ROBS Transactions as a Financial Investment Tool: Legal Traps for the Unwary

Brian S. Weinstock

By Brian S. Weinstock



Over the last few years, ROBS transactions have dramatically increased which means that the funds being used to capitalize these transactions has significantly increased too. I wrote about ROBS transactions last June in a post called “ROBS transactions: the Department of Labor and IRS Regulation.”

Recently, Mr. Alan Lavine interviewed me for an article in Financial Advisor Magazine about ROBS transactions with regard how they are being used as financial investment tools and whether investors should participate in this type of transaction. The article, “Rolling Over, Starting Up,” appears in the in the December 2010 issue. The article’s subtitle is: Clients can tap into retirement savings to start new businesses, but there are legal traps for the unwary.

It was an honor to be quoted by Mr. Lavine who is an accomplished author and syndicated columnist. Mr. Lavine and his wife, Gail Liberman, wrote Rags to Riches which was featured on Oprah and hit two best seller lists.

Will There be a 3.8% Sales Tax When You Sell Your Home?

Patrick J. Murphy

By Patrick J. Murphy



With the passing of the health care bill, there are a number of new tax code provisions and many people are concerned about how these new provisions will affect them. One of these new tax code provisions is the 3.8% Medicare tax that applies to “net investment income,” which is such items as interest, dividends, annuities, royalties, rents, and net gain on the sale of property (like your primary residence). One of the misconceptions about the new 3.8% Medicare tax is that it will affect a number of people when they sell their primary residence for a gain. Fortunately, this new tax will only affect a small percentage of people who are high income taxpayers.

One reason the new tax will not impact many taxpayers is the current exemption for gain on the sale of your primary residence. For single individuals, they are able to exclude the first $250,000 in gain from the sale of their primary residence. For married couples, the first $500,000 in gain from the sale of their primary residence is excluded. As a result, depending upon the taxpayer, the first $250,000 or $500,000 may be excluded from gross income and would not be subject to the 3.8% tax. The only individuals who should be concerned about the 3.8% Medicare tax is individuals who sell a second home or a have a very large gain on the sale of their primary residence.

Another reason that the new 3.8% Medicare tax will not affect many people is that it only applies to high income individuals. The tax will only be incurred when a single individual has adjusted gross income over $200,000 or when a married couple filing jointly has adjusted gross income over $250,000. Only a small percentage of taxpayers earn incomes over these threshold amounts, even for taxpayers who sell their primary residence for a gain over the $250,000/$500,000 exemption.

Therefore, due to the $250,000/$500,000 income exemption and the tax’s income thresholds, the only individuals who will be affected by this tax are high income taxpayers. If you believe you may be subject to the 3.8% Medicare tax due to a sale of your primary residence or otherwise, it is important that you speak with your tax attorney or accountant to develop a tax planning strategy to minimize the impact of this new tax. The goal behind the tax planning will be to minimize your adjusted gross income through such strategies as recognizing losses at the time you sell your primary residence or purchasing municipal bonds which pay tax-exempt interest. Through proper planning, you can minimize the impact of this new tax.

A New Headache for Business Owners – The IRS Form 1099

Patrick J. Murphy

By Patrick J. Murphy



Buried within just 23 lines of Section 9006 of the Healthcare reform bill, The Patient Protection and Affordable Care Act, H.R. 3590, 111th Congress, signed into law by President Obama on March 23, 2010 is a dramatic change to the 1099 reporting requirements.

Prior law IRS reporting laws required, generally, that if a business made payments in excess of $600 to a person or a business over the course of a year, the business was required to file a Form 1099 to report those payments. One copy would be sent to the IRS, another copy was sent to the person/unincorporated business to whom you paid in excess of $600. Payments made to a corporation and payments made in exchange for merchandise were generally not required to be reported.

Now, beginning January 1, 2012, every business, both large and small, will be required to issue additional tax documents to any vendor of services or property to which the business has paid more than $600 to in a tax year. As before, the business will need to send the tax form to both the IRS and to the person who received payments. The Form 1099 will need to be issued for basic business expenses such as airlines, hotels, rental cars, and restaurants, according to the Small Business Legislative Council. Also, for a business who sells or distributes goods, all of their suppliers of inventory are also considered vendors under this law. This new 1099 trail would expose payments to small operators that might now be going unreported, and which the federal government expects to cause a dramatic revenue increase to offset the cost of the health bill.

