The Bored Ape Yacht Club is one of the most prestigious NFT collections in the world. A collection of 10,000 NFTs, each depicting an ape with different traits and visual attributes, Jimmy Fallon, Steph Curry and Post Malone are among their star-studded owners. Right now the price of entry is 52 ether, or $210,000.

Which is why it's so painful to see that someone accidentally sold their Bored Ape NFT for $3,066.

Unusual trades are often a sign of funny business, as in the case of the person who spent $530 million to buy an NFT from themselves. In Saturday's case, the cause was a simple, devastating "fat-finger error." That's when people make a trade online for the wrong thing, or for the wrong amount. Here the owner, real name Max or username maxnaut, meant to list his Bored Ape for 75 ether, or around $300,000. Instead he accidentally listed it for 0.75. One hundredth the intended price.

It was bought instantaneously. The buyer paid an extra $34,000 to speed up the transaction, ensuring no one could snap it up before them. The Bored Ape was then promptly listed for $248,000. The transaction appears to have been done by a bot, which can be coded to immediately buy NFTs listed below a certain price on behalf of their owners in order to take advantage of these exact situations.

"How'd it happen? A lapse of concentration I guess," Max told me. "I list a lot of items every day and just wasn't paying attention properly. I instantly saw the error as my finger clicked the mouse but a bot sent a transaction with over 8 eth [$34,000] of gas fees so it was instantly sniped before I could click cancel, and just like that, $250k was gone."

"And here within the beauty of the Blockchain you can see that it is both honest and unforgiving," he added.

Fat finger trades happen sporadically in traditional finance -- like the Japanese trader who almost bought 57% of Toyota's stock in 2014 -- but most financial institutions will stop those transactions if alerted quickly enough. Since cryptocurrency and NFTs are designed to be decentralized, you essentially have to rely on the goodwill of the buyer to reverse the transaction.

Fat finger errors in cryptocurrency trades have made many a headline over the past few years. Back in 2019, the company behind Tether, a cryptocurrency pegged to the US dollar, nearly doubled its own coin supply when it accidentally created $5 billion-worth of new coins. In March, BlockFi meant to send 700 Gemini Dollars to a set of customers, worth roughly $1 each, but mistakenly sent out millions of dollars worth of bitcoin instead. Last month a company erroneously paid a $24 million fee on a $100,000 transaction.

Similar incidents are increasingly being seen in NFTs, now that many collections have accumulated in market value over the past year. Last month someone tried selling a CryptoPunk NFT for $19 million, but accidentally listed it for $19,000 instead. Back in August, someone fat finger listed their Bored Ape for $26,000, an error that someone else immediately capitalized on. The original owner offered $50,000 to the buyer to return the Bored Ape -- but instead the opportunistic buyer sold it for the then-market price of $150,000.

"The industry is so new, bad things are going to happen whether it's your fault or the tech," Max said. "Once you no longer have control of the outcome, forget and move on."

The Bored Ape Yacht Club launched back in April 2021, with 10,000 NFTs being sold for 0.08 ether each -- about $190 at the time. While NFTs are often associated with individual digital art pieces, collections like the Bored Ape Yacht Club, which allow owners to flaunt their NFTs by using them as profile pictures on social media, are becoming increasingly prevalent. The Bored Ape Yacht Club has since become the second biggest NFT collection in the world, second only to CryptoPunks, which launched in 2017 and is considered the "original" NFT collection.

Let's examine the differences between the three main token types and their functions.

As Ethereum grew, the term "token" became a catch-all term for all assets built on the Ethereum blockchain. However, different tokens were grouped based on their applications and features, causing some confusion. Let's examine the modification of three main token types: security, utility, and non-fungible.

