Tag: cryptocurrency

What is a Security Token Offering (STO) and How Do I Use It In My Business?

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A security token offering (or STO) is a 21st century blockchain-based alternative to a traditional equity or debt sale to raise company funds. Instead of selling units or shares, a company sells digital tokens to investors. Instead of selling SAFE (simple agreement for future equity) notes, companies can offer a SAFT (simple agreement for future tokens).

But why would a company want to sell tokens in the first place? STOs and traditional equity offerings fall within securities laws and must either be registered with the SEC or comply with exemptions (Regulation A+, D, or S for example). State-level “blue sky” laws may also apply. Also, like traditional securities, STOs represent fractional ownership in a tangible asset, either an equity interest in the company, a profit share, or debt instrument.

An STO does have certain benefits over selling traditional securities:

  • Unlike traditional securities, the STO eliminates third parties and middlemen inherent in a traditional securities offering, leading to greater efficiencies, lower costs, and a faster issuance process.
  • Blockchain technologies are inherently transparent, as the digital ledger is public. This makes the offering inherently more secure.
  • By selling tokens, companies can tap into financial markets across the world that would not be normally accessible. An investor from Asia or Europe can easily buy into a company STO, just as an investor from the United States.
  • Security tokens are considered more liquid because investors can buy, sell, and trade tokens around the clock.
  • The digital nature of the tokens makes corporate governance and voting easier and more transparent.

Another distinguishing characteristic of an STO is that a company can tokenize and sell fractional ownership in almost any real world asset – such as real estate, a machine, or even intellectual property. This opens up a host of possibilities and financing options that would otherwise be limited or unavailable with traditional securities. This is especially attractive to high-tech startups whose business model is already based on or related to the blockchain.

STOs should not be confused with ICOs (initial coin offerings). ICOs boomed in 2017, as some companies turned to unregistered token sales to raise funds outside of the traditional securities disclosure, registration, and other legal requirements. In 2017, the SEC issued an investor bulletin and clarified that these digital token sales constitute “investment contracts” that meet the SEC v. W.J. Howey Co., 328 U.S. 293 (1946) test and therefore must be registered as securities under federal law. ICOs also are associated with several high-profile “exit scams,” where cryptocurrency promoters claimed big plans for a new crypto project, collected funds from investors, and then simply disappeared with the funds. Other ICOs purported to be “high-yield investment programs” that turned out to be nothing more than Ponzi schemes.

As cryptocurrency, NFTs, and other blockchain-based technology became more mainstream in 2021, it is important to recognize that the STO is a new way for innovative companies to raise funds. While these are still securities offerings that must comply with applicable regulations, the flexibility, transparency, and efficiency that these digital instruments offer are certainly attractive.

Want to know more? Contact Dan Artaev by email or call or text to set up your initial consultation.

Disclaimer: This guide is for general informational and promotional purposes only. Nothing herein constitutes legal, investment, or tax advice. Every situation is different and faces its own unique set of challenges. Do not take any action or sign any contract until you have obtained specific guidance from a qualified professional.

© 2022 Artaev at Law PLLC. All rights reserved.

What Every Business Owner Must Know About Cryptocurrency Systemic Risk

Whether your business is a full-scale investor in cryptocurrency and blockchain technology or whether you are simply using cryptocurrency to diversify your balance sheet or facilitate international transactions, you are assuming systemic risk. Systemic risk is basically the risk that the “system” in question will fail. The 2008 financial crisis is a recent example of the financial system’s failure due to overleveraged institutions and opaque and risky lending practices. Cryptocurrency and blockchain tech are quickly growing and becoming an integral part of the global financial markets – essentially evolving into another system. For example, sophisticated investors can self-direct their retirement accounts into cryptocurrencies and stake their entire savings on this growing tech.

Risk is part of any business. However, so is effective risk management, which particularly critical in the blockchain/cryptocurrency context, which operates outside of the safeguards and regulatory oversight common to traditional financial institutions. At the same time, existing tax, securities, commodities, and finance regulations still apply to crypto, and compliance is critical to the smooth functioning of your business. At a minimum, any business involved with blockchain tech should involve an experienced business attorney to develop their internal risk management protocols and have a plan for legal compliance, as well as systemic risk.

