Category Archives: Risk Management

The Need to Comply With the CTA comes Into Focus

October 8, 2024 was a bellwether date for those waiting on a court to clarify whether the statutory requirement for filing BOI Reports sits on solid ground.  It was on October 8, 2024 when the oral argument in the pending Eleventh Circuit appeal from Small Bus. United d/b/a Nat’l Small Bus. Ass’n v. Janet Yellen, Case No. 5:22-cv-01448, Dkt. No. 52 (N.D. Ala. Mar. 1, 2024) was released to the public.   

Given the tempo and questions raised during this September 27, 2024 hearing, reporting companies can now reasonably assume there is likely no longer any reason to delay filing their BOIR Report based on any perceived lack of judicial clarity.  Before the end of the year – the deadline for over 30 million reporting companies, subject companies should likely file their BOI Report because there is no Judge that will likely remove that obligation. 

While it is never easy to predict which way the judicial winds blow, it seems likely the Eleventh Circuit will at least remand the Alabama decision for further review of the Fourth Amendment argument raised during that hearing – something not touched upon by the court below, if not just rule outright for reversal.  The appellee raised the Fourth Amendment argument because federal, state, local and foreign law enforcement can access BOIR data without the need for a Court Order.  Overall, the Judges – especially the Honorable Andrew L. Brasher who was appointed in 2020, seemed skeptical of this and all other arguments suggesting that Congress passed in 2021 the Corporate Transparency Act (“CTA”) without proper Constitutional footing.

The Eleventh Circuit hearing is on the heels of a District Court Judge in Oregon denying requested injunctive relief, in part, by ruling the CTA was likely constitutional.  See Michael Firestone, et al. v. Janet Yellen, Case No. 3.24-cv-1034, Dkt. No. 18 (D. Or. Sept. 20, 2024).  Indeed, in the second of two supplemental filings with the Eleventh Circuit, the appellee tried to distinguish the Oregon case as well as a recent Supreme Court case that may have shifted the burden in this case slightly in favor of the government – a case the Eleventh Circuit requested supplemental briefing on in its August 14, 2024 Order.  Not surprisingly, the government filed a contrary reply with the Court

As it stands, the Eleventh Circuit and the Court of Appeals of the Ninth Circuit – by way of the likely appeal from the Firestone decision, will squarely rule upon the constitutionality of the CTA – setting up the exact sort of case the Supreme Court likes to hear, namely an appeal where more than one Circuit Court rules on the constitutionality of a far-reaching federal statute. 

Indeed, there are other Courts of Appeal that could also likely chime in on this issue given pending District Court cases, including the First Circuit (William Boyle v. Janet Yellen, Case No. 2:24-cv-00081 (D. Me. filed Mar. 15, 2024) and Black Econ. Council of Mass., Inc. v. Janet Yellen, Case No. 1:24-cv-11411 (D. Mass. filed May 29, 2024)); the Fifth Circuit (Texas Top Cop Shop, Inc. v. Merrick Garland, Case No. 4:24-cv-00478 (E.D. Tex. filed May 28, 2024)), the Sixth Circuit (Small Bus. Ass’n of Mich. v. Janet Yellen, Case No. 1:24-cv-00314 (W.D. Mich. filed Mar. 26, 2024) and Robert J. Gargasz Co. LPA v. Janet Yellen, Case No. 1:23-cv-02468 (N.D. Ohio filed Dec. 29, 2023)); and the Tenth Circuit (Taylor v. Janet Yellen, Case No. 2:24-cv-00527 (D. Utah filed July 29, 2024)).

This mosaic of potentially conflicting upper court decisions leaves little doubt that in the short term FinCEN holds the upper hand and might use such built-up judicial equity to aggressively enforce its BOIR regulations in 2025.  One thing is for sure – the only way this fast-approaching BOIR Train gets derailed is by either the Supreme Court – which is unlikely given the very case the Eleventh Circuit sought briefing on, or by Congress – which is even less likely given the treasure trove of information derived from the CTA may be useful for tracking individuals with large cryptocurrency holdings and eventually bringing in more money into federal coffers as well as potential crime prevention.

Practical Steps for Advising on BOIR Compliance

When advising clients on filing FinCEN’s Beneficial Ownership Information (BOI) reporting obligations, professionals should offer clear, practical guidance to ensure compliance and mitigate potential risks. 

It is obviously helpful to start out by educating small business clients on the fundamentals of BOIR filing:

   – Who needs to file: Explain that most small corporations, LLCs, and similar entities must comply unless specifically exempt.

   – What needs to be reported: Discuss the required information, such as names, dates of birth, addresses, and ID numbers of beneficial owners (anyone with 25% or more ownership or substantial control).

   – Filing deadlines: Highlight the deadlines—new businesses must file upon formation, and existing businesses have until the start of 2025.

