Saturday, December 30, 2017

The Backdoor Roth

It has come up often enough that I decided to talk about it.

The backdoor Roth.

What sets up this tax tidbit?

Being able to contribute to a Roth in the first place. More accurately, NOT being able to contribute.

Let’s say that you are single and work somewhere without a retirement plan. No 401(k), SIMPLE, SEP, nothing. You make $135,000.

Can you fund an Roth IRA?



Because you do not have a plan at work.

How much can you fund?

$5,500. That becomes $6,500 if you are age 50 or over.

Let’s say you have a plan at work.

How much can you fund?



Because you have a plan at work and you make too much money.

What is too much?

For a single person, $133,000. I question what fantasyland these tax writers live in where $133 grand is too-much-money, but let’s move on.

A Roth is a flavor of IRA. It is like going to Baskin Robbins and deciding whether you want your chocolate ice cream in a sugar cone or waffle cone. Either way you are getting chocolate ice cream.

Let’s say that someone wants to fund a Roth. Say that someone is a well-maintained, moderately successful, middle-aged tax CPA with diminishing dreams of ever playing in the NFL. He is married. His wife works. His back hurts during busy season. His daughter never calls ….

Uhh, back to our discussion.

He has a no plan at work. His wife does.

So we know the income limits will apply, as (at least) one of them is covered by a plan.

For 2017 that limit is $196,000.

Let’s say our tax CPA makes $18,000. His wife makes $180,000.

I see $198,000 combined. He is over the income limit.

Our CPA cannot contribute into a Roth, because a Roth is a flavor of IRA and he has exceeded the income limits for an IRA.

I suppose our CPA can ask his wife to dial it back a notch. Or get divorced.

Or consider a back door.

There are two things to understanding the backdoor:

(1)         We have discussed two types of IRAs: the traditional (that is, deductible) and the Roth. There is a third, although he has moved out of the house and rarely attends family events (at least willingly) anymore.

The third is the nondeductible. He is the wafer cone.

You get no deduction for putting money in. You will pay something when you take money out.

When you pull money out, you calculate a ratio:

 * Nondeductible money you put in/total value of account *

That ratio is not taxable; the balance is.

There is even a tax form for this - Form 8606. You are supposed to use this form every year you make a nondeductible contribution. I understand that there is a penalty for not doing so, but I have never seen that penalty in practice.

And no one would do this if a Roth is available. When you pull money out of a Roth, all of the distribution is nontaxable (if you followed the rules). That result will always beat a nondeductible.

The Roth effectively killed the nondeductible, which perhaps explains why the nondeductible is the unfriendly and distant family member.

But the nondeductible has one trick to its game: there is no income test to a nondeductible. Our tax CPA cannot fund a Roth (went over the limit by a lousy $2 grand), but he can fund that nondeductible. There is no deduction, but there will be no penalty for overfunding an IRA, either.   

(2)         But how to get this nondeductible into a Roth?

Call the broker and have him/her move the money from an account titled “Nondeductible IRA FBO Cincinnati Tax Guy” to one titled “Roth IRA FBO Cincinnati Tax Guy.”

This event is called a “conversion.”

You have to pay tax on a conversion.


Because you are moving money that has never been taxed to an account that will never be taxed. The government wants its vig, and the conversion is as good a time to tax as any.

How much tax?

Here is the beauty: since our tax CPA did not deduct the thing, tax law considers him to have dollar-for-dollar “basis” in the thing. If he put in $5,500, then his basis is $5,500.

Say he converts it when it is worth $5,501.

Then his income is $5,501 – 5,500 = $1.

Yep, he has to pay tax on $1 to convert the nondeductible to a Roth.

But there is ONE MORE RULE. Too often, tax commentators fail to point this one out, and it is a biggie.

He is probably hosed if he has ANY traditional (that is, deductible) IRAs out there. This triggers the “aggregation” or “pro rata” rule, and the rule is not his friend.

Let’s calculate a ratio.

The numerator is the amount he is converting: $5,500 in our example.

The denominator is ALL the money in ALL his traditional/deductible IRA accounts.

Say our tax CPA had $994,500 in his regular/traditional/free-range IRA before the $5,500 backdoor.

He now has $1 million after the backdoor.

His ratio would be 5,500/1,000,000 = 0.0055.

