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    NY Weed Biz Goes All-In on Risky Tax Move

    Nobody likes paying taxes, least of all cash-strapped businesses struggling for their lives.

    That’s why a new business strategy has taken off over the past year in the legal cannabis trade: claiming exemption from a burdensome federal tax provision that has — until now — been effectively taxing much of the industry to death.

    Since early 2024, state-licensed cannabis companies in New York and across the country have been changing up their approach to filing and paying federal taxes — specifically to claim exemption to a little-known 1982 provision in the Internal Revenue Code called Section 280E — in a move that is saving many of them eight or nine figures apiece. 

    The sector-wide tax pivot has saved the national cannabis industry billions of dollars over the past year, industry insiders estimated to Crain’s New York Business.

     The 280E section bars any company from claiming standard business tax deductions if it traffics in Schedule I or Schedule II controlled substances. Marijuana has been a Schedule I narcotic since the federal Controlled Substances Act was signed into law in 1970.

    Because of 280E, state-legal marijuana companies often wind up paying an effective tax rate of 70% to 90% to the Internal Revenue Service each year, which effectively kills the bottom line and often results in net losses for cannabis businesses.

    That includes multistate operator Curaleaf Holdings Inc., which runs a dispensary in Queens and five others scattered around upstate New York, as well as a cultivation facility. Curaleaf reported a net loss of $222 million in 2024, largely due to 280E. That’s a figure which could change significantly within the next year or two, depending on how this new tax strategy pans out for the industry, insiders said.

    “For us, it's millions. For the industry, it's billions in terms of cash flow,” said Mario Pinho, CFO of Massachusetts-based MariMed Inc.

    Those savings are a lifeline for many companies because of how punitive 280E is in practice, said Justin Botillier, founder of Oregon-based Calyx CPA, an accounting firm that serves legal marijuana companies. Botillier emphasized that the effective tax rate under 280E can even be 100% or more if a given company isn’t turning a profit pre-tax.

    “If they're not profitable, like they're losing money, they can still pay tax on phantom income (under 280E),” Botillier said. “And so they could be losing hundreds of thousands, if not millions of dollars, and still pay tax on hundreds of thousands and millions of dollars. That's how bad it is.”

    The catalyst for marijuana businesses to begin claiming they were exempt from 280E came two years ago, when the high-profile New York City law firm Boies Schiller Flexner LLP filed a federal lawsuit in Massachusetts with an eye toward eventually landing a hearing before the U.S. Supreme Court. They argued that the Controlled Substances Act is unconstitutional and outdated, based on the development of state-legal cannabis industries over the past few decades.

    The first to break the mold was Florida-based Trulieve Cannabis Corp. — with a footprint in 11 states — which announced in the first quarter of 2024 that it had filed amended tax returns with the IRS for 2019 to 2021, and had obtained a refund from the IRS of $115 million.

    That news set off a firestorm in the cannabis industry, and other companies rushed to follow suit in the race to keep their doors open.

    ‘Billions’ of dollars in taxes saved

    Chicago-based Verano Holdings Corp., for instance, has saved $177.5 million in working capital through the tax maneuver, according to securities filings. Other cannabis companies doing business in New York have also saved millions, industry insiders told Crain’s.

    “It's keeping most of these companies solvent and afloat. I mean, its impact cannot be understated,” said James Mann, a tax attorney who counts several high-profile multistate operators in the cannabis industry among his clients.

    Mann said he’s obtained millions of dollars in refunds for his clients alone, and there’s a wide swath of both public and private cannabis companies actively changing up their tax positions to follow suit.

    “It’s got to be billions” of dollars saved already by the sector as a whole, Mann said, based on how much just a few public companies such as Trulieve have saved thus far by claiming exemption to 280E.

    New York impact
     

    There are at least three high-profile cannabis companies with have a footprint in New York that have adopted some sort of 280E mitigation strategy, from amending prior year tax returns and obtaining refunds from the IRS to simply claiming 280E exemption for current years and onward, according to a review of securities filings and earnings calls by Crain’s. All three have dispensaries in New York City or on Long Island.

    In March, Cresco Labs Inc. reported a $73.9 million increase in net cash from operating activities, due to “a reduction in our income taxes payable related to our updated position on 280E.” In the second quarter earnings call last year, CFO Dennis Olis said the company projected $65 million in tax savings for 2024 due to its claiming 280E exemption. Chicago-based Cresco has four dispensaries that operate under its Sunnyside brand in New York, including one in Brooklyn and one on Long Island, and two cultivation facilities. The company’s in-house product brands include Cresco-branded products, High Supply, Floracal, Good News, Wonder Wellness Co., Mindy’s edibles and Remedi.

    Curaleaf Holdings Inc. claimed a 280E exemption for 2023 and 2024, which it reported in March had already increased working capital by $117.2 million. The Stamford, Conn.-based company said it intends to file amended tax returns for 2020-2022, and that it will file “as a normal corporate filer” for 2023 and beyond. Curaleaf operates six dispensaries in New York, including one in Queens that sells both recreational and medical marijuana, and one cultivation facility. Its in-house product brands include Grassroots Cannabis Co., Find, Jams edibles, Zero Proof beverages and B Noble pre-rolls.

