Choice of Entity for Sole Business Owners Part III

This is the final part of a three-part series on choosing a business entity for sole business owners. Click here for my previous posts on Corporations, and here my first post on Sole Proprietorships.

Limited Liability Company (L.L.C., L.C.)

Limited Liability Companies are another popular option for sole business owners. LLCs are owned by members who hold membership interests/units, managed by, uh, managers, and governed by an Operating Agreement. An LLC combines the limited liability protection of a corporation with the pass-through taxation of a sole proprietorship or partnership. It’s also highly flexible. LLCs are given fairly broad discretion to manage themselves, and they have a wide selection of tax treatment options.

By default, a single-member LLC will be taxed as a sole proprietorship (income reported on Form 1040 Schedule C), and a multiple-member LLC will be taxed as a partnership (LLC income reported on Form 1065 and members’ pro rata share reported on Form 1065 Schedule K-1). However, an LLC may alternatively elect to be taxed as a C corporation or an S corporation.

Another advantage of an LLC is that there are no formalities. The manager and her responsibilities are typically designated by the operating agreement, and thus there is no requirement for members to hold elections or regular meetings. In light of this, however, it’s wise for even a single-member LLC to have an operating agreement, both to set forth the rules, regulations, and policies of the company and, as with corporations, to document that the company is separate from the owner for limited liability purposes.

In Massachusetts, LLCs are formed by submitted a Certificate of Organization with the Secretary of the Commonwealth. As with corporate bylaws, an operating agreement is not filed with the Secretary.

With all this flexibility comes a cost, however. At $500 apiece, LLCs have the highest initial filing fee and annual report fee (equivalent to that of a Massachusetts Limited Liability Partnership). Nevertheless, LLCs are a favored option because they combine the benefits of corporations, sole proprietorships, and partnerships, with added flexibility and without the strict formalities. Additionally, licensed professionals may form a Professional Limited Liability Company (P.L.L.C.), which confers the same professional liability insulation between members as a professional corporation.

In Sum:

  • + Flexible
  • + Limited liability protection
  • + Pass-through taxation by default
  • + Numerous alternative tax treatment options
  • + Ease of formation
  • + No formalities
  • + Allows for growth
  • + Survives departure of members
  • - Expensive to form and maintain

Massachusetts Limited Liability Company Resources

LLC Forms

Massachusetts Limited Liability Company Act, Mass. Gen. Laws. ch. 156C

LLC Tax Treatment Options (IRS)

In honesty, this series was originally one short post that ended up about five times longer than I expected it to be. In any event, hopefully this has been a helpful little basic primer on business entity considerations for sole owners. Again, selecting an entity is a decision that depends on your preferences, budget, and long- and short-term goals among other things. While my intention here is to provide you with general information to help you make a more educated decision, this is no substitute for consulting with a business attorney and a CPA who can give you a more personalized recommendation based on your specific situation.

As always, if you have any questions, feel free to contact me!

Choice of Entity for Sole Business Owners Part II

This is a continuation of a series about choosing an business entity for sole business owners. Here's my first post, about Sole Proprietorships.

Corporations (Corp., Inc., Ltd.)

At the opposite end of the spectrum from Sole Proprietorships are corporations. Corporations are treated as separate from the individuals who own, manage, and operate them. The defining feature of a corporation is the governance structure: it’s owned by shareholders, who elect directors, who appoint officers. Officers typically manage day to day operations, while directors often handle broader strategic decisions, such as whether to reinvest profits or declare dividends. For our purposes, though, you’ll be the sole shareholder, director, and possibly the sole officer. Unlike sole proprietorships (and partnerships), the corporation survives the death of its owners.

Corporations provide “limited liability” to their shareholders, meaning that the shareholders are generally not responsible for the debts, liabilities, and obligations of the corporation. However, the limited liability protection does not shield professionals, such as doctors, lawyers, architects, engineers, etc., from liability for committing malpractice. Additionally, a claimant suing a corporation may seek to “disregard the corporate form” (commonly called “piercing the corporate veil”) in order to hold the shareholders personally liable. Owners of one-person corporations can be at particularly high risk if they don’t carefully comply with all formalities and record keeping.

