Category Archives: Self-Directed Roth IRA

Roth IRA Conversions and Re-Characterizations

Question: Dear Mr. Long, I enjoyed you video on the Lifestyles Unlimited website about IRAs.  I am new to Lifestyles here in Dallas and have a question for you if you have time. (I’m 61.)

In your video, “The top 10 things you need to know about Self-Directed IRAs”, you mentioned that a 401k can be rolled over into a Roth IRA and you pay taxes on that rollover.   The Roth IRA can then be used to make a profit from Real Estate (no debt financing).

If I understood you correctly, you then have till Oct 15th to change you mind and put the Roth IRA money back into your 401K and presumably not pay have to pay the taxes incurred from the initial rollover.   (same calendar year)

My question: Can the profit that was incurred within the Roth IRA remain in the Roth IRA while the initial rollover amount is returned to the original 401k?
If this happened, I am assuming the tax liability would be zero or minimal?

Question 2:  My company now offers a Roth 401k.  Can a Roth401k be used like a Roth IRA or must the Roth 401k be converted to the Roth IRA?

Question 3: Do you have an office in the DFW area?

Thank you for your time.

Answer: Yes, it’s true that you have until October 15 of the following year to recharacterize, or “unconvert” to use a more colloquial but not technically correct name.  If you do, then there are no tax implications for the initial conversion.

 Unfortunately, the answer to your first question is no, you cannot leave the profit in the Roth IRA.  Boy, that would be a neat trick, but it just isn’t so!  Also, when you recharacterized it would go back into a traditional IRA, not back into the 401(k).

 On your second question, assuming you mean to ask whether or not you can self-direct your Roth 401(k), the answer is no, unless it is an individual 401(k) plan like what is offered at Entrust.  The company controls what you can do as long as it is there.  When you separate from service you can always roll the Roth 401(k) into a Roth IRA and self-direct it, but you generally cannot access the funds until you leave employment or have another distributable event.  Depending on your situation, it may be an excellent idea to participate in your company’s Roth 401(k) just to build up Roth funds for when you do finally retire.

 Yes, we do have a DFW office just north of downtown Dallas.  Mr. Ryan Kimura runs that office, and I have copied him on this email.

 I’m sure you and Mr. Kimura can get together soon.  We have a “Fright Night” event coming up in Dallas which might be fun to attend.  Have a great day!

How do I Calculate Required Minimum Distributions (RMD)s and What is the Penalty for not taking the RMD?

Question:  I have been delinquent in requesting the RMD’s for the years since my father’s death on December 19, 2006.  At that time I was 49 years of age.

 Now it is at the 5 year mark and I don’t wish to incur a 50% penalty.  Attached is the signed document authorizing withdrawal as RMD for these years MINUS 2009, as the RMD was not required in that year.  It is absolutely my intent to use this email to provide additional instruction and provide authorization for this purpose.

 I’ve copied my attorney on this email, as he is also doing my taxes this year and needs to know immediately the withdrawal amount and information for tax purposes.  Please feel free to reply to both of us with all correspondence on this request.

 Please note that I’ve not completed the withdrawal amount; I request that you/Quest calculate this based on my age at the time of my father’s death and withdraw the appropriate amount.  I acknowledge that time is very short, as 2010 taxes are due this coming Friday.  I’m traveling on business this week, but can be available by phone and email to resolve this, this week. 

Answer:  I would be happy to help as far as I can, but there are limits on what I can do at this point.  The way the rules work for Required Minimum Distributions (RMDs) from IRAs inherited from non-spouses is that you must take distributions either based on your life expectancy beginning in the year following your father’s death or you can wait as long as 5 years and then take the entire amount out.  As you know, if you fail to take the RMD there is a 50% penalty on the amount you should have taken.  To calculate the amount to be taken requires you to take the balance in the account at the end of the prior year and divide it by a factor which is initially retrieved from IRS Publication 590, Appendix C, Table I, and in subsequent years is reduced by one.  In your case, since you turned age 50 in 2007, your initial factor would be 34.2 (see page 88 of IRS Publication 590 for 2010 tax returns).  So your factors for the years 2007 through 2011 would be as follows:

 2007 – 34.2

2008 – 33.2

2009 – 32.2

2010 – 31.2

2011 – 30.2

 An example of how you make the calculation is as follows, assuming that the balance in your IRA was $100,000 at the end of the prior year each year:  $100,000 /34.2 = $2,923.98 for 2007, $100,000/33.2 = $3,012.05 for 2008, etc.

