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Jan 10, 2019

Jeff Neumeister, Founder and CEO of Neumeister & Associates, joins us today to talk about cryptocurrency taxes, a confounding area of tax law (what isn’t?) and one that you should master if you are an investor in digital currency. Because what you don’t know could have an adverse impact on your pocketbook. That’s what happened to one U.S. college student in 2017 who invested $5,000 in Ethereum and somehow would up owing the IRS $400,000 in taxes. Yes, you stand to benefit greatly from understanding how the IRS views crypto (Hint: It’s in the same category as your house). And you’ll learn the cardinal rule of crypto taxation: The buck stops with you.


This is specially important this year after the 2018 market crash since many investors are selling their cryptocurrency and fleeing the market, without full knowledge of the tsunami of capital gains liabilities that these transactions may be triggering.


A forensic accountant by trade, Jeff brings great credibility to the task of walking us through the minefields of crypto taxes. He offers practical tips on everything from what constitutes a taxable event to what makes crypto taxes so challenging and how mined coins are taxed. That’s just a few of the questions Jeff answers in this episode. You’ll come away feeling a lot more confident about understanding your tax burden as you stagger into your tax prep marathon.  


Topics Covered in this Conversation with Jeff Neumeister


  • What makes crypto taxes so challenging.
  • What constitutes a taxable event?
  • What is the difference between short-term and long-term gains?
  • How are mined coins taxed?
  • What happens if I give some coins as a gift, or someone gives me crypto?
  • Do I have to pay tax on coins that were hacked?
  • What happens if I lose some coins?
  • What are the acceptable ways to report coin gains?
  • What are the biggest obstacles to easily filing crypto taxes?
  • Increasingly, there are charities that accept crypto. Is that something that would be helpful at tax time?
  •  How are exchanges doing in terms of making it easy for investors to file taxes?
  • Can crypto losses be balanced against traditional fiat capital losses.
  • What’s the craziest thing you’ve ever seen or heard with it comes to filing or not filing crypto taxes.
  • Let’s step back a bit and look at the process involved - let’s look at two scenarios:
    • Scenario A: Let’s say you are Sally Fey, a beginner investor in 2017 and you got all caught up in the buying and selling during the Bull Market and you didn’t track all the coins you traded across multiple exchanges nor did you jot down the buy/sell price  for each transaction. Now your taxes are looming and you have your head in your hands. How do you regroup?
    • Scenario B: Unlike Sally Fey, you are Matt Jones -- a beginner investor in 2019 and it’s a Bear Market and you’ve been told now is the time to buy. You’re starting with a clean slate. You’ve set up your exchange accounts, you are ready to trade. What’s good tax hygiene you should follow from Day One and on to Day 365 to simplify your tax headache for the year?
  • Can you get away with NOT paying crypto taxes?
  • What are the penalties for non-compliance?
  • Any closing thoughts on how to make our crypto tax lives easier?


Questions and Comments?


Guest Contact Information

Jeff Neumeister

Website | LinkedIn | Twitter

Resource Links:

Transcript: Interview with Jeff Neumeister

Interview Recorded On: November 12

Topic: Crypto Taxes

Chitra: Hello, and welcome to Running with Unicorns, your portal to the world of cryptocurrency. I'm Chitra Ragavan, Chief Strategy Officer at Gem. It's that time of year again, and your crypto taxes are looming. Here's what you can do about it. Our guest today is going to walk us through the ins and outs of crypto tax filing. Jeff Neumeister is CEO and Founder of Neumeister & Associates, an LA-based tax advisory firm with a growing practice in crypto taxes.


Jeff, welcome to the program.


Jeff: Thank you.


Chitra: What makes filing crypto taxes so challenging?


Jeff: It'd be probably because there are so many different things that are happening in the crypto world. It's not just mining coins or just trading coins, but there are forks, airdrops. There's just a lot happening. Because it's a new space, it's a lot that the taxing authorities are still trying to wrap their heads around.


Chitra: Let's start with the basics. What constitutes a taxable event in cryptocurrency?


Jeff: A taxable event is anything that results in a tax obligation or a potential tax obligation. That could be selling something, it could be generating income, it could be incurring a expense.


Chitra: Is it different than in regular taxes? What are the differences and similarities?


