Prohibited Transaction Rules, Part IV: IRA LLC Examples

In Part I, we talked about prohibited transaction rules in general; in Part II, we talked about prohibited parties specifically; and in Part III, we talked about prohibited entities.  Now that we’ve covered some ground, let’s put it all together and look at some examples of how this would play out in real life, specifically with an IRA LLC.  Reading through the tax code can, and generally does give one a headache, so let’s go through how this might actually work.

In one of my favorite movies The Philadelphia Story, Cary Grant remarks to Katherine Hepburn’s character “…you’re far and away your favorite person.”  It’s safe to say that we relate well to ourselves, and if we use you and your CheckBook IRA LLC in these examples instead of some fictional character, you’ll probably come away with a better understanding of the rules.

Example 1:

Aerate your lawn with an IRA LLCYour father calls one day and remarks in passing that he has invented a pair of shoes to the bottom of which are attached a set of spikes, allowing the user to arriate his lawn while taking a stroll.  He plans to begin production right away, but he needs some start-up capital and would like you to provide it by loaning some of your self directed IRA LLC money to his newly formed Corporation, of which he is the sole shareholder.


Can your CheckBook IRA LLC provide the necessary startup capital to your father’s Corporation?  Or to your father individually?


No, and no.  The first question to ask is whether or not the parties involved in this transaction are disqualified or prohibited parties.  According to IRC 26 § 4975 (e)(6), your father is a prohibited party or disqualified person, because he is your lineal descendant, so you couldn’t loan the money directly to him.  What about a loan from the your Check Book IRA LLC to his company?  If we refer to 26 § 4975 (e)(2)(G) we’re reminded that any entity owned 50% or more by a disqualified person is a prohibited or disqualified entity.  Since your father, a prohibited party, is the sole or 100% owner of the Corporation, that company is a prohibited entity and is therefore off-limits as well.

It’s important to note here that any transaction of any form with your father or his Corporation would be a prohibited transaction.  Even if the proposed deal was not a loan but something else.  For example if the IRA LLC bought some equipment to build the shoes and then rented or leased that equipment to your father’s Corporation, or if you were to actually buy shares in the Corporation with the IRA LLC.  You can see that it doesn’t matter what form the transaction takes, it’s still a transaction.  So, with a prohibited party, the form of the transaction is not important.  The point is that a transaction will take place, whatever form it may take.

Example 2:

Property in an IRA LLCYou’ve purchased a lovely little house in the downtown area with your CheckBook IRA LLC.  You bought the house from the bank in a short sale, and given the purchase price, you’re confident the rental income will pencil out to a profit.  A week later you find that your son has been accepted to a University which sits not three block from the house.  After having recovered from heart palpitations induced by the fact that the tuition fees amount to a small fortune, you come up with the idea that you could rent the lovely little house to your son; partly out of parental affection, but also so that you can recover some of those blasted tuition fees.


Could the CheckBook IRA LLC rent or lease the lovely little house to your son?  Or could your son stay there for free?


No, and again, no.  Your son is a lineal descendant, and is therefore a prohibited party.  So, if the IRA LLC rents or leases the house to him it would be a prohibited transaction.  What about if he stayed there for free?  There wouldn’t be any “deal or transaction” would there?  Actually the code covers that as well.  In IRC 26 § 4975 (c)(D) it states any use by or for the benefit of a disqualified person by the assets of the plan is a prohibited transaction.  So, even though your son wouldn’t be paying any rent, he would be using an asset of the CheckBook IRA LLC.  Result?  Prohibited transaction.

Example 3

IRA LLC LoanWhile reclining in your favorite lawn chair at the annual family picnic, your brother-in-law mentions he’s thinking of getting a home improvement loan.  You know that his house is debt-free because he inherited it from his parents.  When he tells you the amount he intends to borrow, you quickly do the math in your head and conclude that, assuming you could get a first mortgage position or trust deed, the loan amount compared to the value of the property is very low and would therefore be a low-risk investment.


Could the CheckBook IRA LLC loan the money to your brother-in-law with the property as collateral?


Yes.  If we look at the disqualified or prohibited parties list, we find that your brother-in-law does not fit within that category.  He is not a lineal descendant, nor is he the spouse of a lineal descendant; neither is he a “fiduciary” to the IRA LLC.  He is therefore not a prohibited party.  As a result, any deal or transaction between him and the CheckBook IRA LLC would be allowed.  Note that the transaction must be at fair market value; you couldn’t offer an unsecured loan with 0% interest.

Example 4

Skin GunA friend of yours named Bob has invented and is close to securing a patent on a medical device that regrows skin by extracting a burn victim’s stem cells and spraying them back onto the burned area.  Your friend needs an infusion of funds to complete the last leg of the patent process and would like you to provide it by holding an equity position in his company Skin ReGen, Corp.  He is offering a 20% share for let’s say $100,000.  There are several owners of Skin Regen, Corp. and a couple of them are members of your family.  The ownership breakdown of Skin ReGen, Corp. is:

  • Bob  –  80%
  • Your son  –  8%
  • Your mother  –  12%

Neither your son, nor your mother have any management control of Skin Regen, Corp.


