Retaining Key Employees in a Privately-Held Company through Equity Compensation – Part 4: “Profits Interests” in LLCs and Partnerships

This post is the fourth in a series exploring techniques to attract and retain key employees, directors, and other service providers of privately held companies through equity-based compensation arrangements and alternative arrangements that provide cash payments tied to the value of the company’s stock or ownership interests.

Previously, I provided an overview and discussed the tax treatment of various equity compensation arrangements typically used by corporations, such as stock options, restricted stock, phantom stock, and stock appreciation rights. In this post, I’ll discuss a popular technique, called a “profits interest,” which is available to entities taxed as partnerships, such as limited liability companies (or “LLCs”). Profits interests can provide a tax efficient way to reward key service providers. Since LLCs are the most popular type of entity taxed as a partnership, for the rest of this post, I will assume that the entity in question is an LLC.

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When does a deal involve securities regulation? Part 1: Introduction

Business owners and attorneys without a securities background will often engage in transactions that, while on first blush do not involve securities regulation, but actually are a securities transaction, and thus subject to federal and state securities laws.  For instance, real estate developers often finance projects by bringing in outside investors as limited partners.  They are likely to hire a real estate attorney to complete the deal, who will dutifully draft a limited partnership agreement for the transaction.  What neither of them often realize is that a securities transaction is occurring as part of the deal.  The sale of limited partnership interests is usually a securities transaction under federal and state law.  This means that the interests are subject to registration with the SEC and with the state of each investor’s residence[1], unless an exemption can be found. In addition, all statements made in discussions with limited partners are subject to the anti-fraud rules. [Read more...]

How the Federal Government Taxes LLCs

One of the benefits to using a limited liability company is the flexibility of being able to choose how the entity is taxed. After a new LLC is formed, its owners must decide the method by which they would like their business taxed. By default, an LLC is treated as a pass-through entity, which means that it does not pay federal taxes directly, but its income or loss is allocated to the owners, who then pay taxes on that income. If the LLC has only one member, it files no tax return and all transactions of the LLC are treated as transactions of the owner for tax purposes. If the LLC has more than one member, the LLC files a partnership tax return, which reports the LLC’s income and how that income is to be allocated to each owner. Partnership style taxation is governed by Subchapter K of the Internal Revenue Code. However, the owner(s) of an LLC, whether the LLC has a single member or multiple members, may choose to have their LLC taxed as a corporation. In this case, the LLC can be taxed as a so-called “C Corporation,” which is governed under Subchapter C of the Internal Revenue Code, or an “S Corporation,” which is governed by Subchapter S. This ability of LLC owners to elect the company’s means of taxation is called the “check the box” regulations. Below are summaries of the four methods of taxation of an LLC:

  • Disregarded Entity – This is the default rule for any LLC that has only one member. A single member LLC is treated as though it does not exist for tax purposes and thus the owner is treated as if he were running a sole proprietorship. All transactions — income and expenses — are included on the owner’s tax return. Therefore, no separate tax return need be filed for the LLC.
  • Subchapter K (aka partnership taxation) – This is the most flexible form of taxation for a multi-member LLC. All income and losses of the LLC are allocated to the owners, who pay taxes on that income regardless of the amount of cash they received from the company. A distribution of cash to owners is itself a tax-free event. The owners of the LLC can be compensated for service to the company (called “guaranteed payments”) in which case the payments are treated as an expense to the partnership and income to the owner. Subchapter K is quite flexible, and allows the owners to allocate the income between themselves in a variety of ways, sometimes in quite complex formulas (subject to certain limited restrictions in the Internal Revenue Code). One downside to using a partnership taxation structure is that the income of the partners is generally subject to the self-employment tax.
  • Subchapter C – If an LLC elects to be taxed under Subchapter C, it is treated for tax purposes, as if it were a corporation. The company must file a corporate tax return (regardless of whether there is one member or multiple members) and the LLC itself pays taxes. Any income that is paid to owners in the form of dividends is also taxable income to the owner (so-called “double taxation”), though the dividends are taxed to the owner at the capital gains rate. Because of this, many C Corporation owners pay themselves a salary or bonus. Such income is deductible to the corporation, though the compensation must be “reasonable.” If the IRS were to deem the salaries paid to an owner as higher than what would be reasonable if the owner were just an ordinary employee, it could reclassify part of the salary as a constructive dividend, subjecting the company to additional taxes and potential penalties.
  • Subchapter S – If an LLC elects to be taxed under Subchapter S, it is treated for tax purposes, as if it were a corporation that had elected to be treated as an S Corporation. In this form, the company will still file a corporate tax return but does not itself pay taxes. Instead, each owner is allocated a portion of profits or losses based on the percentage interest that they each own. As in a partnership, the owners must then pay the taxes themselves, regardless of whether any cash has been distributed to them. Any cash payments to owners (called distributions or dividends) are tax-free. Active owners are considered employees of the company and can also be paid for their services to the company in the form of a salary or other payments, in which case, the payment will be deductible to the company and will be taxable wage income to the owner. The benefit of taxing an LLC as an S Corporation is that income that is not paid out as a salary is not subject to self-employment taxes. However, the IRS can scrutinize the salaries paid to owners and if it deems that the owners have been underpaid, it may reclassify some of the LLC’s income as wages, subjecting the LLC and the owners to additional payroll taxes and potential penalties. Another disadvantage to using Subchapter S is that the designation is very “fragile.” There are a number of requirements the company must adhere to (such as having only one class of stock and no more than 100 owners). If the company fails to adhere to these requirements, it will automatically be converted to a C-Corp and face double taxation. The single class of stock requirement is especially easy to violate inadvertently. If the LLC gives any owners preferred distributions or distributes distributions in any way except through a straight pro rata method, it could be deemed as having more than one class of stock. In addition, many of the default provisions in LLC statutes violate the single class of stock requirement, which means that the operating agreement of an LLC taxed under Subchapter S must be carefully written to override the default provisions.