What does this mean?

It means that the inverse: 100% – 0.55% = 99.445% of every dollar will be taxable.

Counting with fingers and toes, I say that $5,470 is taxable.

The nondeductible saved him tax on all of $30, which appears to meet the definition of “near useless.”

So much for that $1 of conversion income he was hoping for. He got hung on the aggregation rule.

This is an extreme example, but any significant ratio is going to trigger significant taxable income on the conversion.

Is this deliberate by the IRS?

Does Tiger chase little white balls?

Our heroic and stoic tax CPA has other IRAs. The backdoor Roth has become unreachable for him.

Or has it?

Here is a thought: what if our tax CPA rolls ALL of his IRAs into the company 401(k)?
COMMENT: I know I previously said he did not have a plan at work. Work with me here, folks.
He would have to call the 401(k) people and see if they permit that. Federal tax law says he can, but that does not mean that his particular plan has to allow it.

Let’s say he can.

He now has zero/zip/zilch in traditional/deductible/sustainable IRAs.

Seems to me that he is back to converting for $1 in income, per our first example.

And there is your backdoor.

Friday, December 22, 2017

Individual Changes In The New Tax Bill

We have a new tax bill, and it is considered the most significant single change to the tax Code over the last 30 years. Here are some changes that may affect you:
·     Your tax rate is likely going down. A single person making $150,000, for example, will see his/her rate dropping from 28% to 24%. A married couple making $250,000 will see their rate drop from 33% to 24%. Whether married or not, the top rate has gone from 39.6% to 37%.
·     You will lose your personal exemptions next year. For 2017 the exemption amount is $4,050 for you, your spouse and every tax dependent. 
·      To make up for the loss of the personal exemptions, your standard deduction is going up in 2018. A single taxpayer will increase from $6,350 to $12,000. A married taxpayer will go from $12,700 to 24,000.
·      Many of your itemized deductions will be limited or go away altogether next year:
o   For 2017 you can deduct interest on up to $1 million on a mortgage used to buy your home.  In 2018 that limit will drop to $750,000.
o   For 2017 you can deduct interest on (up to) $100,000 of home equity loans. In 2018 you will be unable to deduct any interest on home equity loans.
o   For 2017 you can deduct your state and local income and real estate taxes, without limit. In 2018 the maximum amount you can deduct is $10,000.
o   For 2017 you can deduct a personal casualty loss (such as a car flooding), subject to a $100-deductible-per-incident and-10%-of-income threshold. You will not be able to deduct such losses in 2018, unless you are in a Presidentially-declared disaster zone.
o   For 2017 you can deduct contributions up to 50% of your income. In 2018 that increases to 60%.
o   If your contribution provides the right to purchase seat tickets to an athletic event – say to Tennessee or Ole Miss – you can presently deduct a percentage of that contribution.  In 2018 you will not be able to deduct any portion.
o   In 2017 you can deduct employee business expenses, certain similar or investment expenses, subject to a 2% disallowance. Starting in 2018 no 2% miscellaneous deductions will be allowed.
·     Medical expenses – for some reason – go the other way. Congress reduced the threshold from 10% to 7.5%, and it made the change retroactive to January 1, 2017. It is one of the few retroactive changes in the bill, and it will exist for only two years – 2017 and 018.
·     Get divorced and you might pay alimony. For 2017 you can deduct alimony you pay, and your ex-spouse has to report the same amount as income. Get divorced in 2019 or later, however, and your alimony will not be deductible, and it will not be taxable to your ex-spouse.
·      Move in 2017 and you may be able to deduct your moving expenses. There is no deduction if you move in 2018 or later.
·      You still have the alternative minimum tax to worry about in 2018, but the exemption amounts have been increased.
·      If you own a business, chances are the new tax law will affect you. For example,
o   If you own a C corporation, you will now pay tax at one rate – 21%. It does not matter how big you are. You and Wells Fargo will pay the same tax rate.
o   If you are self-employed, a partner or a shareholder in an S corporation, you might be able to subtract 20% of that business income from your taxable income. There are hoops, however. The new law will limit your deduction if you do not have payroll or have no depreciable assets, although you can avoid that limit if your income is below a certain threshold.
·     Your kid will provide a larger child tax credit. The credit is $1,000 for 2017 but will go to $2,000 in 2018.
What can you do now to still affect your taxes?
·      Rates are going down. Delay your income if you can.
·      For the same reason, accelerate your expenses, especially if you are cash-basis.
·      Prepay your real estate taxes. Yes, that means pay your 2018 taxes by December 31.
·      Pay your 4th quarter state (and city) estimated tax by December 31. You may even want to sweeten it a bit, although the tax bill does not permit one to prepay all of 2018’s state tax by December 31.
·      Remember that you are losing your 2% miscellaneous deductions next year. If you use your car for work and are not reimbursed, you will lose out. It is the same for an office-in-home. 