1. Existing Tax, Securities, and Other Laws Still Apply to Cryptocurrency.

First, and foremost, cryptocurrency is an asset and blockchain enterprises are businesses that are subject to general state and federal laws. While there is no central authority in the United States responsible for policing crypto markets, that does not mean that crypto business operate independent of the law. Government regulators are playing catch-up, and have repeatedly asserted their authority over cryptocurrency and related tech under existing laws. For example, 2020 was the first year that the IRS asked taxpayers about their crypto holdings. Enforcement units are gearing up to address tax evasion and close the multi-million dollar gap between actual income and what is reported to the IRS. The SEC and CFTC are also stepping up enforcement actions to head off fraudulent activity and lack of transparency in certain financial offerings. The Department of Treasury (through FinCen) is also stepping up oversight to enforce existing anti-money laundering frameworks.

The existing regulatory framework is far from perfect and is not well-suited to the unique characteristics of cryptocurrency. For example, why are some ICOs (initial coin offerings) securities, but established coins like Bitcoin and Ethereum are not securities? Capital gains taxes apply to cryptocurrency and stablecoins. But the IRS has not issued any guidance on NFTs. Are they going to be taxed like “property” or like collectibles, art, gold bullion, or something else? Will NFT tax rates depend on what the NFT is supposed to represent?

Stablecoins are a whole separate issue. Recently, a group of Treasury, SEC, and CFTC officials urged Congress to pass legislation to regulate stablecoins. In the “Report on Stablecoins,” the group noted existing SEC and CFTC authority to regulate these markets, but urged reform and legislation that is specific to the new technology.

For investors and innovators, legal compliance is the essential first step. Nothing stifles innovation like an IRS audit or an SEC investigation. Make sure to consult with an experienced attorney for guidance on the latest state of the quickly changing law in this area.

2. Decentralization Does Not Mean Risk-Free or Safe.

Second, the decentralized nature of cryptocurrency and blockchain tech in general lends itself to a false sense of security among investors and businesses. Some crypto advocates consider regulation unnecessary because blockchain tech is “decentralized.” The public ledger system purportedly means total transparency, equity, and fairness. In reality, a decentralized system is not immune from tampering or malfeasance.

For example, blockchain at its core is software that depends on coders and engineers upgrading the “chain,” fixing bugs, and making improvements. Someone somewhere determines forks and chain upgrades. Also, what about miners? What precludes off-chain influence (i.e. bribes) to miners that would impact the whole chains or cause them to verify certain blocks or transactions out of sequence?

Stablecoins are considered “safe” because the tokens are purportedly backed by fiat or equivalent reserves. But there is a lack of transparency between various stablecoins, different liquidity thresholds between reserves (for example, cash vs. money market vs. short term bonds), and variable redemption mechanisms and minimums. Additionally, is your stablecoin of choice based on a public blockchain or a permissioned blockchain? Permissioned blockchains limit access to the blockchain, providing more certainty as to who is responsible for the chain’s operation and integrity. At the same time, they reduce transparency and accountability.

Further, the federal government does not insure stablecoin or cryptocurrency deposits. If you stake cryptocurrency for a return, you are not insured or protected against the coin’s failure, a run, or illiquidity. If you are using a stablecoin to facilitate DeFi transactions, have a plan in case of network problems, chain disruptions, or backing failures. For instance, use several stablecoins to diffuse the risk.

As illustrated by the recent examples of the SQUID token and the Evolved Apes NFT, crypto tech is full of bad actors. The chain itself is not immune from malfeasance. Any business that fully depends on the integrity of the blockchain for its day to day operations must have safeguards. At a minimum, a crypto company must have a robust security system and team dedicated to detecting network health and chain anomalies. Financial hedging that diffuses the risk over multiple chains, cryptocurrencies, and other assets is also critical. Finally, established and documented due diligence protocols to assure investors, regulatory authorities, and lenders are a must.

3. Do Not Take the Internet For Granted.

Third, there is an inherent systemic risk to anything that depends wholly on the operation of the internet. Outages of certain sites or even network-wide service providers are not uncommon. Just recently, Facebook and Instagram were down for almost a full day. Comcast made headlines for its network outages across the United States on November 9, 2021. Directly related to cryptocurrency markets, exchanges like Coinbase have connectivity issues and other disruptions in times of market volatility. This can have direct adverse financial consequences for a business that depends on access to the crypto markets.

