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One of the most fundamental questions facing any businessperson in the cannabis industry and every other industry is: “What type of business entity should I use?”

This is such a loaded question that your lawyer or accountant will first respond with, “That depends,” and then they will need to ask you at least ten follow-up questions to understand your goals and expectations, as well as the goals and expectations of your business partners and financiers. Some of these follow-on questions are tax-driven; others are regulatory-driven; others are dictated by financing relationships; and still others deal with control and flexibility within your business.

This is Part 1 of a two-part series. In Part 2, I will discuss more in depth the difference between and among various legal entities from which you can choose. For those who are wondering whether it is “really necessary” to use a business entity instead of just hanging out your shingle, know that your properly established and maintained business vehicle puts the “limited” in “limited liability.” And don’t forget insurance (here and here) and clean business contracts (here), both of which are also essential in helping you sleep at night.

Some types of industries are relatively low risk (NOT cannabis); some business owners are relatively judgment-proof (but it’s hard to start a business if you have no assets); and some business owners like to drive their cars without windshields and seat belts (neither they nor their businesses tend to last very long). I get that many potrepreneurs are used to taking on more than their fair share of risk, but my short response is: forming a business entity is a relatively inexpensive foundation upon which to build a solid business. Don’t ever cut corners in your business, but really don’t cut corners when it comes to your business entity (or getting good insurance or having great contracts in place).

Let’s go over some of these important questions to help you decide how to move forward with your entity selection.

The tax-related questions:

• Do you or any of your fellow owners need to offset revenue in other business ventures?
• Do you or any of your fellow owners need to maximize losses in this business venture? (i.e. will you be 50/50 in the business ownership, but your business partner wants to capture 100% of the losses in the startup years of the business?)
• Are any of your owners non-residents?
• If taxed as a pass-through, will you and other owners be prepared to pay all taxes owed while the company builds out its balance sheet?
• Does your business plan involve real estate ownership?
• Will your business own other assets that are likely to appreciate over time?
• What is the anticipated impact of IRC 280E on your business model?

The regulatory questions:

• Do your state’s cannabis regulations require you to use a particular business entity? (i.e. some states required all licensees to be nonprofit entities or “entities operated on a not-for-profit basis”).
• Do your state’s regulations require full transparency in entity ownership?
• If possible, do you want to keep some of the business’ owners out of the public eye?

The purpose-related questions:

• Are you going to operate your business with a specific mission so that you can draw investment funds from particular types of investors?
• Are you going to operate your business with a specific mission so that you can provide something good to the world by furthering education, providing charitable assistance, or stepping in to help where governmental resources cannot address needs in your community?

The financing-related questions:

• Do you intend to have outside financiers involved, such as private equity or venture capital? If so, have your prospective investors made any requests regarding the type of entity in which they prefer to invest?
• Do you intend to give all owners equal rights to profits, or do you intend to have different classes of ownership (i.e. preferred vs. common ownership interests and voting vs. nonvoting interests)?
• How many owners do you expect to have in the first five years of the business?
• Will any of your owners consist of C corps or S corps?
• Do you intend to take the company public as soon as your business model and U.S. laws permit it?
• How do you intend to get funds from the company to the owners: via salary, debt payments, distributions, or something else?

The control and flexibility-related questions:

• Do you intend to have a small group of owners or a larger group?
• Do you intend that all owners will have equal rights to profits and to decide when profits are distributed?
• Are you a part of the minority owner group or majority group?
• What type of governance structure do you envision working best for your company? Small or large?
• Do you intend to hire outside management for the business?

The answers to these questions will help your legal or tax advisor help you make the right decision on what type of entity to choose and what to do with that business entity. For instance, just because you are already using an LLC does not mean that you cannot take advantage of making a Subchapter S election with that LLC. You just need to have a good reason for doing so, time it correctly, and your accountant needs to know and agree with you. The same is true if you want your business to be taxed as a C corporation or you want to convert your entity to another type of entity.

In a future post we will dig in more deeply to the advantages and disadvantages in the various types of entities you can choose. Stay tuned!