·   Congress is limiting or taking away many popular itemized deductions and replacing them with a larger standard deduction. This means your remaining deductions – mortgage interest, taxes (what’s left) and contributions are under pressure to exceed that standard deduction. If you do not think you will be able to itemize next year, you may want to accelerate your contributions to 2017. Remember that the check has to be in the mail by December 31 to claim the deduction in 2017.
There are some surprises to be had, folks. I was looking at an estimated 2018 workup for a routine-enough-CPA-firm client. The result? An over 16% tax increase. What caused it? The loss of the personal exemptions. It was simply too much weight for the increased standard deduction and slightly lower tax rates to pull back up. 

I hope that is not the norm. This is a hard-enough job without having that conversation. 

Merry Christmas

Friday, December 15, 2017

How Often Can The IRS Audit You For The Same Thing?

How often can the IRS audit you for the same thing?

I would have to ask two more questions before answering:

(1) Is the IRS auditing the same year?
(2) Is the IRS auditing the same issue?

Here is the relevant Code section:

            IRC Section 7605(b):

No taxpayer shall be subjected to unnecessary examination or investigations, and only one inspection of a taxpayer's books of account shall be made for each taxable year unless the taxpayer requests otherwise or unless the Secretary, after investigation, notifies the taxpayer in writing that an additional inspection is necessary.

Focus in on the lawyered wording:

            “unnecessary examination or investigations”
            “an additional inspection is necessary”

If I were the IRS, I would argue that all examinations and inspections are “necessary” and be done with the matter.

Fortunately, it does not work that way.

Let say that you are self-employed and deducted a bad debt – a sizeable one – in 2014. The IRS takes a look at it and raises some questions, as bad debts are a notorious area of contention with the IRS. After some back and forth the IRS agrees to the deduction.
Question: Can the IRS audit your 2014 tax return again?
Answer: Of course it can, at least until the statute of limitations expires. What it cannot do is audit your 2014 bad debt again. It already looked at that issue and did not propose an audit adjustment. There is only one bite at the apple.
This does not mean that you are untouchable, however.

Let’s say that you incur a huge net operating loss in 2016. You decide, after meeting with your tax advisor, to carryback the loss to 2014 and get a tax refund. You could really use the cash, with that loss and all.
Question: Can the IRS audit your 2014 bad debt again?
The answer may surprise you: Yes.

Here is the Court:
This is not a case where the IRS is subjecting the Taxpayer to onerous and unnecessarily frequent examinations and investigations. The reexamination of Year 1 is not a unilateral action on the part of the IRS, but in response to the Taxpayer’s election to carry back net operating losses and claim a refund.”
In other words, you started it.

Let me give you a second scenario: 

You have a large donation in 2014 and another large donation in 2015. You were audited for 2014. The IRS made no change to your return.
Question: Can the IRS audit your 2015 for the donation? 
Here is Internal Revenue Manual
(1) Repetitive audit procedures apply to individual tax returns without a Schedule C or Schedule F, when the following criteria are met:
·        a. An examination of one or both of the two preceding tax years resulted in a no change or a small tax change (deficiency or overassessment), and
·        b. The issues examined in either of the two preceding tax years are the same as the issues selected for examination in the current year.  
Answer: You should be able to stop this audit. The IRS looked at the same issue in the preceding year and found nothing.

BTW, note the references to Schedule “C” and “F” in para 1 above. Schedule C means that someone is self-employed, and Schedule F means that someone is a farmer. Those are two situations where a tax advisor would love to have this IRM protection. The IRS knows that too, which is why the IRS left out self-employeds and farmers.  
Question: What if the IRS audits you in 2014 for mileage and in 2015 for office-in-home expenses?  
Answer: You being are audited for two different things. What we are talking about is the IRS looking at the same thing, either more than once for the same year or more than once over a three-year period.