Small business ownership structures can be complex.   Professionals should emphasize that beneficial ownership extends to anyone with substantial control, even if their equity stake is less than 25%.  For example, CPAs should direct their clients to experts who can help them identify all individuals who qualify as beneficial owners, ensuring no key person is missed.  Discuss how trusts are to be handled.

The importance of accurate and up-to-date documentation should be stressed:

   – Maintain records: Recommend that clients keep detailed records of beneficial owners and any changes over time. Establishing a system for periodic updates will help ensure compliance in the future.

   – Secure documentation: Encourage clients to securely store identifying information, such as government-issued ID numbers, to ensure data privacy and protection.

Professionals should inform clients of the risks of non-compliance:

   – Fines and penalties: Non-compliance can result in daily fines of $591 per day, potentially leading to substantial financial liability.

   – Business risks: Emphasize that failing to comply could lead to regulatory investigations or civil penalties, which can be costly and damaging to the business’s reputation.

For businesses that may find the filing process challenging, you should either:

   – Assist with filing: Offer to help prepare and file the BOIR on behalf of the client or coordinate with professionals focused on such filings.

   – Refer to a Compliance specialist: CPAs can also recommend working with a compliance expert or other professional specializing in corporate governance and regulatory filings.

Clients should be told to approach BOI filings proactively:

   – Plan for future updates: Encourage clients to set up procedures for regularly reviewing and updating beneficial ownership information to avoid missing future reporting obligations.

   – Consult early: Suggest addressing BOIR filing well in advance of deadlines to prevent rushed submissions that could lead to errors. Professionals who are diligent and invest the time can easily help their clients navigate FinCEN’s BOI reporting obligations effectively, minimizing risk and ensuring ongoing compliance.

Risks of Non-Compliance with FinCEN’s BOI Reporting Rule

Non-compliance with FinCEN’s Beneficial Ownership Information (BOI) reporting requirement could expose your business to significant financial and legal risks. Here’s what you need to know about the potential consequences of failing to comply with this critical regulation.

FinCEN has the authority to impose hefty fines on businesses failing to meet the BOI reporting requirement. Penalties for non-compliance is $591 per day, with no maximum cap. This means even small delays in filing could result in substantial financial costs if FinCEN targets your company.

Non-compliance with BOIR can be seen as an attempt to obscure ownership information, which could trigger further investigation into potential financial crimes.

Businesses found to be in non-compliance with the BOI reporting requirements may also suffer reputational damage. Investors, clients, and partners expect transparency in ownership structures, and failure to comply could result in a loss of trust and business opportunities.

Non-compliant businesses may find it harder to secure loans, attract investors, or engage in mergers and acquisitions. Transparency in beneficial ownership is becoming a key factor in financial and business transactions, and non-compliance could hinder growth opportunities.

As of today, there are no reported instances of fines being assessed against a company for violation of the BOI reporting rule.  Nevertheless, the risks of non-compliance with FinCEN’s BOIR requirement far outweigh the effort of filing. Businesses that take proactive steps to meet the reporting deadlines and maintain accurate information will avoid fines, legal action, and reputational harm. Make compliance a priority to safeguard your business.

Five Common Mistakes to Avoid Before Filing Your BOI Report

Business owners preparing to file their Beneficial Ownership Information (BOI) reports should be aware of common pitfalls that might lead to civil penalties or worse.

The most common mistake is identifying one owner but not identifying every individual qualifying as a beneficial owner. Even if someone owns less than 25% of the business, that person may still be considered a beneficial owner if they hold significant decision-making authority evidencing “substantial control” over the reporting company.

For example, an indirect way to exercise substantial control over a reporting company is by controlling one or more intermediary entities that separately or collectively exercises substantial control over a reporting company. The best way to avoid this mistake is to review your company’s structure carefully and consult an expert if you’re unsure about who is a potential beneficial owner.

Another likely common mistake is submitting incorrect or incomplete details for beneficial owners. Mistakes in names, dates of birth, or identification numbers can lead to rejected filings or regulatory scrutiny – and possibly even fines and jail time if done deliberately. This mistake can easily be avoided by double-checking all information before submission and ensuring you’ve provided accurate and up-to-date details.

A third common mistake is failing to timely file. Businesses underestimate how long the process can take, leading to missed deadlines. For new businesses, filing is required 90 days after formation or registration, while companies formed or registered prior to 2024 have until January 2025 to comply. Companies can avoid this potential problem by marking important dates on your calendar and preparing your filing early to avoid a last-minute rush and a possible $591 a day fine for an untimely filing.

A fourth mistake would be the failure to update information as it changes. As set forth in the applicable regulations, the failure to update beneficial ownership information as changes occur can result in non-compliance. Any changes in ownership or control must be reported within thirty days of the change. This can be avoided by Implementing an internal system to track changes in ownership and file updated reports with FinCEN when necessary.