Utility tokens

They provide a specific utility benefit (or a number of such). A utility token is similar to a casino chip, a table game ticket, or a voucher. Depending on the terms of issuing, they can be earned and used in various ways. A utility token is a type of token that represents a tool or mechanism required to use the application in question. Like a service, a utility token's price is determined by supply and demand. Tokens can also be used as a bonus or reward mechanism in decentralized systems: for example, if you like someone's work, give them an upvote and they get a certain number of tokens. This is a way for authors or creators to earn money indirectly.

The most common way to use a utility token is to pay with them instead of cash for discounted goods or services.

Utility tokens are the most widely used by blockchain companies. Most cryptocurrency exchanges accept fees in native utility tokens.

Utility tokens can also be used as a reward. Companies tokenize their loyalty programs so that points can be bought and sold on blockchain exchanges. These tokens are widely used in decentralized companies as a bonus system. You can use utility tokens to reward creators for their contributions to a platform, for example. It also allows members to exchange tokens for specific bonuses and rewards on your site.

Unlike security tokens, which are subject to legal restrictions, utility tokens can be freely traded.

Security tokens

Security tokens are essentially traditional securities like shares, bonds, and investment fund units in a crypto token form.

The key distinction is that security tokens are typically issued by private firms (rather than public companies) that are not listed on stock exchanges and in which you can not invest right now. Banks and large venture funds used to be the only sources of funding. A person could only invest in private firms if they had millions of dollars in their bank account. Privately issued security tokens outperform traditional public stocks in terms of yield. Private markets grew 50% faster than public markets over the last decade, according to McKinsey Private Equity Research.

A security token is a crypto token whose value is derived from an external asset or company. So it is governed as security (read about the Howey test further in this article). That is, an ownership token derives its value from the company's valuation, assets on the balance sheet, or dividends paid to token holders.

Why are Security Tokens Important?

Cryptocurrency is a lucrative investment. Choosing from thousands of crypto assets can mean the difference between millionaire and bankrupt. Without security tokens, crypto investing becomes riskier and generating long-term profits becomes difficult. These tokens have lower risk than other cryptocurrencies because they are backed by real assets or business cash flows. So having them helps to diversify a portfolio and preserve the return on investment in riskier assets.

Security tokens open up new funding avenues for businesses. As a result, investors can invest in high-profit businesses that are not listed on the stock exchange.

The distinction between utility and security tokens isn't as clear as it seems. However, this increases the risk for token issuers, especially in the USA. The Howey test is the main pillar regulating judicial precedent in this area.

What is a Howey Test?

An "investment contract" is determined by the Howey Test, a lawsuit settled by the US Supreme Court. If it does, it's a security and must be disclosed and registered under the Securities Act of 1933 and the Securities Exchange Act of 1934.

If the SEC decides that a cryptocurrency token is a security, a slew of issues arise. In practice, this ensures that the SEC will decide when a token can be offered to US investors and if the project is required to file a registration statement with the SEC.

Due to the Howey test's extensive wording, most utility tokens will be classified as securities, even if not intended to be. Because of these restrictions, most ICOs are not available to US investors. When asked about ICOs in 2018, then-SEC Chairman Jay Clayton said they were securities. The given statement adds to the risk. If a company issues utility tokens without registering them as securities, the regulator may impose huge fines or even criminal charges.

What other documents regulate tokens?

Securities Act (1993) or Securities Exchange Act (1934) in the USA; MiFID directive and Prospectus Regulation in the EU. These laws require registering the placement of security tokens, limiting their transfer, but protecting investors.

Utility tokens have much less regulation. The Howey test determines whether a given utility token is a security. Tokens recognized as securities are now regulated as such. Having a legal opinion that your token isn't makes the implementation process much easier. Most countries don't have strict regulations regarding utility tokens except KYC (Know Your Client) and AML (Anti Money-Laundering).

As cryptocurrency and blockchain technologies evolve, more countries create UT regulations. If your company is based in the US, be aware of the Howey test and the Bank Secrecy Act. It classifies UTs and their issuance as money transmission services in most states, necessitating a license and strict regulations. Due to high regulatory demands, UT issuers try to avoid the United States as a whole. A new law separating utility tokens from bank secrecy act will be introduced in the near future, giving hope to American issuers.

