Effective January 1, 2013, the American Taxpayer Relief Act of 2012 (“ATRA”) and the Patient Protection and Affordable Care Act (“PPACA”) introduced the new Net Investment Income Tax (“NIIT”), raised the top federal income tax rate on ordinary income, dividends, long-term capital gain, and increased the Medicare tax. This article provides an overview of these tax increases, and their effect on choice of business entity.
The PPACA and ATRA Tax Increases. PPACA and ATRA increased federal income taxes for individuals with income exceeding certain thresholds. PPACA introduced the NIIT, equal to 3.8% on net investment income of individuals with modified adjusted gross income (“MAGI”) in excess of $200,000 for single taxpayers and $250,000 for married taxpayers (“PPACA Threshold”). Specifically, NIIT is imposed on the lesser of (i) net investment income, or (ii) the amount by which MAGI exceeds the PPACA Threshold.1
Net investment income includes (i) interest, dividends, annuities, royalties, and rents, which are not derived in the active, ordinary course of business (excluding business of trading in financial instruments or commodities), (ii) income derived from a business that is a passive activity (or business of trading in financial instruments or commodities), and (iii) gain from disposition of property that was used in a business that was a passive activity, a business of trading in financial instrument or commodities, or was not used in business.2 PPACA also increased the Medicare tax by 0.9% (from 2.9% to 3.8%) on wages and self-employment income in excess of the PPACA Threshold.3
ATRA increased the top tax rates on ordinary income, dividends, and long-term capital gains. The top tax rate for individuals increased from 35% to 39.6% on taxable income in excess of $400,000 for single taxpayers and $450,000 for married taxpayers (“ATRA Threshold”).4 The top tax rates on dividends and long-term capital gains also increased from 15% to 20% for individuals with taxable income in excess of the ATRA Threshold.5
Prior to examining the effect of these tax increases upon the choice of entity decision, it is helpful to review the various taxable entities available when organizing a business entity to conduct business.
ENTITY TAX CLASSIFICATION Selection of Entity’s Tax Classification. The form of business entity is dictated by state law, while the federal income tax classification of the entity is controlled by federal law, specifically the Internal Revenue Code (the “Code”).6
Under state law, the entity can be formed as a corporation or one of the many unincorporated entity forms: limited liability company, general partnership, limited partnership, or limited liability partnership. The Code prescribes four main tax classifications for the state law entity: C corporation, S corporation, partnership, or disregarded entity. The C corporation is a separate taxpayer that pays taxes on its earnings. When the C corporation distributes its earnings in the form of dividends, the corporation’s shareholders are also taxed on the dividends they receive. In essence, the earnings are taxed twice (“Double Tax Regime”); the first time at the corporate level and second time at the shareholder level. After PPACA, the dividend income received by the shareholder may also be subject to NIIT.
The S corporation and the partnership are very popular tax classifications. Their popularity stems from the fact that neither an S corporation nor a partnership is a separate taxable entity for federal income tax purposes. Instead, the two entity forms are conduits through which income, losses, and other items flow to the owners.7 This flow-through relationship insulates the entity from being subject to federal income tax. The owner of the entity is the taxpayer for his/her or its share of the income or loss. Generally, the character of income and losses is determined at the entity level.8
However, for purposes of NIIT, net investment income may be determined at both the entity level and the owner level. 9 The IRS publishes on its website the number of tax returns filed by different tax classifications. Interestingly, the number of “partnership” tax classifications that formed after 1997 grew significantly. During the 10 years preceding 1997, the number of tax returns filed for partnerships grew by less than 1%.10 However, during the 10 years following 1997, the number of tax returns filed by partnerships grew by more than 67%;11 the number of tax returns for corporations (S and C corporations) grew by only 24%.12
The strong growth in partnership filings can be attributed to the “check-the-box” regulations that became effective as of January 1, 1997.