Due diligence protocols and internal safeguards are essential in this context. Offline copies of books and ledgers, at least backing up transactions history on a periodic basis. If you are storing crypto, look into offline (hardware) storage options for your code and data. Consider hedging and diversification.

Most important of all, have a plan. Cybercrime and ransomware insurance options are also worth looking into. Crypto and blockchain are existing, but are not without substantial risk. While government regulators are playing catch-up and are urging Congress to pass a risk control framework, legislation is not an instant process. In the meantime, plan for systemic risk as part of your business plan.

Want to know more? Contact Dan Artaev by email or call or text to set up your initial consultation.

Disclaimer: This guide is for general informational and promotional purposes only. Nothing herein constitutes legal, investment, or tax advice. Every situation is different and faces its own unique set of challenges. Do not take any action or sign any contract until you have obtained specific guidance from a qualified professional.

© 2021 Artaev at Law PLLC. All rights reserved.

Stablecoin Taxation and Securities Regulation: What Every Investor Must Know.

Stablecoins are cryptocurrencies backed by other assets like fiat currency reserves, precious metals, commercial paper, and even portfolios made up of other cryptocurrencies. By pegging their value to another asset, stablecoins attempt to decrease price volatility and achieve a more “stable” price than uncollateralized cryptocurrencies like Bitcoin and Ethereum. As I previously wrote, stablecoins may be particularly useful for international trade and business due to their predictable value and the ability to avoid wire delays and to minimize transaction costs. Stablecoins are also not targets of speculation or artificial price increases due to external events like Elon Musk’s SNL appearances or even China’s clampdown on Bitcoin mining. If the stablecoin is pegged to the value of the dollar, it will still be worth $1 regardless of whether there is a sudden spike in demand or supply.

Other than potential business use, stablecoins are also a popular investment medium. Certain exchanges have offered attractive interest rates on stablecoin holdings, ranging from Coinbase offering 4% on USD Coin (USDC) to double-digit returns on some lesser exchanges and stablecoins. As always, do your due diligence and make sure you know where your money is going before transferring any significant amount of cash. Also, it may be worthwhile to test the liquidity or withdrawal time with smaller deposits before investing any large amounts.

Just like with traditional cryptocurrency, there are two main legal areas that affect stablecoins: tax and securities regulation. Here are the latest “must knows” in each area:

Stablecoins are taxed like property and are subject to capital gains tax. Cryptocurrency is not “currency” as far as the IRS is concerned – rather, for taxation purposes, it is treated like property and subject to capital gains tax. This gets tricky, especially with stablecoins that are pegged 1:1 to the dollar. Buying stablecoins (or any crypto) for dollars is not a taxable event. However, using stablecoins to purchase goods and services is a taxable event that must be reported, even if your capital gains are zero.

For instance, if you buy 1,000 USDC for $1,000, that is not taxable. Then, when you pay a Romanian engineer 1,000 USDC in exchange for a circuit board design, the IRS deems that you have sold the USDC at the market rate in exchange for the engineering services. The difference between your cost basis and your sell price is the capital gain. Where the stablecoin is pegged 1:1 to the dollar, the capital gain will be $0 (your purchase price and sale price are the same). In fact, you may even realize a loss that you can use to offset your income if you paid a transaction fee. Transaction fees are added to your cost basis, so if you paid a $10 transaction fee to buy 1,000 USDC, your cost basis is $1,010 and when you sell for $1,000, you just netted a $10 loss. Also, you can end up with capital gains or losses if you are transacting large amounts of stablecoin – for example if you sell 50,000 USDT (Tether) when it’s price fluctuated slightly to $1.01, you just received a $500 capital gain.

Additionally, if you are earning interest on your USDT holdings, interest is taxable like ordinary income. In other words, buying stablecoin for fiat currency is not taxable, but earning stablecoin through staking is taxable. Just like you pay income tax on interest earned from your savings account, you will incur income tax on cryptocurrency gains. Finally, when you use your earned USDT to buy something or convert to cash or another cryptocurrency, that is a reportable taxable event subject to capital gains tax because for IRS purposes, you just sold property – your cryptocurrency.