Jeff: It's similar in concept, except with cryptos there's just, again, so much more going on. Normally, if someone is just, say, a W2 earner, they have a paycheck, and that's the sole source of income that is subject to tax. With cryptos, however, if you're mining and trading in the ICO world, there's so many things that are happening that you're constantly subjected to different types of taxes.


Chitra: One of the basic things one needs to know is short-term and long-term gains. How does that work?


Jeff: Short-term gains just refer to anything, anytime you hold an asset or a piece of property for less than 12 months. Long-term is anything above that. Now, they also come along with different taxable rates. With long-term capital gains, it could be anywhere from 0 to 20%, so much better than what most of us pay with taxes for our income earnings. For short-term gains, it's anywhere from 10 to 37%. Short-term capital gains are essentially the same as ordinary income tax rates.


Chitra: Let's look at different types of crypto and how they will be impacted by taxes. Let's start with if you're mining cryptocurrency. How do you account for those?


Jeff: Mining's interesting, because it's kind of two things at once. When you mine a coin, or a fraction of a fraction of a coin, you're generating ordinary income, so whatever the value of the mined coin was, or fraction of a coin was, you have to pay ordinary income taxes on that. Then, that also establishes your cost basis in the coin that you now hold. If you do something else with it later on, trade it or sell it, you'll have capital gains on top of that.


Chitra: Then, let's look at crypto gifts. If you get a gift of Bitcoin, or Ether, or EOS, how do you handle that when it comes to tax time?


Jeff: If you're the receiver of a gift, then you just need to be aware of what the holder's or the donor's cost basis was. If they acquired something for, say, $100 and gave it to you, you need to make sure that you have that down in your records that your cost basis is $100.


There's no tax owed on a gift received. However, if you're the gift giver, you might have to do a informational filing, a form 709. What that is is anytime you gift more, at least in 2018, more than $15,000, you have to file a form 709. You don't have to pay gift tax on that, but if you exceed your gift-giving of $5.6 million during the course of your lifetime, then you have to start paying gift taxes.


Chitra: If only we could all be so lucky.


Jeff: Right. Most of us will never have to worry about that, but make sure that you file a form 709, because there are penalties with not filing.


Chitra: Then, can you give crypto to charity? I see that increasingly, there are a lot of, even the Red Cross and other organizations accepting crypto. When that happens, is that a good thing to do, when it comes to tax time? Obviously, it's a good thing to do in any case, but it probably helps with taxes, doesn't it?


Jeff: Absolutely. It's just like any charitable contribution, except instead of giving clothes, or fiat, or artwork, or jewelry, you're giving cryptos, yeah.


Chitra: It's taxed similarly?


Jeff: Yes, mm-hmm (affirmative).


Chitra: Then, if you're hacked, what happens? You're losing a bunch of coins because you got hacked. Do you have to pay taxes on that?


Jeff: No, but you have to make sure that it's documented. It's the same thing as if someone came into your house and burglarized it, right? It's a casualty loss. That would be an itemized deduction. You have to make sure that you record those things.

Chitra: What if you just lose your crypto? Like, they're on some exchange, you don't know where it is, or you've lost the password. Can they figure it out that you have this crypto? How do you account for the missing crypto?


Jeff: That's a little bit more challenging. If you no longer have access, say, to your key, and you'll never obtain access, then that could be construed as a casualty loss, as well. If you just say, "I don't know which exchange it's on," hopefully that won't come up if you're audited, yeah.


Chitra: And if you are?


Jeff: Then, as long as you show a good faith effort in being consistent and transparent with taxing authorities, and they could see that you're not trying to hide anything, then you should be okay.


Chitra: Do you hear of people that are trying to hide crypto by claiming losses, that they've lost it?


Jeff: Some folks, yeah, yeah. More egregious than that, though, we've had, there was one gentleman that was seeking out a CPA, who made a little over 2.5 million in cryptos, and said, "No, I'm just not going to file. If they want the money, they have to come after me."


Chitra: Did they?


Jeff: Well, that's what's going to happen over the next couple years, yeah. The IRS has started mounting a task force specialist specifically to investigate cryptocurrency filings.


Chitra: Is that going to be an easy task? Will they find people that are scofflaws?