Let’s clarify a crucial point: what halts the second audit is NOT that you were previously audited on the same issue. What halts it is that you were audited and there was no change or an insignificant change. If you owed big bucks on the audit then you are fair game. 

A word of advice: you will have to let the examiner know. My experience is that he/she will be unaware until you bring it up. Address this issue early – for example, when the examiner is trying to schedule the visit – and you can stop the audit altogether. 

Saturday, December 9, 2017

Bitcoin and Fred

I am going to dedicate this post to Fred.

Fred likes to talk about Bitcoin. He is a believer. He may as well be on the payroll.

I do not want to talk about blockchain or cryptocurrencies or any of that.

Let’s talk about the taxation of the thing, in case Fred has gotten to you.

As I write this Bitcoin is selling for around $15 grand.

On January 1, 2017 – less than a year ago – it sold for around $1 grand.
COMMENT: There is a reason why we are still working, folks.
There are even Bitcoin ATMs. I understand there around 70 or so locations around Miami alone. You can tap into one if you are going to the Orange Bowl at the end of this month.

Mind you, if you withdraw dollars-for-Bitcoins you probably have a tax consequence.

You see, the IRS has said (in 2014) that Bitcoin is not a currency. Given this thing’s propensity to swing hundreds if not thousands of dollars of day, it makes sense that it is not a currency. Currencies are supposed to have some stable value, at least until politicians run them into the ground.

No, Bitcoins are property, like stocks or a mutual fund. Like a stock or mutual fund, you have a tax consequence on the sale.

Let’s use the following numbers for the sake of discussion:

          Bought on 1/1/17                    $1,000
          Cashed-in on 12/31/17           $16,500

Let’s say you cash-in a Bitcoin while you are at the Orange Bowl. What have you got?

Way I see it, you have ...

    $16,500 (proceeds) - $1,000 (cost) = $15,500 gain

You are supposed to report $15,500 as income on your tax return.

What type of income is it?

I see a buy. I see a sell. I would argue this is capital gain. It would be short-term, as you did not own it for a year.

Let’s throw a curve ball.

Let’s say that you did some work for somebody in 2016. The paid you with that Bitcoin on January 1, 2017 – the one worth $1,000 at the time.

What are your tax consequences now?

You got paid with a Bitcoin worth $1,000. You have $1,000 of ordinary income. If you got paid for work, it is also subject to self-employment tax.

Then you sell it.

I see the following …

   $1,000 (ordinary) + $15,500 (capital gain) = $16,500   

This is what happens when Bitcoin is considered “property” rather than “currency.” It would be the same as you writing checks on your Fidelity or Vanguard mutual fund. Every time you do you are selling some of your mutual fund. And it all gets reported to the IRS at year-end.

Except that most of Bitcoin does not get reported to the IRS at year-end. Not yet, at least. In fact, in 2015 only 802 people reported Bitcoin on their tax return. You know that doesn’t make sense.

Which is why the IRS served a “John Doe” summons on Coinbase in November, 2016. Coinbase is an exchange for virtual currencies like Bitcoin and Ethereum. A “John Doe” summons substitutes a group or class or people for a specific person. It could be as easy as “anyone who sold more than $600 of Bitcoin between 2013 and 2015.”

Coinbase fought back, of course, but in the end the two wound up compromising. Coinbase will not provide 100% of its account data, but the IRS is getting information on over 14,000 account holders and almost 9 million transactions.

Bitcoin and other virtual currencies have become the new overseas bank accounts. It is time to come clean on this stuff, folks.

And yes, I believe there will be IRS reporting – akin to what the stock brokerages do – in the near-enough future. The government is flipping the sofa cushions for every nickel it can find. Until they get us to a 100% tax rate, they are going to keep looking for new sofas.

Someone – probably Fred - was telling me about a Bitcoin credit card.

That is a tax nightmare


Say that you bust to Starbucks in the morning. You put your coffee on the card. You stop for fuel – on the card. You go to lunch – on the card. You stop at the dry cleaners and Krogers on the way home – both on the card.

You have 5 “sales” that day. Each one has a cost, and who knows how we are going to come up with that number. Say that you do something comparable almost every work day. I will probably “fee discourage” you from using me as your tax advisor.