Some stablecoins may be regulated like securities. The Securities and Exchange Commission (SEC) enforces U.S. securities laws, which apply to a wide range of publicly-available investment products like stocks, bonds, mutual funds, and investment contracts where investors provide capital in exchange for expected returns. Cryptocurrencies like Bitcoin and Ethereum are not considered securities because they are exchange mediums and in the SEC’s view, are no different than a foreign currency like the Euro or the Japanese Yen. At the same time, the SEC has scrutinized new coin offerings (also called initial coin offerings or ICOs) and concluded that they may constitute investment contracts if there are facts that indicate the buyer is “expecting a profit to be derived from the efforts of others.” See generally SEC v W.J. Howey Co., 328 US 293 (1946) (where the Supreme Court held that shares in a citrus grove operation were investment contracts subject to securities laws because the investors provided capital with the expectation that workers’ efforts in harvesting oranges would yield profits). Certain stablecoins, especially those that seek capitalization through ICOs and promise a percentage return through “staking,” will be considered “investment contracts” required to register with the SEC and provide public information like any other security.

There are also some stablecoins that are backed by securities like corporate and municipal bonds, mutual funds, and other publicly-traded instruments that are themselves regulated by the SEC. There is little doubt that these security-backed stablecoins are considered derivatives because their value is derived from the value of regulated securities. SEC regulation will require stablecoin issuers to disclose additional information about their companies to the public. Already there is some concerning information release ahead of Circle’s (the issuer of USDC) intent to go public – USDC reserves are only61% cash and money market funds, with the rest divided between U.S. and foreign treasury bonds, municipal, and corporate debt. Previously, the 1:1 stablecoin issuers represented that each coin was backed by actual cash reserves, which were regularly audited. Apparently, that is not the precise reality.

Finally, stablecoins are also facing increased regulatory scrutiny from central bank authorities. Federal Reserve officials have expressed their concerns about the effect of stablecoins on the credit markets. Stablecoins also threaten the ability of the Federal Reserve to regulate monetary supply to stimulate the economy and control inflation. For instance, if a coin like USDC gains widespread adoption, a private company like Circle will be able to regulate monetary supply by increasing and decreasing interest rates. Expect to see increased guidance and regulation from the U.S. Treasury and the Federal Reserve in the near future. It would not be surprising to see stablecoin issuers to be treated as banks in certain circumstances.

Want to know more? Contact Dan Artaev by email or call or text to set up your initial consultation.

Disclaimer: This guide is for general informational and promotional purposes only. Nothing herein constitutes legal, investment, or tax advice. Every situation is different and faces its own unique set of challenges. Do not take any action or sign any contract until you have obtained specific guidance from a qualified professional.

© 2021 Artaev at Law PLLC. All rights reserved.

Ask the Crypto Tax Lawyer: Offsetting Capital Gains Through Loss Harvesting.

Update: As of November 10, 2021, Congress is in the process of considering legislation to preclude loss-harvesting through cryptocurrency sales. Congress is also considering other amendments to the Tax Code and other laws to address cryptocurrency specifically. As this is a rapidly developing issue, it is critical that you consult with a tax attorney or other professional about your specific situation and the current state of the law before making any transactions or business decisions.

More than half-way through 2021, cryptocurrency remains an extremely popular investment. Although volatile and subject to unpredictable regulation (yes, that means China), the market has experienced substantial growth. Exchanges like Coinbase and integration with PayPal make owning, trading, and speculating in cryptocurrency easy. Sophisticated investors have even added cryptocurrency into their self-directed retirement portfolios, banking on the continued growth and popularity of the decentralized exchange medium.

As I have previously written, the IRS is keeping a close eye on cryptocurrency investors, transactions, and markets, looking to capture taxes on hundreds of millions in underreported or unreported income. In other words, crypto taxes are going to be an issue for many in the coming tax years, especially after the Biden administration’s mandatory $10,000 or more transaction reporting rule goes into effect in 2023. However, with proper planning and strategy, there are ways to reduce your tax liability even if you are planning to liquidate your crypto positions in the near term.