The fifth common mistake is simply assuming the existence of an exemption without really confirming it applies. Certain businesses, like larger companies already subject to similar rules, are exempt from the BOI reporting requirement. Assuming you are covered by an exemption without having proper confirmation could lead to fines. This can be avoided by double checking your exemption status by consulting the list of exempt entities or seeking expert advice. For example, even if your company has filed for dissolution, that would not automatically exempt you as an inactive company if that dissolution took place in 2024.

Avoiding these five common mistakes will help ensure a smooth BOI reporting process. By simply taking the time to understand key requirements and double-checking your information, you can protect your business from most of these unnecessary risks.

Preparing Your Business for FinCEN’s BOI Reporting Rule

With the Beneficial Ownership Information (BOI) reporting requirement now in effect, many businesses are wondering how to comply with this new rule issued by the Treasury Department’s Financial Crimes Enforcement Network (FinCEN). Preparing early will help you avoid fines and penalties, ensuring a smooth filing process.

The first step is determining who qualifies as a beneficial owner. This includes anyone who exerts substantial control or has ownership of 25% or more in your business. It’s crucial to assess both direct and indirect control, so be sure to evaluate individuals who might have critical influence over decision-making even if they don’t own a large percentage of equity.

You will need the following details for each beneficial owner:

  • Full name
  • Date of birth
  • Residential or business address
  • A government-issued identification number (such as from a driver’s license or passport)

Having this information on hand before filing will streamline the process and ensure accuracy.

If filing for an entity formed in 2024, you will also need to provide similar details for “applicants”, namely those persons who filed formation or registration documents with the state of formation or registration.

New businesses must file their BOI reporting information upon formation. For existing businesses, FinCEN has provided a one-year grace period to comply, meaning the deadline for companies formed or registered prior to 2024 is January 1, 2025. Don’t wait until the last minute — start preparing now.

Develop internal procedures to ensure ongoing compliance. This could involve creating a system for regularly updating beneficial ownership information when ownership or critical management changes over time.

Consider seeking advice from compliance experts to ensure whether you meet all the requirements. While the BOIR filing might seem straightforward, nuances in ownership or control structures could complicate the process. Ensuring your business is prepared for BOI reporting compliance long before the applicable deadline is the exact sort of proactive approach that will save you time, reduce stress, and help avoid costly penalties.

What Every Business Owner Needs to Know About FinCEN’s BOIR Requirement

The Beneficial Ownership Information (BOI) reporting requirement, introduced by FinCEN (the Treasury Department’s Financial Crimes Enforcement Network) increases transparency in business ownership with the stated goal of reducing financial crimes such as money laundering and tax evasion. As a business owner, it’s essential to understand what this regulation means for you and your company.

The BOIR rule mandates that certain companies report information about their beneficial owners to FinCEN. A “beneficial owner” is any individual who directly or indirectly exercises substantial control over the company or owns 25% or more of its equity

Corporations, limited liability companies (LLCs), and similar entities created or registered by a state to do business in the United States are required to file their BOI Report. Larger companies, regulated financial institutions, and inactive companies, are exempt because they largely already have to conduct this disclosure.

Businesses must report identifying information about each beneficial owner, including:

  • Full legal name
  • Date of birth
  • Current residential or business address
  • A unique identification number from a government-issued document (such as a driver’s license or passport)

The BOIR requirement officially went into effect in January 2024, and new companies must file within 90 days after their formation. Existing companies have until the end of 2024 to comply, so it’s essential to immediately start gathering the necessary information. Compliance with FinCEN’s BOIR requirement is a crucial regulatory obligation so take the time to understand these requirements and prepare your business for the upcoming changes.

Constitutionality of FinCEN’s BOIR Requirement

Found in the nearly 1,500-page National Defense Authorization Act of 2021, is the 21-page Corporate Transparency Act (“CTA”), 31 U.S.C. § 5336.  The CTA currently requires most entities incorporated or doing business under State law to disclose personal stakeholder information to the Treasury Department’s criminal enforcement arm, Financial Crimes Enforcement Network (“FinCEN”), including Tax ID numbers, date of birth, government identification number and copies of government identification documents of all beneficial owners and company state formation applicants (collectively a Beneficial Ownership Information Report or “BOI Report”).

According to Congress, this law is intended to prevent financial crimes such as money laundering and tax evasion committed using shell corporations.  The relevant Constitutional question recently put before an Alabama federal court was whether Congress’ broad powers to regulate commerce, oversee foreign affairs and national security, and impose taxes and related regulations were enough to power such a massive information grab. 