We’ve written about the potential benefits of harnessing the power of blockchain technology to track and trace cannabis from seed to sale and provide an effective regulatory tool for governments (see here and here). We’ve also warned of the risks and dangers (and outright scams) associated with many cryptocurrencies and the heightened risks that come when a federally prohibited substance is combined with use of typically anonymous cryptocurrencies.

I have been writing and speaking about the potential benefits of blockchain in a variety of contexts, not limited to cannabis. Last month, I spoke about the benefits of blockchain for local governments on a panel hosted by the International City Managers Association, Government Finance Officers Association, and National League of Cities. The consensus in terms of local government use is that blockchain technology has the potential to provide tremendous benefits to local governments in terms of efficiency and transparency, but that it is still very much in the development stages and great skepticism should be exercised when presented with opportunities to implement it. There are still a great deal of scams and misinformation surrounding blockchain technology, especially in the context of cryptocurrency.

A handful of cities and states are pioneering the way forward in adoption of blockchain technology use. This week, California Assembly Members Ting and McCarty introduced AB 953, which would allow local governments accept city or county cannabis license tax amounts due by payment using “stablecoins.” The bill would authorize local governments to either accept stablecoins directly into a digital wallet controlled by that jurisdiction or to utilize a third-party digital asset payment processor that allows for the immediate conversion of any payments made by stablecoins into United States dollars and deposit into an account of that jurisdiction. The vulnerability of digital wallets is explained in my white paper.

A stablecoin is defined in the bill as: “a digital asset that has price stable characteristics pegged to United States dollars and United States dollars serve as collateral to that digital asset.”

Digital asset is defined as “a digital representation of value that is used as a medium of exchange, unit of account, or store of value and is not legal tender, whether or not denominated in legal tender.”

We are very interested in watching how this bill plays out in the Assembly, and will keep the blog updated as things progress. We are skeptical that this particular proposal will succeed, but encouraged that the State Legislature continues to search for viable banking solutions for the cannabis industry. Stay tuned: the bill may be heard in committee on March 24.

In this case, Alternative Health Care Advocates provided medical marijuana to individuals in California under California law. Another company, Wellness Management Group, Inc., provided management services to Alternative Health Advocates. These services included hiring employees and managing HR for those employees, paying wages for those employees, paying advertising expenses, paying rent, etc. Wellness did not provide services of that nature or any nature to any other business entity. Wellness made money by collecting fees for its services from Alternative Health Care Advocates.

Under Section 280E of the Internal Revenue Code, businesses that are engaged in trafficking controlled substances cannot take regular business deductions, so they end up paying taxes on their gross receipts less their allowed cost of goods sold (COGS). If an expense doesn’t fit into the category of COGS, a company that is considered to be “trafficking” would have to pay taxes as if the expense hadn’t been incurred in the first place. This is how the effective tax rate for marijuana businesses can be outrageously high.

Marijuana businesses set up management companies for a few reasons. Tax avoidance under 280E can be one of them, but trying to set up a management company structure to avoid 280E-related tax problems can be complex and can backfire. Instead, most of the value of the management company model comes from the ability of the management company to get banking and enter into regular electronic transactions with third parties, including running payroll services.

But the model backfires if the management company is considered to be trafficking, because a management company introduces new transactions to the system involving the same pot of money. Imagine that a marijuana retail company generates $1 million and has $500,000 in 280E non-deductible expenses. That company standing alone would pay tax on the full $1 million. Now imagine that a management company is set up to handle the $500,000 in expenses and charges the marijuana company $500,000 to do so. The marijuana company now has $1 million in revenue and a non-deductible $500,000 bill to the management company and pays taxes on $1 million. The management company receives $500,000 from the marijuana company and pays salary and other expenses that also equal $500,000. If the management company is treated like any other business, the transaction is a wash and ends the same way as if there were no management company. If the management company is deemed to be “trafficking” however, then the marijuana business will find itself paying tax on both entities for the same revenue. The $500,000 paid to the management company ends up being taxed twice.