Check-the-Box Regulations. Prior to January 1, 1997, the IRS used the corporate resemblance test, sometimes known as the “four factor test” to determine whether an entity would be taxed as a corporation or a partnership for federal income tax purposes. If the entity had more “corporate” characteristics, it would be classified as a corporation rather than a partnership. The four characteristics that the IRS reviewed were: continuity of existence, centralized management, limited liability for owners, and transferability of ownership interests.13
The four factor test proved unworkable, particularly after every state followed Wyoming’s lead and adopted limited liability company legislation.14 Limited liability companies did not fit easily into the four factor test and forced the IRS to reconsider its entity classification process. Effective January 1, 1997, the IRS adopted the so called “check-the-box” regulations to replace the “four factor” test and simplify entity tax classification. Under “check-the-box” regulations, a state law corporation by default will be taxed as a C corporation unless it affirmatively elects to be taxed as a Subchapter “S” corporation. An unincorporated state law entity (i.e., limited liability company) with only one owner will be disregarded as a separate entity for federal income tax purposes, unless it elects a different tax classification by filing IRS Form 8832 and affirmatively elects to be taxed as a corporation.15 An unincorporated state law entity with more than one owner, whether that is a limited liability company, general partnership, limited partnership, or limited liability partnership, will have a default tax classification of a partnership, absent filing of Form 8832 election to affirmatively elect the tax treatment as a corporation.16 The “check-the-box” regulations provided flexibility and certainty to the tax treatment of entities, particularly for partnerships and limited liability companies, and consequently spurred the growth of partnership tax classification. The following sections will compare and contrast, based upon the entity tax classification, the federal tax treatment of different transactions during the life cycle of a business entity, and how the recent tax increases may affect entity choice.
However, this article does not address the implications that state tax laws may have on entity selection. START UP PHASE The flow-through tax structure is very attractive, because it permits the flow-through entities (i.e., S corporation and partnership) to escape the draconian Double Tax Regime of the C corporation. Prior to ATRA, the individual owners of the entity were subject to the same top tax rate of 35% that was imposed on C corporations. However, ATRA increased the individual top tax rate from 35% to 39.6% on taxable income exceeding ATRA Threshold,17 while the corporate top tax rate of 35% remained.18 The tax rate on dividends did increase from 15% to 20% for taxpayers with income exceeding ATRA Threshold.19 ATRA’s increases in individual top tax rates, may in certain circumstances, cause taxpayers to reconsider the use of a C corporation rather than a flowthrough entity.
Start Up Losses. Loss is an inherent risk in any business. This is particularly the case during the start-up phase when the business has little, if any operating income. Entity selection analysis must consider whether the entity’s losses would provide value to certain owners of the entity, particularly investors with other taxable income which can be reduced by available losses from the entity. Partnerships and S corporations are popular choices in this scenario, because losses can be allocated to the owners who can use these losses to reduce their taxable income, subject to the limitations described below. With PPACA’s and ATRA’s tax increases, the tax benefits generated by these flow-through losses also increased, as illustrated in the following example.
EXAMPLE 1: A company allocates $100,000 of its ordinary income loss to a passive owner that has $700,000 of ordinary income from other passive activities, thereby decreasing the owner’s net taxable income to $600,000. This $100,000 loss, assuming it is not subject to any limitation, produces a federal tax benefit to the owner of approximately $43,400, based upon the owner’s marginal federal tax rate of 39.6% and NIIT 3.8%. Prior to PPACA and ATRA, the $100,000 loss would have produced a federal tax benefit of only $35,000.
The owner’s use of the entity’s losses is subject to the three limitations described below. The first limitation is the passive activity rule. Generally, passive activity losses may only be deducted from passive activity income.20 A passive activity is “any activity which involves the conduct of any trade or business, and in which the taxpayer does not materially participate” (i.e., is not involved on a regular, continuous, and substantial basis). Any disallowed passive activity loss can be applied in the future years against passive activity income. In addition, the disallowed passive activity loss can be deducted upon the disposition of the investment from which the passive activity loss arose. The second limitation is that the owner cannot deduct losses in excess of the amount that he/she actually has “at risk” in the company.21 The amounts “at risk” include the owner’s cash, property, other invested assets, and entity’s liabilities for which the owner is liable. Disallowed losses can be applied to future years when the owner has amounts “at risk”.
