Ep. 137 | Digital Asset Reporting 101
Download MP3Welcome back, everybody, to the Teaching Tax Flow podcast. We know we are your favorite tax related podcast out there in the ecosphere. So today, episode 137, we are exploring digital assets and how the IRS treats these. So before we do it, as always, let's take a brief moment and thank our episode sponsor.
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John Tripolsky:Hey, everybody, and welcome back to the Teaching Tax Full podcast. Obviously, as you've seen in the title, read in the show notes, your friend told you, we are here today talking about digital assets one zero one and how the IRS looks at those, how you're expected to report on those, etcetera, etcetera. Again, I do not have the information. If anybody's watching this and you know this very well, I love being the dumbest guy in the room, which is why we bring the good guests. And I guess we bring Chris Pacquero back too.
John Tripolsky:Welcome to your own show, sir. How are doing today?
Chris Picciurro, CPA:It's great to be back, John. I am stoked about today's topic and our guest. It's it's one thing to have, and we have some amazing guests come on throughout the last, whatever, 30 some episodes here, but it's also great when we have fellow tax professionals come in. And as you know, whenever we bring in a tax professional, it's going to be someone that is at the level that they teach their peers. Because it's one thing to be a tax professional.
Chris Picciurro, CPA:It's another when you teach the teachers, then you are you simply master something. So very excited to have our guest today. This is a topic that, as you know, John, I'm not an expert in, hence why we've been searching for the right person, and I'm so excited to to have that guest. We are gonna talk about digital assets one zero one, definitely a elevated enforcement level by the IRS. That doesn't mean you should be afraid of them.
Chris Picciurro, CPA:That doesn't mean you shouldn't be involved with them, but we're gonna get right to that. Excited to introduce our guest, Ty Gaines, enrolled agent. She is, super respected in our industry, a presenter. If you follow her LinkedIn, her LinkedIn will be connected to this. She is speaking on a weekly basis and adding regional and national level.
Chris Picciurro, CPA:But also fun facts that I found out that she has given back to this profession. She was named enrolled agent of the year in by the Virginia Society of Enrolled Agents a few years back. She was also the president of that organization and really involved with the NAEA, which is the National Association of Enrolled Agents. She also was a mentor of the year for that organization, has her own tax practice, is the project manager for Token Tax LLC, which we're gonna talk about as well. So honored to have you.
Chris Picciurro, CPA:Ty, welcome to the Teaching Tax Slow podcast.
Tynisa (Ty) Gaines, EA:Well, thank you for having me. Every time somebody reads my bio, I'm always like, wow. That girl is awesome. So I guess I'm me.
John Tripolsky:And Ty, that that intro was so long. I feel like I was out of breath as Chris was reading it. Mean, I thought myself
Chris Picciurro, CPA:like too, but it's like, hey. That that that person That
Tynisa (Ty) Gaines, EA:was a nice little succinct tie up. I like it. Sounds great. Thank you.
Chris Picciurro, CPA:Oh, one more fun fact, John, for you. Ty is a avid
John Tripolsky:Oh, I know where this is going.
Chris Picciurro, CPA:Nope. She's an avid yoga. She's an avid she practices yoga, but also she's such a physical specimen. I'm sure she plays pickleball, which I know she does play. Absolutely.
Chris Picciurro, CPA:A game one Absolutely. And she's gonna get us on the yoga mat, and that's gonna be ugly. We're gonna need some bandages and some and we're gonna need some ice packs, John.
John Tripolsky:I have no words.
Tynisa (Ty) Gaines, EA:Have no words to do. You gotta play pickleball, the whole thing.
John Tripolsky:Oh, yeah. Alright, Ty. We're gonna rearrange your bio, and we're gonna have some fun with that here eventually. So just k. I see where this is going.
Chris Picciurro, CPA:Well, let's jump in. I'm sorry, Ty. Yeah. Tell us a little bit about yourself. I know I gave you did the introduction, but what led you into becoming a tax professional and then specifically into working in that niche of digital assets?
Tynisa (Ty) Gaines, EA:So real quick, I guess, the I think I've been a tax professional. I've been an enrolled agent since 02/2007, but I believe I started my first tax season in 02/2002. So, sadly, I can do all complex tax things, but the math on that is really throwing me off. Twenty three years, I don't know, something like that. I've been preparing taxes.