Could the CheckBook IRA LLC purchase a 20% equity position in Skin ReGen, Corp.?


Yes…but.  Let’s deal with the yes first.  Since this transaction would be between the CheckBook IRA LLC and Skin ReGen, Corp., we must first see if Skin ReGen is a prohibited entity.  Here’s the sequence: 1.  Your son and mother are both prohibited parties to the IRA LLC.  2.  Your son’s and mother’s combined ownership in Skin ReGen is 20%.  3.  Any entity owned 50% or more by any one or more prohibited parties is a prohibited entity.  Your son’s and mother’s combined interest is less than 50%…  4.  Therefore, Skin ReGen (at least in terms of ownership) is not a prohibited entity.

But we have more to consider before you go ahead with this investment (this is the “but” part :))

We have to look at two more things: control and indirect benefit.  In this example we know that neither your son nor your mother have any control over Skin ReGen.  They aren’t Officers of the Corp., they’re not on the Board.  They hold no fiduciary position whatsoever with the company; they’re just shareholders.  That solves the control issue.  Neither of them has sufficient control of the company to taint a possible transaction between Skin ReGen and the CheckBook IRA LLC.

Remember back in Part I, we pointed out language in the code that said a prohibited party could not benefit directly or indirectly from an investment of the IRA LLC.  So, will your son or mother benefit directly or indirectly from this transaction?  Using the information given in the example, they would not benefit directly or indirectly.  But, here is an example of what could constitue a benefit thereby triggering a prohibited transaction:

  • What if your son had been wanting to sell his shares in the company, but Skin ReGen had placed a restriction on his ability to sell the shares until more capital was brought into the company?  There’s a good chance that by purchasing 20% of Skin ReGen, the CheckBook IRA LLC would be guilty of a prohibited transaction because it would enable your son to then sell his shares back to Skin ReGen.  This is commonly referred to as an “enabling investment.”  Look at it this way: if the IRA LLC had not bought shares in Skin ReGen, your son would not have been able to sell his shares.  The investment by the IRA LLC makes possible something that was not (your son’s ability to sell his shares), and it makes it possible for a prohibited party (your son).  Result?  Prohibited transaction.

There are endless examples one could go through, and we’ll be posting more in the future.  For now, try to focus on the underlying concept and principles.  Understanding the prohibited transaction rules is of paramount importance because there are consequences for failing to abide by them.  If you don’t understand these rules yet, you’re not ready for a CheckBook IRA LLC.  Don’t hesitate to call us if you have questions about the rules, or a particular deal you’re thinking of doing.  In the meantime…

Invest intelligently.  Enjoy the rewards.

Prohibited Transaction Rules, Part I: An IRA LLC Primer

Prohibited Transaction Rules, Part II: Who is a Prohibited Person?

Prohibited Transaction Rules, Part III: Disqualified Entities


(Visited 1,474 times, 2 visits today)

About Jordan Sheppherd

I am co-owner of one of the oldest companies in the nation to offer the CheckBook IRA LLC structure. The structure gives our clients immediate, total, and local control of their IRA funds, allowing them to escape costly transaction and assets fees, and to invest in areas they never imagined were possible using IRA money.
This entry was posted in IRA LLC, Prohibited Transactions and tagged , , . Bookmark the permalink.

15 Responses to Prohibited Transaction Rules, Part IV: IRA LLC Examples

  1. Steve M. says:

    I have a situation where I want to loan money to my sister’s company. It would be a good normal deal, so nobody would be playing favorites. Could I do something like that? I know you talk about loaning money to your brother-in-law, but would my sister be ok?

    • Steve,

      Your sister is not a prohibited party, so loaning money to her would be fine. If you want to loan money to her company, you’ll need to make sure that her company is a non-prohibited entity. If your sister owns the company outright, then a loan from your IRA LLC to her company is perfectly fine. On the other hand, if her company has multiple owners, you’ll need to make sure the other owners are not prohibited parties. If they are, you’ll need to look at the amount of ownership those prohibited parties have to ensure they total less than 50%. If there are multiple owners, and if they are prohibited parties, you are looking at a tricky transaction. I’ll be more than happy to review the transaction with you to ensure you aren’t running afoul of the rules.

      Feel free to contact me directly at or (541) 749-0780.

  2. Dan says:

    I have 2 questions.

    1: I purchased a vacation rental with my checkbook Ira LLC. I hired a management company to find renters in the summer time for revenue. If I wanted to let a friend or non-disqualified person use it, do I have to charge them for staying there?

    2: if I purchased new furniture for the place using Ira funds can I actually be inside the unit when it gets delivered and help to stage it or would this be considered a prohibited contribution?

    Thank you

    • Hi Dan,

      Thanks for the questions; they’re good ones.

      1. Its probably not a good idea to let your friends stay at the house for free. The purpose of the IRA is to make money for your retirement, and as the Manager of the LLC, you have a fiduciary responsibility to act in the best interest of the company. Someone walking in off the street who wanted to stay in the house would be required to pay the normal rent, and to give it to anyone for free would run against normal business practices; the fact that they are personal friends of yours would muddy the waters even more.

