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Sole Proprietorship Or LLC: Is It Time To Rethink Your Business Structure?

Denice Sakakeeny is the founder and principal consultant of Denice Sakakeeny & Associates, a Boston-based boutique finance and operational consulting practice focused on anticipating and solving the unique challenges of high-growth organizations. With over 20 years of finance experience, including working in and for organizations spanning publicly held software and media companies, and startups, Denice guides companies through critical stages of growth including launch, transition and expansion. Here she compares different business structures and discusses the advantages of each.


What are the primary differences between sole proprietorships, limited liability companies and corporations?

With a sole proprietorship, the owner and the business is one in the same. There is no distinction. Thus, the sole proprietorship can only have a single owner, the actual sole proprietor. As such, the profit and losses of a sole proprietor are recorded in Schedule SE — Form 1040. Generally, this is called pass-through taxation, as this schedule is included in the owner's personal income tax filings. In this situation, the profit and losses of the business are literally passed through to the owner. Additionally, as there is no distinction between the owner and her business, the business' liabilities are the owner's liabilities.

A limited liability corporation differs from a sole proprietorship in two main ways. First, the LLC could have more than one owner, whereas a sole proprietor only has one owner. Secondly, the LLC is a separate and distinct legal entity than the owners. This concept is called corporate personhood, and this is important because if the LLC owes another party money, generally the owners are not personally liable.

A corporation differs from an LLC in one primary way. A corporation, generally, files its own tax returns. The federal return for a U.S. corporation is Form 1120. Generally, the owners of the corporation receive profit distributions by means of dividends. There generally is no pass through accounting on corporations.

At what point should an entrepreneur consider forming an LLC?

The first reason an entrepreneur should consider forming an LLC is if they do not wish to be personally liable for the activities of their business. If you have no tolerance for personal risk, then an entrepreneur should contemplate forming an LLC from day one and consider the additional expenses an investment in protecting their personal assets. The second reason an entrepreneur should consider forming an LLC is when the sole proprietorship would like to have more than one owner. The third reason an entrepreneur should consider forming an LLC is when the sole proprietor has employees, and would like to offer these employees certain benefits. A sole proprietorship cannot provide the range of tax efficient benefits, such as a 401k, to its employees as an LLC or a corporation is able to under current regulations.

What are the financial benefits and costs of an LLC?

In Massachusetts, as sole proprietor, you're required to register your business with your city or town. There is a small cost associated with this. Generally, a sole proprietor with some financial literacy or experience could prepare her own Schedule SE on her own personal income taxes. As an LLC, you must register with the Commonwealth of Massachusetts Department of Corporations, and need to pay a qualified attorney to draft formation documents and operating agreements. Also, an LLC generally needs specialized tax accounting as profits are distributed to members according to the operating agreement. Whereas a sole proprietor with some level of sophistication, could file their own Schedule SE. The vast majority of small business owners outsource entirely the tax filing and distribution calculations for the LLC.

There are vast differences in the personal liability limits of the business owner. Regardless of the structure, each company should seek to invest in business liability insurance. Talk to a qualified commercial insurance broker, and get insurance to protect you. There are packages meant for self-employed sole proprietors, and it's well worth the investment.

What provisions do you recommend business owners include in their operating agreement when forming an LLC?

I recommend including two key areas.

  1. Distribution of profit and losses. How are the proceeds of the company distributed to the members? Specifically, what is the math behind allocating the profits and losses of the LLC to the owners?
  2. Adding new members and rights of departing members. If a member was to depart, due to death or otherwise, the LLC should know how things will proceed in advance. Do the existing members have the rights to buy out the departing owner? At a certain price? Also, how does the corporation take on new members? What is the cost of each unit of membership, or what is the process to determine the cost?


This article was written by Gillian Burdett for CBS Small Business Pulse.

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