 You are correct when you state that no RMDs were required for 2009, but the factor still was reduced by one in that year, as it is in all years.  Unfortunately, I do not have all the information needed to calculate your RMDs.  For 2007, you would need to provide us with a statement dated 12/31/2006 from your prior custodian, since you didn’t open the account until March, 2007.  In subsequent years, you will need to provide me with a Fair Market Value form as of 12/31 each year signed by you and a qualified third party appraiser so that I can adjust the value of your account each year before making any calculations.  In reviewing your file I see no updates to the value since the initial investment of $100,000.  I have attached the needed form and the instructions.

 When you do arrive at a figure you will need to submit a revised and legible Distribution form.  I cannot complete the amount for you, and the form must be legible because we have to transmit it to our central processing facility.  Unfortunately, the one you submitted was not legible.  I’m not sure why, perhaps the ink was not a color that scanned well or something.

 I hope that helps get you started.  Fortunately, this year the tax filing deadline is April 17, not April 15.  Good luck, and let me know if you have any further questions.

Can an IRA be used to start a husband’s new business?

Question: A husband & wife borh have Roth IRA’s & husband has a 401k. He plans to leave his corporate job & start his own business. If Roth & 401k funds are transferred to Quest self directed IRA’s, can husband & wife use IRA funds to loan start up money to husbands new business, as long as they pay interest on loan to IRA’s? Is this an acceptable or prohibited transaction & how should the loan be structured? If prohibited, is their a way to structure the loan so as to be an acceptable transaction?Is there an Quest form for this type of loans?

Answer: Thank you for your inquiry.  The short answer to your question is no, neither the Roth IRAs nor your 401(k) which is rolled into an IRA can loan start up money for your new business venture.  There is a list of persons with whom the IRA is not permitted to do business, called disqualified persons.  A business owned entirely by you would be a disqualified person, and therefore the proposed loan would be a violation of Internal Revenue Code Section 4975(c)(1)(B), which says that the direct or indirect “lending of money or other extension of credit between a plan and a disqualified person” is a prohibited transaction.   

I have heard of people using their 401(k) plans to start a new business by using what the IRS terms a ROBS arrangement (Rollovers for Business Startups), but the IRS clearly does not like these arrangements and believes that the way many of them operate result in a prohibited transaction.  I have attached some information in this regard.  If you do want to go down this path, be sure that whoever you choose is very familiar with the IRS position and that you feel they have adequately dealt with the issues.  Certainly there are many companies out there offering the ROBS set up.  It is fairly expensive to do, though, since it involves setting up a C corporation, having the C corporation adopt a 401(k) plan, rolling the IRA or former 401(k) into the 401(k) for the new company, and purchasing shares of the company as employer securities.  You cannot roll your Roth IRAs into the 401(k) plan, only traditional IRAs. 

Finally, you should be aware that Quest cannot give you tax, legal or investment advice, and so we could never advise you on how to structure a particular investment or provide you with the forms to do so.  Good luck with your new business venture.  Have a great day!

Tax Treatment of Flipping Promissory Notes in an IRA

Question: The debate continues:)  I actually have an account with another SDIRA company in FL. I use their company website as a resource but, it does not seem to give much information regarding the the tax treatment of Flipping notes in an IRA:  I am networking with a lot of younger investors and there seems to be a lot of questions and little information.  When we ask our tax professionals they “look at us like-you can’t do that.”  Most tax and legal professionals do not seem to understand much, if anything about Self Directed Investing.  So here is a follow up to the conversation if you can help us clear this up.  Just to put this into context, the original question was, “what would you do with $50k in a Self Directed IRA.”  I would say the average reader is in their late 30’s. 

Investor: I find it very hard to believe that flipping notes could be considered appreciably different than transacting stocks quickly.

