Read the transcript

Steven (00:52):

Hello everyone and welcome to the next episode of the Retirement Tax Services podcast, financial Professionals edition. I’m your host, Steven Jarvis, CPA, and I’m really excited for this week’s episode to dive into a topic that can feel controversial, but we’re going to cover a piece of it that everyone really should understand. We can’t just pretend it’s not there. And joining me this week to talk about this is Tyrone Ross and we’re going to dive into all things crypto and taxes. So Tyrone, welcome to the show.

Tyrone (01:18):

Thank you so much for having me. I’m excited for this. It’s not everyday advisors are wrote in to talk taxes, but crypto is my way in, so it’s an important time for it as well. So excited to chat.

Steven (01:30):

Yeah, definitely. Very timely topic as this is releasing here in the middle of February. Before we dive into some of the details, just give a little bit of background for the audience of how you’ve ended up with what you’re doing today and why the passion around crypto.

Tyrone (01:41):

Yeah, so I started my career at a small boutique investor relations and PR firm actually on Wall Street called Financial Dynamics and eventually through different paths, ended up at Merrill Lynch and then got introduced to Bitcoin in 2014 and it completely changed my life and I was like, all right,

(02:01):

And once you understand Bitcoin and crypto is one of those things you can’t unsee. And I was like, I have to bet my whole career on this. And I walked into my mentor’s office and was like, I need to leave here. I know I can’t do crypto here. And started another REA with an old partner of mine and was working with a lot of young clients who owned crypto on a very wealthy, this is prior to the runup of 2017. The first one they kind of went nuclear and they were young, they had millions of dollars in crypto and there was no way to help. You couldn’t see it, we couldn’t manage it. It’s still bad, but it was horrible then. And it kind of planted the seed and at the same time I kind of got into the startup space as well. 2016 or so started really getting into startups. So I was blessed to have this unique lens of watching Jason Wang Star altruist. There’s a company in a space called Eagle Brook. I was the Eagle Brook very early and also just helping founders is kind of like an outsource CFO type of thing based on my advisor background.

(03:02):

And then eventually had the chance to start my own company OnRamp in 2020, which was exactly that. It was an OnRamp for advisors in the crypto. And I had started ranting about crypto and how advisors should be paying attention years before that. And Josh Brown is a really good friend of mine. He kind of caught wind of it.

(03:23):

Anyway, so I’ve been educating advisors all along the way. So built on ramp up and we were rocking and rolling. And then I resigned in 2022 March of 2022 because I had this really, really clear vision of what I thought the future of wealth management looked like and how it was going to play a role in that. So in May of 22, I started one of my companies called Turnqey Labs. So think of Turnqey Labs for those. Watching this as a combination of plaid and adipar, we basically go get all of your clients held away crypto data to help with text, and we reconcile all of that data and then we push it to the platforms that the advisors use.

Steven (04:05):

Interesting

Tyrone (04:06):

Big gap right now, which we’re trying to solve. And in September of 22, I launched 4 0 1 financial. So 4 0 1 financial is an RIA, which we believe we say is the next gen RIA for the right now investors. So 4 0 1 we feel like is the wealth management firm of the future. So non discretion, a UM, we don’t trade or we don’t custody. We’re a big believer in a non-custodial future. So obviously we have a deep crypto expertise. My partner’s a CFP, huge defi dj and he is punch drunk off crypto as am I. So we have a deep expertise in crypto, but we do full blown financial planning, cash and debt management all the way to estate planning,

(04:46):

Tax planning. And then the goal was to have 4 0 1 almost be this conduit of what we were experimenting with on the Turnqey side. And it worked well because our target market is some 25 to 45 year olds, those working with an advisor for the first time. We have a subscription model, we have an hourly model. We don’t bill on assets or anything like that. So that’s essentially what I’m doing now and how I got here. And with that I have a really unique view being an advisor and an entrepreneur, building solutions for advisors around crypto assets.

Steven (05:20):

Well, I really appreciate that background. And it’s so interesting we were chatting before we hit record some of the nonsense that goes on online and on social media. And I think a lot of that is just driven by the fact that you can’t have context like that, right? I felt like I knew a little bit about you. I just learned so much just from that description and a couple of things really resonated with me there. But in a previous life I used to work with a lot of financial institutions and so I was introduced to the idea of blockchain actually before I had any idea what Bitcoin was. And so I probably knew before a lot of people that there are two different things going on. As you well know, a lot of people when crypto first started getting a lot more buzz, they were interchangeable and no one really understood that there were different concepts going on there and that there was more to it than just the meme coins that people see.

