Sell Today And Pay Tax in Thirty Years

Sometimes I am amazed to the extent people will go to minimize, defer or avoid taxes altogether.

I get it, though. When that alarm clocks goes off in the morning, there is no government bureaucrat there to prepare your breakfast or drive you to work. Fair share rings trite when yours is the only share visible for miles.

I am looking at an IRS Chief Council Advice.

Think of the Chief Counsel as the attorneys advising the IRS. The Advice would therefore be legal analysis of an IRS position on something.

This one has to do with something called Monetized Installment Sale Transactions.

Lot of syllables there.

Let’s approach this from the ground floor.

What is an installment sale?

This is a tax provision that allows one to sell approved asset types and spread the tax over the years as cash is collected. Say you sell land with the purchase price paid evenly over three calendar years. Land is an approved asset type, and you would pay tax on one-third of your gain in the year of sale, one-third the following year and the final third in the third year.

It doesn’t make the gain go away. It just allows one to de-bunch the taxation on the gain.

Mind you, you have to trust that the buyer can and will pay you for the later years. If you do not trust the buyer’s ability (or intention) to do so, this may not be the technique for you.

What if the buyer pays an attorney the full amount, and that attorney in turn pays you over three years? You have taken the collection risk off the table, as the monies are sitting in an attorney’s escrow account.

You are starting to think like a tax advisor, but the technique will almost certainly not work.

Why?

Well, an easy IRS argument is that the attorney is acting as your agent, and receipt of cash by your agent is the equivalent of you receiving cash. This is the doctrine of “constructive receipt,” and it is one of early (and basic) lessons as one starts his/her tax education.

What if you borrow against the note? You just go down to Fifth Third or Truist Bank, borrow and pledge the note as collateral.

Nice.

Except that Congress thought about this and introduced a “pledging” rule. In short, a pledge of the note is considered constructive receipt on the note itself.

Not to be deterred, interested parties noticed a Chief Council’s Memorandum from 2012 that seemed to give the OK to (at least some of) these transactions. There was a company that need cash and needed it right away. It unloaded farm property in a series of transactions involving special purpose entities, standby letters of credit and other arcane details.

The IRS went through 11 painful pages of analysis, but wouldn’t you know that – at the end – the IRS gave its blessing.

Huh?

The advisors and promoters latched-on and used this Memorandum to structure future installment sale monetization deals.

Here is an example:

(1)  Let’s say I want to sell something.

(2)  Let’s say you want to buy what I am selling.

(3)  There is someone out there (let’s call him Elbert) who is willing to broker our deal – for a fee of course.

(4)  Neither you or I are related to Elbert or give cause to consider him our agent.

(5)  Elbert buys my something and gives me a note. In our example Elbert promises to pay me interest annually and the balance of the note 30 years from now.

(6)  You buy the something from Elbert. Let’s say you pay Elbert in full, either because you have cash in-hand or because you borrow money.

(7)  A bank loans me money. There will be a labyrinth of escrow accounts to maintain kayfabe that I have not borrowed against my note receivable from Elbert.

(8)  At least once a year, the following happens:

a.    I collect interest on my note receivable from Elbert.

b.    I pay interest on my note payable to the bank.

c.    By some miraculous result of modern monetary theory, it is likely that these two amounts will offset.

(9)  I eventually collect on Elbert’s note. This will trigger tax to me, assuming someone remembers what this note is even about 30 years from now.

(10)      Having cash, I repay the bank for the loan it made 30 years earlier.

There is the monetization: reducing to money, preferably without taxation.

How much of the original sales price can I get using this technique?

Maybe 92% or 93% of what you paid Elbert, generally speaking.

Where does the rest of the money go?

Elbert and the bank.

Why would I give up 7 or 8 percent to Elbert and the bank?

To defer my tax for decades.

Do people really do this?

Yep, folks like Kimberly Clark and OfficeMax.

So what was the recent IRS Advice that has us talking about this?

The IRS was revisiting its 2012 Memorandum, the one that advisors have been relying upon. The IRS lowered its horns, noting that folks were reading too much into that Memorandum and that they might want to reconsider their risk exposure.

The IRS pointed out several possible issues, but we will address only one.

The company in that 2012 Memorandum was transacting with farmland.

Guess what asset type is exempt from the “pledging” rule that accelerates income on an installment note?

Farmland.