In a 53-page opinion, Judge Liles C. Burke of the Northern District of Alabama answered this question in the negative and struck down the CTA as unconstitutional.  See Mem. Op. at 3 (“Because the CTA exceeds the Constitution’s limits on the legislative branch and lacks a sufficient nexus to any enumerated power to be a necessary or proper means of achieving Congress’ policy goals, the Plaintiffs are entitled to judgment as a matter of law.”).   As recognized by Judge Burke, there was no comparable State or federal law to the CTA.  Mem. Op. at 35.

As a result of Judge Burke’s March 1, 2024 ruling – which began its appellate journey on March 11, 2024, all the plaintiffs in that case are for the time being exempt from filing a BOI Report – including the over 65,000 businesses and entrepreneurs located in all 50 states who are members of Plaintiff National Small Business Association (“NSBA”).  As for everyone else who may be a Reporting Company, the CTA very much still applies.

By way of background, FinCEN issued a final rule implementing the CTA on September 29, 2022 and made that rule effective as of January 1, 2024.  87 Fed. Reg. 59498.  Because only the plaintiffs in the Alabama action are safe from the CTA’s reporting reach all other businesses operating in the United States who are considered Reporting Companies will have to comply with the Rule. 

More specifically, the CTA requires disclosures from “reporting company[ies],” defined as “corporation[s], limited liability company[ies], or other similar entit[ies]” that are either “(i) created by the filing of a document with a secretary of state or a similar office under the law of a State or Indian Tribe, or (ii) formed under the law of a foreign country and registered to do business in the United States.” 31 U.S.C. § 5336(a)(11)(A). The CTA exempts twenty-three kinds of entities from its reporting requirements, including banks, insurance companies, and entities with more than twenty employees, five million dollars in gross revenue, and a physical office in the United States. 31 U.S.C. § 5336(a)(11)(B).  In other words, this statute not only targets shell companies involved in criminal conduct or fraud, it expressly hits most small business owners in the country as well.

“FinCEN estimates that there will be approximately 32.6 million reporting companies in Year 1, and 5 million additional reporting companies each year in Years 2–10.”   87 Fed. Reg. at 59549. The CTA requires these millions of entities to disclose the identity and information of any “beneficial owner.” 31 U.S.C. § 5336(b)(1)(A). A beneficial owner is defined as “an individual who . . . (i) exercises substantial control over the entity; or (ii) owns or controls not less than 25 percent of the ownership interests of the entity,” with some exceptions for children, creditors, and a few others. 31 U.S.C. § 5336(a)(3).

For new entities formed or operating in the United States after January 1, 2024, the CTA requires them to disclose the identity and information of both Beneficial Owners and “Applicants,” defined as “any individual who files an application to form a corporation, LLC, or other similar entity under the laws of a State or Indian Tribe; or registers [a foreign entity] to do business in the United States.” 31 U.S.C. § 5336(a)(2).  Such filings must be made within 90 days of the relevant state filings and those companies formed or operating in the United States prior to January 1, 2024 have until year end.

Reporting entities must give FinCEN a Beneficial Owner or Applicant’s full legal name, date of birth, current address, and identification number from a driver’s license, ID card, or passport. 31 U.S.C. § 5336(a)(1), (b)(2)(A).   Under the final rule, reporting entities are also required to submit an image of the identifying document. 31 C.F.R. § 1010.380(b)(1)(ii)(E). If any of that information changes, the reporting company must update FinCEN, 31 U.S.C. § 5336(b)(1)(D), and FinCEN retains Applicant and Beneficial Owner information on an ongoing basis for at least five years after the reporting company terminates. 31 U.S.C. § 5336(c)(1).  Determining whether someone is a Beneficial Owner can be somewhat difficult given it requires a determination of who “has substantial influence over important decisions made by the reporting company” among other potentially vague criteria.  31 C.F.R. § 1010.38 (d)(1)(i)(C).

A willful provision of false or fraudulent beneficial ownership information or failure to report “complete or updated beneficial ownership information to FinCEN” by “any person” is punishable by a $500 per day civil penalty and up to $10,000 in fines and 2 years in federal prison, 31 U.S.C. § 5336(h)(1), (3)(A); a knowing and unauthorized disclosure or use of beneficial ownership information by “any person” is punishable by a $500 per day civil penalty, along with a $250,000 fine and 5 years in federal prison, 31 U.S.C. § 5336(h)(2), (3)(B); and a knowing and unauthorized use or disclosure while violating another federal law “or as part of a pattern of any illegal activity involving more than $100,000 in a 12-month period” by “any person” is punishable with a $500,000 fine and 10 years in federal prison, 31 U.S.C. § 5336(h)(3)(B)(ii)(II). Over time, this daily penalty increased to $591 per day.