Jeff: They will absolutely find people, right? It's going to be interesting in the tax world for the next couple of years, and tax courts, people fighting them.


Chitra: You're seeing a lot of new developments in tax filings, in tax law as a result of this?


Jeff: Not yet. Really, they're just kind of testing the waters, now. The last, about a year ago, they started issuing subpoenas to exchanges, and they were winning, to get transaction records from them, so they could see what people are trading and how much people are earning, so they could compare that with individual tax returns, to find evidence of those that are evading their taxes. They're just starting to institute those audits now and will be taking these folks to tax court as needed. There's a lot of things that will come out of it, but it hasn't happened yet.


Chitra: Because I think, particularly in the early days, there were probably a lot of people who weren't filing taxes. Is there like a statute of limitations, or does it matter if like 10 years ago you weren't filing taxes, and now the IRS is starting to think about this and starting to do these audits?


Jeff: There is a statute. It's, generally speaking, three years from the date of which a filing was due, but that's only if it was an innocent mistake. If you're intentionally evading, there's no statute on that.


Chitra: How do you report, typically, gains and losses? What's the process?


Jeff: The process is usually, you want to have everything calculated, all the transactions. Coin for coin, coin for fiat, and those will be itemized on a form 8949, and summarized on a schedule D, which are attached to the tax returns.


Chitra: Having done my crypto taxes this year, it's fairly complicated. It's just, you have to look at every single transaction. Talk a little bit about what that process is like. It's fascinating for me to see the level of detail and how you actually go about finding those records, if somebody hasn't kept those records, and being able to trace the flow of that currency from the exchange to your wallet, or if you're trading, you've got all of these multiple transactions that have taken place, hundreds, maybe thousands of them.


Jeff: Yeah, it could get very complicated. That's why a lot of our clients have come to us, to help them untangle these complex array of transactions, ranging from, if they have a few hundred coins that they're trading across multiple years, you can end up having thousands and thousands of cost pulls, because you have to trace every single transaction to its cost basis. Its cost basis depend on whether you used FIFO, LIFO, or HIFO.


Chitra: Explain that a little bit.


Jeff: Sure, yeah. Those are the manners in which you inventory the cells of different coins. LIFO, last in, first out, that's saying, when you sell a coin, you go to the last time that you had acquired that coin, and you sell it out of that pool. If you're buying and selling coins all day long, go across multiple months, you have many cost pulls, even thousands or tens of thousands of cost pulls.


FIFO, first in, first out, is where you sell your oldest coin. What that does is it will result in fewer long-term capital gains, but you're kind of eating up your tax obligation now, versus deferring it to later on.


Chitra: Let's say I'm trading, okay? I'm on exchanges, and I'm trading. I'm not really thinking about ... It's not something you think during your trading process, right? It's something you do after the fact. I'm not thinking LIFO and FIFO when I'm like, "Let me find what's my oldest Bitcoin, and let me trade that for Ether." I'm just like, trading. Am I doing the right thing? Is this something you go after the fact, and start to look through it and make those calculations?


Jeff: The easiest thing is to maintain good records, so that whoever, whether you're doing it yourself or outsourcing it to a professional like us, then they could go through those records a lot easier, because it does get complicated. As long as you have the information, it could be all untangled.


Chitra: What's the largest number of transactions you've done, filing taxes, that you've seen? Thousands, hundreds of thousands?


Jeff: Probably in the hundreds of thousands. I think our largest client had a little shy of 200,000 transactions across about 2.5 years. It was a lot. It took a massive amount of manpower, because there isn't a way to fully automate it, yet. We've established a proprietary method to semi-automate portions of it, but not the whole thing. There's still a lot of manual touches that have to be done to it.


Chitra: Were you able to do it?


Jeff: Yeah, yeah. We were able to untangle all of it. He had a massive tax obligation, but most importantly, it'll keep him compliant with the IRS. He had the cash, right? If you make a million dollars in cryptos, and if you have to pay a few hundred thousand in tax, you know, you're still coming out ahead.


Chitra: This is true. What are some of the biggest obstacles today for average investors, when it comes to filing taxes?


Jeff: I think having an understanding about how complex the tax aspect is with cryptos, if you're trading, mining, doing anything else. I think just being aware and mindful of that.