Tynisa (Ty) Gaines, EA:So I think I started digital assets around 02/2019. So I have been in the tax field for a while and was actually getting a little tired of regular tax. I think the Tax Cuts and Jobs Act had just passed. We had all this new stuff, and then there was something like cryptocurrency. And I'm like, hey.
Tynisa (Ty) Gaines, EA:What's that? You know? So I kinda took some classes, some trainings. I actually worked for two different startups before I ended up at TokenTax, which was a new startup at the time. We've grown tremendously since then, probably because I worked there.
Tynisa (Ty) Gaines, EA:But, no, seriously Exactly. It's it's it's been a, you know, it's been a ride. The the crypto market has been, as we can talk about as we go up and down and around, and I personally didn't invest in it until 2020. I wanna say I jumped in at COVID when the markets dropped, is when I invested in in, like, Ethereum and Bitcoin. And and if I told you what I paid for them, I wanna say Ethereum was, like, $200, and it's over 2,000 now, which is even low for for its standards, but it's over 2,000 now.
Tynisa (Ty) Gaines, EA:And then Bitcoin was maybe 6 or 7,000. It's in the nineties now. I I wish I could have bought a whole one. I didn't because that seems so high. Like, $7,000 for a coin seemed ridiculous back then, and now it's almost a hundred thousand.
Tynisa (Ty) Gaines, EA:Right? Because you're buying stocks. Like, I buy Ford, and it's $8. And then you say something like Bitcoin, and it's 8,000. You're like, I'm not buying that.
Tynisa (Ty) Gaines, EA:So you buy you buy parts of cryptocurrency. You don't buy the whole thing. Well, unless you're rich. I'm not. But, you know, you buy you buy fractions of it.
Tynisa (Ty) Gaines, EA:So when you buy Bitcoin, you buy point zero zero zero zero whatever of a Bitcoin, and you spend a hundred dollars and that's what you get. But, yeah, taxes in general, I just I was a military spouse. We traveled a lot. It's a great thing to travel with, and I ended up building a virtual practice as a result of having to travel as a military spouse. So that's kind of where it started and where it where it flowed to.
Tynisa (Ty) Gaines, EA:Oh, really? So I I work remotely still, yet it's more remote because of technology. Right? So at first, it was like people dropping stuff off at the house, and if you moved, you could keep the clients with you. Now it's all completely virtual.
Tynisa (Ty) Gaines, EA:So Uh-huh. It's great.
Chris Picciurro, CPA:Well, I have a question for you that no one jump in. I promise. A little birdie told me that you are an alum of the University of Illinois.
Tynisa (Ty) Gaines, EA:Oh, of course. I l l.
Chris Picciurro, CPA:And you're so I went to Michigan State, so we got big 10 going for
Tynisa (Ty) Gaines, EA:us. One Big 10.
Chris Picciurro, CPA:Yes. The the one program we don't love on this show is the University of Michigan, but that's alright because John lives outside Ann Arbor. So we're not a big Michigan fan here.
John Tripolsky:Oh, don't worry. People people here are pretty used to not being liked, you know, because it's always the the popular people and the really good ones. They they take a lot of heat. It's all good. I didn't
Tynisa (Ty) Gaines, EA:know this,
John Tripolsky:so I'm not smart enough.
Chris Picciurro, CPA:Also, you got your I should have mentioned this. You got your master's degree from Troy University. And guess what? That's not in Troy, Michigan. That's not in Troy, New York.
Chris Picciurro, CPA:It's in Alabama. Right?
Tynisa (Ty) Gaines, EA:It's in Troy, Alabama.
Chris Picciurro, CPA:Yeah. That's that's so we drive through there. I live in Franklin, Tennessee, which is just South of Nashville, Fifteen miles. So when we go to the beach, we go right through where Troy University is.
Tynisa (Ty) Gaines, EA:Have you seen the campus? It's the most beautiful campus in the state, they say, and it is a really pretty campus. I didn't actually attend on campus. It wasn't until two years ago that I actually visited it. I went through the military.
