Value is in the eye of the beholder; or was that beauty? This is especially true for those infamous monkey portraits on the internet. Non-fungible tokens (NFTs) have exploded in popularity and can carry with them substantial tax consequences. Due to the volatile nature of the digital asset market and coupled with the lack of similar assets, it can be exceptionally difficult to determine the fair market value (FMV) of NFTs. Gift giving and donations can become much more complicated when NFTs are involved.

New Fangled Technology

For the noobs, an NFT is a type of cryptographic token that exists on a blockchain. As the name suggests, the tokens are not fungible, meaning each asset is unique and can’t be interchanged for one another, the way that dollars or bitcoins can. Every NFT represents a unique asset with a unique value, however, determining what that value is can be quite difficult; The market for buying and selling NFTs can be extremely volatile. Some NFTs may quickly lose value or have no value at all. When a taxpayer donates an NFT to a qualified charitable organization as a way to reduce tax, the FMV is a required piece of information.

To find out how to do this properly, keep reading.

When recognizing capital gains during a tax year, it can often make financial sense to sell assets that have lost value to offset profits in other investments or regular income. In this situation, you swap stocks, bonds, or mutual funds by buying a similar asset, selling the old asset and taking a loss.

This strategy is called tax-loss harvesting, and it can be applied under certain circumstances which will lower your taxes. Yet while the tax deduction might seem appealing, you might have a hard time locking in that loss forever, and you may be inclined to repurchase the same investment in case the value rebounds.

This strategy may appear brilliant on paper; however, the IRS doesn’t allow such manipulation just to reduce taxes.

The Wash Loss Rule prevents traders from realizing a tax loss on a position that the taxpayer reacquires within 30 days after (or before) selling a security.

But a little known loophole may allow you to complete a wash sale and claim your deduction without recognizing the loss forever as long as it is crypto.

Cryptocurrency continues to be an area where the rules don’t always seem to make sense. Most experienced investors are already familiar with the “Wash Loss Rule,” while many newer investors have recently learned about it the hard way.

To learn this valuable strategy for offsetting your capital gains while remaining in the investment gain for expected future growth, continue reading to learn more.

Every tax professional has at least one client that when asked about business mileage replies, “I don’t know; what did I have last year?” You may have read that last sentence and thought, “most of them.” Self-employed taxpayers generally know they must track their mileage, but it’s seldom done correctly, or at all. Vehicle deductions are an area frequently challenged by the IRS on examination as well as an area the taxpayer is unlikely to prevail without strong, contemporaneous documentation. That said, very few taxpayers keep perfect records, so what are the best practices for mileage deductions in the real world?

Keep reading to find out!

Think back to January 2021. A new President was sworn in; Twitter was obsessed with “Bean Dad,” and the term “Meme Stock” entered popular culture. A previously obscure subreddit called “Wall Street Bets” began making front page headlines. Average Americans took their “Stimmies” and invested them into unpopular companies, some on the verge of failure, and started making double digit percentage gains per day by pitting their collective holdings to short squeeze institutional investors.

Companies that no analyst listed as a good buy, such as a retail video game store (retail is still a thing?), a movie theater chain (in the middle of a pandemic) and multiple cell phone companies (that don’t produce Apple or Android phones) all began to skyrocket overnight. As of this writing, GameStop Corp. ($GME) was up nearly 2000 percent in the last year. It’s likely while riding the adrenaline rollercoaster, most investors were not thinking about taxes. There are no taxes on the moon, but it’s not too late to plan for tax consequences here on Earth.

So, you bought an NFT of a unicorn riding a unicycle. That sounds nifty. Turns out, though, even though you paid $500 for it with the expectation of a tidy profit, no one actually wants to buy it from you. It’s now so worthless you can’t even give it away. Is there a way to at least deduct the loss and save a bit in tax?

Let’s find out.

The trick to any tax preparation or tax planning engagement is to do the work as if you would have to defend it in an audit. And when it comes to an audit, “Google said I could” is about as defensible as saying “I saw it on TikTok,” “I read it on Reddit,” “My cousin’s friend said I could,” or the Twinkie Defense. What you need to defend in an audit and win is substantial authority (and really good books and records, but that is a topic for another day). This article provides some tips for conducting tax research that will get you to the authority you need.