As recognized by Judge Burke, “[t]he ultimate result of this statutory scheme is that tens of millions of Americans must either disclose their personal information to FinCEN through State-registered entities, or risk years of prison time and thousands of dollars in civil and criminal fines.”  Mem. Op. at 8.  Given the importance of this information, FinCEN already compels banks and other financial institutions to obtain nearly identical information from State entity customers and provide it to FinCEN.  

More specifically, FinCEN’s 2016 Customer Due Diligence rule requires “covered financial institutions” to “identify and verify beneficial owners of legal entity customers.” 31 C.F.R. § 1010.230(a).   As with the CTA, this rule defines a “legal entity customer” as “a corporation, limited liability company, or other entity that is created by the filing of a public document with a Secretary of State or similar office, a general partnership, and any similar entity formed under the laws of a foreign jurisdiction that opens an account,” unless the entity fits into one of sixteen exemptions – seven less than the CTA exemptions. 31 C.F.R. § 1010.230(e)(1)-(2).

The CDD rule also defines beneficial owners in the same manner: “Each individual . . . who owns, directly or indirectly, 25 percent or more” of the entity; has “significant responsibility to control, manage, or direct a legal entity,” including “a Chief Executive Officer, Chief Financial Officer, Chief Operating Officer, Managing Member, General Partner, President, Vice President, or Treasurer)” and “[a]ny  other  individual  who  regularly  performs  similar  functions.”  31 C.F.R. § 1010.230(d)(1)-(2).

In other words, FinCEN’s CDD rule and the CTA provide FinCEN with nearly identical information.  The CTA itself acknowledges the similarity. See 31 U.S.C. § 5336(b)(1)(F) (requiring the Secretary of the Treasury to promulgate regulations that “collect [beneficial owner and applicant] information . . . in a form and manner that ensures the information is highly useful in . . . confirming beneficial ownership information provided to financial institutions.” (emphasis added).  See also Pub. L. 116-283 § 6402 (6)(B) (134 STAT. at 4604 – 4605) (“It is the sense of Congress that . . . [collection of] beneficial ownership information . . . [will] confirm beneficial ownership information [already] provided to financial institutions.”).

According to FinCEN’s compliance with the Paperwork Reduction Act of 1995: “The estimated average burden associated with this collection of information from Reporting Companies is 90 to 650 minutes per respondent for reporting companies with simple or complex beneficial ownership structures, respectively. The estimated average burden associated with Reporting Companies updating information previously provided is 40 to 170 minutes per respondent for reporting companies with simple or complex beneficial ownership structures, respectively.”

Given the appellate route will likely take well over a year to resolve and the NSBA plaintiffs no longer have any injury to adjudicate – which might have expedited an appeal if they had, it is incumbent on business owners to take the CTA at its face value and comply with the implemented regulations of FinCEN.

The NFT Growth Tax

Between Amazon launching next month its NFT Marketplace – tentatively called the “Amazon Digital Marketplace”, Sotheby’s already launched high-end secondary marketplace for “digital artwork”, and Christie’s launching last year its Christie’s 3.0 – a platform allowing for fully on-chain sales that demonstrates “the auction house’s commitment to both artists and collectors in the Web3 space”, programmable digital assets/NFTs are simultaneously entering both ends of the mainstream market.     

Probably the most important takeaway from such broad initiatives turns on the fact foundational brands have decided to supplant the prior NFT free-for-all initiated by PFP projects, artists and collectors.  Despite potentially risking the same fate of Dapper Labs, Amazon will rely on a private blockchain that takes credit cards while Sotheby’s eliminates “NFTs” from the equation altogether to focus on what it calls “digital artwork” even though digital art has already been around for decades.  What is clear is that Amazon’s use of its own “brand worthy” naming convention – “Amazon Digital”, elevates rather than hinders this new ecosystem. 

Being swept aside by this establishment wave is OpenSea – the newly-displaced old guard and wild-west pioneer who likely never contemplated insider trading as a risk until a former OpenSea Manager was recently convicted of it.  Not surprisingly, OpenSea offloads tax obligations and refers its users to CoinTracker for tax calculations.  OpenSea even explicitly points out to users of the marketplace that “[y[ou are responsible for determining what, if any, taxes apply to your purchases, sales, and transfers of NFTs. If you have specific questions regarding taxes, please consult with a professional tax advisor.”  OpenSea’s sole Help Center entry regarding taxes further drives home the point:  “Users are responsible for determining what, if any, taxes apply to their purchases, sales, and transfers of NFTs. If you have questions about taxes, please consult with a professional tax advisor.”

In sharp contrast, the government is certainly rooting for reliable tax collectors such as Amazon, Christie’s and Sotheby’s to enter the NFT sandbox.  Since 2018 – when the Supreme Court overruled decades of precedent, taxation of online sales no longer depends on physical presence within a particular state.  The new guard will create the proper recipe for mass profitable usage, namely removing tech geek elements, improving user interfaces, adding brand allure, and ensuring government is happy and remaining on the right side of the regulatory fence. 