The rest of the world has much simpler rules requiring issuers to create basic investor disclosures. For example, the latest European legislation (MiCA) allows businesses to issue utility tokens without regulator approval. They must also prepare a paper with all the necessary information for the investors.

A payment token is a utility token that is used to make a payment. They may be subject to electronic money laws. 

Because non-fungible tokens are a new instrument, there is no regulating paper yet. However, if the NFT is fractionalized, the smaller tokens acquired may be seen as securities.

NFT Tokens

Collectible tokens are also known as non-fungible tokens. Their distinctive feature is that they denote unique items such as artwork, merch, or ranks. Unlike utility tokens, which are fungible, meaning that two of the same tokens are identical, NFTs represent a unit of possession that is strictly one of a kind. In a way, NFTs are like baseball cards, each one unique and valuable.

As for today, the most recognizable NFT function is to preserve the fact of possession. Owning an NFT with a particular gif, meme, or sketch does not transfer the intellectual right to the possessor, but is analogous to owning an original painting signed by the author.

Collectible tokens can also be used as digital souvenirs, so to say. Businesses can improve their brand image by issuing their own branded NFTs, which represent ranks or achievements within the corporate ecosystem. Gamifying business ecosystems would allow people to connect with a brand and feel part of a community. 

Which type of tokens is right for you as a business to raise capital?

For most businesses, it's best to raise capital with security tokens by selling existing shares to global investors. Utility tokens aren't meant to increase in value over time, so leave them for gamification and community engagement. In a blockchain-based business, however, a utility token is often the lifeblood of the operation, and its appreciation potential is directly linked to the company's growth. You can issue multiple tokens at once, rather than just one type. It exposes you to various investors and maximizes the use of digital assets.

Which tokens should I buy?

There are no universally best tokens. Their volatility, industry, and risk-reward profile vary. This means evaluating tokens in relation to your overall portfolio and personal preferences: what industries do you understand best, what excites you, how do you approach taxes, and what is your planning horizon? To build a balanced portfolio, you need to know these factors.

Conclusion

The three most common types of tokens today are security, utility, and NFT. Security tokens represent stocks, mutual funds, and bonds. Utility tokens can be perceived as an inside-product "currency" or "ignition key" that grants you access to goods and services or empowers with other perks. NFTs are unique collectible units that identify you as the owner of something.

Financial regulators have for years attempted to apply existing laws to the multitude of issues created by digital assets. In 2021, leading federal regulators and members of Congress have begun to call for legislation to address these issues. As a result, 2022 may be the year when federal legislation finally addresses digital asset issues that have been growing since the mining of the first Bitcoin block in 2009.

Digital Asset Regulation in the Absence of Legislation

So far, Congress has left the task of addressing issues created by digital assets to regulatory agencies. Although a Congressional Blockchain Caucus formed in 2016, House and Senate members introduced few bills addressing digital assets until 2018. As of October 2021, Congress has not amended federal laws on financial regulation, which were last significantly revised by the Dodd-Frank Act in 2010, to address digital asset issues.

In the absence of legislation, issues that do not fit well into existing statutes have created problems. An example is the legal status of digital assets, which can be considered to be either securities or commodities, and can even shift from one to the other over time. Years after the SEC’s 2017 report applying the definition of a security to digital tokens, the SEC and the CFTC have yet to clarify the distinction between securities and commodities for the thousands of digital assets in existence.

SEC Chair Gary Gensler has called for Congress to act, stating in August, “We need additional Congressional authorities to prevent transactions, products, and platforms from falling between regulatory cracks.” Gensler has reached out to Sen. Elizabeth Warren (D-Ma.), who has expressed her own concerns about the need for legislation.

Legislation on Digital Assets in 2021

While regulators and members of Congress talked about the need for legislation, and the debate over cryptocurrency tax reporting in the 2021 infrastructure bill generated headlines, House and Senate bills proposing specific solutions to various issues quietly started to emerge.