The third limitation is that the owner cannot deduct losses in excess of his/her outside basis in the company (“Basis Limitation”).22 “Basis” generally refers to the amount that the owner has paid for his/her interest in the company. Losses that are disallowed because of the Basis Limitation can be applied to future years when the owner has basis. The application of the Basis Limitation rule favors a partnership over an S corporation; because of the way it permits partners in a partnership to increase their basis in a way that is not available to shareholders of an S corporation. An increase in a partnership’s liability, for example obtaining a loan, increases the partners’ basis.23 On the contrary, the same increase in an S corporation’s liability does not increase the shareholders’ basis, even if the corporation’s liability is guaranteed by the shareholders.24 This difference generally makes partnerships more advantageous than S corporations with respect to an entity’s losses, as shown in the following example.
EXAMPLE 2: Two equal owners own Company Y. Bank loans Company Y $1 million, which is personally guaranteed by each owner. Prior to taking out the loan, each owner had zero basis in Company Y. During the year, Company Y suffers a $200,000 loss. If Company Y is a partnership and allocates ½ of the basis for the $1 million loan to each partner, then each partner’s basis would increase to $500,000; assuming there are no other limitations, each partner would be able to use his or her share of the partnership’s loss. 25 However, if Company Y is an S corporation, then the shareholders’ basis would not increase by their share of the $1 million loan, and none of the losses would be deductible.
On the other hand, a C corporation is a separate taxable entity, so its losses do not flow-through to the shareholders and cannot be used to offset their income. Instead, the losses may only be used to offset the previous two years or future twenty years of the corporation’s taxable income.26 This is illustrated in the following example:
EXAMPLE 3: C corporation has a total loss of $1 million, and one of its shareholders has income (from other sources) of $500,000. The shareholder cannot use his/her portion of the $1 million loss suffered by the C corporation to offset part or all of his/her $500,000 taxable income.
As the first example illustrates, after ATRA and PPACA, for individuals in the highest tax brackets, losses generally became more valuable, in some cases by as much as 24%.27 Hence, for these individuals, the ability to use the flowthrough entity’s losses to offset their other income became more valuable.
OPERATING PHASE Flexibility of Partnership Form. Each owner of a company has unique circumstances, needs, and wants. Owners may be in different tax brackets, and may be seeking different returns and risks on their investments. Once an entity generates income, entity choice will determine the manner in which income is allocated to the owners. An S corporation does not offer flexibility in allocating income and loss. It cannot have more than one class of stock. The S corporation’s profits and losses are allocated to each shareholder according to his/her percentage ownership of the stock.28 The partnership, on the other hand, is very flexible, and permits allocation of income, losses, and other transactions as the owners agree in their operating agreement, given the allocation has a “substantial economic effect” in accordance with I.R.C. §704.29 For individuals in the highest tax bracket, the flexibility of the partnership in allocating income and loss becomes even more valuable after ATRA increased the individual top tax rate. The value of the partnership flexibility over the S corporation is illustrated in the following example.
EXAMPLE 4: Active member A and passive member B equally own LLC Y. Member A is married and has filed a joint tax return with $70,000 of taxable income, which is taxed at an average rate of 13.7%.30 Member B is single and has filed a tax return with $700,000 of taxable income, which is taxed at a marginal rate of 39.6%. LLC Y has $140,000 of income and $70,000 of deductible depreciation during the year. LLC Y allocates $70,000 of income and $70,000 of depreciation to member B. Due to member B’s high individual tax rate, member B’s tax savings are 43.4% (ordinary income tax and NIIT) of $70,000 or $30,380. Half of those tax savings ($15,190) are generated from the $35,000 of depreciation that could have been allocated to member A, had they shared the depreciation equally. On the other hand, if owners A and B are shareholders of an S corporation, the S corporation must allocate the depreciation expense equally to owners A and B. Upon the S corporation allocating 50% of the depreciation ($35,000) to owner A, then instead of the $15,190 tax savings that owner B realized, owner A would have realized a tax savings worth only $4,358 (due to owner A’s lower tax rate),31 which is $5,250—or 3.5 times—less than the tax savings that owner B realized.
Use of C corporation at lower income levels. Once the entity starts generating profits, the proper tax classification will assist in reducing the tax costs of the business and preserving the value of the entity. After ATRA’s increase in the top federal rates for individuals, there may be circumstances in which use of the C corporation should be considered, particularly at lower income levels. A C corporation’s initial $50,000 of taxable income is taxed at 15%, and the next $25,000 of income is taxed at 25%.32 This is considerably lower than the post-ATRA individual top tax rate of 39.6%. If the C corporation does not distribute these earnings to its shareholders, there will be more after tax earnings available to finance and grow the company. The potential savings are illustrated in the following example.