As Grace Kyne of EY informed attendees at the April 13, 2023 NFT.NYC session “NFTs and Marketplaces: Opening Pandora’s Box”, there are state-specific marketplace facilitator rules that make most marketplaces subject to state tax.  Not surprisingly, Amazon is front and center in pointing that hard fact out to its market participants: “Marketplace Facilitator legislation is a set of laws that shifts the sales tax collection and remittance obligations from a third party seller to the marketplace facilitator. As the marketplace facilitator, Amazon will now be responsible to calculate, collect, remit, and refund state sales tax on sales sold by third party sellers for transactions destined to states where Marketplace Facilitator and/or Marketplace collection legislation is enacted.”

In other words, pushing digital asset sales to Amazon is really every state treasurer’s dream.

This should not come as any surprise.  Ever since the 2019 tax year, IRS Form 1040 has included a question regarding a taxpayer’s cryptocurrency activity. In 2021, the IRS slightly broadened the scope of its inquiry:  “At any time during 2021, did you receive, sell, exchange, or otherwise dispose of any financial interest in any virtual currency?”  In 2022, the scope of the latest IRS Form 1040 broadened yet again: “At any time during 2022, did you: (a) receive (as a reward, award, or payment for property or services); or (b) sell, exchange, gift, or otherwise dispose of a digital asset (or a financial interest in a digital asset)?

In other words, the IRS expressly seeks disclosure of all digital asset transactions and not merely those involving cryptocurrencies.  The IRS now wants to know about a taxpayer’s NFT sales and any income generating activities where digital assets are received as payment.  On April 5, 2023, the IRS released its IRS Tax Tip 2023-45 which elaborated on this new position regarding a taxpayer’s obligation to report digital asset transactions – including citation to applicable supplemental forms.  By informing taxpayers of their new obligations – by way of tax forms and “tax tips”, it becomes increasingly difficult for them to argue any lack of knowledge on the topic.   The easiest approach will always be one which just assumes all realized digital asset gains are taxable.   

And, to the extent there was any ambiguity regarding more specific tax treatment of NFTs, that might soon evaporate given the IRS – in its March 13, 2023 Notice 2023-27, seeks to classify most NFTs as “collectibles” – a lesser form of asset for purposes of capital gains and other tax purposes.

Specifically, Notice 2023-27 – which seeks comments before June 19, 2023, announces the IRS’s and Treasury’s intention to issue guidance as to whether certain NFTs are “collectibles” under IRS Section 408(m).  Currently, the only available categories of “collectibles” under this section are:  “(A) any work of art, (B) any rug or antique, (C) any metal or gem, (D) any stamp or coin, (E) any alcoholic beverage, or (F) any other tangible personal property specified by the Secretary for purposes of this subsection.”  See 26 USC § 408(m)(2).  The IRS recognizes that NFTs do not presently constitute any of the above – including “art” given an NFT is not the art itself, it is a digital file pointing to the actual digital art typically found using an IPFS gateway such as Pinata.  Moreover, Section (F) expressly references “tangible personal property” so that catchall also does not squarely fit. 

While waiting for comments, the IRS will deploy a “look-through” analysis:  “Under the look-through analysis, an NFT constitutes a section 408(m) collectible if the NFT’s associated right or asset is a section 408(m) collectible. For example, a gem is a section 408(m) collectible under section 408(m)(2)(C), and therefore an NFT that certifies ownership of a gem constitutes a section 408(m) collectible. Similarly, an NFT does not constitute a section 408(m) collectible if the NFT’s associated right or asset is not a section 408(m) collectible. For example, a right to use or develop a “plot of land” in a virtual environment generally is not a section 408(m) collectible, and therefore, an NFT that provides a right to use or develop the “plot of land” in the virtual environment generally does not constitute a section 408(m) collectible.”  See IRS Notice 2023-27.

It is not clear whether the “look-through” approach would be limited to an underlying physical asset tied to the NFT or whether it might include potential money-generating components of an NFT.  More than likely, however, the relevant IRS section could not be broadly interpreted to include future gains unrelated to specific associated assets.  Moreover, earning rewards by way of an NFT should not be taxable given rewards are generally treated as a rebate or discount on purchases – that should be treated no differently than frequent flyer miles.

The lesson learned for businesses seeking to grow NFT adoption is that market validation and future growth opportunities are now inevitable given the tax hounds have gotten the scent.  To the extent there were any previous regulatory barriers to growth opportunities, those will be lifted so long as the government gets it take.