As cryptocurrency continues to become more popular, its reach into areas not normally associated with crypto has expanded dramatically. One of the largest areas of growth is the DeFi Gaming sector. DeFi games function like regular video games with one major difference: They are either built on or rely on a blockchain to record activity. This can allow in-game assets to be NFTs that can be bought, sold, or even used in different gaming platforms. While this is a highly desirable ability for the player, it also carries with it tax consequences that gamers have previously not had to consider. With careful planning however, these tax consequences can be mitigated.

Continue reading to learn more!

At least once a week in the cryptocurrency community, there is a new post or article encouraging crypto investors to relocate to Puerto Rico to avoid tax. Relocating to the Caribbean is certainly an attractive proposition, but is it too good to be true? In the words of every good tax professional everywhere, “It depends.” Becoming a resident of Puerto Rico does have some potential tax benefits that come with it, but it is no slam dunk decision. Let’s take a trip together to the Island of Enchantment, grab a cocktail on the beach, and lower our tax bill!

Those of us who are parents of Gen Z children know it’s “no cap ” that we have no clue what our children get up to on the internet. My son, for example, makes a lot of YouTube videos of our cat for some reason. Thankfully, he hasn’t monetized his videos (yet!), so they don’t carry any tax consequences. However, many taxpayers are finding out that their dependents have spent their time in the metaverse, defi gaming, or nfts, and as a result have engaged in dozens to thousands of taxable transactions without even being aware it. Those transactions may also trigger the “Tax on a Child’s Investment and Other Unearned Income,” also known as the “Kiddie Tax.” Read on to learn more…

I love pizza. No, like I really love pizza. I have a pizza tattoo. I’m a member of the Rare Pizzas DAO. It is my go-to meal whenever the question “What’s for dinner?” gets asked. There really isn’t a better combination of cheese and deliciousness in the world. At least not in the flesh and blood “real” world. Loving pizza that much can clearly get oneself into trouble. I just never expected it to be tax trouble.

Enter the “metaverse,” although I’m not sure if that is metaphorically or digitally. The metaverse is a term used to describe many digital environments that contain aspects of online gaming, virtual reality, social networking, and cryptocurrency. Generally, a metaverse is a fully immersive digital universe which combines elements of augmented reality, virtual reality, and the internet to create a seamless and interconnected space where users can explore, create, and engage with others in a virtual world. In the metaverse, users control an avatar, which represents the user in the digital universe and functions similar to a video game character. Avatars can be customized and accessorized with clothing and other items represented in the metaverse through NFTs.

The metaverse holds the potential for new forms of entertainment, communication, commerce, and social interaction on a global scale. The metaverse economy is based on digital assets, making it possible for taxpayers to engage in a substantial number of taxable transactions without realizing it. And herein lies the crux of our problem.

As many of us become more accustomed to working from home, it is easy to forget that some industries were regularly working remotely prior to the COVID-19 pandemic. It might be easy to forget altogether that real estate businesses also qualify for the same deductions as other businesses. Yet, it is often easy to overlook something like a home office for a real estate rental operation, but the home office typically functions as the glue holding these businesses together.

To learn more about the how and the where to grab this deduction, keep reading.

The COVID-19 pandemic has altered many aspects of our society, perhaps permanently. One of these is the need to physically go to the office to get work done. Like all businesses, partnerships are no exception. While the Tax Cuts and Jobs Act of 2017 (TCJA) suspended this deduction for employees of the partnership until 2025 . However, partners may still take advantage of this often-overlooked tax benefit. The key is in how to report it. Read on to learn how!

2020 saw a huge increase in taxpayers working from home. A good internet connection can allow taxpayers in many industries to work almost anywhere. Whether it is because the typical workspace has closed or there’s a need to be home to care for a family member, the shift to working from home can come with substantial tax savings. Claiming the home office deduction allows the taxpayer to take a typically non-deductible expense and make it deductible, reducing the amount of income subject to tax.