Unfortunately, the Tax Court decided that Wellness’s management activities were “trafficking” as much as Alternative Health Care Advocates’ activities were. In response to the taxpayers’ arguments that disallowing the 280E deductions for both businesses was inequitable, the Tax Court simply stated that the tax consequences were a direct result of the organizational structure the taxpayers put together.

Here are the takeaways for existing businesses, especially management companies. First, it’s worth noting that this case will likely be appealed, so keep an eye on that. Second, businesses have to plan their transactions involving management companies as if management company revenue is subject to 280E. Some management companies that offer broader services to a variety of different businesses may have some additional arguments that they are not engaged in “trafficking.” But if your management company is just a stand-in for your operating marijuana company, the Tax Court has indicated that it will approve of the IRS considering you to be trafficking as well. This case is one more reminder that Section 280E presents an ever-present obstacle to the ongoing health of marijuana businesses. Advocates must continue to concentrate their efforts to finally get Congress to repeal Section 280E.

All in all, Tuesday was a good day at the state and national level. But cannabis wasn’t just on the ballot at the state or national level—many cities had measures on that would regulate cannabis in one form or another. This post discusses some of the more impactful ballot measures that won and lost in California.

To start, dozens of cities and counties in California had cannabis taxation measures, which is a good sign for the expanding market. Oakland voters, for example, approved of Measure V, which amends the local code to allow cannabis manufacturers and cultivators to deduct the value of raw materials when calculating gross receipts for tax purposes. Fresno voters approved of Measure A, which adopts a cannabis business license tax. As noted above, numerous cities had tax measures on the ballot—and they are quite literally all over the map.

El Dorado County had a number of cannabis measures on its ballot. Measures P, Q, R, and S each passed, allowing the retail sale, delivery, distribution, and outdoor/indoor cultivation of commercial cannabis for recreational and medicinal purposes. Interestingly, El Dorado County’s Measure N (a tax measure), didn’t pass.

Los Angeles County’s well-publicized Measure B, which would have established a municipal bank, failed. This was a closely watched measure in the cannabis industry, as many had hoped for a local bank in which to bank their earnings. Because the California effort to charter a state bank has cooled, local businesses may have limited options until a federal fix occurs.

Elsewhere, the City of Malibu passed Measure G, which will now allow retail sales of commercial cannabis and deliveries. Before, Malibu only allowed medicinal sales. But wait before delivering into Malibu from other cities; you’ll need a regulatory permit from the City of Malibu to do so. No word yet on what that application process will look like.

As noted above, these are just a few of the measures that were adopted (or not) on Tuesday. California, like many other places nationally, is certainly moving toward a more open marijuana landscape.

Well, not any longer. In addition to the seven-month lockup, Price was ordered to pay the I.R.S. $262,776 in restitution on the nearly $1 million in taxable income he raked in from 2011 to 2014. He will probably never be allowed to participate in the OLCC program again, given the agency’s recent tightening of the screws, and its authority to bar anyone with a federal conviction “substantially related to the fitness and ability of the applicant” to obtain a license.

Generally speaking, marijuana businesses are liable for lots of tax under IRC 280E. As cannabis business lawyers, we work with CPAs and others to attempt to mitigate our clients’ tax liability, but at the end of the day, that liability is always there. Tax obligations do not end at the federal level, of course: Most states have income tax programs, and all states with legal cannabis programs seem to collect additional taxes on the sale of marijuana. In Oregon, for example, that sales tax must be escrowed by OLCC retailers and paid to the state Department of Revenue. As to Matthew Price, the news reporting was silent on whether he was also shirking those payments.

Having advised state-legal cannabis businesses since 2010, we have seen a lot of monkey business when it comes to tax. We have seen bad lawyers advise clients not to pay taxes, on the theory that tax programs violate business owners’ rights against self-incrimination. We have seen businesses attempt to claim “non-profit” status and avoid taxes in that manner, despite the impossibility of receiving an I.R.S. exemption. And we’ve seen lots of “management company” schemes, most of which are nonsense. At the end of the day, a baseline level of tax is unavoidable.