As a basic matter, know that the IRS classifies cryptocurrency as “property,” which means that it is subject to capital gains tax. General capital gains reduction strategies work for cryptocurrency as well as they do for more traditional property like investment real estate, stocks, and bonds. For instance, waiting at least 365 days to sell lets you take advantage of the lower long-term capital gains tax rate. Selling in a lower income year where your overall income puts you in a lower tax bracket is another strategy.

One advanced tax strategy involves taking advantage of the so-called wash sale rule. Or rather, it is taking advantage of the fact that the wash sale rules does not apply to cryptocurrencies (yet). Under Treasury Regulation 26 CFR 1.1091-1, an investor cannot sell “stock or securities” at a loss, use the loss to reduce taxable income, and then immediately repurchase the stock or security. Under the wash sale rule, there is a 30-day waiting period before purchasing the same or substantially the same stock or security – if an investor repurchases the security within the 30-day restricted period, the loss will be added to the cost basis of the repurchased security and reduce capital gains on the sale of the repurchased security, but it will not be treated as an investment loss to reduce general tax basis. In other words, you cannot manufacture losses in a bear market to reduce your taxable income that you receive from other investments, rentals, or wages.

The IRS has been clear that cryptocurrency is treated as “property” for tax purposes. However, whether it is a “stock or security” remains unanswered and both IRS Notice 2014-21 and the recently amended FAQ are silent on the issue. There is no express definition of “stock or securities” for the purposes of the wash sale rule. Looking elsewhere in the Internal Revenue Code, the definitions of stock and securities in various other sections include traditional shares, notes, bonds, and the like. Indeed, in 1988 the United States Tax Court adopted a narrow interpretation of the Code, holding that stock options were not considered “stock or securities.” Gantner v. Commissioner (91 T.C. 713 (1988). Congress responded by amending the wash sale rule to expressly include stock options, but still did not enact a definition of “securities” for the purpose of the rule.

Based on the current Code and Regulations and the lack of IRS guidance on the issue, there is a strong argument that cryptocurrencies are not “stock or securities” for the purposes of the wash sale rule. What this means is that crypto investors can take advantage of loss harvesting to accrue losses and use those losses to offset income. For example, if you buy one Bitcoin for $30,000 and the next day the price drops to $20,000, you can sell the Bitcoin at a loss of $10,000, “harvest” the loss, and repurchase the Bitcoin for $20,000 shortly thereafter. You still own 1 Bitcoin, but now you have accumulated a loss that you can use to offset capital gains income.

If your losses exceed capital gains, you can use up to $3,000 of loss to reduce regular income. Any excess loss can be carried over to future years to offset future gains.

At the same time, the Securities and Exchange Commission (“SEC”), the Commodities Futures Trading Commission (“CFTC”), and certain United States courts have ruled that cryptocurrencies are indeed “securities” within those Commissions’ regulatory scope. This regulatory effort was generally to stem the fraud and abuse through “initial coin offerings” or ICOs that sought to evade strict regulations designed to protect investors. While there is currently no indication that the IRS would consider cryptocurrency as “stocks or securities,” there is precedent for that conclusion from these other agencies and remains possible that the IRS could issue supplemental guidance and interpretations to that effect.

At the time of this writing, the IRS has not issued any such interpretation and savvy investors can consider the loss harvesting strategy if appropriate for their particular situation. As with all cryptocurrency transactions, good record keeping is paramount. It is especially critical to have accurate records to substantiate your losses if you are repurchasing the same crypto. Good and accurate records are the best tool in defending your position to the IRS, should the IRS take a position and disallow your claimed losses.

Contact Dan Artaev by email or call or text to set up your initial consultation.

Disclaimer: This guide is for general informational and promotional purposes only. Nothing herein constitutes legal, investment, or tax advice. Every situation is different and faces its own unique set of challenges. Do not take any action or sign any contract until you have obtained specific guidance from a qualified professional.

© 2021 Artaev at Law PLLC. All rights reserved.

Ask the Crypto Tax Lawyer: What Are the Tax Implications of Cryptocurrency and NFT Investing?