Digital Token Sales

Several House bills attempt to address securities law barriers to digital token sales—some of them by building on ideas proposed by regulators in past years.

Exclusion from the definition of a security. Congressional Blockchain Caucus members have been introducing bills to exclude digital tokens from the definition of a security since 2018, and they have revived those bills in 2021. They include the Token Taxonomy Act of 2021 (H.R. 1628), successor to identically named bills in 2018 and 2019, and the Securities Clarity Act (H.R. 4451), successor to a 2020 namesake.

Safe harbor. SEC Commissioner Hester Peirce proposed a regulatory safe harbor for token sales in 2020, and two 2021 bills have proposed statutory safe harbors. Rep. Patrick McHenry (R-N.C.), Republican leader of the House Financial Services Committee, introduced a Clarity for Digital Tokens Act of 2021 (H.R. 5496) that would amend the Securities Act to create a safe harbor providing a grace period of exemption from Securities Act registration requirements. The Digital Asset Market Structure and Investor Protection Act (H.R. 4741) from Rep. Don Beyer (D-Va.) would amend the Securities Exchange Act to define a new type of security—a “digital asset security”—and add issuers of digital asset securities to an existing provision for delayed registration of securities.

Stablecoins

Stablecoins—digital currencies linked to the value of the U.S. dollar or other fiat currencies—have not yet been the subject of regulatory action, although Treasury Secretary Janet Yellen and Federal Reserve Chair Jerome Powell have each underscored the need to create a regulatory framework for them. The Beyer bill proposes to create a regulatory regime for stablecoins by amending Title 31 of the U.S. Code. Treasury Department approval would be required for any “digital asset fiat-based stablecoin” to be issued or used, under an application process to be established by Treasury in consultation with the Federal Reserve, the SEC, and the CFTC.

Serious consideration for any of these proposals in the current session of Congress may be unlikely. A spate of autumn bills on crypto ransom payments (S. 2666, S. 2923, S. 2926, H.R. 5501) shows that Congress is more inclined to pay attention first to issues that are more spectacular and less arcane. Moreover, the arcaneness of digital asset regulatory issues is likely only to increase further, now that major industry players such as Coinbase and Andreessen Horowitz are starting to roll out their own regulatory proposals.

Digital Dollar vs. Digital Yuan

Impetus to pass legislation on another type of digital asset, a central bank digital currency (CBDC), may come from a different source: rivalry with China.
China established itself as a world leader in developing a CBDC with a pilot project launched in 2020, and in 2021, the People’s Bank of China announced that its CBDC will be used at the Beijing Winter Olympics in February 2022. Republican Senators responded by calling for the U.S. Olympic Committee to forbid use of China’s CBDC by U.S. athletes in Beijing and introducing a bill (S. 2543) to require a study of its national security implications.

The Beijing Olympics could motivate a legislative mandate to accelerate implementation of a U.S. digital dollar, which the Federal Reserve has been in the process of considering in 2021. Antecedents to such legislation already exist. A House bill sponsored by 46 Republicans (H.R. 4792) has a provision that would require the Treasury Department to assess China’s CBDC project and report on the status of Federal Reserve work on a CBDC, and the Beyer bill includes a provision amending the Federal Reserve Act to authorize issuing a digital dollar.

Both parties are likely to support creating a digital dollar. The Covid-19 pandemic made a digital dollar for delivery of relief payments a popular idea in 2020, and House Democrats introduced bills with provisions for creating one in 2020 and 2021. Bipartisan support for a bill on a digital dollar, based on concerns both foreign and domestic in nature, could result.

International rivalry and bipartisan support may make the digital dollar a gateway issue for digital asset legislation in 2022. Legislative work on a digital dollar may open the door for considering further digital asset issues—including the regulatory issues that have been emerging for years—in 2022 and beyond.