Tynisa (Ty) Gaines, EA:It was a you know, through the military bases, you could go to the schools long distance distance learning, I guess, back then. It wasn't really remote or online, but they had classes on the bases that were linked to the university, and that's how I attended. But a couple years ago, my son, who's active duty military, army, Apache helicopter, by the way, was in aviation school at Fort Novicell, and it's, like, thirty minutes from the the campus, so we drove through. So I took pictures, like I graduated from there in 1999, so I took pictures, like, twenty years later. Like, yeah.
Tynisa (Ty) Gaines, EA:It's why we made it to the campus.
Chris Picciurro, CPA:Token tax goes goes public and and you're on the stock exchange. You're gonna ring the bell, and then and then there's gonna be a tie gains. There's gonna be a statue next to the football stadium by all the all the stars.
Tynisa (Ty) Gaines, EA:So I love it. Because we definitely went to the field. I have selfies. I can tell you of us on the field. That was the the whole thing.
Tynisa (Ty) Gaines, EA:So
John Tripolsky:yeah. And we know why Chris has a bit of that campus because every time he goes to that state, he stops at Buc ee's for about two and a half hours.
Chris Picciurro, CPA:Oh, no.
John Tripolsky:That's his favorite place.
Tynisa (Ty) Gaines, EA:A Buc ee's ten minutes from my house here. So yeah.
John Tripolsky:U of M campus, University of Michigan, and Buc ee's. Chris would be an absolute paradise.
Chris Picciurro, CPA:I'm I'm more of a wah wah or Busy Bee person, but that's alright.
Tynisa (Ty) Gaines, EA:I love wah wah. I love wah wah.
Chris Picciurro, CPA:Me too. Not a fan of Buc ee's, but you know what? That's okay. I like to go against the grain a little bit. Just just to you know?
Chris Picciurro, CPA:Well, let's jump into this the the the digital assets. And, you know, a lot of time there's a lot of confusion, right, from taxpayers thinking that they you know, that that that how do I report that on my tax return? And, let's chat through, like, why do people you know? I know that the the first the question on the first page of the return, which actually the IRS slipped in there the last few years, right, about digital assets, and then it changed of how you're even supposed to answer that. But tell us about why why do people need to report the digital assets on their tax return?
Tynisa (Ty) Gaines, EA:So they are considered property, and they hold value. So, generally, the IRS wants money for anything you sell that's valuable. It's funny because if you sell something at a yard sale, it has technically decrease in value, so you generally don't have to report that unless you sell it on eBay, in which case you do have to report it. But, you know, the decrease in value versus increase is the thing here. And although crypto can increase and decrease, it is similar to a stock where you're buying it as an investment.
Tynisa (Ty) Gaines, EA:So your intent when you buy it is to make money, you would hope. Right? So because of that, in general, you have to report it. So any sales, anytime you sell it, anytime you trade it or buy it, or guess what? Starbucks accepts it.
Tynisa (Ty) Gaines, EA:If you buy coffee at Starbucks and use cryptocurrency to do so, that is a taxable event that you must report on your tax return. Now that's the crazy thing.
Chris Picciurro, CPA:Segue because you you nailed it. A lot of times people say, well, I just exchanged it. I didn't take it out of my account. Well, just like if you're you're you you have a brokerage account and your portfolio rebalances and you sell one stock to buy another one. That's that's That's Maybe that's gonna be reportable.
Tynisa (Ty) Gaines, EA:It is. And then it's very close, although not a security like stock, very much like a stock in terms of handling on your tax return. So if in fact you do buy stocks or are familiar with stocks, that process is exactly the same. It's reported on a form eighty nine forty nine individually. It you report if it's short term, which means you've had it for less than a year, or if it's long term, which means you've had it for longer than a year.
Tynisa (Ty) Gaines, EA:And that the reason you would do that is because taxes are more favorable for long term gains versus short term gains. And Right. We can talk about that later, but the point is you have to report it, and it is generally taxable. If you have a loss, that could help you, but you still have to put that on the tax return. Right.
Chris Picciurro, CPA:So let's talk yeah. Let's talk about that where so we know that, like you've said, the digital assets are property. They're not foreign currency. They are reported just like you would sell a mutual fund or a stock. What are some of the best practices for for people or taxpayers to keep track of their cost basis, and can they u what kind of methods are available?
