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The Ins and Outs of LLCs

A Well-drafted Operating Agreement Is Critical for Success

Michael Simolo

Michael Simolo

Limited Liability Companies (LLCs) have in many cases become the preferred choice of entity for passive income investments, particularly rental real estate. In addition, LLCs are a valuable tool for facilitating family ownership of valuable property, such as vacation homes.  While LLCs are often not the best choice for operating entities, there are exceptions, and LLCs can and do serve this role.
In short, LLCs are an increasingly popular alternative to the traditional corporate structure, and there are many reasons for this, as this article will explain.
First, it is helpful to first consider why LLCs continue to increase in popularity among business owners and holders of income producing real estate. There are several reasons, but here are the three most prominent:
• First, LLCs offer their owners liability protection. In fact, in many states, LLCs with multiple owners offer greater liability protection than corporations due to additional protections against the creditors of co-owners;
• Second, LLCs permit significantly greater flexibility than corporations in structuring the financial arrangements and rights of owners; and
• Third, LLCs can serve as a ‘pass-through’ entity for tax purposes without the need to qualify for so-called S corporation status. (S corporations incur no tax at the corporate level, with all income being taxed to the shareholders.)
The default rule is that LLCs are taxed as partnerships, meaning that income taxes are applied only at the partner level. In keeping with the general flexibility of LLCs, however, an LLC may elect to be taxed as a corporation, including as an S corporation (the taxation of which differs siginficantly from partnerships, nothwithstanding that both are pass-through entities). Such an election may be preferable if the LLC is an operating entity.
These benefits may be unavailable if the LLC’s governing document — the operating agreement — fails to properly address the numerous issues that can arise with any ongoing business. The operating agreement, while similar in some ways to the bylaws of a corporation, is an agreement among the owners that allows for nearly unlimited flexibility in the governance of the LLC. As a result, operating agreements should always be narrowly tailored to address the unique characteristics of each business.
In particular, the operating agreement should be used to address issues that are not covered by the applicable state’s LLC statute, or to override provisions in the LLC statute that are inconsistent with the owners’ objectives. For example, the Massachusetts LLC statute provides owners with the right to resign from the LLC upon six months notice and have their interest bought out by the LLC at fair value (i.e., not discounted). For obvious reasons, owners may wish to override this provision through an operating agreement.
Crafting such an agreement requires both detailed knowledge of the underlying LLC statute for the state in which the LLC is formed and a thorough understanding of the intentions and concerns of the LLC’s owners. For these reasons, use of a form LLC operating agreement can often do more harm than good.
Here is a partial list of 11 common issues that should be addressed in virtually all operating agreements:
1. Under which state’s law should the LLC be formed?
2. How many classes of ownership interests will the LLC have? Will different classes of owners have different rights (i.e. voting) and preferences (i.e. return of capital)? Does the underlying state LLC statute allow for different classes of ownership?
3. Who will manage the day-to-day affairs of the LLC? Which decisions will be made by the manager, and which will be put to a vote of the owners?
4. What types of fiduciary obligations will the owners and managers have to each other? Under what circumstances will managers and/or owners have a right to sue the LLC (i.e. derivative action) or the other owners or managers?
5. Upon what terms (if any) will owners be required to contribute additional capital to the LLC?
6. Upon what terms (if any) will owners be entitled to be paid back their contributions to the LLC?
7. How will the LLC’s profits, losses, and cash flow be allocated to the owners?
8. How will distributions be allocated among the owners? Under what circumstances will the LLC be required to make distributions to owners (i.e. to pay income taxes on LLC income, liquidation, etc.)?
9. Will owners be permitted to transfer their ownership interests? If so, to whom?  What happens if an owner dies?
10. Will the LLC and/or other owners have the right to redeem or purchase the owner’s interest prior to such transfer?  If so, how will the purchase price of the owner’s interest be determined?
11. How will the entity be taxed (i.e. sole proprietorship, partnership, subchapter S-corporation, etc.)? Note that the validity of certain tax elections may hinge on a properly drafted operating agreement being in place. This is particularly true if the LLC desires S-corporation tax status.
More complicated arrangements may require additional terms, such as non-compete clauses, indemnification provisions, ‘tag-along’ and ‘drag-along’ rights, call-and-put options, and others.
A look at these issues reveals that the flexibility offered by LLCs is the proverbial double-edged sword. On one hand, the entity can be structured in virtually any manner to address its purpose and the goals of its owners. On the other, reliance on the LLC statute — or, perhaps worse, a form operating agreement improperly tailored to the entity it governs — can result in significant consequences, including the premature liquidation of the entity or an ownership interest being seized by a co-owner’s creditors.
A well-drafted operating agreement can eliminate these risks and prevent disputes among owners from leading to litigation.

Michael Simolo is an attorney with the law firm Robinson Donovan, P.C., specializing in estate planning, estate and trust administration, business law, and fiduciary litigation; (413) 732-2301. Nicholas P. Lata, Esq. assisted in drafting this article.