    Vireo Growth Inc. filed amended tax returns for 2020 to 2022 to claim 280E exemption, is filing as a normal taxpayer for 2023 and beyond, and finished 2024 with an uncertain tax position of $33.3 million, according to securities filings. Minneapolis-based Vireo has four dispensaries, including one in Queens, and a cultivation facility in New York. Its in-house product brands include the Vireo Selects, Vireo Spectrum, and HiColor.

    Also worth noting is that Chicago-based Green Thumb Industries Inc. is the only real outlier in the industry, according to its filings. Instead of trying to offset 280E or claim exemption, GTI has instead paid its full 280E bill to the IRS with regularity. GTI has a cultivation facility and five dispensaries in New York, including one in Manhattan and one on Long Island, that operate under its Rise brand. Its in-house brands include Rythm, Dogwalkers pre-rolls, Good Green, Beboe, Doctor Solomon’s, Shine and Incredibles.

    IRS tax interest cheaper than borrowing

    The trend has not been relegated to publicly traded businesses either, but is growing in popularity among privately held marijuana companies, sources told Crain’s.

    The motives of companies claiming 280E exemption are obvious, industry insiders said: cannabis businesses are desperate for cash to fund their operations and more expansion, and it’s cheaper to potentially pay taxes plus interest further down the road than it is to go find lenders on the open debt market right now.

    “A lot of companies have to essentially raise capital to pay their taxes, because there’s not enough cash coming in. And so the cost of capital is cheaper than if you have the IRS charge you interest, than if you go to the capital markets and try and raise money,” said Matt Karnes, founder of New York-based GreenWave Advisors.

    Private lenders in the cannabis space these days are easily charging between 10% and 15% interest for capital, Karnes said, while IRS interest on unpaid federal taxes is usually only 7% to 9% depending on the size of the business.

    Karnes said that based on his analysis, four of the top five multistate cannabis companies — Curaleaf, Cresco Labs, Trulieve and Verano — owe the IRS roughly $1 billion under 280E as of early April. The fifth top MSO is Green Thumb Industries, which is up to date on its federal tax bills.

    Penalties by the IRS for cannabis companies trying to claim 280E exemption could likely be waived, even if the agency were to try to claw back some of the refunds obtained by marijuana businesses, said Botillier, the Oregon CPA, who estimated he’s won upwards of $10 million in tax refunds for clients through 280E exemption claims.

    Botillier said that as long as a given company can demonstrate it made a good-faith effort to comply with federal tax law by providing solid books and records — even while attempting to dodge 280E — that’s usually enough to persuade the IRS to ease off with financial punishments. That just leaves the original tax tab plus interest.

    “The worst-case scenario is you have to pay them (the IRS) the money back plus interest,” Botillier said, adding that he believes the trend of 280E exemption will only get bigger with time across the U.S. marijuana trade, and that IRS audit rates are “at an all-time low.”

    “At some point, it's going to be a rush, as more and more of these companies end up winning, going unaffected by audits,” Botillier said. “If we're lucky and if they win in Tax Court (against the IRS), there's going to be a huge rush for amending returns. And we're just kind of at the very beginning of that movement, I think, right now.”

    Not a silver bullet

    Still, the new tax strategy isn’t solving everything for the marijuana industry, and there are several possible pitfalls.

    Verano, for instance, still reported a net loss in 2024 of $341.8 million, and the company still has long-term liabilities of $859.7 million as of March 31 this year. The taxes that Verano hasn’t paid to the IRS are still included in its balance sheet as an “uncertain tax position,” Mann noted, a move that many other cannabis companies have taken, because it’s uncertain as to what — if anything — the IRS may do to counteract the wave of marijuana businesses claiming exemption to 280E.

    Both Verano and MariMed are also already being audited by the IRS; Verano for the 2021 and 2022 tax years, and MariMed for the 2022 tax year, according to securities filings.

    Mann also predicted that 280E exemption claims by many cannabis companies will likely prove only a delay tactic, and noted there has been a wide range of legal tax theories and justifications that have been used to justify the 280E exemption.

    Not all of those rationales are equally effective, Mann said, and not all will be successful.

    The entire reason public marijuana businesses such as Verano are still listing their 280E tax bills as “uncertain tax positions” on their balance sheets is specifically in case the IRS ultimately rejects their reasoning and demands that their 280E obligations be paid in full, he noted.

    Mann’s opinion is that the strongest legal rationale for the 280E exemption is a legal argument based on the 16th Amendment and the Constitution’s Dormant Commerce Clause. The argument asserts that the IRS has no right to impose 280E on the marijuana industry because the entire “legal” industry is all siloed within state boundaries, meaning there’s no interstate commerce for the federal government to regulate or tax.