Seems a critical point, considering that monetization is basically a work-around the pledging prohibition.

Is this a scam or tax shelter?

Not necessarily, but consider the difference between what happened in 2012 and how the promoters are marketing what happened.

Someone was in deep financial straits. They needed cash, they had farmland, and they found a way to get to cash. There was economic reality girding the story.   

Fast forward to today. Someone has a big capital gain. They do not want to pay taxes currently, or perhaps they prefer to delay recognizing the gain until a more tax-favorable political party retakes Congress and the White House. A moving story, true, but not as poignant as the 2012 story.   

For the home gamers, this time we have been discussing CCA 2019103109421213.

Tax Return That Surprised An Accountant

Let’s do something a little different this time.

I want you to see numbers the way a tax CPA does.

Let’s say that you are semi-retired and you bring me your following tax information:

                    W-2                                         24,000

                    Interest income                            600

                    Qualified dividend income      40,000

                    Long-term capital gains          10,000

                    IRA                                         24,000

Looks to me like you have income of $98,600.

How about deductions?

                    Real estate taxes                    10,000

                    Mortgage interest                      5,000

                    Donations                                26,000

I am seeing $41,000, not including your exemptions.

You did some quick calculations and figure that your federal taxes will be about $6,500. You want to do some tax planning anyway, so you set up an appointment. What can you do to reduce your tax? 

What do I see here?

I’ll give you a hint.

Long-term capital gains have a neat tax trick: the capital gains tax rate is 0% as long as your ordinary income tax rate is 15% or lower. This does not mean that you cannot have a tax, mind you. To the extent that you have taxable income in excess of those capital gains, you will have tax.

Let’s walk though this word salad.

Income $98,600 – deductions $41,000 – exemptions $8,100 = $49,500 taxable income.

You have capital gains of $10,000.

Question: will you have to pay tax on the difference – the $39,500?

Answer: qualified dividends also have a neat tax trick: for this purpose, they are taxed similarly to long-term capital gains.

NOTE: Think of qualified dividends as dividends from a U.S. company or a foreign company that trades on an U.S. exchange and you are on the right path.

You have capital gains and qualified dividends totaling $50,000.

Your taxable income is $49,500.

All of your taxable income is qualified dividends and capital gains, and you never left the 15% tax bracket.

What is your tax?

Zero.

How is that for tax planning, huh?

From a tax perspective, you hit a home run.

Let me change two of the numbers so we can better understand this qualified dividend/capital gain/taxable income/15% tax bracket thing.

                    W-2                                         36,000

                    Qualified dividends                 28,000

As you probably can guess, I left your taxable income untouched at $49,500, but I changed its composition.

You now have capital gains and qualified dividends of $38,000. Your taxable income is $49,500, meaning that you have “other” income in there. You are going to have to pay tax on that “other” income, as it does not have that qualified dividend/capital gain trick.

The tax will be $1,153.

You still did great. It is just that no tax beats some tax any day of the week.

It is something to consider when you think about retirement planning. We are used to thinking about 401(k)s, deductible IRAs, Roth IRAs, social security and so on, but let’s not leave out qualified dividends and capital gains. Granted, capital gains are unpredictable and not a good fit for reliable income, but dividend-paying stocks might work for you. When was the last time Proctor & Gamble missed a dividend payment, for example?

OK, I admit: if you leave the 15% tax bracket the above technique fizzles. That however would take approximately $76,000 taxable income for marrieds filing jointly. Congrats if that is you.

BTW I saw scenario one during tax season (I tweaked the numbers somewhat for discussion, of course). The accountant was perplexed and asked me to look at the return with him. The zero tax threw him.

Now he knows the dividend/capital gain thing, and so do you.

The Sale of "American Pie"

Did you see where Don McLean sold his original manuscript for “American Pie” at Christie’s? He sold the work for $1.2 million, and it included his handwritten notes and deletions from the 1971-72 hit that – at 8 ½ minutes – was the longest song to ever top the U.S. charts.

The song of course is famous for its allusions. The “day the music died” refers to the death of Buddy Holly, whereas “the king” supposedly refers to Elvis Presley while “the jester on the sidelines” refers to Bob Dylan after his motorcycle accident. It became an anthem to disillusionment, to the sense of our best days being behind us and the ennui and hopelessness of a society being carted off in the wrong direction.

Sounds eerily contemporary.

