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Showing posts with label nondeductible. Show all posts
Showing posts with label nondeductible. Show all posts

Sunday, January 25, 2026

A Cannabis Business Offer In Compromise

 

Let’s talk reasonable collection potential (RCP).

If the conversation turns to RCP, chances are good that you owe the IRS and are hoping to settle for less than the full amount. A couple of programs come immediately to mind:

  • Offer in Compromise
  • Partial Payment Installment Agreement

 As you might guess, the IRS requires paperwork before agreeing to this. The IRS wants to look at your:

  • Income
  • Expenses
  • Assets
  • Liabilities
  • Future Income Potential

Yes, the process is intrusive. I have had clients balk at the amount of disclosure involved, but in truth it is not much different from what a bank would request. I rarely work with OICs or partial pays these days. Some of it is the client base, but some also reflects past frustration. I have started this process too many times with a client and the first wave of documentation comes in quickly enough; the second wave takes longer. The last wave may take long enough that we must start the first wave over again, and sometimes we never even receive the last wave. It has happened enough that I am now reluctant to get involved, unless it is a client I have known for a while and am confident will follow instructions. The IRS is going reject a partially completed application anyway, so there is no upside to submitting one.

COMMENT: This is a repetitive tactic of the reduce-your-tax-debt mills. They will assemble and file whatever, knowing (or at least should know) that the application will be rejected. That does not matter to them, as they are paid in advance.

The IRS is trying to pin down how much you can pay: the RCP.

And it is not what you may think.

Assets are relatively easy: you must list and value all your assets. You may not want to disclose that restored Corvette or gun collection, but you really should.

Liabilities are tricky. You will submit all your liabilities, but the IRS may not allow them. Credit card debt comes to mind. Let’s just say that the IRS is not overly concerned whether you fail to repay your credit card balances.

Income again is easy, unless you have unusual sources of income. In practice, I have found that the IRS also has difficulty with erratic (think gig) income, sometimes to the point that one cannot get a plan in place.

Expenses can break your heart. Just because you have an expense does not mean that the IRS will allow it. Examples? Think an expensive car lease, private school tuition, even veterinary expenses for an aging dog. For some expense categories, the IRS will look to tables listing normalized allowances for your region of the country. You supposedly can persuade the IRS that your situation is different and requires a larger number than the table. I wish you the best of luck with that.

Future income potential has disqualified many. Let me give an example:

·      A retiree has substantial health issues. It is unlikely that the retiree will (or can) return to work, meaning that current income (sources and amount) is likely all there is into the foreseeable future.

·      A young(er) nurse practitioner is bending under the weight of credit cards, car loan, day care, and aging parents.

The IRS is not going to view the retiree and nurse practitioner the same. One’s earning power is behind him/her, whereas the other likely has many years of above-average earning power remaining. Granted, both may be in difficult straits and both may receive relief, but it is unlikely that the relief will be the same. The retiree may receive an OIC, for example, whereas the nurse practitioner may receive a temporary partial-pay with a two-year revisit. Even then, I anticipate that getting a partial pay for the nurse practitioner is going to be … challenging.

Let’s talk about a recent RCP situation that irritates me. It involves a business.

Mission Organic Center (Mission) is a state legal marijuana dispensary in California.

COMMENT: Two things come into play here. The first is the federal Controlled Substances Act, which classifies cannabis as a Schedule 1 substance. The second is a Code section (Sec 280E) that prohibits businesses from deducting ordinary business expenses from their gross income if the business consists of trafficking in controlled substances. This gives us the odd result of a state-legal business that cannot deduct all its expenses on its federal tax return. Perhaps the state will allow those expenses on its return, but there is no federal equivalent. An accounting firm can deduct its payroll, rent and utilities, by contrast, but a cannabis business cannot (there is an exception for cost of goods sold, but let’s skip that for now).

This raises the question: what is the reasonable collection potential of that cannabis business?

Did you know that there are different accounting methods for different purposes?

Let’s say that you are auditing a Fortune 500 company.  You probably want to keep the accounting on the pavement, something the accounting profession refers to as “generally accepted accounting principles.” Leave the pavement too long or too far and you might have liability issues.

Switch this to the tax return for the Fortune 500, and it is a different matter. The IRS is likely telling you which bad debt – or inventory, or asset capitalization, or depreciation, or deferred compensation, or (on and on) - accounting method to use. The profession calls it “tax accounting,” and that is what I do. I am a tax CPA.

Here is the Supreme Court in Thor Power Tool distinguishing generally accepted accounting income from taxable income:

The primary goal of financial accounting is to provide useful information to management, shareholders, creditors, and others properly interested; the major responsibility of the accountant is to protect these parties from being misled. The primary goal of the income tax system, in contrast, is the equitable collection of revenue; the major responsibility of the Internal Revenue Service is to protect the public fisc. Consistently with its goals and responsibilities, financial accounting has as its foundation the principle of conservatism, with its corollary that "possible errors in measurement [should] be in the direction of understatement rather than overstatement of net income and net assets." In view of the Treasury's markedly different goals and responsibilities understatement of income is not destined to be its guiding light. Given this diversity, even contrariety, of objectives, any presumptive equivalency between tax and financial accounting would be unacceptable.”

Got it: financial accounting provides useful information to stakeholders and tax accounting funds the fisc. Both use the word “accounting,” but they are not the same thing.

Question: what does a business pay bills with?

With cash. Unless somebody is throwing in equity or loaning money, profit is the sole remaining source of cash.

Mission owed a lot of taxes. It submitted an OIC. An IRS Settlement Officer reviewed the OIC and disallowed the Section 280E expenses. The reasoning? The IRS has a policy of disregarding for RCP purposes those business expenses nondeductible under Code Sec. 280E.

I do not see this is an issue of discretion. I see it as a matter of economic reality. Mission needed cash to pay the IRS, and merely making something nondeductible does not create cash. The IRS missed a step here by conflating RCP (an economic measurement of cash) with taxable income (which might mirror cash by luck or accident but then only rarely).

Mission however had a history of filing tax returns without paying. We are not making friends and influencing people here, Mission.

The Tax Court looked at this and decided that the policy was within IRS discretion, and the Settlement Officer did not abuse her discretion by following that policy.

I disagree.

We now have a precedential case that Congressional tax-writing caprice will override an economic evaluation of a business’ ability to generate and retain the cash necessary to pay its tax obligations to the IRS. Let me restate this: Congress - via tax law - can bankrupt you.

Bad facts.

Bad law.

Our case this time was Mission Organic Center v Commissioner, 165 T.C. 13 (2025).

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?

Yep.

Why?

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?

Nada.

Why?

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.

Why?

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.