EXAMPLE 5: Company X requires a loan of $1.5 million, which has annual principal payments of $60,000. If Company X is a flow-through entity and its owners are in the 39.6% tax bracket, then Company X would have to earn a pre-tax income of $99,338, to service the $60,000 of principal payments.33 On the other hand, if Company X is a C corporation, then it would have to earn a pre-tax income of only $73,333, to service the $60,000 principal payments.34 If Company X is formed as a flow-through entity (and its owners are in the 39.6% tax rate bracket) rather than a C corporation, it has to earn 35%35 or $26,005 more of pre-tax income to service the $60,000 of principal payment.
Mitigating the C Corporation Double Tax Regime. With proper planning, and mindful of IRS scrutiny in this area, the effect of Double Tax Regime of a C corporation can be reduced or avoided during the operating phase of the C corporation. The Double Tax arises only when the corporate earnings are distributed to the shareholders in the form of nondeductible dividends. If the earnings are paid to the shareholder in the form of a salary for services performed, the salary is deductible to the corporation so that there is no Double Tax. This is illustrated in the following example.
EXAMPLE 6: If Company X (from Ex. 5) was a C corporation with annual earnings of $99,338, it could pay a salary of $24,157 to its shareholder/employee. Company X would pay $1,848 of employment tax36 on the salary. This would leave Company X with taxable income of $73,333, on which it would pay federal tax of $13,333 or 18.2%, leaving Company X $60,000 necessary for the principal loan payment. The corporation’s salary payment of 24,157 would not be subject to the Double Tax Regime.
Employment Tax. It is also important to consider employment tax issues in the choice of entity analysis, particularly after the PPACA tax increases. For S and C corporations, the corporation and its employees, including any shareholder employees, must each pay (i) a Social Security tax of 6.2% on the first $113,700 of the employee’s wages, and (ii) a Medicare tax of 1.45% on all of the employee’s wages.37 PPACA increased the employee’s portion of the Medicare tax by 0.9% on all wages that exceed PPACA Threshold.38
For partners that are not the equivalent of limited partners, earnings from the partnership will be subject to self-employment tax.39 The self-employment tax consists of (i) a Social Security tax of 12.4% on the first $113,700 of self-employment income, and (ii) a Medicare tax of 2.9% on all self-employment income.40 PPACA increased the Medicare tax by 0.9% (from 2.9% to 3.8%) on selfemployment income that exceeds the PPACA Threshold.41
An individual’s full distributive share of a partnership’s earnings is considered self-employment income,42 and unless an exception applies, the full amount is subject to the self-employment tax. One exception is provided in I.R.C. §1402(a)(13), which excludes a “limited partner’s” distributive share of a partnership’s income from selfemployment tax.43 However, neither I.R.C. §1402(a)(13), IRS regulations, nor the courts have clearly defined “limited partner.”
The vagueness of the proposed regulations, combined with the large and increasing burden of self-employment taxes leads to litigation between taxpayers and the IRS over the amount of income characterized as self-employment income. A recent case, Renkemeyer, Campbell & Weaver, LLP, 136 TC 137 (2011), illustrates the competing tensions. In Renkemeyer, a law firm was organized as a limited liability partnership (“LLP”). The law firm’s partners claimed to be exempt from self-employment tax under the “limited partner” exception. The court recognized that “‘limited partner’ is a technical term which has become obscured over time.” Further, the court found that the legislation of Section 1402(a)(13) did not intend to exclude “partners who performed services for a partnership in their capacity as partners … from liability for self-employment taxes.” In applying Section 1402(a)(13), the court held that the partners’ distributive share of the LLP was not of an “investment nature” but was rather for services performed, and thus, subject to selfemployment tax. In a way Renkemeyer hinted towards the idea that “limited partners” should be passive investors who do not perform services for their partnership. Although such passive investors may be exempt from self-employment tax under the “limited partner” exception, after PPACA the investors’ passive activity income may now be subject to NIIT. If the “limited partner” exception does not apply, the difference in the employment tax between a partnership and an S or a C corporation may be significant. This is due to the fact that in a corporation only the shareholder’s salary, rather than the full distributive share of the corporation’s income, is subject to employment tax. This offers opportunities to review employment tax as illustrated in the following example.