Interestingly and appropriately, the judge in this case didn’t seem to treat Price differently because his income derived from cannabis sales. It was reported that federal prosecutors petitioned the judge to go hard on Price, in order to send a message to the marijuana industry. The judge wasn’t having that:

The fact that the product involved here is marijuana is utterly meaningless to me in passing a sentence,” the judge said. “It’s a tax case to me.”

That didn’t stop the Justice Department from bragging a bit, but it’s encouraging to see cannabis entrepreneurs being treated like everyone else — in theory, anyway — and for better or worse. On that point, we have often said on this blog that just because someone is violating one federal law by trading in cannabis, that doesn’t make it a good idea to violate all the others. And we always advise entrepreneurs to run their cannabis business like real businesses. That includes paying taxes.

On July 20, 2018, the CDTFA released its discussion paper on proposed rulemaking regarding the administration of the cannabis cultivation and excise taxes. This blog post highlights the issues addressed in the proposed regulation.

By way of background, on August of 2017 the CDTFA promulgated two emergency regulations. The first, Regulation 3700, Cannabis Excise and Cultivation Taxes, was promulgated to ensure that essential guidance was available when California’s regulated cannabis market became operational on January 1, 2018. The second, Regulation 3701, Collection and Remittance of the Cannabis Excise Tax, was promulgated to clarify the imposition, collection, and reporting of the Cannabis Excise Tax. We previously discussed these regulations here, and we a discussed the Cultivation and Excise Tax here and here.

The CDTFA will not take action on Regulation 3701. However, the CDTFA has proposed many revisions to Regulation 3700. We summarize them below, and provide some commentary throughout.

• Expands the definition of cannabis flower to include trimmed or untrimmed flower but excludes leaves and stems removed before sale. The consequence of this proposed change is to assure that even trimmed flower will be taxed at the highest tax rate of $9.25 per dry weight ounce.
• Clarifies that “fresh cannabis plant” must be identified as fresh cannabis plant and recorded in the upcoming track-and-trace system. Until the track-and-trace system come online, a paper invoice or manifest must indicate that “fresh cannabis plant” is being transferred. This documentation is important. Fresh cannabis plant is taxed at the lowest rate of $1.29 per ounce; the proposed change clarifies what information is required to support paying tax at the lowest cultivation tax rate.
• Prohibits separately stating the cannabis excise tax on the receipt provided to a retail cannabis customer. Instead, the regulations require the invoice to state “The cannabis excise taxes are included in the total amount of this invoice”. Retailers purchasing from third-party distributors must compute the excise tax based on their wholesale cost plus 60% mark-up as determined by the CDTFA. Separately stating the excise tax allows a consumer to determine the wholesale cost of a cannabis retailer. The proposed prohibition does not provide retailers the flexibility to disclose the computation of the tax to its customers.
• Clarifies that transactions between two distributors must document that no cannabis excise tax was collected or remitted on the transaction. That is, the distributor that sells cannabis to the cannabis retailer is the one responsible for collecting and remitting the cannabis excise tax to the CDTFA.
• Clarifies that invoices documenting the cultivation tax must disclose the weight and category of the cannabis that entered the commercial market. This change is to assure that the receipt a manufacture provides to a cultivator includes the weight and category (i.e., cannabis flower, cannabis leaves, or fresh cannabis plant) of cannabis transferred. The weight and category must match the information in the track-and-trace system.
• Requires a manufacture to provide a distributor (or next party in the transaction) an invoice or manifest that documents the weight and category of cannabis used to produce the cannabis product. This change is to assure that a distributor has the necessary information to properly collect and remit the cultivation tax to CDTFA.
• Clarifies that a cannabis accessory is not subject to the 15% excise tax. When a cannabis product is sold with a cannabis accessory, the cannabis retailer must segregate the wholesale cost of cannabis from the wholesale cost of the cannabis accessory on the customer receipt. If a cannabis retailer is unable to segregate the wholesale cost, the cannabis excise tax will include the wholesale cost of the cannabis accessory in the computation. The proposed regulation places the burden on the retailer to segregate its wholesale costs to avoid including the cost of a cannabis accessory from the excise tax paid by a cannabis consumer.
• Clarifies that a 50% penalty is imposed for unpaid taxes. The 50% penalty is added to the cultivation or excise tax not paid by the due date.  For example, the tax payment for the third quarter of 2018 is due October 31, 2018.  A payment on November 1, 2018 would subject the distributor to the 50% penalty. Although the penalty can be waived for reasonable cause, a best practice is to always file and pay your cultivation and excise taxes on time.
• Introduces proposed Regulation 3702 which requires the following information to be entered into the California track- and-trace system including: name of originating seller of cannabis; name of retailer purchasing cannabis; unique identifying number of cannabis supplied to the retailer; and the retailers wholesale cost. The CDTFA intends to use the track-and-trace system to collect real data to assist in their determination of the appropriate mark-up used in determining the average market price the computation of the excise tax.