For example: If Dr. Shanika Thomas from our last post formed “Thomas Healthcare Center, Inc.,” it defaulted on a small business loan, and the lender sued to collect, Thomas Healthcare Center, Inc. would be responsible for the debt, not Dr. Thomas. However, if Dr. Thomas was the sole shareholder, director, President, Treasurer, and Secretary, the lender could seek to “pierce the veil” and hold Dr. Thomas personally liable for the debt on the grounds that she is essentially a sole proprietor.

Forming a Massachusetts corporation is fairly straightforward. Simply submit your Articles of Organization with the Secretary of the Commonwealth. As of this post, the filing fee is $275, which allows you to issue up to 275,000 shares of stock. Every additional 100,000 shares costs an extra $100. Note that in Massachusetts, business filings are public record and freely searchable at the Secretary’s website.

In addition to Articles of Organization, you should also enact corporate bylaws, even if you’re the sole shareholder, director, and officer. The bylaws set forth how the corporation will be governed. Not only is it generally wise to have bylaws to guide you in managing your company, but they also lend documentary support to your claim of limited liability. Bylaws should also establish how the corporation will carry on in the event that owners and directors die, become incapacitated, or otherwise depart from the corporation. The bylaws are not filed with the Secretary of the Commonwealth.

You must also elect your directors and appoint your officers, even if you’re a sole-shareholder corporation. The Articles of Organization require you to name your initial directors and officers, and during the life of your corporation, you must hold shareholder meetings to elect or reelect the directors, and director meetings to appoint or reappoint the officers. It may sound silly, especially if you run your business out of your own home, but holding shareholder meetings, elections, and director meetings, and carefully documenting the minutes of these meetings can help support your claim of limited liability in the event that a claimant attempts to hold you personally liable.

In order to keep your corporation in good standing, you must file an Annual Report with the Secretary of the Commonwealth. The current annual report filing fee is $125.

Corporations can come in a variety of flavors depending on ownership and tax treatment. Here, I’ll stick to some basic distinctions: the C Corporation, the S Corporation, and the Professional Corporation.

C Corporation

The main distinguishing feature of a C Corporation is tax treatment. You’ve likely heard the phrase “double taxation” regarding C corporations. This is because C corporations are taxed on their income at two levels. First, the corporation itself pays annual income tax just as an ordinary person would. Second, if the corporation distributes dividends to the shareholders, the shareholders pay income tax on those dividends. If a corporation earns a profit or has a surplus, the directors may decide to declare a dividend, in which case the corporation distributes the profits to the shareholders, typically proportionate with the amount of shares owned.

As you might imagine, this usually isn’t very appealing to the sole owner of a small business. Indeed, C corporations are often preferred by larger, more sophisticated businesses. The reason is a little technical. A corporation can’t necessarily decide when it will incur taxable income at the first level – its annual income will likely depend on the external factors such as the market and consumer demand. However, the corporation can decide when to declare a dividend, and thus when to incur a taxable event at the second level. This can be a very powerful tool for tax planning. Of course, there are reasonable limits: the IRS (and likely the Massachusetts Division of Revenue) will penalize a profitable corporation that refuses to declare a dividend solely because it doesn’t want to incur taxes.

In sum:

  • + Limited liability protection
  • + Allows for easy growth
  • + Can defer taxable event
  • - Certain formalities required to sustain liability protection
  • - Incorporation fee and annual report fees
  • - Double taxation

S Corporation

S Corporations are a popular alternative for small businesses. The shareholders still enjoy the same limited liability protection, but the profits and losses are “passed-through” to the shareholders, which they report on their personal income tax returns and pay taxes on at their personal income tax rate. The tax treatment offered by the S corporation tends to be appealing to small business owners.

The flip side is that there are a number of eligibility requirements for S corporation status: there must be no more than 100 “eligible” shareholders (individuals, certain trusts, and estates), the corporation may issue only one class of stock, and certain corporations are ineligible. For many sole-shareholder corporations, the favorable tax treatment may nevertheless strongly outweigh burden of complying with the eligibility requirements.

To form a Massachusetts S Corporation, you follow the same steps as with a C Corporation, except that once you’ve filed your Articles of Organization, you must file IRS Form 2553 (Instructions here) electing S corporation status.

In Sum:

  • + Pass-through taxation
  • + Limited liability protection
  • - Same formalities to sustain liability protection
  • - Can’t issue multiple shares of stock
  • - May have limited number of shareholders
  • - Certain businesses ineligible
  • - Incorporation and annual report filing fees

Professional Corporation (P.C.)