Chitra: There's also the issue of documentation, right? For example, different exchanges can give you different levels of information about your trades, so at the end of the year, some exchanges will give you a lot of information. Other exchanges give you virtually no information. How do you start to do the detective work to find all of your records?


Jeff: That's one of the tricky parts, yeah, because there isn't really any sort of regulation about what all the exchanges have to provide users. There's going to be, and it's moving that direction. For now, it's kind of up to the individual to maintain their own records. If the exchange only provides piecemeal stuff, or in the case of Bittrex that just up and deleted people's information, it's still your obligation to make sure that you're tracking things.


Chitra: What happened in that instance where the information was deleted?


Jeff: Well, they up and decided just to remove information.


Chitra: This was an exchange?


Jeff: Yeah, yeah, Bittrex. It's still the user's responsibility to maintain the records. The individuals that were subjected to that, had they downloaded their transactional information, let's say, every week or every month, they would have been okay, right, just in case something does happen to an exchange. That's something we advise our clients to do is don't wait till the end of the year to start pulling your information, even if you're using a CPA like us, right? Pull the information maybe once a month, just in case something happens.


Chitra: That's interesting. That's something I've never thought to do. It's kind of surprising that they're allowed to even delete information. Is that going to change, in the future?


Jeff: Yeah, there's definitely more pressure in regulation around what the exchanges are doing. Also, keep in mind that a lot of these are foreign exchanges, too, right? The IRS and the federal government only has so much control over what they do.


Chitra: Because this is such a global flow of money.


Jeff: Exactly. It's a global thing. Right.


Chitra: How does the US government, or how is the US government attempting to get a handle on this? Do you feel like the government is kind of playing catch up, now?


Jeff: A bit, yeah. I think there was too much downtime from 2014 to now. You know, the last time the IRS issued any formal guidance was in 2014.


Chitra: What was that initial guidance?


Jeff: It was maybe like a five-page notice, 2014-21, which pretty much just said that it's not legal tender, and to pay your tax on it. There really wasn't much guidance beyond that.


Chitra: What happened before then, like 2009 through '14? Was there any guidance?


Jeff: Nothing formal.


Chitra: What were people doing then?


Jeff: I think, at the time, IRS and other government agencies probably just assumed that this is just a fringe thing, it's a temporary thing, it's not going to last, but look at us now. There are industries being built around blockchain and crypto, and they realize that, now, and the amount of money that people have earned in the sector. They see it as, like, it's a huge nest egg waiting to be tapped.


Chitra: Build your highways and all of that stuff.


Jeff: Right, yeah.


Chitra: Now, when you're filing taxes, can your crypto losses or gains, be balanced against your traditional portfolio?


Jeff: Yes, yeah. The way it works is short-term gains and losses get netted against other short-term gains and losses, regardless of if they're crypto or not. Then, the same thing with long-term.


Chitra: Great. Now, what are the penalties for noncompliance?


Jeff: For failing to file a return, it's a flat 5% of whatever your tax obligation is. For not paying the total amount of taxes owed, it's one half of 1% per month. If it's just one month late, half of 1%, it's not a lot, but if a couple of years go by, a few years go by, it can add up really quick, plus interest.


Chitra: Can you go to jail?


Jeff: Absolutely, unfortunately. If it's deemed that it was tax evasion, like in the example that I gave you of the gentleman that was looking into using our service and decided, no, they can just come after me, a couple million dollars, if they find evidence of tax evasion, then it could be subjected to a felony, which leads up to up to five years in prison and up to a quarter million dollars in penalties.


Chitra: Now, there's a lot of money laundering also going on, right? Does that play a role at all in this?


Jeff: Not so much with the taxes, but it is something that they're mindful about, out there. I see that more in the banking sector, that being an issue. In fact, one of our clients in the crypto space, their bank account was just abruptly closed with no notice. They said, "You can't bank with us," because they are concerned about potential money laundering.


Chitra: What is their fear?


Jeff: I think because they don't know where the money is coming from, right? If you have crypto-related money, it's so easy for it to be maneuvered from overseas. I think that's the concern, because there isn't enough regulation out there yet, right? Some people are just distancing themselves.


Chitra: It seems like there's a whole bunch of areas in which the federal government and governments around the world are now grappling with, how do you make people accountable for all of this wealth that they're generating, and how do we get a piece of that action?