Tax Professional: I don’t think we are saying that they are “appreciably” different, just that the two investment options (stocks on public market vs. private market notes) are different in other means. I have no idea which is the correct and legal answer, but in my opinion, I see how one can argue that notes sold/transfered from flipping which deal with a buyer and a seller who negotiate between themselves and have contact between them in a private manner is functionally different than flipping stocks in a public market where the buyer and seller never negotiate and never have contact. To add to the confusion, what if you bought and immediately sold an actual business inside your 401k/IRA. Would UBIT apply?

Investor: Flipping stocks doesn’t just magically occur either. A buyer and a seller still have to agree on a price for a transaction to occur. There may be fewer things to negotiate in these transactions, but I don’t see how they are really different from a “business standpoint.” What about trading something on the pink sheets? Is that somehow different still?

Tax Professional: I almost always agree with you, but will have to agree to disagree on this. Regardless of who is right, as no final evidence has been discovered clearly (and may never be clear), we just have two different thoughts on this. I see a difference in stocks vs. flipping notes as explained, you do not as explained. No problem.  Not only that, when they discuss the fact that the IRA can use debt leverage on a rehab, it makes no mention of UDFI which also triggers UBIT (unless debt is paid off 365 days before sale). As I have mentioned in the past, unfortunately, find details are often missing from TPA’s such as the one you are dealing with.

It seems like there is a lot of mis information and confusion out there regarding the subject.  I certainly appreciate your thoughts, time and any information you can cite to help us clear this up.  Please note that am not asking for advice-just information on where we can find facts in regards to this subject. 

Quincy’s Answer: I think you’re trying to over analyze this and impose rationality and reason on the US government, which is of course quite impossible.  Step back and ask yourself one question while forgetting entirely about the IRA aspect of it – would note flipping be considered a trade or business if you did it personally?  If the answer is yes, then it is, by definition, a trade or business within the IRA as well, and it will generate UBIT, assuming it is “regularly carried on.”  If the answer is no, then it should not generate UBIT.  Whether something else like day trading stocks is or isn’t a trade or business is irrelevant.  You are focusing on the IRA aspect of it when you should be focusing on whether or not it is a trade or business.  In general terms, anything that you buy as “inventory” for resale to the public is going to be considered a trade or business, whether it is real estate, notes, widgets or anything else.  Unfortunately, the standard of when you cross the line from being an investor to being in a trade or business is fuzzy at best and depends on many factors.  Oh well, that’s the world we live in.

 I have attached my short paper on UBIT.  You may also find more information on UBIT in IRS Publication 598.  The Internal Revenue Code sections dealing with UBIT are 26 USC 511-514.  I hope that helps some.  Good luck!

Response: Thank you for taking the time to help me out with this.  It seems to me that it is best to error on the side of caution with this since the penalties can be so steep.  I see a lot of guys buying and flipping homes in IRA’s.  These guys are considered “Dealers” because they also buy and flip properties outside of IRA’s.  I would say since these are bought with the intention of immediately offering them for sale to the public that they would then be subject to UBIT.  The same would hold tru for a note that is immediately flipped.  When you say “regulatory carried on,” do you mean this is something you do inside the IRA X amount of times per year, X amount of times during the life if the IRA? 

Quincy’s Answer to Reponse: Review Page 3 of IRS Publication 598, which states:  “Business activities of an exempt organization ordinarily are considered regularly carried on if they show a frequency and continuity, and are pursued in a manner similar to comparable commercial activities of nonexempt organizations.”  An example is given in the publication.  I agree that intent is very important.  I’m not sure that an occasional flip in an IRA among many other investments will cause UBIT, but certainly if that’s all that the IRA invests in and the IRA owner also flips properties outside of his or her IRA that would weigh heavily in the consideration of whether the IRA had dealer income.  While IRAs are very rarely audited, it is always important to give the IRS what they are due, because they have what it takes to take what you have. 

One thing I would caution you about is not to confuse the payment of UBIT with the penalties associated with prohibited transactions.  It is perfectly legal to make investments which subject your IRA to taxation, but if you do a prohibited transaction it blows up your entire IRA and you and others may owe excise taxes and penalties as well.  The two subjects are completely separate, but many people, even educated ones, get them mixed together in their minds.