Professional Corporations are a unique type of corporation available exclusively to licensed professionals. Functionally, a professional corporation can be either a C corporation or S corporation, so the same advantages and disadvantages apply. Just as with any other limited liability entity, the professional corporation doesn’t shield shareholders from personal liability for their own individual negligence or malpractice. However, the distinct advantage of a professional corporation is that it does shield shareholders from liability for malpractice caused by other shareholders.

For example: Suppose Dr. Thomas incorporated “Thomas Healthcare Center, P.C.,” where she was the sole shareholder, director, and officer. Wanting to serve patients at all ages, she brings on her classmate, Jackie Wu, a pediatrician, as another shareholder. If a patient sues Dr. Wu for malpractice, then Dr. Thomas is shielded from personal liability as long as she did not participate in the treatment of the aggrieved patient.

In exchange for this added protection, there are certain ownership and governance restrictions on Massachusetts professional corporations. All incorporators, all shareholders, a majority of the directors, and the president and vice president of the corporation must be licensed professionals. Additionally, either the Articles of Organization, bylaws, or a shareholder agreement must include a “corporate share redemption provision” requiring the corporation to redeem the shares of a shareholder who dies, becomes unable to practice (due to incapacity or disciplinary action), or transfers their shares to a non-licensed individual. See Massachusetts Professional Corporation Law § 12, Mass. Gen. Laws ch. 156A, § 12.

To form a professional corporation, you must file Articles of Organization with the Secretary of the Commonwealth, and, unlike non-professional corporations, you must explicitly state the professional services your corporation will provide. Additionally, you must also include a certificate signed by the relevant licensing board stating the name of the corporation and listing the incorporators, officers, directors, and shareholders. Otherwise, formation and maintenance parallels that of a C corporation or S corporation.

A professional corporation is a worthwhile consideration for a licensed professional who finds the corporate entity appealing. A professional corporation might be particularly appealing to professionals hoping to establish a solely owned company while leaving room for potential growth.

In sum:

  • + Limited liability protection
  • + Insulated from liability for other shareholders’ malpractice
  • + Allows for growth
  • - Only available to licensed professionals
  • - Certain formalities required to sustain liability protection
  • - Incorporation fee and annual report fees
  • - Additional incorporation and reporting requirements

Massachusetts Corporation Resources

Corporate Forms (Standard Domestic)

Corporate Forms (P.C.)

Massachusetts Business Corporation Act, Mass. Gen. Laws ch. 156D

Massachusetts Professional Corporation Act, Mass. Gen. Laws ch. 156A

S Corporation Summary (IRS)

This concludes Part II of my three-part miniseries on choice of entity for sole business owners. Look forward to Limited Liability Companies next week!

As always, if you have any questions, leave a comment or contact me!

Choice of Entity for Sole Business Owners

What if you're not only a small business owner, but also the only owner of your business? Maybe you’re currently operating as a sole proprietorship, but for one reason or another, you got the idea that you should form a business entity. How do you choose one? What are the advantages and disadvantages of each one? In this three-part miniseries, I’ll take you on a whirlwind tour of (Massachusetts) business entity options for sole business owners. We'll be talking about Sole Proprietorships, Corporations, and Limited Liability Companies.

Choice of entity is a major decision with certain legal, financial, and tax consequences, so it shouldn’t be taken lightly. Which entity is right for you is a business decision depending on a variety of factors, but I’d wager that the most significant ones are typically

  1. Ownership
  2. Liability protection
  3. Tax implications
  4. Costs
  5. Ease of formation

Your preferences with respect to each of these issues will likely strongly influence which entity you select. Now, without further ado, let’s dive in.

Sole Proprietorship

The Sole Proprietorship is the default business designation. It isn’t actually a business entity at all: it’s just you, you are the company. For better or for worse, there are no layers between you and your business. The big advantage of the sole proprietorship is that it’s cheap and easy to form. There are no registration requirements – if you’re doing business for yourself and haven’t formed an entity, you’re already a sole proprietor. You don’t need to file a separate tax return: you report your business income on Schedule C of your personal Form 1040. You can still hire employees. “Sole proprietor” doesn’t mean one-man or one-woman business, it simply means that you’re the sole owner.

The only filing requirement is that, depending on your business name, you may have to register a DBA (“Doing Business As”) with the city or county in which you do business. If you use a name other than your legal name, also known as a “fictitious name,” you need to register your fictitious name in each city or county in which you maintain a location.