BTW, a similar thing can occur if you accept Bitcoin as payment for your services. Say that you are an independent contractor and two or three of your clients pay you in Bitcoin. You are going to have to price the Bitcoin every time you get paid with one, as your “proceeds” are its value on the day you receive it.

That is an accounting hassle.

Can you think of a nightmare scenario?


What if you get paid with Bitcoin next year when it is worth $20,000. You hold onto it. Let’s say Bitcoin drops to $9,000 by December 31, 2018. You bring me the info for your taxes. How much do you have to report as income from that Bitcoin?

You have to report $20,000.

But it is only worth $9,000 now!

Yep. That is how it works since Bitcoin is not considered a currency.

What can I do to get my taxes down? Should I sell it?

Now you have a different problem. If that thing is a capital asset – and we said earlier that it was – you will have a capital loss upon sale. You will report a $11,000 capital loss on your return.

And unless you have capital gains to absorb those losses, you continue to have tax problems. Capital losses are allowed to offset only $3,000 of your “other” (read: Bitcoin) income on your tax return. You get no bang on the remaining $8,000 ($11,000 - $3,000), at least until the following year when you can use another $3,000. 

Don’t forget that you are also paying self-employment taxes on that $20,000 and not on $9,000.

This is ridiculous. If I were you, I would fire me as your tax advisor.

I do not accept Bitcoin for my fees, but I am waiting for someone to bring it up. I might do it for an isolated transaction or two. 

But no way am I using a Bitcoin credit card.

Saturday, December 2, 2017

Not Filing Because You Expect A Refund

I received a call from a client this past week. He is keen on getting his taxes caught-up.

Mind you, he is not a timely filer.  He files every two or three years, at best.

How does he get away with it?

He has the ultimate tax shelter: a net operating loss (NOL).

You have to have a business to have an NOL. It means a business loss so large that it overwhelms whatever other sources of income you may have. It leaves behind a net negative number, and you can use that negative to recoup taxes paid in a prior year (2 prior years, to be exact) or you can use it to reduce your taxes going forward (up to 20 years).

It makes tax planning easy.

Say you have a $1 million NOL carryforward. You anticipate earning $400,000 next year. What tax planning advice would you give?

Here’s one: stop the withholding on that $400,000, if you can.


$400,000 - $1,000,000 = ($600,000).

There is no tax on minus $600,000. There is no point in withholding.

And that is why my client is somewhat lackadaisical about filing his taxes.

Won’t there be penalties for late filing?

Most likely: No. Penalties are normally calculated on any taxes due. No taxes due = no penalties. This is not always true, but it is true enough in his case.

A more common variation on this theme is a taxpayer who always gets a refund. A refund = no taxes due = no penalties. One has to be careful with this, however, because once enough years go by (more specifically: 3 years), the government will keep your money.

I was looking at the Parekh case this week. Here is the Tax Court:
… we conclude that petitioners did not exercise ordinary business care and prudence and that they have not established reasonable cause for failing to file their 2012 tax return timely.”
COMMENT: if you see the words “ordinary business care and prudence” or “reasonable cause,” rest assured that someone is being penalized. Those are code words when one is trying to remove or reduce penalties.
What did Parekh get into?

Let’s see:
  • Mr and Mrs Parekh filed 2009 only after the IRS prepared a substitute tax return for them.
  • They were late in filing 2010 and 2011.
  • They did not extend their 2012 return. They eventually filed it in 2014.
Wouldn’t you know the IRS decided to audit 2012?

Who cares, right? They are always overpaid.

There was something different in 2012: retirement plan distributions. The IRS determined that they owed over $8 grand of Alternative Minimum Tax (AMT).

Now that there was tax due the IRS also assessed a penalty.

Parekh went to Appeals. He wanted the penalty for late filing abated.

His reason?

He always had refunds. How was he supposed to know that 2012 was different?

Here is Parekh:
I figured, reasonably so I thought, that since I’d be getting a refund it was OK to file late ***. In fact, I had considered the de facto deadline for filing to be three years if one is getting a refund since after that the refund is forfeited. As I take a quick look at some tax advice websites that is pretty much what they say.”
Here is the IRS:
The Appeals officer noted that petitioners had also been delinquent in filing their 2009-2011 returns and that, as of […], they had not filed a return for 2013 or 2014 either.”
One they got to Tax Court – and hired an attorney - the Parekhs added another reason for filing late: his mom was ill and he was routinely travelling to India in 2013 and 2014 to help his father care for her.