    Another factor is the cannabis rescheduling proposal by the Biden administration, to reclassify marijuana to Schedule III from Schedule I — a move that, if completed, would nullify 280E for cannabis companies. But the federal rescheduling process has been stuck in limbo since President Donald Trump took office in January, with its future unclear, leaving marijuana businesses to rely on more speculative tax theories for financial relief.

    There are also other legal tax arguments that marijuana attorneys and CPAs have been relying upon, such as Botillier’s approach of relying on a formal opinion from the U.S. Department of Health and Human Services last year that stated cannabis doesn’t fit the definition of a Schedule I or Schedule II drug, and more properly belongs in Schedule III. That, Botillier said, is very arguably enough to justify cannabis companies’ claims of 280E exemption, because 280E is only supposed to apply to those who deal in the most restrictive of narcotics, not in drugs that are categorized in Schedule III. Botillier said he’s been filing amended tax returns since the middle of last year with that rationale for marijuana businesses.

    Will IRS respond?

    The primary question, sources agreed, is what will the IRS do next? The agency has three years to audit any given tax return, and so far, few cannabis companies have passed that mark and kept their refunds.

    “The big question around all this stuff is what is the IRS ultimately going to do with this? What position are they going to take?” Karnes said. “Because they came out twice publicly on two different IRS bulletins, saying pot companies have to pay 280E basically. And every company's kind of looked the other way in terms of that directive. And it's not a big secret that people are not paying. So it's like, well, why haven't they done anything?”

    The IRS has already rejected many of the 280E exemption positions taken by cannabis companies, Mann added, and a clear consensus on an anti-280E industry playbook hasn’t yet really emerged.

    “Some of my clients have gotten refunds back from the IRS on amended returns and significant amounts, and others in the industry report that as well,” Mann said. “But there are also reports of amended returns that were filed that were not accepted by the IRS. And so no refund was issued.”

    Businesses whose 280E exemption claims are rejected may then try to negotiate some sort of payment plan with the IRS, or simply threaten to shut their doors and not pay the government a dime, depending on how bad their financial situation is, Mann said. Which begs the question, he said, how will the situation play out for those with whom the IRS disagrees?

    “I think they're hoping that even if they are challenged by the IRS on audit, and even if the IRS ultimately prevails, the cannabis companies will say, ‘Okay, you win. And we can't pay the full amount, including penalties and interest. Now what we have to do is compromise,’” Mann said.

    Mann pointed out that such a play worked for the now-defunct California cannabis company StateHouse Holdings, which was put onto a 10-year payment plan by the IRS in 2022 for an unpaid $22 million tax bill, before it went belly-up last year and was auctioned off to repay creditors. Many in the industry cite the StateHouse example as a potential worst-case scenario, Mann said.

    But that, Mann said, is probably not the most sound business strategy for long-term success.

    “They're taking a very big bet on an untested tax position,” Mann said. “They're betting the farm on a bet that you might not make at a casino. They're betting the farm on something that's going to pay off 20% of the time. Well, if it doesn't pay off 80% of the time, their companies go under.”

    Whether the IRS will be willing to actually compromise with cannabis companies on their tax bills is also an open question, Mann emphasized, especially given the multi-million-dollar salary levels of some marijuana company executives.

    “If these big MSOs are going to enter into offer in compromised proceedings (with the IRS), they will have to justify their expenses, including amounts paid as compensation to people at the company, which in some cases are very, the compensation package is significant,” Mann warned.

    All of the cannabis companies identified in this story declined to comment or did not respond, with the exception of MariMed.

    MariMed CFO Pinho said that most public cannabis companies have been transferring their 280E debts to an “uncertain tax position” and listing them on their balance sheet as long-term liabilities, but he also agreed that doing so could invite an IRS audit, meaning the tax savings trend is on notably thin ice from a legal perspective.

    “They might still be subject to further audits. I know there's a lot of cases out there, and most of them are a constitutional type of argument,” Pinho said, adding that MariMed has thus far filed only one restated tax return. “They probably still have the true tax liability because they're hedging, saying, ‘Hey, we're going to file our tax returns based on our view,’ but the IRS might come back and say, ‘Hey, I don't believe you. The tax rules still say you can't deduct these expenses, so then you actually have to pay all these taxes.’”

    At least some of those businesses are clearly ready for a fight with the IRS over the matter, however.

    “We've said all along that the likely outcome here is litigation, which we again are ready for,” Trulieve CEO Kim Rivers said during the company’s fourth quarter earnings call.

    Earlier in the year, Trulieve CFO Wes Getman also warned investors on an earnings call, “Final resolution to our approach may ultimately take years to conclude.”

    Las Vegas-based Planet 13 Holdings Inc.'s CFO Dennis Logan also said during his company’s third quarter earnings call last year that he’s expecting “a $35 million tax refund that the IRS will then fight us for.”

    Pinho and others repeatedly noted that the specific legal justifications for the 280E exemption vary greatly between different companies, and it’s not even clear which rationale Trulieve used to obtain its nine-figure refund from the IRS.

    “It’s company by company,” Pinho said.

    But, he agreed, the cumulative financial effect for the sector as a whole is “huge.”

     

     

    by Crain's New York Business

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