The regulations discussed above are only proposed and may change as CDTFA considers comments and another stakeholder input.  Nonetheless, many of the recommendations contained in the proposed regulations are already on the CDTFA website. For example, the CDTFA website provides that “the flower category includes all dried flowers of the cannabis plant, whether trimmed or untrimmed”. So some of these provisions seem very likely to stick.

California cannabis businesses should continue to monitor these regulations as the CDTFA considers stakeholder comments and likely revises some portion of the proposed regulation. As the regulations develop, business owners should also revisit their tax strategies and operational protocols for tax efficiency.

For more on California’s cannabis tax regime, check out the following:

Alpenglow Botanicals LLC is a medical marijuana business. The IRS audited Alpenglow’s tax returns and determined Alpenglow was trafficking in a controlled substance and so it denied the company’s business deductions under IRC §280E. Alpenglow paid the tax assessment and filed for a refund, which was subsequently denied by the IRS. Alpenglow then went to federal court to recover its refund claim. In court, Alpenglow made the following three arguments:

• The IRS does not have authority to disallow deductions under IRC §280E unless the taxpayer has a criminal conviction for trafficking;
• IRC§280E violates the 16^th Amendment of the U.S. Constitution; and
• IRC §280E violates the 8^th Amendment of the U.S. Constitution.

The Court rejected all of these arguments.

The Court determined that a criminal conviction is not a prerequisite for the IRS to apply IRC 280E and that the IRS has the authority to determine on audit that a taxpayer is trafficking in a controlled substance. The Court relied on its earlier decision  in Green Solutions Retail Inc. where it stated that “the IRS’s obligation to determine whether and when to deny deductions under IRC §280E, falls squarely within its authority under the tax code.” The Court in Alpenglow went further than Green Solutions in ruling that there’s no evidence Congress intended to limit the IRS’s investigatory power here.

Alpenglow cited a line of U.S. Supreme Court cases for the proposition that courts have invalidated regulations involving the taxation of illegal conduct — these cases strike down the imposition of a tax as a violating a taxpayer’s 5^th Amendment right against self-incrimination. The Tenth Circuit Court distinguished those cases, noting that Alpenglow is challenging the IRS’s very authority to tax and investigate illegal activity at all  and held that this prior line of cases don’t apply to the denial of a tax deduction as opposed to the imposition of a tax.

The Court also determined that IRC §280E does not violate the 16^th Amendment, which grants Congress the power to tax “income,” or the 8^th Amendment, which prohibits the federal government from imposing “excessive fines.” The Court ruled that IRC §280E is not an unlawful penalty and disallowing a deduction is not a “punishment.”

Most importantly, this court’s decision on IRC §280E is going to have real life implications for many cannabis businesses. Every cannabis business that has filed a tax return challenging the application of IRC §280E should immediately review its tax returns and reevaluate their options.

By now, the destructive force of IRC §280E is well known. IRC §280E disallows deductions and credits to a business trafficking in a controlled substance. One exception is cost of goods sold (“COGS”). Other than a 2015 IRS General Counsel memorandum, the IRS has not offered much guidance regarding the application of IRC §280E. With this gap in IRS guidance, it is the courts that have outlined the (fairly narrow) parameters of IRC §280E.

