
James F. McDonough
Of Counsel
732-568-8360 jmcdonough@sh-law.comFirm Insights
Author: James F. McDonough
Date: May 18, 2016

Of Counsel
732-568-8360 jmcdonough@sh-law.comRecently, myself and another attorney in the firm met with accountants from a well-established practice with several offices. When I inquired about the biggest problems they encountered in tax season, they replied that it was the use of self-directed IRAs to finance business acquisitions. They described the problem as an epidemic caused by the sluggishness of the economy in the parts of New Jersey served by their offices.
Self-directed IRAs are not new nor are they prohibited. The facts in Thiessen v Commissioner, a Tax Court case, are typical of the circumstances described to us in that recent meeting.
In Thiessen v Commissioner, taxpayers did not want to accept a transfer to a Kroger location in another state. Taxpayers rolled over their respective Kroger 401K account balances to self-directed IRAs. Taxpayers looked for a business to acquire and encountered a broker who located one suited to their skills. A friend recommended a CPA who advised an acquisition structure whereby the 401K account balances would be rolled over to self-directed IRAs (“IRAs”). These transfers in 2003 were reported as tax-free rollovers. The CPA formed a C corporation for the taxpayers. Then, the taxpayers directed the IRAs to purchase all of the stock of a C corporation and then cause the C corporation to acquire the business.
The taxpayers had an attorney to represent them regarding the purchase but he did not participate in establishing the structure, nor did he have ties to the CPA or the broker. The CPA was not involved in drafting the contract of sale nor in the negotiation of the financing terms.
The taxpayers transferred $432,000 to their IRAs and then directed the IRAs to purchase of all shares of stock of the new corporation. The contract of sale called for a purchase price of about $600,000 consisting of $60,000 of a deposit, a $200,000 Note (the “Note”) and the $340,000 balance in cash from the IRAs (presumably from the C corporation). The deposit came from the personal bank account of the taxpayers and the government did not raise the source of these funds as a tax issue. The Note required and contained the personal guarantee of the taxpayers.
In 2010, seven years after the acquisition, the taxpayers received a tax deficiency notice for $180,000 based upon the disqualification of the IRAs in 2003. Disqualification was based upon the fact that the guarantee of the Note by the taxpayers was a prohibited transaction. A prohibited transaction includes the indirect lending of money or extension of credit between a plan and a disqualified person. The later term includes a fiduciary who is one who exercises discretionary authority or control over plan assets. The court held that the guaranties constituted indirect extensions of credit between the taxpayers and the IRAs. The distinction here is that the taxpayer guaranties added to the value of the assets held in the IRAs and circumvented contribution limitations.
The irony here is that the CPA was also involved in a 2013 case, Peek v. Commissioner, that taxpayers also lost. One should also know that the government had other arguments that the Court did not rule upon. A reader should not read Thiessen as giving the government only one line of attack.
No Aspect of the advertisement has been approved by the Supreme Court. Results may vary depending on your particular facts and legal circumstances.

Every New Jersey company should periodically evaluate its governance framework. Strong corporate governance protects directors and officers, builds investor confidence, reduces litigation exposure, and positions a company for sustainable growth. The first quarter of the year is a great time to evaluate your corporate governance practices and perform any routine maintenance needed to keep that […]
Author: Ken Hollenbeck

Being served with a lawsuit is one of the most stressful legal events a business or individual can face. Whether the claim involves a contract dispute, an employment matter, an intellectual property issue, or another legal challenge, the actions you take in the first few days can significantly shape the outcome of your case. Acting […]
Author: Robert E. Levy

Special Purpose Acquisition Companies (SPACs) continue to gain momentum as we move through 2026. After enduring a significant contraction following the 2021 boom and the regulatory scrutiny that followed, SPAC activity rebounded sharply in 2025 and now carries forward into 2026 with real momentum. The SPAC resurgence reflects broader improvements in both market conditions and the […]
Author: Dan Brecher

Compliance programs are no longer judged by how they look on paper, but by how they function in the real world. Compliance monitoring is the ongoing process of reviewing, testing, and evaluating whether policies, procedures, and controls are being followed—and whether they are actually working. What Is Compliance Monitoring? In today’s heightened regulatory environment, compliance […]
Author: Dan Brecher

New Jersey personal guaranty liability is a critical issue for business owners who regularly sign contracts on behalf of their companies. A recent New Jersey Supreme Court decision provides valuable guidance on when a business owner can be held personally responsible for a company’s debt. Under the Court’s decision in Extech Building Materials, Inc. v. […]
Author: Charles H. Friedrich

Commercial real estate trends in 2026 are being shaped by shifting economic conditions, technological innovation, and evolving tenant demands. As the market adjusts to changing interest rates, capital flows, and workplace models, investors, owners, tenants, and developers must understand how these trends are influencing opportunities and risk in the year ahead. Overall Outlook for Commercial […]
Author: Michael J. Willner
No Aspect of the advertisement has been approved by the Supreme Court. Results may vary depending on your particular facts and legal circumstances.
Consider subscribing to our Firm Insights mailing list by clicking the button below so you can keep up to date with the firm`s latest articles covering various legal topics.
Stay informed and inspired with the latest updates, insights, and events from Scarinci Hollenbeck. Our resource library provides valuable content across a range of categories to keep you connected and ahead of the curve.
Let`s get in touch!
Sign up to get the latest from the Scarinci Hollenbeck, LLC attorneys!