In addition to issuing the Form 1099s to all its vendors, a business will also have to obtain Taxpayer Identification Numbers (TINs) from all qualifying vendors. If the business is unable to do so, the business will be required to withhold a portion of the vendor’s payment and send it instead to the IRS. If a business fails to accurately file their 1099s, significant penalties can apply. Hopefully technical corrections will be made to this legislation to lessen the record keeping and reporting burden placed on small businesses by these requirements.

ROBS transactions: the Department of Labor and IRS Regulation

Brian S. Weinstock

By Brian S. Weinstock



Recently, the Department of Labor advised that they are in the process of developing information to provide direction for Rollovers as Business Start-ups known by the IRS as ROBS transactions.

The IRS issued a memorandum on October 1, 2008 warning about potential pitfalls for ROBS transactions particularly related to prohibited transactions. Moreover, the Department of Labor and the IRS have indicated that a large percentage of ROBS transactions do not comply with federal rules and regulations with regard to tax-deferred retirement plans such as qualified 401k plans and IRAs.

According to Louis Campagna, Chief of the Fiduciary Interpretations Division for the Department of Labor’s Employee Benefits Security Administration, the direction being produced by his department shall address the Department of Labor’s apprehension with regard to ROBS transactions initiated with rollovers from employer sponsored qualified plans and individual retirement accounts, such as 401k plans and IRAs, in order to allow a professional to assess whether the ROBS transaction could be a prohibited transaction.

The Department of Labor is concerned with the employer’s intent when the ROBS transaction is initiated.

Specifically, the Department of Labor needs to determine whether the ROBS transaction was initiated to implement a lawful way for employees to save money for retirement or is the ROBS transaction being used to shelter income for taxpayers who want to start a business or capitalize an existing business. The latter would allow for the taxpayer to withdraw funds from the C-corporation with the 401k plan for reasons unrelated to the business. If so, the taxpayer could withdraw funds, which where designated as tax-deferred, before they are allowed to be withdrawn tax free.

The IRS has their own concerns with ROBS transactions such as the valuation of the transaction and their compliance with other rules for qualified retirement plans which invest in employer stock, therefore the IRS may publish their own memorandum with respect to the issues they have concerning ROBS transactions.

Besides the complex rules and regulations governing prohibited transactions, another major concern for the IRS is the ability to “unwind” ROBS transactions which have violated IRS rules and regulations for qualified retirement plans. If a 401k plan participates in a prohibited transaction, the entire 401k plan loses its tax deferred status. Therefore, the entire 401k becomes taxable. Another major issue is deterioration of the initial ROBS valuation. Many small to medium size business holders remove cash from the entity for reasons unrelated to the business. This type of action can cause a decrease in the initial value of the ROBS transaction and violate prohibited transaction rules and regulations.

Time is of the essence with respect to hiring a professional to review your ROBS transaction in order to determine if there have been any violations of federal rules and regulations, such as prohibited transactions. The IRS has a self-correction program for 401ks which taxpayers can take advantage of before an IRS examination.

The Employment Tax Compliance Program—And What It Means for Businesses

Patrick J. Murphy

By Patrick J. Murphy



What Is the Employment Tax Compliance Program?

The Employment Tax Compliance Program (ETCP) is an Internal Revenue Service (IRS) program which aims to lessen the income tax gap. The ETCP plans to do this by auditing 6,000 companies over the next three years to determine if the classification of certain employees within those companies as independent contractors is proper, as opposed to classifying those same individuals as employees. This classification is important for tax purposes as it is easier for taxes to be taken from employees, who are subject to the withholding system, as opposed to independent contractors. Independent contractors are not subject to this same withholding system, which can sometimes lead to the under-payment of taxes. By auditing these companies, the IRS can look to see if individuals who were claiming to be independent contractors are actually employees, and thus would be subject to more regulated taxing.

Who is the Employment Tax Compliance Program Targeted At?