EXAMPLE 7: Company Z, owned by two equal owners who are active in the business, generated net income of $1 million. Each owner pays himself a reasonable salary of $80,000 per year. If Company Z is formed as a partnership, the full $500,000 attributable to each partner would be subject to employment tax, equaling $29,846.44 However, if Company Z is formed as an S corporation, the shareholders are subject to employment tax on their salary only, which equals $12,240;45 their distributive share of the income from the corporation is not subject to employment tax. Thus, the partnership form causes the owners to pay $17,606—or 2.4 times—more employment tax.
After PPACA’s 0.9% Medicare tax increase, using the corporation to decrease employment tax will become even more significant.
EXITING PHASE Exit strategy should always be an important consideration in the entity choice analysis. Although individuals forming a business may not be interested in discussing their exit strategy, it is a critical factor that should be addressed at the onset. The form of sale will either be a sale of the entity’s assets or the owner’s equity. If a C corporation sells its assets, the Double Tax Regime is imposed. First, the C corporation pays taxes on the gain from selling its assets. The sale is treated as if each asset is sold separately, and the corporation’s gain or loss is determined separately for each asset. Second, the shareholders pay tax on the gain they recognize, which equals the difference between the amount they receive for their shares and their basis in these shares.46 Generally, the gain will be characterized as capital gain for the shareholders. On the other hand, a flowthrough entity will not be subject to the Double Tax Regime upon selling all of its assets. Rather, each owner will recognize capital gain and/or ordinary income depending on the nature of the assets sold.
If a seller can persuade a buyer to purchase shares rather than assets, an S or a C corporation may be the preferred entity. A sale of shares, so long as they are held for longer than one year, will be recognized as long-term capital gain.47
Clients are often surprised to learn that a sale of an interest in a partnership may produce capital gain and ordinary income. To the extent that any of the partnership assets consist of its inventory48 and unrealized receivables,49 the gain recognized is treated as ordinary income.50 The remaining gain from the sale of the partnership interest is treated as capital gain. When analyzing the disposition of the entity, ATRA’s increase in tax rates and PPACA’s NIIT must be considered. ATRA increased the long-term capital gain tax rate from 15% to 20% for individuals with taxable income in excess of ATRA Threshold.51 The individual top tax rate on ordinary income increased to 39.6%. In addition, NIIT of 3.8% may also apply in case of passive owners.
CONCLUSION Entity choice analysis is heavily influenced by tax considerations and requires careful analysis. After the ATRA and PPACA tax increases, this analysis becomes more complex because of the increased federal tax rates on ordinary income, dividends, long-term capital gain, together with the new NIIT and increases in the Medicare Tax. After a thorough consideration of the alternatives and their effects throughout the life cycle of a business, appropriate entity choice can help reduce the tax burden for the entity and its owners.
1 I.R.C. §1411(a)(1).
2 I.R.C. § 1411(c)(1).37 I.R.C. §3101.
3 I.R.C. §1401(b)(2) & §3101(b)(2).
4 I.R.C. §1.
5 I.R.C. §1(h).
6 Reg. §301.7701-1(a)(1).
7 See I.R.C. §702 and §1366.
8 I.R.C. §702(b) and §1366(b).
9 Eugene Seago, et al., Working With the Unearned Income Medicare Tax, 118:3 Journal of Taxation 5 (March 2013). If the income that flows to the owner is characterized as net investment income at the entity level it will keep its character and be subject to NIIT at the owner level. Further, even if the income is not net investment income at the entity level, it may still be characterized as net investment income at the owner level if it is allocated to a passive owner.
10 I.R.S. SOI Tax Stats, available at: http://www.irs.gov/uac/SOITax-Stats-Integrated-Business-Data. Calculation: The number of partnership tax returns filed in 1987 was 1,648,032 and in 1996 it was 1,654,256. The growth of partnership tax returns = (1,654,256 – 1,648,032) / 1,648,032 = 0.38%.
11 I.R.S. SOI Tax Stats, available at: http://www.irs.gov/uac/SOITax-Stats-Integrated-Business-Data. Calculation: The number of partnership tax returns filed in 1997 was 1,758,627 and in 2006 it was 2,947,116. The growth of partnership tax returns = (2,947,116 – 1,758,627)/1,758,627 = 67.58%.