NFT vs. FTX

Fine art NFTs slowly but surely prop up blockchain technology while also moving the nascent Digital Fine Art movement – like popcorn placed in a Raytheon microwave oven but in a less pedantic manner.  On November 16, 2022, a burning question for NFTs is whether the unfolding FTX disaster advances or hinders their cause.

Over 230 years ago, Courts recognized that fraud taints everything it touches.  Snyder v. Findlay, 1 N. J. Law (Coxe) 48, 51 (1791).  Notwithstanding the good intentions of respected celebrity endorsers Larry David, Tom Brady and Stephen Curry, the fraudster Sam Bankman-Fried – now derided as “Sam Bankrun-Fraud”, incredibly avoided internal detection by stealing and hiding funds using his own personal backdoor software tool.  By trading client assets, his massive fraud did the exact opposite of what his firm contractually promised clients as a condition of FTX’s custody. 

Fried’s fraud has become a major contagion in the crypto world – some are even posturing FTX as Exhibit “A” in their case against crypto adoption.  Despite the pernicious nature of Fried’s massive fraud, there remains underlying positive news given FTX’s failures shine a light on why NFTs will continue having a long and impactive run and why their decentralized nature will eventually become baked into most financial assets.  Indeed, the term “NFT” will hopefully disappear from our vernacular given the underlying technology’s future ubiquity.  Literally no one cares how “Hypertext Transfer Protocol Secure” works so long as the “https” before a website address gets the job done.  Similarly, few really care about the technology behind a “non-fungible token”.   Owners only care about having transferable digital property self-containing proof of ownership, verifiable uniqueness and programmable contract attributes.

The FTX debacle immediately adversely impacted NFT markets because NFTs are purchased and sold using cryptocurrencies – most of which took a major hit beginning on November 2, 2022, the publication date of Coindesk’s expose on FTXAnd, with Solana’s SOL emerging as this worst-performing crypto asset – losing over 41% in value given FTX was an important backer of the network, several Solana NFT marketplaces, namely Magic Eden and Solanart, felt an even greater FTX sting than other NFT marketplaces.   

Despite the fact NFT sales remain on a slow mass adoption cycle, as of November 16, 2022 OpenSea alone still had nearly $33 billion in total NFT trades.  NFTs are well beyond the proof-of-concept stage but mass adoption will continue a slow journey given the constant press assaults.  For example, in a May 3, 2022 Wall Street Journal hit piece suggesting that it may be “the beginning of the end” for NFTs, Zach Friedman, co-founder and chief operating officer of crypto brokerage Secure Digital Markets, is quoted as saying:  “The ones that continue will be utility-focused for sure.” 

That perspective is both correct – utility is an intrinsic feature of all NFTs, and wrong given it begs the question:  Since when does fine art ever need additional utility for it to gain status as “fine art”?  Utility is always found in great art simply by way of the esthetic utility derived.  As of the same month as the WSJ article – May 2022, collectors sent over $37 billion to NFT marketplaces, putting them on pace to beat the total of $40 billion sent in 2021.  Even though the vast majority of these transactions are not for fine art NFTs, the disrespect shown today for Digital Fine Art remains no different than cubist art in 1910. 

At the 1913 Armory Show in New York City, the most famous collectors of modern art originally shunned what they saw.  Indeed, after the show travelled to Chicago, members of the Art Institute of Chicago – the first museum brave enough to display these works, burned mock-Matisse and Picasso effigies on the museum’s steps. Today, the Art Institute of Chicago proudly hangs over five hundred important works created by Matisse and Picasso.  History will always have an uncanny way of repeating itself.

At an Art Basel panel discussion, Esther Kim Varet, owner of the L.A. and Seoul gallery Various Small Fires, reportedly let the cat out of the bag as to why Digital Fine Art runs against the grain of the fine art world: “There are a lot of barriers and it feels exclusive once you get in. And I fear that the more pricing transparency there is … we’re going to have to invent new ways to create this aura of exclusivity or privilege. Not that those things are things that we should value but it’s just kind of what the art world is built on.”

In other words, pricing opaqueness is positioned as a virtue of the art world community.  Not surprisingly, the pricing transparency and documented provenance inherent in Digital Fine Art in the form of NFTs in some ways runs counter to this view of the art world.   While the actual art in Digital Fine Art provides utility plain and simple, the programmable nature of the smart contracts used in NFTs provides a world of opportunity for collectors and artists. Such underlying contractual rights can create a lifetime relationship between collector and artist – one with ties to direct interactions removed from any centralized control.  More to the point, fine art galleries and dealers can readily join in this new form of relationship.  Ultimately, the only barriers to the heights Digital Fine Art can achieve is driven by a lack of imagination and a fear of the unknown.

