuant to the lease to pay rent to Taxpayer. Corp also fulfilled its duties to Chicken-Co under the Agreement; Taxpayer was not obligated to perform farm-related services under the Agreement. Although Taxpayer participated in Corp’s activity, Corp consistently hired numerous laborers and professionals to carry out its obligations.

Trouble in the Henhouse?

Taxpayer reported: (i) rental income from Corp, which was excluded from self-employment tax; (ii) wages on which employment taxes had been paid; and (iii) a distributive share of Corp’s net income, which was not subject to self-employment tax.

The IRS determined that the “rental income” was subject to self-employment tax because, according to the IRS, it actually constituted net earnings from self-employment.

Taxpayer sought redetermination of the resulting deficiencies in the Tax Court, where the sole issue was whether the rent payments Taxpayer received were subject to self-employment tax; in other words, whether they represented something other than rental income.

Under the Code, the term “net earnings from self-employment” means the gross income derived by an individual from any trade or business carried on by such individual, less any allowable deductions. In computing such gross income and deductions, rental income from real estate is excluded.

The IRS contended that the rent payments Taxpayer received were subject to self-employment tax because, taking into account all the facts and circumstances, there existed an “arrangement” between Taxpayer and both Corp and Chicken-Co that required Taxpayer to materially participate in Corp’s farming activities under the Agreement.

Conversely, Taxpayer contended that the rent payments were not subject to self-employment tax because the rent payments were consistent with market rates, there was no nexus between the lease agreement, on the one hand, and either the Agreement or Taxpayer’s employment agreement with Corp, on the other, and neither of these agreements required Taxpayer’s material participation in Corp’s business.

“What’s It All About, Boy? Elucidate.” – Foghorn Leghorn 

The Court agreed with Taxpayer, stating that a rental agreement may stand on its own in certain circumstances, even despite the existence of a separate employment agreement requiring a taxpayer’s material services.

The fact that the rents in question, the Court stated, were consistent with market rates for farmland “very strongly” suggested that the rental arrangement stood “on its own as an independent transaction” and could not be said to be part of an “arrangement” for participation in the farming business activity. The same could be said where the rents in question were at, or below, fair market value.

The Court explained that Congress intended to apply the self-employment tax so as to provide benefits for individuals “based upon the receipt of income from labor, which old age, death, or disability would interrupt; and not upon the receipt of income from the investment of capital, which these events would presumably not affect.”

Therefore, Congress was careful, the Court continued, to exclude from self-employment income any amounts received as “rentals from real estate”; accordingly, the courts have interpreted this intent “to exclude only payments for use of space, and, by implication, such services as are required to maintain the space in condition for occupancy.”

However, when the tenant’s payment includes compensation for substantial additional services – and when the compensation for those services constitutes a material part of the payment – the “rent” consists partially of income attributable to the performance of labor not incidental to the realization of return from passive investment. In these circumstances, the Court stated, the entire payment is included in “net earnings from self-employment.”

The issue, then, becomes one of separating return of investment from compensation for services performed.

Did the Rent Stand on its Own?

Self-employment income generally is defined as “the net earnings from self-employment derived by an individual”. The Code defines “earnings from self-employment” as “the gross income derived by an individual from any trade or business carried on by such individual.”

The term “derived” necessitates a “nexus,” the Court stated, “between the income and the trade or business actually carried on by the taxpayer.” Under the “nexus” standard, according to the Court, income must arise from some income-producing activity of the taxpayer before that income is subject to self-employment tax.

The Code generally excludes rental real estate income from the computation of a taxpayer’s earnings from self-employment. This exclusion does not apply, however, if the income is derived under an “arrangement” pursuant to which the owner is required to, and actually does, materially participate in a farming activity (i.e., provide services in an active business activity) on his land.

In accordance with general tax concepts, the Court noted that the self-employment tax provisions are to be construed broadly in favor of treating income as earnings from self-employment, while the rental income exclusion is to be strictly construed.

Certain farming-related rental income is properly included in a taxpayer’s earnings from self-employment if the rental income is derived under an arrangement between the owner and tenant that specifies that the tenant will farm the rented land, and the owner will materially participate in the farming activity.

The Court interpreted the term “arrangement” broadly, finding that although the Taxpayer’s rental and employment agreements were separate, the Court would view the Taxpayers’ obligations within the overall scheme of the farming operations; the Court acknowledged that the income derived by one who owns and operates his own farm is often partially attributable to income of a rental character.

However, the Court added that, regardless of a taxpayer’s material participation – actual or required – if the rental income is shown to be less than or equal to fair market rental value, the rental income is presumed to be unrelated to any employment agreement or other business arrangement to which the taxpayer is a party; it does not “convert” included business income into excluded rental income. In that case, the rental agreement stands on its own, separate from the taxpayer’s farming/business activity.

As shown by the evidence, the rent payments Taxpayer received represented fair market rent. This, the Court found, was sufficient to establish that the lease agreement stood on its own. What’s more, Taxpayer had obtained a detailed analysis of the costs of operating the farm as an investment; in turn, Taxpayer priced Corp’s activities, including labor and management costs, to exceed the projected costs. The Court observed that these amounts were not merely remainder payments to Taxpayer after the rent checks were cashed. They were appropriate amounts for Corp to spend for the services required under the Agreement. The structuring of these expenses further illustrated the lengths to which Taxpayer went to operate Corp as a legitimate business, and not as a method to avoid self-employment tax.

Thus, the Court concluded that the rental agreement was separate and distinct from Taxpayer’s employment obligations and, therefore, the rental income was not includible in Taxpayer’s net self-employment income.

Observations

Where an agreement calls for rent payments that exceed what the market would bear, that excess may be evidence that there is an arrangement in which compensation for services is being disguised as rent, so that self-employment tax may be improperly avoided.

On the other hand, an agreement that calls for rent payments at fair market value, may be evidence that the arrangement does not involve disguised compensation for services, and may be relevant to the question of whether there is an arrangement linking rent and services.

The Court indicated that below-market rent is excluded from self-employment income because it does not “convert” taxable income into non-taxable income.

However, is it possible that a lower rent may act as an inducement for a larger payment elsewhere? Does the form of the transaction reflect its economic substance?

Regardless of the business, regardless of the circumstances, and regardless of the tax, the guidance is the same: if a taxpayer wants to avoid “tax surprises,” the taxpayer should treat with others on as close to an arm’s-length basis as possible. In most cases, this will in fact occur; where it doesn’t, the taxpayer has to understand the associated risks.