Chris Picciurro, CPA:Because we know what stock and mutual funds you can do FIFO, LIFO, or specific identification or an average. What what would you recommend?
Tynisa (Ty) Gaines, EA:So same with crypto. Specific ID, can choose. First in, first out, FIFO. Last in, first out. Or highest in, first out is the third option, which generally helps people the most, I think, is what most of our clients generally choose because it's more of giving them a choice in, I'll sell this lot and not this one and things like that.
Tynisa (Ty) Gaines, EA:The the let's see. What was the question? Because I got Well, that's right.
Chris Picciurro, CPA:So can yeah. How can they keep track of cost basis?
Tynisa (Ty) Gaines, EA:So how do you keep track? So there's a new law that actually says you have to keep track. Mhmm. Whereas before, even though you should have, many people didn't. So going back to when the 8949 was born in 02/2010, cause a lot of people don't realize that the 8949 for reporting stocks is not that old.
Tynisa (Ty) Gaines, EA:I've been doing taxes longer than the eighty nine forty nine existed. Used to be able to put it on a schedule d, but now because you but back in 02/2010, there was a law that basically said brokers have to report cost basis for stocks. And so that's when we start getting the new stock, the $10.99 b that's a code a short term covered, code b short term not covered. Same thing is happening with crypto. There was a broker bill passed last July, t d 10,000, that basically said brokers are gonna have to report cost basis for crypto.
Tynisa (Ty) Gaines, EA:They don't know cost basis. So it's your responsibility as a taxpayer to actually keep track of your tax basis because you are gonna actually have to give it to the broker. And when you don't give it to the broker, what happens is they just report the proceeds, and you're taxed on the total proceeds even though you have basis because you paid something for that item. So the best way to track this, obviously, is to use crypto software, and I work for a crypto software company, duh, token tax. So we keep track of your your assets.
Tynisa (Ty) Gaines, EA:We track your bases. If we don't know it, we can look it up. There everything is stored on the blockchain, so we can look for basis. So you can pay professionals any software. I'm gonna plug mine because I work there, but you can look crypto software companies, this is what they do.
Tynisa (Ty) Gaines, EA:So they all do the same thing where they look they help you find any missing cost spaces. Usually, that occurs when people have different exchanges, different wallets, multiple things, and they're like, oh, I bought it from this wallet. I transferred it to this. I don't remember when I bought it. You should keep track of everything.
Tynisa (Ty) Gaines, EA:If you're good with Excel, you can probably do it in Excel if you don't have a lot of transactions. But if you do or you do more complex transactions, you should get crypto software to help you track your base.
Chris Picciurro, CPA:That you you took my next question from me because we have to remember, if you're listening to the well, I always say that, John. Right? Because you have to be listening. Why do I ask you listen? You're freaking listening or watching.
John Tripolsky:We're gonna change it to be like, while you're listening.
Chris Picciurro, CPA:While you're listening.
John Tripolsky:And then a cowbell goes off.
Chris Picciurro, CPA:Your the IRS will credit you with zero cost basis. It's your responsibility to track that basis. And quite frankly, you may have bought these assets ten four or five years ago when so that's why you need that software. And, again, TokenTax is gonna be a very big help for you. We're gonna put those links in the in all the notes.
Chris Picciurro, CPA:But you're responsible because I can't tell you how many times, and this has happened with other this happens all the time with the CP 2 thousands, which is your most common IRS notice. Someone says, oh, I sold I sold my Bitcoin. Yeah. Why didn't you let's let's say I'm the tax professional. Oh, okay.
Chris Picciurro, CPA:Well, why didn't you tell me? Because I didn't make no money, and they always say Right. That. Right?
Tynisa (Ty) Gaines, EA:They
Chris Picciurro, CPA:nobody makes money. But guess what? It's still reportable in the IRS now. It's gonna say, $10,000 sale. I'm gonna assess your short term capital gain rate with zero basis.
Chris Picciurro, CPA:You get the crappiest treatment, and it's your responsibility to prove the better treatment. So do that right away and keep track of these things.
Tynisa (Ty) Gaines, EA:Keeping records.