Jeff: Right, that's what it is. They want their cut. As long as you give them their cut, they're not going to bother you.


Chitra: Now, let's look at two scenarios. Let's say you're a Sally Fay, you're a woman investor. You're just starting out. You're super excited. It's 2017. The bull market is in full swing, and you've learned how to trade, and you're just buying and selling without any regard for keeping tabs on your cost basis or the proceeds that you're making. Then, come December, you're stuck with having done thousands of transactions, and you have no idea how to go about finding those records, because every trade that you've done is potentially taxable, correct?


Jeff: Correct.


Chitra: What do you do?


Jeff: In those kinds of situations, because it's a lot of cleanup, the best thing to do is consult with an expert like us, so we can get you cleaned up and caught up. Then, going forward, you're on the right path, right? And to be mindful just about all the tax consequences of all that trading activity.


Chitra: Do you just sort of systematically start to go back and look at every trade you've made?


Jeff: In order to calculate all the gains and losses, historically, yeah. We have to kind of start from inception. If someone started trading in 2014, right, we have to go back to square one.


Chitra: That's pretty daunting.


Jeff: It is, yeah, yeah. At least once we get you caught up, then you should be okay, right?


Chitra: Let's look at scenario B. Let's say that I am a young man, Matt Jones. I'm not in the crypto market yet. It's the bear market, and people are telling me, "Hey, now's the time to come in. Buy low, and you can sell high." I have a clean slate. I've set up my exchanges, but I haven't done any transactions. What are the kinds of things I need to put in place to have tax hygiene, so to speak?


Jeff: Some best practices.


Chitra: Yes.


Jeff: I'd say, first, be mindful that you do any sort of trade coin for coin, that's all going to be a taxable event. Have at it, but just be mindful that there could be a lot of tax compliance to deal with at the end of the year. That affects some people's volume activity.


Another thing, to make sure to pull their records on a consistent basis. We usually, we're advising our clients now to download their transactional history from each exchange they use about once a month. Just make it a month-end practice, just in case either they got locked out, the data is deleted, or something is hacked, just in case anything happens, at least you have the records.


Then, outside of transactions like that, if you're trading on an exchange, if you're gifting coins, jot down somewhere on a Excel sheet or a Word document who you gave it to, when you gave it to them, and how much you gave, right? Just in case if there's any gift tax compliance to do, we could do that as well.


Chitra: Is it advisable to have a notebook and a pen, and when you're making these trades, to actually just jot it down, or put it on an Excel sheet that on this date, I bought X amount of Bitcoin, or I sold X amount of Ether for X amount, and to have that? Is that going to be helpful at the end of the year?


Jeff: It could, but like all the transactional data within the exchanges usually is going to have all that information. If someone wants to just separately track it, and if they're not doing a lot of trades during the year, that could be just as efficient and make their process easier at the end.


Chitra: Now, tell us some war stories. What are some of the anecdotes that you tell people about folks having challenges in filing taxes, or cases that you've seen, or what the government is doing to come to terms with this new source of income?


Jeff: Sure. Probably a couple examples. We have clients that were trading back from, the oldest one is 2013, maybe about a little over $4 million, and of course, they never reported any of it. Thankfully, in contrast to the other individual I was referencing, he said, "You know what, I just want to be compliant, right?" He came to the table. We went through everything, all the records, and got him up to speed.


Going forward, if he's audited, or maybe I should say when, because it's a lot, a big amount, we have work papers in place that we could provide in response to an audit. 90% of the time, that'll just make it go away, almost immediately. As long as the IRS can see that you've made a good faith effort, that there's been due diligence in being compliant, and you have work papers and a CPA to back it up, the audit will go away, right?


Another example, well, with the IRS, it's not so much a war story, but it's come to my attention that they've selected around 1200 to 1300 cases already from the 2017 filings that they're going to move forward with audits. Now, I don't know which ones those are. That comes from a source I have within the audit community, but we suspect that those are probably the larger ones, mostly, people that have generated hundreds of thousands, if not millions.


Chitra: Is the IRS not only trying to get revenue back from these taxable events but also trying to set precedence in some way?