Important: The information in this article applies to individual investors and LLCs that are taxed as pass-through entities. The rules are different for corporations and LLCs electing to be taxed as a corporation and are not addressed here. This article is for informational and promotional purposes only and, as always, you should consult with a professional about your specific tax situation before taking any action.

2021 is the year of cryptocurrency. Bitcoin and its kin have attracted many institutional investors, smaller individual portfolios, and even some sophisticated self-directed retirement accounts. The accessibility, decentralization, and unlimited upside certainly make cryptocurrency (or crypto) an attractive investment. Or simply a fun way to try to make some extra fun money. Or lose it – the crypto market is extremely volatile and quickly reacts to government action (i.e. China’s ban) and Elon Musk’s tweets or SNL appearances.

Government regulators are watching the crypto markets. The Securities and Exchange Commission (“SEC”) has already applied securities laws to police initial coin offerings and to prosecute Ponzi schemes posing as crypto investments. As early as 2014, the IRS issued guidance (supplemented by a more recent FAQ) classifying cryptocurrency as property for tax purposes. More recently, the Department of Treasury and the IRS have zeroed in on cryptocurrency as a tax revenue source ripe for enforcement. As part of its tax reform plan, the Biden administration announced mandatory reporting of any crypto transaction of $10,000 or more starting in 2023. On May 20, 2021, the Treasury also released a report detailing the plan to close the so-called tax gap, which is the difference between taxed owed and taxes actually paid. In 2019, the gap was $600 million or 15% of all taxes, and is projected to grow to $7 billion in 10 years if left unaddressed. The biggest contributor is unreported income and Treasury and the IRS will be looking very closely at anyone who is trading cryptocurrency in the next few years for any signs of unreported or underreported taxable income.

Why are there taxes on trading crypto and how is crypto even taxed? Despite its name, cryptocurrency is not really currency for tax purposes. It is taxed like property and is subject to capital gains tax. When you purchase crypto with fiat currency (i.e. U.S. Dollars) you do not pay tax on the transaction. Note: States do not consider crypto purchases subject to sales tax – yet. But when you sell crypto, you are taxed on the gain (if any) just like you would be if you sold a stock or investment real estate. The tax rate depends on the length of time you held the asset and other factors related to your income status. Importantly, when you exchange one cryptocurrency for another (for example, you trade Bitcoin for Ethereum) the exchange is taxable. The IRS considers an exchange to be a sale of one asset for cash – income – regardless of what you do with the proceeds. Accordingly, it is critical to keep accurate and clear records of every transaction involving cryptocurrency, regardless of gain or loss. Interestingly, while the IRS considers cryptocurrency “property,” it does not consider it “securities” and therefore investors can take advantage of certain tax benefits. Specifically, crypto investors can do something called “loss harvesting” to offset taxable income from other sources.

How does the IRS verify income from crypto trading? In 2020, the IRS asked taxpayers about their participation in any cryptocurrency transactions as part of their 1040 filing. In large part, the tax system is based on self-reporting, but with third party verification checks. Bigger exchanges like Coinbase report your transaction history to the IRS and you should have received a copy of the 1099-MISC for tax year 2020. The IRS will then flag any returns that do not match the information received from the exchange and what the taxpayer puts on their return. Off-brand or off-shore exchanges may not report to the IRS, but you still have to report those transactions yourself and pay tax on any gains. As mentioned above, the Biden administration is cracking down on underreporting of taxable crypto income. This means expect to see significant and highly-publicized enforcement actions, including penalties, interest, and even jail time for tax evaders. If you do use an off-shore crypto exchange, you should also be aware of your tax obligations in the host country. The United States has tax treaties with many (but not all) countries – for example, while there is a treaty with mainland China, the treaty does not apply to Hong Kong and there is no separate treaty with Hong Kong. International tax law will also come into play if buy and sell crypto abroad or exchange it for goods or services in other countries.