He explained that he had forgotten he had the manuscript. He found it in the proverbial old box that had survived several moves. The sale allowed him to provide for his family, now and into the future.

Yes, $1.2 million will do that.

So what are the tax consequences from the sale of his manuscript?

We are talking about intellectual property and a subset we will call creative properties.

For the most part, self-created properties cannot be a capital asset in the hands of its creator. This causes a problem, as one requires a capital asset if one wants capital gains.

Take it a step further. If someone else owns the asset but its tax basis (that is, its cost for purposes of calculating gain or loss) is determined by reference to the creator’s basis, then it cannot be a capital asset.  How can this happen? Easy. You could gift the property, for example, or you could contribute the property to a family limited partnership. In either case the recipient will “take over” your basis in the creative property. Since the basis remains the same, it cannot be a capital asset.

The vocabulary gets tricky when discussing creative property. For example, an author (say Stephen King) may receive a “royalty.” Coincidently, find oil in your backyard and chances are an oil company will also pay you a royalty. Since the word “royalty” is the same, are the tax consequences the same?

The answer is no. If you write a book or score a movie soundtrack, that royalty is probably ordinary income to you. In fact, it is reported on Schedule C of your individual tax return, the same as your self-employment income from Uber. The oil royalty, on the other hand, is reported on Schedule E, along with rents. The Schedule C royalty will trigger self-employment tax. The Schedule E will not. 

OBSERVATION: We have discussed before that sometimes a word will have different meanings as it travels through the tax Code. Here is an example.

As always, there are exceptions. Let’s say you write one book and never write again. The IRS will likely consider that to be ordinary income but not self-employment income. Why? Supposedly it takes two or more books to establish that you are in the trade or business of writing books.

OBSERVATION: I am curious how the IRS would apply this standard to Harper Lee. She published, you will recall, To Kill a Mockingbird in 1960. It was only this year that she published her second work (Go Set a Watchman) – 55 years later. What do you think: is this self-employment income or not?

Remember when Michael Jackson bought the catalog of Beatles music? He bought it as a non-alternative investment, akin to stocks and bonds. Like a stock or bond, Michael Jackson would have had capital gains had he sold the catalog.

This created a fuss among songwriters. If they sold their own compositions, they would have ordinary and self-employment income. Introduce Michael Jackson and the tax result transmuted to capital gains.

So Congress passed Section 1221(b)(3), which incorporated a provision from the Songwriter’s Capital Gains Equity Act, promoted by the Nashville Songwriters Association International (NASI). It extended capital gains to self-created music owned for more than one year. It requires an election, and the songwriter/creative can elect for one musical composition and not for another. It does require the transfer of a musical composition or a copyright in the same; transfer something less and the result defaults to ordinary income.

NASI argued that the industry had changed. By the 1990s many music artists were acting as their own publishers or co-publishers, meaning they had some control over the exploitation of their songs. Gone were the days of Hank Williams and Bill Monroe, when songwriters sold their songs outright to music publishers with no right to ongoing income.

Congress listened.

Don McLean now has a tax option that he did not have years ago when he recorded “American Pie.” I suppose that there could be a scenario where it would be more advantageous to recognize the $1.2 million as ordinary income rather than as capital gains, but I cannot easily think of any that do not require low-probability tax considerations.

I would say he is making the election.

The Taxation of a Bitcoin

It wasn’t too long ago I was speaking with a friend who has a high-level position in the financial industry. The conversation included a reference to Bitcoins and how they might impact what he and his company do. We spent a moment on what Bitcoins are and how they are used.

I am still a bit confused. Bitcoins are a “virtual” currency. They are not issued or backed by any nation or government. They took off as a vehicle for wealthy Chinese to get money out of the mainland, and their market value over the last year has bordered on the stratospheric: from approximately $13 to over $1,000 and back down again. Understand: there is no company in which you can buy stock. To own Bitcoins, you have to own an actual “Bitcoin,” except that Bitcoins is a virtual currency. There is no crisp $20 bill in your wallet. You will have a virtual wallet, though, and your virtual currency will reside in that virtual wallet. I suppose some virtual pickpocket could steal your virtual wallet crammed with virtual currency.