As you can see, there are many factors to consider in choosing how to have an LLC taxed. Your final choice should be based on your own specific situation. Therefore, before making any decisions on your form of business, you should speak with your attorney or accountant.

© 2011 Alexander J. Davie — This article is for general information only. The information presented should not be construed to be formal legal advice nor the formation of a lawyer/client relationship.

Obama’s Proposed American Jobs Act Contains Tax Increase on Private Fund Managers

The American Jobs Act, recently proposed by President Obama, contains a provision closing the co-called “carried interest tax loophole” that benefits many investment fund managers.  Just about all hedge funds, real estate investment partnerships, private equity funds, and venture capital funds in the U.S. are structured as partnerships for tax purposes.  The incentive fee that the manager is paid (usually 20% of all net gains of the partnership) isn’t actually a fee at all.  Rather, when the partnership is formed, it is structured so that the manager (or an affiliate of the manager) owns a 20% interest in all profits generated by the fund.  The benefit to the manager in structuring the incentive fee this way is that all favorable tax treatment that the fund may receive for certain types of income are preserved for the fund manager.  For instance, if the fund earns a gain on the sale of assets that it owned for over one year or if the fund receives qualified dividends from stock, those gains and dividends are taxed at the lower capital gains rate (15%) rather than being treated as ordinary income.  In addition, the manager of the fund does not pay social security or Medicare taxes on the portion of the fund’s profits allocated to the manager, as he would if he were earning it as wages or were otherwise self-employed.  As a result, the fund manager only pays federal income taxes at a rate of 15% on a large portion of his income, and also pays no social security and Medicare taxes on any of the incentive fee earned by him. [1]  If the law were changed, fund manager incentive allocations would be taxed as ordinary income and would also be subject to the self-employment tax (ordinarily 15.3%) to pay both the employee and employer portions of social security and Medicare taxes on such income.

Arguments can go back and forth whether the current tax treatment of investment partnership incentive allocations is (a) a good idea or (b) fair.  Proponents of changing the law say that it is unfair that investment fund managers should pay a lower level of taxation than people in other professions, especially considering that this income is essentially a fee in substance, if not form.  Opponents counter that fund managers take a huge risk in taking much of their fees in this manner, because (a) it is contingent upon the fund making a profit and thus the fee may never materialize and (b) is often (but not always) deferred for a number of years until gains can be realized.  Because of these unique features, they argue that this favorable tax treatment is fair and reasonable.

Regardless of who you may think is right, luckily for fund managers, the legislation is unlikely to pass in the near term.  Given the gridlock in Washington, and the fact that the Republican-controlled House of Representatives would never approve such a provision, fund managers are currently safe.  However, in the long term, the outlook is far more uncertain.   With tax reform on the horizon, fund managers and their representation in Washington will need to be vigilant.  A change like this to the tax code is likely to be popular with voters and since the people who who would be negatively impacted by it are few, it could be an easy concession for Republicans to make in their quest to lower overall tax rates.  As always, stay tuned.


[1] However, the Health Care and Education Reconciliation Act of 2010, among other provisions, enacted a new additional tax, referred to as the “unearned income Medicare contribution,” on net investment income, like the partnership allocations of income and gain from investment funds at a rate of 3.8% which will, if no additional changes in law are enacted, take effect January 1, 2013.  The tax only affects individual taxpayers with a modified gross income over $250,000 for married taxpayers filing jointly, $125,000 for married taxpayers filing separately, and $200,000 for single taxpayers.


© 2011 Alexander J. Davie — This article is for general information only. The information presented should not be construed to be formal legal advice nor the formation of a lawyer/client relationship.

5 Legal Mistakes Often Made By Startups

Entrepreneur magazine recently posted an article on their blog describing five overlooked legal mistakes that entrepreneurs often make. It’s a good worthwhile read. The mistakes mentioned are:

  1. Making handshake deals (i.e. not in writing) with clients and vendors.
  2. Choosing the wrong business structure (i.e. sole proprietorship, LLC, Corporation).
  3. Entering into a partnership without a detailed written agreement.
  4. Entering into a 50-50 partnership.
  5. Filing a trademark without doing a detailed and extensive search before hand.

I wholeheartedly agree with four out of the five common mistakes. Perhaps the one I may partially disagree with is mistake number 4: entering into a 50-50 partnership. 50-50 partnerships can certainly present challenges when it comes to governing a company and general decision-making when there is a deadlock between the partners. However, I think categorically ruling out such an arrangement is a mistake. Rather, if the partners desire to establish a 50-50 partnership and that relationship is important to them, they should plan ahead and consider adding detailed provisions in their partnership agreement which deals with deadlocks. In addition, the company buy-sell provisions will have to be carefully considered as well.

Article Referenced: Five Overlooked Legal Mistakes Entrepreneurs Make


© 2011 Alexander J. Davie — This article is for general information only. The information presented should not be construed to be formal legal advice nor the formation of a lawyer/client relationship.