The ETCP will mostly be targeting at those industries which traditionally have individuals working for them that are more often than not considered to be independent contractors. This will include industries such as construction, ground delivery, car service and trucking, to name a few. Unfortunately, there is no specific test which can differentiate an employee from an independent contractor. Typically an independent contractor will have and use their own tools, will create their own schedules and will have numerous “employers,” as opposed to working for the same individual or company for 40-hours-a-week for an extended period of time. However, many of those same factors can be used in finding that an individual is an employee. Determining the difference between the two groups is a very fact-intensive process, specific to each situation.

What Will the Audits Consist of?

Typically, the audits will be done on-site and face-to-face with an agent. Other information which will be pertinent to the audit will be documents provided by the IRS and information which can be gathered from the internet. As stated above, the audit will focus on the proper classification of individuals as independent contractors or employees.

What Can You do to be Prepared?

To be adequately prepared if the IRS should contact your business, one must be cognizant of those employees who may garner extra attention. These employees will be those who have been previously been classified as independent contractors, but perhaps for consecutive years have received a W-2 from your company. It would be prudent to gather documentation about these employees which bolster their independent contractor status (e.g. contracts, agreements between parties, etc.). Small changes in your relationships with these employees for the future might also help to bolster their status as independent contractor.

Businesses also should keep in mind Section 530 of the Revenue Act of 1978. This section allows for individuals who have long been classified as independent contractors to remain as such, so long as the requirements for “substantive consistency,” “reporting consistency,” and “reasonable basis” are met.

Missouri Historic Tax Credit

Brian S. Weinstock

By Brian S. Weinstock



Currently, the Missouri legislature is debating on whether to restructure the state’s historic tax credit program given the state’s budget crisis. Governor Nixon apparently believes that the state’s historic tax credit programs are large and have been usurping state funds that could go public schools, colleges and universities. Therefore, his administration believes that these programs need to be reformed to free up cash flow for other state programs. Governor Nixon’s administration has proposed creating new statutes for six separate state historic tax credit programs with discretion on the amount awarded, whether to award any amount at all, whether to award any or all of a particular year’s credits allocation and whether to cap certain tax credits at $314 million a year. No rules or regulations have been set in place for the Missouri Department of Economic Development to even make these types of determinations which will only serve to complicate the process even though the current process has been recognized as a national model.

In 1999, The Wall Street Journal published an article entitled “In St. Louis Developers Bank on Tax Credits” wherein the author called the Missouri Historic Tax Credit program “a national model.” The article explains “the Missouri program provides state income tax credits for 25% of eligible rehabilitation costs of approved historic structures. The credit which has no cap applies to both residential and commercial buildings and can be used in conjunction with the 20% federal historic tax credit. In addition, the state tax credit is transferable: Mercantile Bank (now US Bank) has set up the Missouri Tax Credit Clearinghouse to buy and sell credits.” Rehabilitation construction projects such as Cupples Station, the Chase Park Plaza and projects on Washington Avenue and surrounding areas in downtown St. Louis would not have taken place without these tax credits. Without these tax credits, these properties would most likely continue to be an eye sore for the community and definitely not creating new jobs nor increasing state and local government revenue.

The Missouri Growth Association (MGA) and St. Louis University performed a ten year study with regard to Missouri’s historic tax credit programs. In March 2010, they released their conclusions which revealed that the Missouri historic tax credit program contributed to the creation of over 43,000 Missouri jobs with average salaries of $42,732, $669 million in newsales, use and income tax revenues which directly benefited the state and local governments as well as $2.9 billion in private investment in Missouri. According to the Missouri Department for Economic Development, Missouri Historic Tax Credit projects created 4,900 Missouri jobs in 2007, which according to David Listokin of Rutgers University Center for Urban Policy Research, equals 38 jobs per $1 million invested or more jobs than highway or new construction projects. Moreover, the Missouri Department of Economic Development noted that from 1998 – 2008 over $4 billion of investment had been leveraged throughout Missouri as a result of the Missouri Historic tax Credit Program as well as $858 million being invested in 2008. In addition, the Missouri Department of Economic Development has concluded that over 66 communities in Missouri have taken advantage of these historic tax credit programs.