      2. You could certainly be present in the unit when the furniture is delivered, and stage the furniture if need be. As Manager of the LLC, you have certain responsibilities and powers to direct the investments of the company. Being present to stage furniture is certainly within those powers. To provide a counter example: if the property needed to be painted, re-roofed, and re-carpeted, it would be inappropriate for you as the Manager to go do those things, because those repairs require an involvement beyond your role as Manager. In that case, you would need to hire a third-party contractor to do that work.

      Let us know if you have any other questions.

  3. Kathy says:

    I am the new owner of my checkbook IRA.
    1. So far I’ve been using it to pay mortgage payments on an investment lot in a country in Central America. I have another lot there that I am making mortgage payments on with my own money. Can I sell my investment lot, recoup the money and put it on the lot I am planning on keeping for myself? Or am I able to sell the investment lot and change my checkbook IRA back into a standard IRA so that I can buy and live with the money I want to spend. Is this a complex thing to do?
    2. I’ve found another lot in a close by country that I would like to own and live on. I am guessing that I cannot use my checkbook IRA to put a down payment on it, correct or not?
    3. I will have to pay taxes for the first time this year because I didn’t withhold enough $ from my salary. I suspect I can’t use my checkbook IRA to pay that, correct or not?
    Thank you for your help.

    • Hi Kathy,

      You would not be able to use the funds within the iRA or the LLC to pay for anything you own personally. There can be no crossover between your personal finances and investments, and what the LLC is doing; you have to keep that separate. To use those retirement account funds for personal use, you’d first have to take a distribution and pay taxes on the amount coming out of the IRA.

      I’m a little unclear on your question about the lots. Are you a client of ours? If not, you should contact the company that set you up, as they can probably answer your question about the lots more fully that I can.

  4. Geof says:

    I’m self employed with employees that contribute to a simple IRA. Can I transfer my simple ira into a checkbook ira? Do all of my employees have to follow suit and are they required to get a checkbook ira like I do as employer?

    • Hi Geof,

      It is generally best to avoid setting up a Check Book IRA with a SIMPLE IRA. SIMPLE IRAs are subject to ERISA, and some subtle differences result in regards to what rules apply to the account.

      The best option is to transfer funds from your SIMPLE to a Traditional IRA, but you should be aware that in order to be able to do that, the SIMPLE has to have been open for 5 years or more.

      You’d need to have a CPA look at the plan document for the SIMPLE IRA to find out how any changes would affect your employees. I’d be happy to go over your situation to see what your options are. You can call our office at (541) 749-0780.

  5. Kathy says:

    I am a licensed real estate agent (not the Broker). Can my broker or another agent in my office list a property owned in my IRA LLC? I “assume” I cannot represent myself, which is why I would use another agent in my office.

    Thank you for sharing all your knowledge through this site!

    • Hi Kathy,

      That’s a good question. On first glance, it doesn’t appear that it would be a problem for a broker or another agent in your office to list a property owned by the IRA LLC.

      You’d have to make sure that the broker or agent are not partners with you in any other ventures, as that would most likely make them a prohibited party. The other argument against it, is that you might get undue benefit by having someone in the office list the property, as opposed to going outside the firm. That’s a bit of a weak argument in my opinion, but its just that – my opinion.

  6. Kent Hoggan says:

    I am 66 years old. I have a self directed IRA that I opened on Jan 2010 so my 5 years is on Jan 1st 2015. I think I have created myself a prohibited transaction by working for a company my IRA LLC loaned money to. If so will I have to start a new IRA and start my 5 year waiting period all over again.



    • Hi Kent,

      Its possible that the transaction you describe was prohibited, but its possible it was not prohibited. Merely working for a company your IRA LLC has loaned money to, does not in and of itself create a prohibited transaction. There are a number of things that would need to be taken into consideration before it could be said the IRA LLC did something impermissible.

      Feel free to call our office at (800) 482-2760, and we’ll be happy to at least give you some guidance on the subject.

  7. Bill Schroeder says:

    I am considering a checkbook ira to invest in houses to flip. I will not have any other involvement other than investing and paying the bills for renovation, etc. My wife will be arranging for contractors, workers, buying materials, etc., but for no compensation.

    Your web stated that the founder flipped 50+ homes inside his checkbook ira. Is my plan within the IRS guidelines? If not, what changes would I have to make.


    • Hi Bill,

      Your wife can be a co-Manager of the LLC if you’d like, and I would suggest it, if she is going to be involved in managing the affairs of the LLC.

      Certainly flipping houses is fine within an IRA structure. There is some question as to how many per year you can flip before the IRS would consider your activity a “business activity”, which would make the profits of the flips taxable under the UBIT section of the code. From everything I’ve seen, you would need to be flipping a large number of houses per year to trigger that tax, but its a good idea to talk with someone about it, to get an idea of how many you plan to do.

      Give us a call if you’d like, and I’ll be happy to look at your situation.

Leave a Reply

Your email address will not be published. Required fields are marked *