Reading the IRS guidance and court rulings together, it is clear that selling or growing cannabis is always considered trafficking and expenses related to such activity are disallowed. A cannabis business can deduct all expenses related to a separate trade or business. A court is more likely to accept a separate business activity if that business can operate independently of a cannabis business.

Alterman

Alterman does not offer broad guidance regarding IRC §280E. In part, this is because the Court issued a Memoranda opinion.  A Memoranda opinion does not set a precedent for taxpayers; however, they are useful to illustrate how the Court may analyze the law.

Laurel Alterman and William Gibson operated a Colorado medical marijuana grow and dispensary. These taxpayers also sold cannabis paraphernalia, hats and shirts. The Court held that the sale of paraphernalia, hats and shirts was not a separate trade or business primarily due to the lack of records. Accordingly, costs associated with these activities were not deductible under IRC §280E.

In addition, the Court determined that certain costs were not allowable as COGS because of insufficient records, which should be a lesson to any cannabis business owner: It’s not enough to have potentially deductible costs, if you don’t keep records! Interestingly, the opinion uncharacteristically discusses, in detail, the records available, only to hold that those records were insufficient. (Court cases that disallow deductions because of poor recordkeeping typically do not discuss in detail, the records examined.)

Because of the fact-specific nature of this case, Alterman offers little guidance to cannabis businesses other than recordkeeping must be sufficient to support deductions.

Loughman

In Loughman, the Court did not address the issue of record keeping or substantiation. Instead, the Court addressed the issue of double taxation of income because of IRC §280E. And the Court concluded that double taxation is allowed.

Jesse and Desa Loughman were licensed in Colorado to grow and sell cannabis through a Colorado corporation, Colorado Alternative Health Care (“CAHC”). The Loughmans were the sole shareholders of CAHC and elected to be treated as an S Corporation for federal tax purposes.

An S corporation is not subject to tax; instead shareholders are taxed on S Corporation income at the individual level. Special rules treat S Corporation shareholder/officers as employees and require the S Corporation to pay them a reasonable wage. Under ordinary circumstances, an S Corporation deducts shareholder/officer wages; the shareholder/officer then pays income tax on the wages. The S Corporation’s deduction of wages prevents double taxation.

In this case, the IRS applied IRC §280E and disallowed CAHC’s deduction for wages paid to the Loughmans. Consequently, the amount of S Corporation income passed through to the Loughmans increased. The result is that the Loughmans wages are taxed twice — first as an employee and then as S Corporation shareholders.

The Court rejected the argument that IRC§280E discriminates against S Corporation shareholders operating a cannabis business. The Court reasoned that wage payments to a third-party performing the same services as the Loughmans would not be deductible under IRC §280E. Accordingly, the amount of pass through income to the Loughmans would not change: IRC §280E applies equally to increase S Corporation income, regardless of who receives wages. Furthermore, the Court noted that the taxpayer did not have to, but chose to, elect S Corporation status for their cannabis business.

As in Alterman, the Court issued a memorandum opinion. Accordingly, the Court’s determination only applies to the Loughmans and does not set precedent. Nonetheless, the Court highlighted a serious disadvantage to operating a cannabis business through an S Corporation– namely, double taxation.

The STATES Act

So where does that leave us? These cases highlight the dire need for a legislative fix of IRC §280E. On June 7, 2018, Senators Gardner and Warren introduced the Strengthening the Tenth Amendment Through Entrusting States Act (The “STATES Act”). The STATES Act exempts persons from the Controlled Substances Act, so long as they are acting in compliance with a state’s cannabis law. Specifically, under the STATES Act, the production or sale of cannabis in a cannabis legal state “shall not constitute trafficking”. Because IRC §280E applies to a trade or business that consists of trafficking, the STATES Act would effectively eliminate the impact of IRC §280E.

As more cannabis businesses are audited, expect more cases like Loughman and Alterman to move through the system. In addition, expect similar results on similar facts, unless Congress finally takes action. The STATES Act would do a lot of good for the industry, and eliminating the oppressive impact of IRC §280E is high on the list.