According to the Downtown Community Improvement District (2009), St. Louis City alone has 5,000 new residents as a direct result of Missouri’s Historic Tax Credit programs which caused the city to have its first population increase in fifty years. All of these new residents as well as visitors are paying new local taxes to the state and St. Louis City.

The discussion of removing or capping Missouri’s Historic Tax Program would have zero effect on the 2010 budget since historic tax credits have already been approved for this year. Any change to the Missouri Historic Tax Credits programs would only affect future state budgets. If the state historic tax programs are changed, developers would then analyze the cost to renovate a historic building with the potential revenue. In addition, changes to the programs or uncertainty in the programs will cause more problems for developers in terms of financing a project. At this time, developers are having a hard time financing projects as a result of new internal lending policies and procedures. Many lenders are requiring anywhere from 40% percent equity to 100% collateralization in order to obtain a loan. If the state has a stable historic tax credits program, a developer can leverage those funds to aid in financing a project.

While Missouri is debating whether to institute significant changes to the Missouri Historic Tax Credits programs which was deemed “a national model”, Kansas removed its historic tax credits cap. Further, Iowa increased their historic tax credits cap and Illinois is organizing a historic tax credit program. If Missouri wants to continue to grow jobs, grow revenue for state and local governments as well as increase private investment; particularly, when the country and the state are hopefully coming out of a significant economic recession, the Governor and state legislators need to think long and hard about altering a extremely successful state historic tax credit program which is not only the envy of many other states but has been recognized on a national level.

U.S. Energy Policy, Intangible Drilling Costs (IDCs) and Income Tax Deductions

Brian S. Weinstock

By Brian S. Weinstock



Since 1913, the intangible drilling costs (IDC) tax deduction has allowed oil and gas companies to obtain capital for the huge risk of exploring and developing new locations of oil and gas. This tax deduction is critical when it comes to providing an incentive for oil and natural gas companies to continue to explore and develop new sites for oil and gas. For tax purposes, IDCs get special treatment. Usually, costs that benefit periods in the future must be capitalized and recovered over those periods as opposed to being expensed in the period they are realized.

Under the special rules, an operator or working owner can either expense or capitalize these costs if they pay for or incur IDCs in association with the exploration and development of gas or oil on property located in the U.S. IDCs include all payments made by an operator or working owner for wages, fuel, repairs, hauling, supplies, drilling or development work done by contractors under any contract which is necessary for the drilling of a well including drilling, shooting, cleaning, clearing, roads, surveying, geological work, and in the construction of tanks, pipelines, and any other physical structure necessary for the drilling and preparation of the well which are incidental and necessary to the drilling and preparation of a well for oil and gas.

If elected to expense these items, the owner or working operator deducts the amounts of the IDCs as an expense in the taxable year the cost is paid or incurred. If IDCs are not expensed but capitalized, they can be recovered via depreciation. If the well is dry, the IDCs can be deducted.

The ability to expense IDCs is critical for the exploration and development of new sources of oil and gas. Natural gas and oil is a key component with respect to U.S. demand for sources of energy. Currently the Obama Administration wants to repeal the expensing of IDCs.

This could crush the domestic U.S. oil and gas industry.

There would no longer be any incentive for small to medium sized oil and gas companies in the U.S. to explore and develop new wells. Moreover, the repeal would essentially wipe out millions U.S. jobs associated with this industry at a time when many state governments are bankrupt, unemployment levels are high and revenues for state governments and the federal government are declining.

In addition, some estimates have indicated that a repeal of IDCs could wipe out $3 billion of U.S. business investments in oil and gas development and exploration at a time when the U.S. needs these types of investments. Moreover, a repeal of IDCs would destroy corporate financial value which would directly impact securities such as mutual funds as well as 401(k) plans or other retirement plans.

There is no doubt that America must develop alternative sources of energy including renewable sources but oil and gas remains a key ingredient for the U.S. energy policy including national security. Repealing the tax benefit for IDCs would put a significant dent in America’s security and ability to compete in a global economy during a severe economic downturn which does not appear to be showing any signs of quick recovery.