Legal and Compliance

 


Business Entity Summaries

Limited Liability Companies (LLCs)

LLCs are suitable for many business and investment endeavors, including but not limited to the following:

  • Corporate joint ventures (where the corporate co-owners desire both pass-through taxation and limited liability);
  • Real estate investment and development activities (because the partnership taxation rules allow investors to obtain basis from entity-level debt, and special tax allocations can be made to investors);
  • Oil and gas exploration and development (where the partnership rules can be used to make special allocations of intangible drilling cost deductions to investors);
  • Venture capital investments (where the partnership rules allow pass-through taxation and creation of "customized" ownership interests with varying rights to cash flow, liquidating distributions, and tax items);
  • Business start-ups expected to have tax losses in the initial years (which can be passed through to investors);
  • Professional practices - if allowed under state law and applicable professional standards (where pass-through taxation can be combined with specially tailored ownership interests that reflect each member's contributions to the practice); and
  • Estate planning vehicles (where the older generation can gift LLC ownership interests to younger family members while retaining control by functioning as the managers, and where all taxable income is passed through to the members).

Accordingly to a survey in the December 1995 issue of Journal of Accountancy, the top 10 types of businesses operated as LLCs were:

  • Engineering and management support services;
  • Real estate services;
  • Construction and general contracting;
  • Investment companies;
  • Retailers;
  • Health Services;
  • Agriculture;
  • Oil and gas extraction;
  • Restaurants; and
  • Leasing companies.
Some states do not permit the use of LLCs in certain lines of business, such as banking, insurance and farming.

Most advisors agree that the LLC is the best entity alternative if pass-through taxation is desired (such as with a service business that has no need to retain significant amounts of earnings within the business entity). However, empirical evidence shows that LLCs are seldom formed to operate capital-intensive and high-growth businesses such as manufacturing and high-tech ventures. Such businesses typically need to retain all earnings to finance capital expenditures and growing receivables and inventory levels. These businesses are most often operated as C corporations in order to maximize cash flow by minimizing current outlays for federal income taxes.

Because LLCs allow all members to participate in management without the risk of losing limited liability protection (unlike a partnership), they are ideally suited for closely held entrepreneurial businesses.

In summary LLCs may be the best choice for business and investment ventures if:

  • There will be more than one owner (but not so many owners that the ownership interest would be considered publicly traded);
  • Limited liability protection for the co-owners is an important consideration;
  • Pass through taxation is desired;
  • The advantages of partnership taxation are significant compared to the alternative of S corporation taxation, or the entity cannot qualify for S corporation status;
  • The business activity can be operated as an LLC under the state law and applicable professional standards; and
  • The co-owners can tolerate certain legal and tax uncertainties of LLC status;
Although LLC statutes place no limits on the number of members, there is a tax problem if ownership interests are so widely held that they are "publicly traded" within the meaning of IRC s. 7704. If an LLC's ownership interests are publicly traded, the LLC will be treated as a C corporation for federal income tax purposes. LLC's are generally only appropriate for privately held businesses.


Limited Liability Partnerships (LLPs)

LLPs are probably the best entity choice for professional service ventures if:

  • Pass through taxation is desired;
  • LLC status is unavailable or the state LLP statute offers LLC like liability protection;
  • LLP status is permitted under state statutes and applicable professional standards;
  • Qualifying as an S corporation would be inconvenient, difficult, or impossible or the entity could qualify as an S corporation but the benefits of the partnership taxation rules are significant compared to those of the S corporation taxation rules; and
  • The co-owners can live with their exposure to the entity's contract liabilities.

General Partnerships

General Partnerships may be suitable for business and investment activities including, but not limited to, the following:

  • Corporate joint ventures (where the corporate co-owners desire both pass through taxation and limited liability);
  • Real estate investment and development activities (because the partnership taxation rules allow partners to obtain basis from entity level debt and special tax allocations can be made to investors);
  • Oil and gas exploration and development (where the partnership rules can be used to make special allocations of intangible drilling cost deductions to partners);
  • Venture capital investments (where the partnership rules allow pass through taxation and the creation of customized ownership interests with varying rights to cash flow, liquidating distributions and tax items);
  • Business start-ups expected to have tax losses in the initial years (which can be passed through to investors); and
  • Professional practices (where pass through taxation can be combined with specially tailored ownership interests that reflect each member's contributions to the practice).
General Partnerships can be particularly advantageous for oil and gas ventures, because general partners are exempt from the passive loss limitations if they qualify for the so called working interest exception under IRS s. 469©(3)(A). This exception applies to oil and gas working interests, which basically mean operating mineral interests that are burdened with the costs of developing and operating the property. Royalty interests, production payments, and net profits interests don't qualify as working interests under this definition (because they are burdened with development and operating costs).

