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The Tragic Case of the Self-Directed IRA That Never Was

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  |  By Bryan Ellis

Just last week, John (not his real name) lost nearly 60% of the value of his self-directed IRA in a single day.  There wasn’t a horrible crash in the stock market or an act of fraud that caused this calamity.  Instead, John’s misfortune was the result of an esoteric mistake that rendered John’s IRA invalid months before it was even created.

Here’s how it happened:

On a bright, beautiful day in 2009, John finally rolled over his old 401k plan into a new self-directed IRA.  He’d watched in the past two years as the stocks in his 401k had been slashed in half by a rapidly falling market, leaving John with only $150,000 of the $300,000 he started with.

John was an accomplished real estate investor, and he decided to use his new self-directed IRA to buy cash flowing properties.  John quickly encountered success, acquiring one property which he sold a year later for a very large profit, which enabled him to buy 3 more properties.

John’s success as an investor continued onward for many years.  He was very careful and very precise, always seeking legal and tax expertise whenever he needed it.  That’s why, when he was selected for a random audit by the IRS, John wasn’t worried about the outcome.

Unfortunately for John, the IRS found a single 9-word clause in a service agreement that John had signed on behalf of his IRA.  This clause, the IRS claimed, involved “cross-collateralization” of John’s IRA, which is strictly prohibited.

The Instant Effects of John’s Prohibited Transaction

What happened as a result of John’s error?  When John signed the fateful service agreement in late 2009, three things happened immediately:

Instant Effect #1:  SILENCE.  That’s right… silence.  John heard nothing.  John saw nothing.  There were no red flags waving or IRS agents knocking down John’s door.  He experienced a whole lot of nothing.

Why?  It’s because neither the IRS nor John knew that he’d committed a prohibited transaction at that time.  The IRS doesn’t monitor these things in real time, and John certainly didn’t know that he’d stepped over the line.  In fact, he thought he’d taken great care to avoid such a fate.

Had John not been randomly selected for audit, it’s possible that nobody would ever have known of the transgression, and presumably at some point, a statute of limitations would apply in John’s favor.  Unfortunately for John, he wasn’t so lucky.

Instant Effect #2:  RETROACTIVE DOWNGRADE.  The very moment that John’s IRA committed the prohibited transaction, his IRA was permanently downgraded, effective as of January 1 of the same year.  In John’s case, his prohibited transaction happened in October of 2009, so his IRA was permanently downgraded as of January 1, 2009.
What does this downgrade mean?  The best way to answer that is to think of all of the benefits that an IRA offers, and to realize those benefits are gone, retroactively.  For example:

  • John lost the right to make tax-deductible deposits
  • John lost the right to defer taxes on the profits of his transactions
  • John’s account was no longer protected from creditors, bankruptcy and other legal problems

These things are huge problems by themselves, but the biggest problem for John – and for anyone who commits a prohibited transaction – is that you don’t know it’s happened, so you continue to use your IRA as if it was never downgraded.  You make deposits, you buy assets, you sell assets and you generally proceed as if everything was totally right with you IRA…

…But it’s not.  You no longer have an IRA, and you don’t even know it. You have no idea whatsoever that you’re taking deductions and other tax benefits to which you’re no longer entitled, which gives rise to…

Instant Effect #3:  RETROACTIVE TAXES & PENALTIES.  Unbeknownst to John, he began accumulating taxes, penalties and interest at a blistering rate.  This is where the real pain of a prohibited transaction is felt.

John didn’t know that his IRA was downgraded, effective the first year that he opened.  As a result:

  • He continued to make deposits into his IRA each year, and took income tax deductions for those deposits to which he was no longer entitled
  • He continued to buy and sell assets through his account without paying taxes on the profits, falsely believing he was shielded from tax consequences through his IRA
  • With each new deduction John took for his deposits, and with each new profitable investment he made, John’s tax liability to the IRS grew

By the time the IRS caught up to John’s error in 2016, he’d been taking deductions and making successful investments for many years, during which time John’s tax liability grew and grew.

But the painful part of a growing tax liability isn’t the taxes, it’s the penalties and interest.  That is why the tax liability for prohibited transactions routinely cost taxpayers 50% or more of their IRA balance.  In John’s case, he lost 60% of his retirement savings because of this error.

How to Avoid John’s Fate with Your Self-Directed IRA

John was actually quite careful with his self-directed IRA, and the error that the IRS found in his account was rather esoteric and strange.  He did consult with – and receive the blessing of – his attorney before each transaction.

But that wasn’t enough.  John should have done these things to protect himself:

  • Only use attorneys with specific experience in self-directed IRA’s.  John’s attorney was his family attorney who “did some research” for John, but had no actual experience with self-directed IRAs.  This is an area of law with substantial nuance, and should only be trusted to the most knowledgeable counsel.
  • Have your attorney review every document you sign, not just the “big” ones.  Obviously, your attorney should review your purchase and sale agreements, LLCs, etc.  But you should have them also review documents required for your bank accounts, insurance policies and anything else involving your self-directed IRA.  In John’s case, the problematic clause was in the documents he signed when opening a bank account, and not in any document related to his investments.
  • If you qualify to do so, consider using a Solo 401(k) for risky assets.  The rules for prohibited transactions in 401(k)’s are far more forgiving than the equivalent rules for IRA’s.

John’s outcome was tragic.  Fortunately for other self-directed investors like you and me, his fate is avoidable by understanding the profound severity of prohibited transactions, and working proactively to avoid them.

Mr. Bryan Ellis is a guest contributor and is not affiliated to PENSCO Trust Company or its affiliates.  Opinions expressed by Guest Contributors are their own and is not endorsed nor does it represent PENSCO Trust Company or its affiliates.

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Copyright © 2016 Bryan Ellis.  All rights reserved.  You may publish this article in full without modification, including all links and meta content.  If adjustments are necessary to accommodate your specific needs, contact Bryan Ellis at for authorization prior to publication.

This Blog does not provide investment, tax, or legal advice nor does it evaluate, recommend or endorse any advisory firm or investment vehicle. Investments are not FDIC insured and are subject to risk, including the loss of principal.

PENSCO Trust Company performs the duties of an independent custodian of assets for self-directed individual and business retirement accounts and does not provide investment advice, sell investments or offer any tax or legal advice. Clients or potential clients are advised to perform their own due diligence in choosing any investment opportunity as well as selecting any professional to assist them with an investment opportunity. Alternative investments are not FDIC insured and are subject to risk, including loss of principal. Other than the Opus Affiliates, PENSCO is not affiliated with any financial professional, investment, investment sponsor, or investment, tax or legal advisor.