Sometimes the simplest of tax questions can trigger the most complex of discussions.
The question put to the ABA-TAX listserve was simple. Can a sole proprietor elect, under the check-the-box regulations, to be treated as a corporation for federal tax purposes? The question was raised by someone who attended a CPE session, was told that a sole proprietorship COULD elect to be treated as a corporation, and who had trouble, understandably, accepting the correctness of the statement.
Those voicing an opinion offered all sorts of rationales and explanations to support one or the other of the championed answers. How could that be? A look at the check-the-box regulations reveals not only the absence of any statement addressing the question directly, but also the absence of definition of organization.
The definition of organization is critical because the check-the-box regulations, and almost every flow-chart portraying their rules, begin analysis with the existence of an organization. If there is an organization, , then the door is open to deciding if it will be a corporation, partnership, sole proprietorship, or division of a corporation for federal tax purposes.
The regulations technically begin by stating that they apply for purposes of determining "the classification of various organizations" and specify that "whether an organization is an entity separate from its owners for federal tax purposes is a matter of federal tax law and does not depend on whether the organization is recognized as an entity under local law."
The next logical step would be to define organization. But the regulations don't do that. Instead, they proceed to identify certain "joint undertakings" (such as joint ventures and other contractual arrangements) that "may" create a separate entity for federal tax purposes. They do, if the participants in the undertaking carry on a trade, business, financial operation, or venture and divide the profits from it.
So are the regulations saying, in effect, "In addition to organizations, which may or may not be treated as separate entities for federal tax purposes, certain ventures and arrangements that are not organizations may qualify as separate entities for federal income tax purposes"? In other words, do the regulations provide that an entity can exist even though there is no organization?
The regulations then kick out of the analysis certain organizations out of the analysis. Presumably, there is no question that they are organizations. Thus, organizations wholly owned by a state aren't recognized as separate entities. Considering that states are tax-exempt, this is not an earth-shattering conclusion. Certain Indian tribes are treated as not being entities.
The regulations then point out, specifically, that organizations with a single owner can choose to be recognized or disregarded as entities separate from the owner. Of course, what first comes to mind is the single-member LLC, which is disregarded as an entity (and thus treated either as a sole proprietorship or as a division of a corporation depending on whether the owner is an individual or corporation) unless it elects to be treated as a corporation.
But the fascinating question is this: Is a sole proprietorship an "organization"? If so, it is a single-owner organization and can follow the same path down the flow-chart or through the analysis as does a single-member LLC.
The regulations then push aside organizations that have separate, special treatment under the Code. For example, a REMIC is an organization (or so one can presume), but it is a REMIC and not a partnership, corporation, trust, sole proprietorship, or division of a corporation.
One would expect the next rule to be "An organization is treated as a separate entity if...." but that's not where the regulations go. Instead, on the assumption that organizations treated as separate entities have been identified, the regulations state that "the classification of organizations that are recognized as separate entities is determined under" specified sections of the regulations. Technically, that makes no sense, because it is under one of those specified regulations that a single-member LLC (presumably an organization) is disregarded and NOT recognized as a separate entity. Literally, the provision that treats a single-member LLC as a disregarded (and not separate) entity is in a Regulations provision that one doesn't reach unless one is dealing with an "organization recognized as a separate entity." I'm beginning to wonder what the flow chart used by the regulations drafters looked like. But, just as too many computer programmers don't flow-chart their projects and end up paying a price or causing their customers to pay the price, so, too, failure to flow-chart this sort of regulation means that at some point the IRS, or its customers, we taxpayers, will pay the price.
The regulations then jump to the definition of a business entity, which primarily pushes trusts (and presumably estates) into their own special corner of the tax classification world. These regulations state: "a business entity is any entity recognized for federal tax purposes (including an entity with a single owner that may be disregarded as an entity separate from its owner) that is not ... a trust .. or otherwise subject to special treatment." Again, the use of the language is deficient. If the IRS wants to treat disregarded entities as a subset of recognized entities, which perhaps it is trying to do, it needs to use better phraseology. Otherwise, we end up with recognized entities that are disregarded.
This is the point at which the question, can sole proprietorships elect to be treated as corporations, runs aground. The rest of the regulations, which take business entities and provide for their treatment, don't impact on the specific question.
One argument that was made is that a sole proprietorship is an organization, because it is organized by a person as a means of doing business. In response, one argues that the sole proprietorship is simply an individual and that no separate organizational structure or procedures exist. Even so, under state law X can set up a sole proprietorship under a business name such as "X doing business as Arf's Biscuits." Is Arf's Biscuits an organization?
Another argument that was made is that if a sole proprietorship is not an organization, it can't be an entity as an undertaking or contractual arrangement because the definition requires that there be "participants" who divide the profits. A sole proprietorship has one participant and the profits are not divided.