The Court did not like the attorney slapping the India thing into the record at the last minute.
Even if we were to credit petitioner husband’s testimony about his heavy travel schedule, it is inconceivable that he could not have found two days in which to fulfill petitioners’ filing obligation, as opposed to filing that return 15 months late.”
The Court said no reasonable cause for not extending and not filing on time. They had to pay the penalty.

Did Parekh’s track record with the IRS hurt him with the Court?

No doubt.

And there is the risk if you routinely file your returns late – perhaps because you expect a refund or because you have always gotten refunds. Have your taxes spike unexpectedly, and it is unlikely you will avoid the penalties that will come with them.

Friday, November 24, 2017

When The IRS Says Loan Repayments Are Taxable Wages

Here is a common-enough fact pattern:

(1) You have a company.
(2) You loan the company money.
(3) The company has an unprofitable stretch.
(4) Your accountant tells you to reduce or stop your paycheck.
(5) You still have bills to pay. The company pays them for you, reporting them as repayments of your loan.

What could go wrong?

Let’s look at the Singer Installations, Inc v Commissioner case.

Mr. Singer started Singer Installations in 1981. It was primarily involved with servicing, repairing and modifying recreational vehicles, although it also sold cabinets used in the home construction.

After a rough start, the business started to grow. The company was short of working capital, so Mr. Singer borrowed personally and relent the money to the company. All in all, he put in around two-thirds of a million dollars.
PROBLEM: Forget about the formalities of debt: there was no written note, no interest, no repayment schedule, nothing. All that existed was a bookkeeping entry.
The business was growing. Singer had problems, but they were good problems.

Let’s fast-forward to 2008 and the Great Recession. No one was modifying recreational vehicles, and construction was drying up. Business went south. Singer had tapped-out his banks, and he was now borrowing from family.

He lost over $330 grand in 2010 and 2011 alone. The company stopped paying him a salary. The company paid approximately $180,000 in personal expenses, which were reported as loan repayments.

The IRS disagreed. They said the $180 grand was wages. He was drawing money before and after. And – anyway – that note did not walk or quack like a real note, so it could not be a loan repayment. It had to be wages. What else could it be?

Would his failure to observe the niceties of a loan cost him?

Here is the Court:
We recognize that Mr. Singer’s advances have some of the characteristics of equity – the lack of a promissory note, the lack of a definitive maturity date, and the lack of a repayment schedule …”
This is going to end poorly.
 … but we do not believe those factors outweigh the evidence of intent.”
Wait, is he going to pull this out …?
 … because intent of parties to create [a] loan was overwhelming and outweighed other factors.”
He won …!
However, we cannot find that all of the advances were loans.”
Then what would they be?
While we believe that Mr. Singer had a reasonable expectation of repayment for advances made between 2006 and 2008, we do not find that a similarly reasonable expectation of repayment existed for later advances.”
Why not, Sheldon?
 After 2008 the only source of capital was from Mr. Singer’s family and Mr. Singer’s personal credit cards.”
And …?
No reasonable creditor would lend to petitioner.”

The Court decided that advances in 2008 and earlier were bona fide loans. Business fortunes changed drastically, and advances made after 2008 were not loans but instead were capital contributions.

This “no reasonable creditor would lend” can be a difficult standard to work with. I have known multimillionaires who became such because they did not know when to give up. I remember one who became worth over $30 million – on his third try.

Still, the Court is not saying to fold the company. It is just saying that – past a certain point – you have injected capital rather than made a loan. That point is when an independent third party would refuse to lend money, no matter how sweet the deal.

Why would the IRS care?

The real-world difference is that it is more difficult tax-wise to withdraw capital from a business than it is to repay a loan. Repay a loan and you – with the exception of interest – have no tax consequence.

Withdraw capital – assuming state law even allows it – and the weight of the tax Code will grind you to dust trying to make it taxable – as a dividend, as a capital gain, as glitter from the tax fairy.

It was a mixed win for Singer, but at least he did not have to pay taxes on those phantom wages.