What about NFTs? Non-fungible tokens or NFTs are unique digital-only objects or unique digital versions of real-world objects. This is basically computer code. Mostly associated with collectibles and art, NFTs use blockchain technology like cryptocurrency but can represent almost anything, including virtual real estate and personalized avatars. The IRS has not issued definitive guidance on how NFTs will be taxed, but most commentators agree that they will probably be considered property like cryptocurrency and be subject to capital gains tax. If you buy an NFT for U.S. Dollars, you do not pay tax on that transaction. If you sell an NFT for a profit, you just incurred capital gains tax liability, even if you are exchanging an NFT for another NFT or trading it for cryptocurrency. If you are buying an NFT with cryptocurrency, the purchase will also be subject to capital gains tax, as the IRS treats the transaction as a sale of an asset (cryptocurrency), income, and then use of that income to purchase the NFT. Currently, there are no tax exemptions or safe-harbor periods that allow traders avoid capital gains tax on exchange type transactions.

An additional question with NFTs is whether the tax rate will change based on what the NFTs represents. Is it a collectible piece of art? Then there is a special collectibles tax rate. Is it real estate? Something else? There are a lot of unanswered questions about NFT taxes at this time. But like with cryptocurrency trading, make sure to keep meticulous records of all transactions, including any gains or losses on sales.

A final item of note – estimated quarterly tax payments. The IRS (and state tax authorities) require the payment of estimated quarterly taxes from self-employed individuals or independent contractors. If you buy and sell crypto (and NFTs) make sure you are reporting and paying expected capital gains tax before the due date for payments that apply to the quarter of the sale. If you wait until the end of the year to pay taxes, you may be subject to penalties and interest for failing to pay quarterly. Additionally, you may have to liquidate other investments to pay taxes, instead of simply setting aside the capital gains estimate at the time of the original sale.

In short, if you are investing and trading crypto or NFTs, keep good records. Pay attention to any new guidance issued by the IRS. Beware false or misleading information on the internet. And above all, retain a trusted advisor to answer your questions and guide you through your tax obligations in this evolving field.

Contact Dan Artaev by email or call or text to set up your initial consultation.

Disclaimer: This guide is for general informational and promotional purposes only. Nothing herein constitutes legal, investment, or tax advice. Every situation is different and faces its own unique set of challenges. Do not take any action or sign any contract until you have obtained specific guidance from a qualified professional.

© 2021 Artaev at Law PLLC. All rights reserved.

Can a Self-Directed IRA (“SDIRA”) Invest in Cryptocurrency and NFTs?

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Self-directed IRAs (“SDIRAs”) can be a powerful investment tool when used the right way. Instead of relying on a bank or brokerage to hold and invest your retirement accounts, the SDIRA gives you direct control over what to invest in for your retirement. Best of all, the SDIRA is not limited to the traditional stock and bond market portfolios. Savvy and knowledgable investors willing to take on high levels of risk can direct their tax-advantaged savings into private companies, debt portfolios, real estate, and other non-traditional assets. While the personalized control and expanded investment opportunities may sound great, SDIRAs are subject to complex tax rules and other pitfalls, including extreme volatility and investment risk. The government rules and regulations ensure that individuals are not abusing the tax advantaged status of their retirement accounts. The Internal Revenue Code (“IRC”) governs what retirement accounts (including SDIRAs) can and cannot invest in.

What about cryptocurrency like Bitcoin? Can an SDIRA invest in cryptocurrency? Yes. In general, the IRC prohibits any IRAs (including self-directed ones) from owning life insurance, S-Corporation stock, and collectables. 26 USC 408. The term “collectable” includes art, antiques, collectable stamps, coins, alcoholic beverages, and “any other tangible personal property” specified by the IRS. Pursuant to Notice 2014-21, the IRS considers cryptocurrency to be intangible property for the purpose of taxation. This means it is treated the same as stocks or bonds – if you sell at a profit, you are paying capital gains tax. Note that cryptocurrency is not treated the same as cash – this also means that if you are paying for a product with Bitcoin, it is a taxable event. For the purposes of an SDIRA and retirement investment, you can certainly buy and hold (or HODL) cryptocurrency. Or sell it for a gain – the tax consequences are the same as they would be with a stock or bond portfolio (depending on whether you have a 401k or Roth-type setup). Remember that any profits that an SDIRA makes go right back into the SDIRA and may only be withdrawn for the benefit of the individual under certain conditions (like being 59 and a half years old) to retain the tax advantage. With cryptocurrency, it is critical to set up an SDIRA-owned LLC to establish and own the cryptowallet in conjunction with a bank account. The LLC structure allows the SDIRA beneficiary to act as a manager and direct investments right from the bank account rather than going back to the SDIRA custodian and waiting for an approval of a particular transaction. However, remember that the manager cannot receive compensation or commingle personal and SDIRA assets, accounts, or cryptowallets.