Jeff: Yeah. It serves both purposes, yeah. One, it's a huge amount of revenue just sitting there for the government that hasn't been tapped yet. The second is going through this process, and going through these audits, and taking some people to tax court will set precedence, so that it's clear to everyone else that, one, you need to be compliant. Don't play games with them. I wouldn't be surprised if they send at least a few people to jail over this that have evaded their taxes.


Also, it allows them to kind of establish authoritative guidance, because they're going to take everything they find. They will undoubtedly issue some pronouncements about, "Here's how you calculate this. Here's why you file things this way," which right now, we don't have.


Chitra: What about moving out of the US, like just moving abroad so you don't have to pay your taxes, or even moving to Puerto Rico. You hear a lot about that. Is that going to help you or hurt you, in the long run?


Jeff: I think for taxes, temporarily, it would help, right? But, do you really want to expatriate yourself, denounce the US, in order to just save some money temporarily on taxes? I don't know.


Chitra: Depends, I would say.


Jeff: It depends, yeah, yeah.


Chitra: On what the amount is. Are you hearing about people who are actually doing that?


Jeff: No one I know has actually done it. Some folks that we know have been debating it, and they asked to do some research on expatriation process.


Chitra: It's a fascinating area. When you're doing the forensic work, you've been asked to help, I think, with investigations and things like that. How do you go about collecting the forensic evidence on these cases?


Jeff: Really kind of the same way we do crypto calculations for our clients, right? We pull all the underlying third-party documents. In this case, transactional records. We get their narrative about what happened, hear the story, because any forensic case, anything that we do, it's not just the numbers. It's also the context. It's also what happened, the story, if you will.


With forensic cases, there's usually a lot of other moveable parts, as well, particularly like divorce cases, where people are sometimes hiding funds. Partnership disputes, where one partner is embezzling money. We see that kind of stuff a lot more often than what people realize.


Chitra: What happens in the case of a divorce? Who gets the crypto? How do you actually even split the proceeds, if that's what happens?


Jeff: Same thing with kind of like a house, right? If it was community property, assuming it's a community property state like California, then any assets would be split 50/50, unless it was bought with separate property. If you don't want to cash out the portfolio, then usually one partner would buy out the other half from the other partner, just like a house. If you don't want to literally split the house in half, one person wants to keep it, one partner would buy out the house from the other.


Chitra: Well, that actually raises an interesting question, because let's say one partner is very crypto-savvy and the other partner is not crypto-savvy. It probably is pretty easy to hide your assets in the form of crypto, because the other person has no way of finding out how much you have and where you have this.


Jeff: True. Yeah, there's an opportunity there for someone to try to take advantage. Part of the divorce proceedings process is to come to the table and be transparent with both partners. Usually, like, you're essentially signing off to the court that let the partner know 100% of the assets out there. To try to hide it is essentially perjuring with the court.


Chitra: Where do you see all of this going in the next few years, as more and more people get into the space? There is a prediction that you're going to have a billion new crypto investors, over the next five years, entering the market. Where do you see the field of taxation going?


Jeff: Yeah, definitely, I see a second adoption, as well, coming in the coming years. I think, by the time that happens, there'll be a little bit more infrastructure in place with the taxation piece. One, with the exchanges. They'll start being a little bit better about what they record for their clients and what they issue out at the end of the year. I think we'll get to a point where exchanges are very, very similar to brokerage accounts, where you just get a 1089 of, "Here's your cost basis, here's your proceeds, here's what you report on your tax," and make it much easier for folks.


Chitra: Just as the industry is growing up, the tax piece will grow up, as well.


Jeff: Yup.


Chitra: Yeah. Great. Is there anything I haven't asked or anything really important, closing thoughts?


Jeff: One closing thought, just, I think it's good for everyone to remember that almost everything is a taxable event. If the question is, "Do I have to pay tax on this?" 9 times out 10, it's yes.


Chitra: Sadly.


Jeff: Yes.


Chitra: Thank you so much for joining us. Where can people learn more about you and find out more about the work that you're doing?


Jeff: Sure. Our website is, that's We're a full-service accounting consulting firm, but we specialize in things like cryptos.


Chitra: Great. Thanks so much for joining us.


Jeff: All right, thank you.


Chitra: That's all for now. Join us again next time for another edition of Running with Unicorns. Until then, enjoy your crypto journey, unicorns.