Another argument was simply that nothing in the regulations states that a sole proprietorship cannot be an entity, or an organization, or a business entity. Of course, nothing in the regulations states that a sole proprietorship CAN be an entity, organization, or business entity.
To the same effect was an argument that referred to the Preamble to the regulations, which state that protective elections, made when there is uncertainty about status, are not prohibited. Of course, a protective election is simply that, a contingent protection that would fail if, in fact, the organization, entity, or other existence does not qualify to make the election.
I argued somewhat more obliquely. If a tenancy-in-common, "mere cownership" to use the technical phrase, cannot be an entity, can a tenancy-by-one's-self (a sole proprietorship) be an entity? The response is that joint ownership can be an entity, under the joint undertaking or contractual arrangement rule, if there is sufficient "activity" so why can't a sole proprietorship that engages in the same sort of activity rise to the level of an entity? The counter-response is the absence of participantS to divide the profits.
Another response to my argument brought an interesting twist. The regulations state "Mere co-ownership of property that is maintained, kept in
repair, and rented or leased does not constitute a separate entity for federal tax purposes. For example, if an individual owner, or tenants in common, of farm property lease it to a farmer for a cash rental or a share of the crops, they do not necessarily create a separate entity for federal tax purposes." This language suggests that an individual owners does not necessarily create a separate entity, but because it doesn't state that an individual owners can NEVER create a separate entity, it leaves open the possibility that an individual can create a separate entity in the form of a sole proprietorship.
Several cases were cited, including Williams v. McGowan, in which the court held that the sale of a sole proprietorship is the sale of the assets of the sole proprietorship and not the sale of a single business, or presumably, entity. Also pointed out was the Supreme Court's decision in Morrissey, suggesting that entities are limited to corporations, partnerships, and trusts, but the decision does not explicitly so state. And, of course, that sort of definition of entitly leaves out things not in existence when Morrissey was decided, such as the LLC, and it says nothing of estates, which surely are separate from their executors and beneficiaries (and are very similar to trusts for many purposes).
Some interesting arguments were raised on the basis of what would happen if a sole proprietorship were permitted to elect to be treated as a corporation for federal tax purposes. One, citing Braswell v US, asks if the individual would lose the right to raise, as a sole proprietor, the "act of production" privilege under the Fifth Amendment? Would profits retained by the individual generate dividends or interest? If the sole proprietor ceases doing business, is the corporation dissolved, with its attendant liquidation consequences? If not, would retention of interest-bearing accounts create a personal holding company?
Well, one enterprising participant in the discussion, sought a response from the IRS Email Tax Law Assistance. Having known this particular participant for many years, I'm not surprised that he took the initiative to find out what the IRS thinks. The short answer is that the IRS said, "No, a sole proprietorship cannot elect to be treated as a corporation."
The longer analysis is interesting. The IRS cited the regulations that apply to the definition of business entity, but not the regulations that deal with organizations and joint undertakings, which is where most of the discussion, and my analysis, turned its attention. The IRS stated "A business entity does not include a sole proprietorship not classified as a single owner entity disregarded from its owner (an LLC under state law). A sole proprietor is not an entity in and of itself thus, this election cannot be made." Of course, the cited regulations do NOT make this statement. The IRS also quoted the regulations that deal with the consequences of changing classification, but those, to me, provide nothing in the way of guidance.
So now we know what the IRS thinks. I agree with its position. But I don't think the IRS provided persuasive reasoning. The arguments raised by those discussing the question, on both sides, were far more cogent. Why not simply state, "A sole proprietorship is not an organization, and because it does not have more than one participant, it is not a joint undertaking. Accordingly, it is not an entity, and because it is not an entity it is not a business entity for which an election to be treated as a corporation is available."? Isn't that the gist of what the IRS wants to say?
I learned two other things from this discussion. Well, maybe I ought to say that two things I knew or suspected were reinforced. First, the active members of the ABA-TAX listserve can really get into a tax law discussion, of the quality and scope one likes to see from a law school class on a Blackboard virtual classroom discussion board. Second, things get said at CPE and CLE sessions that are flat out wrong, and risking intrusion into another topic, there's no supervision of what is said, and no evaluative mechanism to determine if those attending the sessions have learned anything. Of course, most CLE and CPE sessions are of high quality, and some attendees learn at least something, but there's more education experienced on the ABA-TAX listserve by its active participants and readers than happens for some people in some CLE and CPE sessions.
And, oh won't my students be so appreciative, that another examination question has crawled out of the many pages of discussion that traversed the ethernet during the past few weeks. The best part, for many, I suppose, was that I deliberately sat back and said nothing until near the end. I think some people thought I had email laryngitis. No such luck.