What about non-fungible tokens or NFTs? Can an SDIRA invest in those? Maybe. NFTs are digital property that exist only online, but unlike “traditional code,” NFTs are unique and cannot be copied. More accurately, they can be copied (like a print of the Mona Lisa can be copied), but there can be only one original. In that sense, they are like real-world property and their non-fungibility creates scarcity, and theoretically value. Although NFTs are based on the Ethereum blockchain (and Ethereum is a cryptocurrency like Bitcoin), cryptocurrency and NFTs are not necessarily treated the same way. As explained above, the IRS treats cryptocurrency the same as intangible property for the purposes of taxation – meaning like stocks, bonds, and mutual funds. Section 408 of the Internal Revenue Code prohibits any IRA from investing in art, antiques, collectable stamps, coins, alcoholic beverages, and “any other tangible personal property” specified by the IRS. 26 USC 408. Will the IRS treat NFTs like cryptocurrency and therefore permitted SDIRA investments? Or will NFTs be treated like restricted collectables?

The IRS has not issued guidance on this matter. Some commentators (including the top search result on Google as of the writing of this article) have concluded that the IRS treats NFTs as collectibles and therefore they subject to a “higher minimum gains tax rate of 28%.” This is simply not true. While the IRS certainly treats NFTs as taxable property, it remains uncertain exactly how the IRS will tax these digital assets.

At its core an NFT is code. Cryptocurrency is also code, which the IRS expressly treats like “property” for the purpose of taxation. It follows that NFTs are also “property” for the purpose of taxes. But what kind of property? Are NFTs always considered art or collectibles? Or are they cryptocurrency and can be owned by an SDIRA? What about NFTs that represent virtual real estate in “worlds” like Decentraland, Cryptovoxels, Somnium Space, Sandbox? What if the NFT is an avatar, a name, a virtual outfit? There are several possible ways for the IRS to treat NFTs:

  • One, the IRS can take a pragmatic approach and tax them in accordance with what they would represent in the real world. Some NFTs have real-world counterparts – for example, Forbes reported that a digital collectible startup called Ethernity is set to auction limited edition real world baseball bats that include an NFT counterpart. Nike also patented something called “CryptoKicks,” which presumably will tie real sneakers to some sort of digital authentication certificate. If an NFT represents art, then it is treated like art for tax purposes. If an NFT is a trading card, then it is treated like a collectible. If the NFT represents virtual real estate, it is treated and taxed like real estate (which raises a whole different set of questions).
  • Two, the IRS can take a simple approach and classify NFTs as “property” that is treated exactly like cryptocurrency regardless of what the NFT “represents.” This second approach avoids litigation over what how a particular NFT should be taxed – for example, is an in-game avatar “art”? The second approach also would give SDIRA investors the flexibility to invest in virtual assets, including virtual real estate.

Finally, is the IRS really going after unreported cryptocurrency and NFT transactions? Absolutely. In 2020, the IRS established the Office of Fraud Enforcement and announced in 2021 that a special investigative team was conducting “Operation Hidden Treasure” to identify individuals who failed to report cryptocurrency (and presumably NFT assets).

Investing in cryptocurrency and NFTs is a hot trend in 2021. Although these digital assets may “exist” only as part of the virtual blockchain, the IRS considers them very real and very taxable. This is a constantly changing and developing area, so it is especially critical to consult a tax and legal professional before making any investment decisions. As I pointed out in my earlier post about SDIRAs, even if you are right, you may still end up litigating against the IRS in Tax Court.

More questions? Thinking about investing in cryptocurrency or NFTs? Funding your retirement through an SDIRA? Contact Dan Artaev by email or call or text to set up your initial consultation.

Disclaimer: This guide is for general informational and promotional purposes only. Nothing herein constitutes legal, investment, or tax advice. Every situation is different and faces its own unique set of challenges. Do not take any action or sign any contract until you have obtained specific guidance from a qualified professional.

© 2021 Artaev at Law PLLC. All rights reserved.

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