Chris Picciurro, CPA:So, Ty, you mentioned something that was I want I've first question would be is so, typically, that's gonna get reported on the $89.49. You mentioned the Starbucks example. Let's say someone is owns a coffee shop in a in a hip cool area, and you accept yeah. You know, you accept Bitcoin. How does that get reported?
Chris Picciurro, CPA:Let's say you're a sole proprietor.
Tynisa (Ty) Gaines, EA:If I'm I'm the sole proprietor Yes. Accepting it as payment Yes. I have to report that as income as well as fair market value upon receipt. So whatever it's worth at the time that I receive it is ordinary income to me as a as a business owner.
Chris Picciurro, CPA:Right. And then let's say you keep it in your in your your wallet or or something as in the business, and then subsequently sell it, you might have a gain or loss there. But yeah. And and there's some and there's actually gonna be some real estate transaction done with digital assets coming up. Because think about this.
Chris Picciurro, CPA:If a lot of your wealth is in digital assets, especially for that younger generation, it's not like you can go to the mortgage company and say, hey. I've got all this money in my wallet. You might have to pay cash for a property, but really cash. And and when you the point is is once that digital asset leaves your ownership, it is considered transferred and reportable
Tynisa (Ty) Gaines, EA:Yes. By
Chris Picciurro, CPA:Absolutely. House, a car, coffee. Anything. Anything. And you
Tynisa (Ty) Gaines, EA:could actually have a loss on it. You could have paid, you know, $10 for this cryptocurrency, and then Mhmm. It could have decreased in value by the time you you you you sold it, and then you purchased something that wasn't even worth that. Like, it could be that you do lose money. It just doesn't mean that you don't report it.
Chris Picciurro, CPA:I mean, you could very well have a situation. We were talking about this in some of our educational seminars for the tax pros. Let's say you had a young person that bought $5,000 worth of cryptocurrency and went up to a half a million dollars. They sell it, pay cash for a house.
Tynisa (Ty) Gaines, EA:Mhmm.
Chris Picciurro, CPA:They gotta remember, you've gotta pay tax on that. Hope it's probably a long term gain.
Tynisa (Ty) Gaines, EA:Yeah. Long term, hopefully, for five years.
Chris Picciurro, CPA:Shingle off the house and pay the tax. Right? You're gonna have a taxable event.
Tynisa (Ty) Gaines, EA:Yes. You are. Yep. And it yeah. It it people you're gonna have to pay the tax.
Tynisa (Ty) Gaines, EA:You have to put that aside. A part of the problem we have at TokenTax, where we're preparing taxes, is that the markets go up and down. Right? So people file their taxes one year. Markets are up.
Tynisa (Ty) Gaines, EA:They pay, you know, millions of dollars on taxes. The next year, the bill is due. Guess what? Value went down. They can't pay it because you're talking about the difference in we cut off the tax year 12/31 and the value of Bitcoin at 12/31 may have been a hundred thousand dollars.
Tynisa (Ty) Gaines, EA:We filed taxes April 15 and it's dropped to $80,000 or less or whatever. We have a loss. The portfolio balance drops and people can't pay the tax liability because you're taxed at the time, the fair market value at the time. Digital assets can be volatile and can up and down as they have been even just this year. And so you can you can definitely lose lose money or basically run short.
Tynisa (Ty) Gaines, EA:When you were rich last year, you could be poor this year.
Chris Picciurro, CPA:It's volatile. That is a great way to put it. Well, Ty, I'm gonna wrap this up because I guarantee you, we are go John's already making some notes over there. It's rare that he's paying attention half the time. No.
Chris Picciurro, CPA:He I know. He's the general's talking about anymore. I well, we'll work on those skills, We'll get back you. But I know we'll have Ty back on. We're gonna we're gonna we're gonna we're gonna entice her to to add some content to our YouTube channel.
Chris Picciurro, CPA:But to wrap
Tynisa (Ty) Gaines, EA:it up on
Chris Picciurro, CPA:this one zero one, digital assets one zero one, can you give us just a couple minutes on the aforementioned new reporting requirement called a ten ninety nine DA? Stands for digital assets. Many people are aware of ten ninety nine NEC miscellaneous interest dividend. What are the rules with the ten ninety nine DA that are gonna be new here for the 2025 tax year, which would be filing in '26 as as we and we'll and yeah. Can you leave us with those those rules?