You can own a gold miner stock, for example, although the decision to do that would have proved disastrous in 2013. Then there are Bitcoin “miners,” if you can believe it. Bitcoins presents near-unsolvable mathematical problems, and – if you answer them correctly – you might receive Bitcoins in return. That is how new Bitcoins are created. There a couple of caveats here, though: first, the problems are so complicated that you pretty much have to pool your computer with other people and their computers to even have a prayer of solving the problem. There is also a dark side: the computer security firm Malwarebytes discovered that there was malware that would conscript your computer and its processing power to aid others mine for Bitcoins. Second, only 21 million Bitcoins are supposedly going to be created. Call me a cynic, but look at our government’s fiscal death wish and tell me you believe that assertion.

Bitcoins are tailored made for illegal activities. The currency is virtual; there are no bank accounts or financial institutions to transfer information to the government - yet. China has banned their financial institutions from using Bitcoins, and Thailand has made it illegal altogether. Bitcoins was tied into Silk Road, which was an eBay (of sorts) for drugs and who knows what else. One apparently had to be a computer geniac to even get to it, as Silk Road resided in the dark web and required specialized access software (such as Tor) to access. Its founder was known as Dread Pirate Roberts (I admit, I like the pseudonym), and Silk Road accepted only Bitcoins as payment. The Pirate gave an interview to Forbes and was subsequently arrested by the FBI. You can draw your own conclusion on the cause and effect.

Did you know that there are merchants out there who will accept payment in Bitcoins, and in some cases only in Bitcoins? There is even a small town in Kentucky that agreed to pay its police chief in Bitcoins.

So how would Bitcoins be taxed? It depends. Let’s say you are trading the Bitcoins themselves, the same way you would trade stocks or baseball cards. You then need to know whether the IRS considers Bitcoins to be a currency or a capital asset.

There is a downside to treating Bitcoins as a currency: IRC Section 988 treats gains and losses from currency trading as ordinary gains and losses. This means that you run the tax rates, currently topping-out at 39.6% before including the effects of the PEP and Pease phase-outs and as well as the ObamaCare taxes.

What if Bitcoins are treated as a capital asset? We would then have company. Norway has decided that Bitcoins is not a currency and will charge capital gains taxes. Germany has said the same. Sweden wants to subject Bitcoins to their VAT. The advantage to being a capital asset is that the maximum U.S. capital gains tax is 20%. However, remember that capital losses are not tax-favored. Capital losses can offset capital gains without limit, but capital losses can offset only $3,000 of other income annually.

There is a capital asset subset known as commodities. Futures trades on a currency (as opposed to trading the actual currency itself) are taxed under Section 1256, which arbitrarily splits any gain into 60% long-term and 40% short-term. Now only 60% of your gain is subject to the favorable long-term capital gains tax. However, futures contracts on Bitcoins do not yet exist.

What if you are not trading Bitcoins but rather receiving them as payment for merchandise or services? This sounds like a barter transaction, and the IRS has long recognized barter transactions as taxable. What price do you use for Bitcoins? There are multiple exchanges – Mt. Gox or coinbase, for example – with different prices. One could take a sample of the prices and average, I suppose.

I also question what to do with the price swings. Say you received a Bitcoin when it was trading at $900. Under barter rules, you would have $900 in income. You spend the Bitcoin a week or month later when the Bitcoin is worth $700. You have lost $200 in value, have you not? Is there a tax consequence here?

If it were a capital asset, you would have “bought” it for $900 and “sold” it for $700. It appears you have a capital loss.

This doesn’t necessarily mean that that the loss is deductible. Your home, for example, is a capital asset. Gain from the sale of your home is taxable if it exceeds the exclusion, but loss from the sale of your home is never deductible.

If it were a currency AND the transaction was business-related, you would have a deduction, but in this case it would be a currency loss rather than a capital loss. A currency loss is an ordinary loss and would not be subject to the $3,000 annual capital loss restriction.

If it were a currency AND the transaction was NOT business-related, you are likely hosed. This would be the same as vacationing in Europe and losing money from converting into and out of Euros. The transaction is personal, and the tax Code disallows deductions for personal purposes.

What do you have if you “mined” one of those Bitcoins? When are you taxed: when you receive it or when you dispose of it?

Bitcoins are virtual currency. Do you have to include Bitcoins when you file your annual FBAR for financial accounts outside the U.S. with balances over $10,000? Where would a Bitcoin reside, exactly?

The IRS has not told us how handle the taxation of Bitcoins transactions. Until then, we are on our own.