The most important item to note is the Tax Cuts and Jobs Act of 2017 (TCJA) suspended this deduction for employees until 2025. However, this deduction is still available to taxpayers who are self-employed or independent contractors. (Some states may still allow a deduction for an employee).

While it’s not as easy as claiming the expenses and calling it a day, home office deductions provide fantastic ways to get a tax deduction for amounts you ordinarily would spend but are not eligible as write-offs. Keep reading to learn the details and how to deduct things like your homeowner’s association dues, security systems, and other home improvements.

Many taxpayers lost substantial amounts of money in the crypto collapse of 2022, but what tax consequences come with that loss? Taxpayers may be expecting to be able to deduct the full amount of their crypto losses, and may, unfortunately, find out it isn’t as straightforward as they would like…

COVID-19 has affected every aspect of our lives, and tax filing status is no exception. Couples who have filed jointly for their entire marriage may find that for 2021 it is more beneficial to file separately. This is in large part thanks to the many stimulus bills the Congress passed in 2020 and 2021.

The addition of Economic Impact Payments (EIP) and the associated Recovery Rebate Credits (RRC) have complicated what was once a simple tax calculation to now include these additional factors. In some scenarios, a couple would pay more tax filing separately than if they filed jointly, but because of pandemic-related credits, end up with more money in their pockets. Filing separately is not without its own potential headaches, though. Keep reading to find out when to switch your filing status.

I’ve been spending too much time thinking about wrapping. You might picture presents neatly wrapped under a Christmas tree, or surprise birthday gifts next to the cake, but I’m thinking of something very different: cryptocurrency token wrapping.

A wrapped token is a token that represents a cryptocurrency from another blockchain or token standard. A wrapped token can be used on certain non-native blockchains and redeemed in the future for the original currency. It is typically worth the same as the original cryptocurrency, but when it isn’t, the question arises that when you exchange virtual currency for other property (including other virtual currency) is there tax due, and if so, how much?

Like many areas of cryptocurrency tax, the IRS has yet to issue guidance on this topic, resulting in taxpayers having to fend for themselves. The primary question you need to answer is, “Is wrapping cryptocurrency a realization event?” The answer to this question will influence the ultimate tax treatment.

Keep reading to learn more.

Self-directed IRAs (SDIRAs) have long been a vehicle for less traditional investments that can’t be held in a normal IRA, such as precious metals, real estate, or tax liens. Cryptocurrency is the newest addition to that list of alternative retirement savings and has exponentially grown in popularity in recent years. The rules governing SDIRAs are complex, and taxpayers can easily and unknowingly violate the rules, resulting in the entire IRA being deemed distributed and potentially subject to tax. As the famous adage says, “with great [investment] power comes great responsibility.”

Keep reading to learn more!

“I’m going to get a pedicure later,” my wife said to me one Saturday morning. I quickly replied, “You should start an OnlyFans so you can deduct it.” (Everything has a tax angle when you’re married to a tax person.) “Is that really a thing?” she inquired. “Well…” I said, “It depends…” (Nothing is certain when you’re married to a tax person.) “…ordinarily I would say no, but in this case, it might be necessary.” (Everything is a tax pun when you’re married to a tax person.)

In the “post” covid era, many taxpayers have turned to the gig economy. (Aside from the number of companies paying workers as contractors when they should actually be employees, but that’s a different topic for a different time.) Many of these gig workers are new to being self- employed and wonder what exactly they can “write off.”

To the non-crypto enthusiast, the term “airdrop” may conjure an image of a pallet of relief supplies parachuting in from above. In the cryptocurrency world, the term has a very different meaning, but conjures the same mental image.

In the simplest terms, a crypto airdrop is a token that appears in your wallet without being purchased, although in some cases additional actions may be necessary to facilitate the transfer of the asset.

An airdrop can take several different forms, the most basic of which is an unsolicited token that simply shows up in your wallet. This is typically done as a marketing campaign, to try to expand the user base of a new project. Generally, only a nominal amount of the token is distributed.

Many times, this type of airdrop is done maliciously as part of a phishing or dusting attack. The vast majority of these airdrops are unwanted; they function as cryptocurrency’s version of “junk mail.”