General Partnerships are probably the best entity choice when:

  • There are at least two co-owners, all of whom have a high degree of trust in each other;
  • Pass through taxation is desired;
  • LLC and LLOP status are unavailable;
  • Liability concerns can be managed with insurance;
  • Qualifying as an S corporation would be inconvenient, difficult, or impossible, or the entity could qualify as an S corporation, but the benefits of the partnership taxation rules are significant compared to those of the S corporation taxation rules; and
  • The co-owners can live with the fact that the general partnership will not have an unlimited legal life or free transferability of ownership interests.
In most cases the desire to limit owners' liability is so significant that only a limited partnership, as opposed to a general partnership, will make sense. In the case of professional practices, operating as an LLC, LLP or C Corporation should be explored. Most advisors agree that general partnerships and sole proprietorships are by far the least attractive entity option.

Limited Partnerships

Business and investment activities where Limited Partnerships make sense include, but are not limited to, the following:

  • Real estate investment and development activities (where the partnership taxation rules allow investors to receive preferred returns, special allocations of tax losses, and additional basis from partnership level debt);
  • Oil and gas exploration and development (where the partnership taxation rules allow preferred returns and special allocations of deductions from intangible drilling costs);
  • Venture capital investments (where the partnership rules allow pass through taxation and the creation of ownership interests with varying rights to cash flow, liquidating distributions, and tax items);
  • Business start ups expected to have tax losses in the initial years (which can be passed through to the partners);
  • Estate planning vehicles (where the older generation can gift limited partnership interest to younger family members while retaining control by functioning as the general partnership, and where all taxable income is passed through to the partners);
Limited partnerships can be attractive if;
  • There are at least two co-owners (but not so many co-owners that the ownership interests would be considered publicly traded under IRC s. 7704);
  • Pass through taxation is desired;
  • LLC status is unavailable;
  • Qualifying as an S corporation would be inconvenient, difficult or impossible;
  • The entity could qualify as an S corporation, but the benefits of the partnership taxation rules are significant compared to those of the S corporation taxation rules;
  • The cop-owners who will be limited partners can live with the fact that they cannot become too actively involved in management of the venture without losing their limited liability protection; and
  • The co-owners can live with the fact that the limited partnership will not have an unlimited legal life or free transferability of all ownership interests.
Most advisors agree that LLC's when available are superior to limited partnerships. However, when pass through taxation is desired, limited partnerships are often the second best choice.

C Corporations

In general, C corporations may be preferred to LLCs, LLPs, General and Limited Partnerships, and Sole Proprietorships if:

  • Limiting owner liability is a critical concern;
  • There will be only one owner (making partnership taxation unavailable by definition) and the S corporation restrictions make operating an S corporation difficult or impossible); or
  • The activity cannot be operated as a limited partnership, because the owners who would be limited partners cannot live with the fact that they must avoid management involvement to maintain their limited liability protection; and
  • The activity cannot be operated as an LLC or LLP under state law and/or applicable professional standards; or
  • The business cannot be operated as an LLC, because the owners cannot live with the legal uncertainties associated with LLC status; or
  • The benefits of pass through taxation are not required (because the graduated corporate rates counteract the ill effects of double taxation or because the venture's income can be drained with deductible payments to or for the benefit of the owners); or
  • Being able to borrow against their qualified retirement plan accounts is a critical issue for the owners.
C Corporations are often underrated because of the issue of double taxation. However, the differences between corporate tax rates and individual tax rates mean that pass through taxation often results in higher current outlays for federal income taxes. Recent empirical evidence shows that C Corporations are still being formed to operate capital intensive and growth businesses, such as manufacturing and high tech ventures, because such businesses typically need to retain all earnings to finance capital expenditures and growing receivable and inventory levels. Operating as a C Corporation maximizes cash flow by minimizing current outlays for federal income taxes. And for very successful businesses, the C Corporation format lays the best groundwork for going public.