UPDATE: December 13, 2022

On December 13, 2022, the SEC filed criminal charges against Bankman-Fried. The complaint alleges he “orchestrated a years-long fraud to conceal from FTX’s investors (1) the undisclosed diversion of FTX customers’ funds to Alameda Research LLC, his privately-held crypto hedge fund; (2) the undisclosed special treatment afforded to Alameda on the FTX platform, including providing Alameda with a virtually unlimited “line of credit” funded by the platform’s customers and exempting Alameda from certain key FTX risk mitigation measures; and (3) undisclosed risk stemming from FTX’s exposure to Alameda’s significant holdings of overvalued, illiquid assets such as FTX-affiliated tokens.”

In parallel actions, the U.S. Attorney’s Office for the Southern District of New York and the Commodity Futures Trading Commission also announced their own charges against Bankman-Fried.

Given that he was about to testify before Congress, the timing of the SEC and CFTC actions are not nearly as important as that of the criminal indictment. In effect, the DOJ has prevented a potential treasure trove of wholly admissible statements from being elicited. Now that he has been indicted and arrested in the Bahamas, lawyers will be the only ones talking for money-runner SBF. That’s too bad.

Another Day, Another Phishing Exploit Seeking NFTs

On July 15, 2022, several of DeeKay Kwon’s Twitter followers were the latest victims of scammers feasting in the NFT space.  DeeKay is an animator and part of a growing number of innovative artists developing the Digital Art Movement spurred on by NFTs.  One of DeeKay’s admirers is Calvin Cordozar Broadus Jr. also known as Snoop Dogg also known as Cozomo de’ Medici – who acquired DeeKay’s “Life and Death” for “$1m USD, or 310 ETH.”  According to this very important art collector, “all of this [NFT profile picture] mania is bringing massive attention to NFT. And when they come in for an azuki, punk, bored ape, or their choice of “culture token” . . . But then stumble across an @XCOPYART, a @fewocious, a @deekaymotion . . . That’s when one realizes the true power DIGITAL art can have, beyond any traditional art they have ever seen before.”

DeeKay reported his Twitter account was hacked and “and the hacker has been tweeting a fake mint site.  I reacted to it ASAP and spread the word but could not stop the damage in time.”  An unknown number of DeeKay’s over 179,000 followers clicked on a phishing link found in the below fake Tweet – a Tweet that purportedly brought them to a new collection from the artist:

According to Deekay, “[t]he fake mint site was made two weeks prior, 100% copied my original website. I assumed he studied my time when I am inactive too.”   While trying to claim the purported free NFTs on the fake site, victims instead approved transactions granting the scammer access to their wallets and allowing the removal of various digital assets. It is not yet fully known how many NFTs or other crypto assets were stolen from Deekay’s Twitter followers.  Most reports currently peg the number at $150,000 worth of digital assets. 

DeeKay has been trying to “work something out” with those have been scammed.  For example, one victim was gifted “something special” by DeeKay to “help ease” his loss.  Interestingly, DeeKay recognizes the problem with reimbursing victims given that it “also encourages hackers to keep doing their thing since I am the one covering the mess. Part of me says reimbursement should not be a standard way to react, and another part of me says I should still find a way to compensate and find a balance.”  This is no different than the problem caused by insurers who continually reimburse ransomware victims and why ransomware payments should be self-insured.

DeeKay’s Twitter phishing scam comes on the heels of another phishing exploit days earlier targeting Uniswap liquidity providers that used a similar scheme but obtained a much larger $8.6 million in crypto assets.  As reported in Crypto Briefing, the Uniswap fake site “instructed the victims to claim the malicious UNI tokens as a reward for providing liquidity on the exchange, but when the victims agreed to the claim, they inadvertently approved a transaction that granted the attacker access to their wallets. From there, the attacker could make token transfers to drain their wallets.”

The phishing technique used in these scams is relatively easy to pull off given most folks still click on links without really thinking and many users of crypto wallets such as MetaMask have no clue as to what they are really providing consent for when clicking on the consent button.  After going to what appears to be a genuine site, they just assume they are obtaining what they are pitched as the reason for going to the site in the first place, namely freebies of some sort.  In a similar way an email address can be spoofed in a phishing exploit, consents can say whatever a scammer wants it to say. 

Whether it’s DeeKay’s Twitter followers or Uniswap’s liquidity providers, these pools of potential victims are publicly known and easily reached by scammers.  One way of getting away from this vulnerable crowd is by using multiple wallets and intermediaries such as fine art galleries that can work with collectors to improve their security hygiene.  More to the point, until art galleries become a mainstay part of the Digital Art Movement, these sort of scams will continue to proliferate.

UPDATE: July 20, 2022

On July 19, 2022, DeeKay let everyone know he was targeted again – likely by way of another phishing exploit. He suggested that his collectors be aware that he would “NEVER do a free mint.”