12 I.R.S. SOI Tax Stats, available at: http://www.irs.gov/uac/SOITax-Stats-Integrated-Business-Data. Calculation: The number of corporate tax returns filed in 1997 was 4,710,083 and in 2006 it was 5,840,799. The growth of corporate tax returns = (5,840,799 – 4,710,083) / 4,710,083 = 24%.
13 Morrissey v. Commissioner, 296 U.S. 344 (1935).
14 Heather M. Field, Checking in on Check-the Box, 42 Loy. L.A. L. Rev. 451 (2009).
15 Reg. §301.7701-3.
16 Reg. §301.7701-3.
17 I.R.C. §1.
18 I.R.C. §11(b)(1).
19 I.R.C. §1(h).
20 I.R.C. §469.
21 I.R.C. §465.
22 I.R.C. §704(d) and §1366(d)(1).
23 I.R.C. §752(a).
24 I.R.C. §1366(d).
25 Subject to the “at risk” and “passive activity” limitation.
26 I.R.C. §172(b).
27 Calculation: Increase in losses value = (43.4% - 35%) / 35% = 24%.
28 I.R.C. §1366 and §1377.
29 I.R.C. §704.
30 Calculation: Tax liability on $70,000 is $9,608. Average tax rate = $9,608 / $70,000 = $13.7%.
31 Calculation: Member A tax liability with no depreciation deduction is $9,608. If member A has $35,000 of depreciation deduction, then he/she would have $35,000 of taxable income. Tax liability on $35,000 of taxable income is $4,358.
32 I.R.C. §11(b)(1). However, a tax rate of 35% applies to all taxable income of a personal service corporation (I.R.C. §11(b) (2)).
33 Calculation: $99,338 is the total income. Tax liability = 39.6% X $99,338 = $39,338. $99,338 pre-tax income – 39,338 tax liability = $60,000. This example ignores the implications of employment tax.
34 Calculation: $73,333 is the total income. $50,000 is taxed at 15% which equals $7,500. Then next $23,333 is taxed at 25% which equals $5,833. Total tax = $7,500 + $5,833 = $13,333. Pre-tax income of $73,333 – tax liability of $13,333 = $60,000.
35 Calculation: ($99,338-73,333) / 73,333 = 35.46%.
36 Calculation: Employer’s Social Security Tax = $24,157 X 0.062=$1,498. Employer’s Medicare Tax = $24,157 X 0.0145 = $350. Total Employment Tax = $1,498 + $350= $1,848.
38 I.R.C. §3101(b)(2).
39 I.R.C. §1402.
40 I.R.C. §1401.
41 I.R.C. §1401(b)(2).
42 I.R.C. §1402(a).
43 I.R.C. §1402(a)(13).
44 Calculation: (i) Social Security Tax: $113,700 X 0.124 = $14,099;(ii) Medicare Tax: $500,000 X 0.9235 X 0.029 = $13,391; (iii) Additional Medicare Tax: ($500,000 X 0.9235 – $200,000) X 0.009 = $2,356; and (iv) Social Security Tax + Medicare Tax + Additional Medicare Tax = $29,846.
45 Calculation: (i) Social Security Tax: $80,000 X 0.124 = $9,920; (ii) Medicare Tax: $80,000 X 0.029 = $2,320; and (iii) Social Security Tax + Medicare Tax = $12,240.
46 I.R.C. §331(a).
47 I.R.C. §1221(a).
48 Inventory includes property held for sale in the ordinary course of business, and any other property that would not result in capital or §1231 gain. (I.R.C. §751(d))
49 Unrealized receivables include payments for goods or services not previously included in income, and recapture property, but only to the extent unrealized gain is ordinary income. (I.R.C. §751(c))
50 I.R.C. §751.
51 I.R.C. §1(h).
Oleg Polyatskiy, JD, MBA, CPA, is an associate at Clingen, Callow & McLean, LLC. He is currently pursuing his L.L.M. in Taxation at the Northwestern University School of Law. Oleg received his JD/MBA degree from The University of Iowa College of Law and Henry B. Tippie School of Management in 2010. He also received his bachelor’s degree in finance from The University of Iowa in 2006.