Other airdrops are used to reward users of a particular protocol for their past behavior. Typically, this will take the form of a governance token or some other newly minted token.

Occasionally, the new token will automatically be deposited in the recipient’s wallet, but most of the time the user will need to connect their wallet to a website and actively claim the reward.

You may also be required to pay a gas fee to enable the transfer. Many airdrops of this type contain tokens of substantial value, so proper determination of when receipt takes place and what the fair market value (FMV) is can have considerable impact to tax.

While the two previous examples are the most common form of airdrops, they are not limited to the above. In practice, any unsolicited token received is generally considered an airdrop. This can also apply to non-fungible token (NFT) and game-based environments.

Small differences in the facts and circumstances of the airdrop may have outsized impacts on taxability and your planning opportunities. Keep reading to learn more.

As cryptocurrency grows in popularity, so do the complications of tax reporting. At present, there is no consistent 1099 reporting for crypto transactions.

This is primarily because no 1099 form currently exists to adequately report cryptocurrency. The IRS has yet to issue third party reporting requirements to exchanges, so companies must determine on their own what information to report to the IRS and how they will report it.

Some exchanges will attempt to report transactions on a traditional 1099-B, but the easily accessible transferability of crypto makes it nearly impossible for an exchange to correctly report basis information.

Incorrect reporting can result in the IRS sending an unnecessary CP2000 notice, which can be both expensive and time-consuming for the taxpayer to resolve.

Other exchanges issue a 1099-Misc for certain transactions, but again this doesn’t reflect the full picture. Some exchanges choose to issue a 1099-K to customers, showing only the gross proceeds of crypto transactions and also doesn’t show the full picture.

Here’s what to do to avoid getting a dreaded notice from the IRS.

In our recent issue, we discussed the exponentially growing universe (or metaverse if you will) of DeFi or blockchain based gaming. In that article, I shared how dedicated players support their livelihood, especially in places with a low cost of living, by playing the games.

In this issue we will explore the concept of a “Trade or Business” as defined by § 162, and how specifically how blockchain gaming meet this threshold. For a quick refresher of what constitutes a § 162 activity, see our article “Pros and Cons of Cryptocurrency Mining as a Trade or Business.

Why become a trade or business? Meeting these requirements can make a difference between video games being treated as a hobby and becoming a tax benefit.

Click here to keep reading.

Cryptocurrency is currently one of the hottest topics in taxation. The use cases of crypto are continually evolving, and official IRS guidance is perpetually several years behind the types of transactions investors engage in. We are left trying to force a crypto transaction to fit into the existing code that was not written with crypto in mind. Additionally, with the lack of official guidance, we are forced to attempt to anticipate how the IRS will interpret novel transactions or worry about potential penalties and interest down the road. Staking is a transaction that has become extremely common among crypto users, yet the IRS is silent on how to report and tax it.

Read on to learn more about cryptocurrency “mining”, staking, and how the current IRS interpretations of the tax code (or lack thereof) may affect your income reporting.

Beanie babies, Pokémon cards, POGs, and digital pictures of monkeys on the internet, one of these things is not like the others. All these are items that people may collect or at least have collected in the past. Maybe they were just collecting for fun, or perhaps they acquired in hopes of selling their items in the future for a profit. However, the IRS has highlighted only one of the items on this list as potentially being a collectible.
A non-fungible token (NFT) “is a unique digital identifier that is recorded using distributed ledger technology and may be used to certify authenticity and ownership of an associated right or asset. Ownership of an NFT may provide the holder a right with respect to a digital file (such as a digital image).” NFTs run the gamut from bored apes (computer generated pictures of monkeys that sell for hundreds of thousands of dollars, not to be confused with board apes, which are monkey pictures on sandwich and surf boards and do not sell for hundreds of thousands of dollars) to Ruish Bronzelight (a DeFi Kingdoms online video game Warrior Wizard we met in “Tax Planning for DeFi Based Games”), and even event tickets (especially popular with crypto conferences). There is even at least one CPA who sells access to his tax practice via NFT.

Click here to continue reading…