Tynisa (Ty) Gaines, EA:So the ten ninety nine d a will be similar to what I was discussing the stock's ten ninety nine b. It's not as cute. It's not as neat. It doesn't look as good, but it reports the same thing. The name of the asset, the date it was purchased, the date it was sold, the cost basis, the sale, That type of information is the information taxpayers will need to have for their tax preparer to put that information on their $89.49.
Tynisa (Ty) Gaines, EA:So those forms will come out. The problem with them that I see so far is that there may be multiple forms where the ten ninety nine b would just say code a, code b, k code c, and they would all be on one form. It looks like the digital ten ninety nine d a is set up to put one code per form. So the codes are like GHJKY. Yeah.
Tynisa (Ty) Gaines, EA:Y. And that's like the unknown one. But when that code is on a form, like, there's only spot for one code. So, like, anything short term could be on one form, and then something long term, even though it's the same stock, will be on a second form. So the problem with that form is that they're killing trees for one.
Tynisa (Ty) Gaines, EA:But, you know, it it it could be to where do we have everything because there's multiple pages. And we know in the digital age, clients like to give you page one of something. So as a taxpayer, give all the pages of everything you receive and make sure you receive all pages because this is a new thing. And they don't have to report cost basis in 2025. That was actually pushed to 2026.
Tynisa (Ty) Gaines, EA:So a lot of the forms may be missing cost basis, which is another reason taxpayers will need to keep track of that so they can give that information and say, no. This is what I paid for it, and tax professionals will be able to use that basis to help lower any gains.
Chris Picciurro, CPA:In that form, I I you know, I looked at a draft of that form because that's because I don't have a very good social life. But they're asking for, like, you know, short term, long term, ordinary. There's a lot of information on that form
John Tripolsky:It is.
Chris Picciurro, CPA:That that's gonna get really tricky. But I I can't thank you enough for joining us here, and and I can't wait to have you back and get some more information. Go ahead, Johnny t. I know you're
John Tripolsky:Oh, I'm itching, man. I'm sitting in here in my head just playing it back because you're let you're you're going off with all those letters that are on that form. And in my head, I'm trying to think of a a really dumb way to do, like, a a version of the YMCA.
Tynisa (Ty) Gaines, EA:Oh. You know, for
John Tripolsky:the village people where it's like, bee, sing, bee, bee, What? Yeah. Crazy with it. They're that's why I'm here. Right?
John Tripolsky:The poor comic relief.
Tynisa (Ty) Gaines, EA:For sure. That's why. And I'm here for it, as you can see.
John Tripolsky:Well, I'm glad you are. We can get rid of everybody else. Chris and Gong know. But, honestly, Ty, thank you so much for joining us. And, obviously, as Chris has said multiple times too, we're we're gonna have you back on.
John Tripolsky:You don't have a choice. You know?
Tynisa (Ty) Gaines, EA:We're just
John Tripolsky:gonna find you. You know, we'll we'll take the blockchain approach. Right? We'll do a little bit at a time, and then we'll we'll get you back. But for anybody that is listening to this as well, as mentioned a little bit earlier on too, we will drop Ty's contact in the show notes as well as anywhere you're listening to this.
John Tripolsky:Obviously, subscribe to it. You'd be on the lookout for some more content we're gonna put out. But, also, Chris, I don't know if you mentioned it, but if you did, awesome. I'll say it again. Hop on the YouTube channel.
John Tripolsky:If that's if you're watching this on YouTube, awesome. Don't be lazy. Hit the subscribe button. It's somewhere, you know, in the y m you know, not with the, like,
Tynisa (Ty) Gaines, EA:Madonna logo here. Subscribed. I found it.
John Tripolsky:So Good. Good. You can come
Chris Picciurro, CPA:back then.
John Tripolsky:You can come back. But, yes, anybody that's listening to this, reach out to us. Reach out to anybody, your tax pro, anybody you have in your proverbial Rolodex, and they will help you out. This is something you do not wanna tackle necessarily by yourself. But if you do, do a little bit of a DIY with this.
John Tripolsky:Hopefully, this helped you along the way. So as always, we will see you back here again next week. Same day of the week, different date, completely different topic. Have a good week, everybody.
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