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.

Deducting “Tax Insurance” Premiums

 There is an insurance type that I have never worked with professionally: tax liability insurance.

It is what it sounds like: you are purchasing an insurance policy for unwanted tax liabilities.

It makes sense in the area of Fortune 500 mergers and acquisitions. Those deals are enormous, involving earth-shaking money and a potentially disastrous tax riptide if something goes awry. What if one the parties is undergoing a substantial and potentially expensive tax examination? What if the IRS refuses to provide advance guidance on the transaction? There is a key feature to this type of insurance: one is generally insuring a specific transaction or limited number of transactions. It is less common to insure an entire tax return.  

My practice, on the other hand, has involved entrepreneurial wealth – not institutional money - for almost my entire career. On occasion we have seen an entrepreneur take his/her company public, but that has been the exception. Tax liability insurance is not a common arrow in my quiver. For my clients, representation and warranty insurance can be sufficient for any mergers and acquisitions, especially if combined with an escrow.

Treasury has been concerned about these tax liability policies, and at one time thought of requiring their mandatory disclosure as “reportable” transactions. Treasury was understandably concerned about their use with tax shelter activities. The problem is that many routine and legitimate business transactions are also insured, and requiring mandatory disclosure could have a chilling effect on the pricing of the policies, if not their very existence. For those reasons Treasury never imposed mandatory disclosure.

I am looking at an IRS Chief Counsel Memorandum involving tax liability insurance.

What is a Memorandum?

Think of them as legal position papers for internal IRS use. They explain high-level IRS thinking on selected issues.

The IRS was looking at the deductibility by a partnership of tax insurance premiums. The partnership was insuring a charitable contribution.

I immediately considered this odd. Who insures a charitable contribution?

Except …

We have talked about a type of contribution that has gathered recent IRS attention: the conservation easement.

The conservation easement started-off with good intentions. Think of someone owning land on the outskirts of an ever-expanding city. Perhaps that person would like to see that land preserved – for their grandkids, great-grandkids and so on – and not bulldozed, paved and developed for the next interchangeable strip of gourmet hamburger or burrito restaurants. That person might donate development rights to a charitable organization which will outlive him and never permit such development. That right is referred to as an easement, and the transfer of the easement (if properly structured) generates a charitable tax deduction.

There are folks out there who have taken this idea and stretched it beyond recognition. Someone buys land in Tennessee for $10 million, donates a development and scenic easement and deducts $40 million as a charitable deduction. Promoters then ratcheted this strategy by forming partnerships, having the partners contribute $10 million to purchase land, and then allocating $40 million among them as a charitable deduction. The partners probably never even saw the land. Their sole interest was getting a four-for-one tax deduction.

The IRS considers many of these deals to be tax shelters.

I agree with the IRS.

Back to the Memorandum.

The IRS began its analysis with Section 162, which is the Code section for the vast majority of business deductions on a tax return. Section 162 allows a deduction for ordinary and necessary expenses directly connected with or pertaining to a taxpayer’s trade or business.

Lots of buzz words in there to trip one up.

You my recall that a partnership does not pay federal tax. Instead, its numbers are chopped up and allocated to the partners who pay tax on their personal returns.

To a tax nerd, that beggars the question of whether the Section 162 buzz words apply at the partnership level (as it does not pay federal tax) or the partner level (who do pay federal tax).

There is a tax case on this point (Brannen). The test is at the partnership level.

The IRS reasoned:

·      The tax insurance premiums must be related to the trade or business, tested at the partnership level.

·      The insurance reimburses for federal income tax.

·      Federal income tax itself is not deductible.

·      Deducting a premium for insurance on something which itself is not deductible does not make sense.

There was also an alternate (but related argument) which we will not go into here.

I follow the reasoning, but I am unpersuaded by it.

·      I see a partnership transaction: a contribution.

·      The partnership purchased a policy for possible consequences from that transaction.

·      That – to me - is the tie-in to the partnership’s trade or business.

·      The premium would be deductible under Section 162.

I would continue the reasoning further.

·      What if the partnership collected on the policy? Would the insurance proceeds be taxable or nontaxable?

o  I would say that if the premiums were deductible on the way out then the proceeds would be taxable on the way in.

o  The effect – if one collected – would be income far in excess of the deductible premium. There would be no further offset, as the federal tax paid with the insurance proceeds is not deductible.

o  Considering that premiums normally run 10 to 20 cents-on-the-dollar for this insurance, I anticipate that the net tax effect of actually collecting on a policy would have a discouraging impact on purchasing a policy in the first place.

The IRS however went in a different direction.

Which is why I am thinking that – albeit uncommented on in the Memorandum – the IRS was reviewing a conservation easement that had reached too far. The IRS was hammering because it has lost patience with these transactions.