For example: if a physician named Shanika Thomas wanted to open a primary care clinic called the “Thomas Healthcare Center,” with her main office in Newburyport and a second location in Boston, she would need to register DBAs with both Newburyport/Essex County and with the City of Boston. However, if Dr. Thomas was operating her clinics under the name “Shanika Thomas, M.D.,” she wouldn’t need to register any DBAs.

Additionally, some banks may wish to see a city/county business registration certificate in order to open a business bank account.

The major disadvantage of a sole proprietorship is that, because the owner is legally the business, there’s no liability protection. This means that the sole proprietor is personally responsible for the debts and liabilities of the business.

For example: if Dr. Thomas defaulted on a small business loan she borrowed to lease the clinic spaces, she would be personally liable for the debt.

Another disadvantage is that expansion is somewhat limited. You can certainly grow your company, hire more employees, and open additional locations, but you can’t take on partners or co-owners. Moreover, the business terminates upon the death of the sole proprietor. That said, depending on the nature of your business, a sole proprietorship might be a good option. I think that the sole proprietorship can be a particularly good option for licensed professionals because, as I’ll discuss further in the post covering Corporations, the liability protection afforded by a corporation or limited liability company does not cover professional liability. If you’re a licensed professional with no employees, a mainly virtual/online practice, and you already carry professional liability insurance, a sole proprietorship might be a reasonable option.

In sum:

  • + Little to no filing requirements
  • + No filing fees or annual fees
  • + Taxed as an individual
  • + May hire employees
  • - No limited liability protection
  • - No co-ownership
  • - Doesn’t survive owner

In my next post, we'll discuss Corporations! 

As always, if you have any questions, don't hesitate to contact me!

SCORE Intellectual Property Basics Recap

On Thursday I had the privilege of giving a presentation on intellectual property law along with my friend, Michael Gu, to some of the small business owners at Boston SCORE. We covered patents, trademarks, copyrights, and trade secrets. Here’s a quick recap of some of the main takeaways.

Trademarks

Use it or Lose it

Trademark rights arise from use, whether your mark is registered or not. If you’re using your trademark on a "common law" basis (using it without registering it), your rights cease when your use ends. Even if you have a registered trademark, your registration will be cancelled if you fail to show proof of continued during your renewal period.

U.S. Registration is a Legal Proceeding – Get Assistance

Applying for a federal trademark registration is a process involving substantive legal analysis and adherence to strict deadlines. It isn’t as straightforward as applying for a business certificate or filing to create a new entity. For example, responding to an examining attorney’s refusal to register a trademark requires legal argumentation similar to that of a motion in litigation. To that end, it’s strongly recommended that you hire an attorney. Even the USPTO recommends retaining a lawyer. *cough*

Use your Mark Properly

You threaten your trademark rights when you don’t use your mark properly. Some tips for proper use include

  • Using the trademark consistently
  • Using the trademark as an adjective, not a noun or a verb
  • Using trademark notices (TM/SM if it isn’t registered, ® if it is)

Copyrights

Check out my AIGA presentation recap for an overview of basic copyright law.

Patents

Patentable Subject Matter

“Anything under the sun that is made by man” may be patentable. However, patents don’t protect abstract ideas, laws of nature, and natural phenomena. Moreover, the invention must be useful, novel, and non-obvious.

Rights Granted

Patents grant the exclusive right to exclude others from making and using your patented invention. The right must be affirmatively asserted, it isn’t automatic. The right is also limited in geographic scope: a U.S. patent cannot be enforced outside of the U.S.

Visit www.uspto.gov/patent or contact a licensed patent agent or patent attorney for more information.

Trade Secrets

What is a Trade Secret?

A trade secret is information that (1) derives independent economic value from its not being generally know and not being readily ascertainable by other persons; and (2) is subject of reasonable efforts to maintain its secrecy.

The Law Varies from State to State

While many states have adopted the Uniform Trade Secrets Act in some form, a number of states, including Massachusetts, have not. Some protect trade secrets by separate statute, and others protect them under common law.

Closing Thoughts

This was another fun presentation with a very active audience. My Kevin James joke bombed – I guess even I can’t make Paul Blart funny, but you can’t win ‘em all. Thanks again to Boston SCORE for letting us give the presentation, and thanks to Harvard Ed Portal for letting us use their cool location.

As always, if you have any questions about copyright or trademark, don’t hesitate to contact me!