Qualified Small Business Corporations (QSBCs)

QSBC shareholders (other than C Corporations) potentially qualify to exclude from taxation 50% of their gains upon the sale of shares. However, the shares must be held for more than five years, and a number of other restrictions apply.

In general C Corporation that meet the definition of a QSBC may be preferred over LLC's Partnerships, and Sole Proprietorships, if:

  • Limiting owner liability is a critical concern; and
  • There will be only one owner (making partnership taxation unavailable by definition) and the S Corporation restrictions make operating as an S corporation difficult or impossible; or
  • The activity cannot be operated as a limited partnership, because the owners who would be limited partners cannot live with the fact that they must avoid management involvement to maintain the limited liability protection; and
  • The activity cannot be operated as an LLC under state law; or
  • The business cannot be operated as an LLC, because the owners cannot live with the legal uncertainties associated with LLC status; or
  • The benefits of pass through taxation are not required (because the graduated corporate rates and QSBC tax benefits counteract the ill effects of double taxation, or because the venture's income can be drained off with deductible payments to or for the benefit of the owners); or
  • Being able to borrow against their qualified retirement plan accounts is a critical issue for the owners.
The same comments as apply to C Corporations apply regarding a QSBC, except that the QSBC's are more attractive than regular C corporations because of the 50% gain exclusion tax break.

S Corporations

In general S corporations may be preferred over C Corporations, LLCs, LLPs, partnerships and sole proprietorships if:

  • Limiting owner liability is a crucial concern;
  • Pass through taxation is desired;
  • The S corporation eligibility rules can be met without undue hardship;
  • The restrictions on eligible S shareholders do not cause undue hardship with regard to the owners' future plans to transfer ownership interests to others for estate planning, family tax planning, or business succession planning purposes;
  • There will be only one owner (making partnership taxation unavailable by definition);
  • The activity cannot be operated as an LLC under state law and/or applicable professional standards;
  • The business cannot be operated as an LLC, because the owners cannot live with the legal uncertainties associated with LLC status;
  • · The activity cannot be operated as limited partnership because the owners who would be limited partners cannot live with the fact that they must avoid management involvement to maintain their limited liability protection;
  • The business either cannot be operated as an LLP, or the liability protections offered by LLPs are considered inadequate; and
  • The benefits of partnership taxation compared to those of S corporation taxation are not considered significant enough to warrant setting up a partnership, LLC or LLP.
Most advisors agree that LLCs and limited partnerships are superior to S corporation. However, when there is a single owner and double taxation must be avoided, the S Corporation is the only alternative to sole proprietorship status unless single member LLCs are permitted under state law, and applicable professional standards.

Sole Proprietorships

The sole proprietorship may be the preferred form of doing business if:

  • Single member LLCs are not permitted by state law and/or applicable professional standards;
  • Adequate liability insurance is available at an accept able cost;
  • The major liability exposures are from the owner's practice of a profession (a problem that generally is not cured simply by operating as a liability limiting entity;
  • The business is in the early stages, and minimizing administrative expenses and paperwork is a major objective;
  • There are no employees;
  • At this time the owner does not wish to deal with the issue of how ownership interests will be transferred in the future (for estate planning, succession planning or other reasons);
  • At this time, the owner does not wish to deal with the issue of how additional equity capital might be raised in the future; and
  • The business is small enough that operating as a sole proprietorship is still a rational choice in light of all the above considerations.
The primary attraction of sole proprietorships is their administrative simplicity. As soon as a business begins to generate significant income and wealth for the owner, however, the use of a liability limiting entity is highly advisable. Generally, the S Corporation or single member LLC (if permitted by state law and applicable professional standards) will prove the best choice for single owner business, because double taxation is avoided. However, when it is critical to retain the maximum amount of capital to finance growth, the C Corporation's lower graduated tax rates can make it the better choice particularly if the corporation can meet the definition of a QSBC.

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Laura Anthony, Founding Partner
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Legal & Compliance, LLC
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