(06:05):

So I’m not going to sit here and speculate about what the price of Bitcoin is going to be in a year. I am really convinced that the concept of cryptocurrency and blockchain and those kinds of things are not just going to go away. And the other thing that really stood out to me in your description is that you work with people who are 25 to 40. Because when I first started working with financial advisors and the first couple of financial advisors I worked with were more traditional in the sense that they worked with baby boomers, pre-retirees, retirees, they working with people in their sixties plus. And none of those people owned any Bitcoin or cryptocurrency. And so it’s easy for advisors in that world to say, well, I’m just going to ignore that. It’s not relevant, it’s silly. Well, let’s move on. And as the tax guy, as I started working with more and more advisors, especially as I worked with advisors who worked with younger clients, I said, timeout, you guys can’t just ignore whatever your feelings about it are. You can’t ignore it because as you move into a, we use sarcastic air quotes, younger clientele, people, thirties, forties even, they all have some crypto.

(07:02):

I mean you mentioned about gathering that data. Some of them, they’ve bought some Bitcoin through Coinbase or Robinhood or some platform that’s going to do some level of tax reporting, but it’s still pretty minimal. There’s a lot of risk out there right now of people who’ve dabbled in crypto not really knowing what they’re doing and having no idea how it’s going to hit their tax return.

Tyrone (07:23):

I mean so much there to parse through that I could comment on. But

Steven (07:27):

Please,

Tyrone (07:27):

That’s one of the things that I think CPAs and advisors need to understand is that it’s happening away from you whether you feel it’s tulip bulbs or not, right? It’s happening, clients are doing it

(07:42):

And they are leaving themselves open to a lot of risk with you not knowing about it and using the centralized platforms, which is why that’s where we start pulling data from centralized platforms because the data is not good. Now, that is going to change with some of the IRS and treasury guidelines of what’s to be expected of them with 1099s coming up and everything else. And again, what I say is not tax advice. We own two tax advice, but that’s the thing about crypto. So now it’s still so early you can’t pull those two apart right now it’s like you almost got to blur the lines to be able to give advice. You always have to talk tax because without it, you can’t give advice. So to that point, the one example that I give all the time, if you have a client at Coinbase, yeah, they give some type of tax reporting, but if they’re trading at Coinbase come tax time, they have to manually go in and identify what the purpose of that transaction was. If they don’t do that, then they’re in trouble. Which is why I also let folks know, Coinbase, Gemini, Kraken, all of those folks now are acting like exchange custodian and broker and they don’t generate individual statements for clients.

(08:56):

And one of the reasons why there are some tax changes is that so that they can track basis across one. If I’m moving to the other and all these other things, if you don’t know that you’re setting your client up for massive tax bill amongst other things possibly being hacked, they’re draining, centralized wallets, pig butchering, all these other things. So anyway, to that point, I think the more advisors understand that, and this is why I’m building Turnqey, is just see it. If you could just see it, what would you do differently? Read only, Hey, you got a $5 million Coinbase account and you made 10,000 trades last year. What? And a lot of advisors also don’t notice no wash sale rule. There’s so many different things here that if advisors understood, they could add so much value to clients, you won’t ever have to talk crypto. You could talk about the stuff that you normally talk about.

Steven (09:54):

Yeah. Something else I want to throw out here and be curious to hear your experience. I mean, having seen tax reporting on crypto transactions and then talking to other CPAs and just knowing how CPAs work in general, I would imagine there are a lot of mistakes going on right now around crypto. Unfortunately, just the way that the tax prep world works right now, most tax repairs, not all of ’em, most of them, they work with a client. They say, Hey, send me your tax documents. Great, I’m going to put your tax documents in. I’m going to move on.

(10:17):

And the first couple of times I got any kind of tax documents around crypto, it was a CSV file. The client had to go and download all of their transactions for the year and say, Steven, this is what I found. Good luck. And honestly, those first few, what I would do, Tyrone, is I would go through their CSV file, I’d kind of summarize it for ’em, and I’d say, Hey, does this feel like what you did last year? And there was some learning we had to do up there? No, that seems way too big of a number. And then we’d go back and parse through it again together and say, ah, okay, now I see how this CSV file is set up. But most tax preparers are not doing that. They’re just saying, there’s the document you gave me, great. I put the numbers in and they moved on. And crypto is this kind of mysterious thing to so many people that there aren’t as many obvious red flags of, oh, well it shouldn’t be X or it shouldn’t be Y. They’re like, oh, it just kind of is what it is.

Tyrone (11:02):

And that’s part of why we’re building Turnqey that it’s that, right? Earlier today we’re testing some data from a platform and they send this massive file with all of these transactions or whatever. And then what we do is we basically reconcile that. We do all the cost basis, realize and realize all that other stuff. And we are launching, which I think you’ll love and everyone will love. We’re actually launching a full on, almost like a TurboTax for crypto, where you give us your wallet address and we give you interesting, all of the data of your taxable gains, everything else, losses, everything. We do it all

(11:42):

Because that’s a big need right now. And no one is doing it correctly. But that’s the thing right now, they got to pull all these different CSV files, then I may have some on chain stuff. So we got to track basic across all these different wallets. And then am I using specific id? Is it fifo, is it, and no one in crypto wants to use fifo, right? Is it, hi O, what am I? So it’s a mess. And that’s the thing. If you don’t know those things, then it makes it really hard and everyone in the space agrees the taxes are a mess. What I loosely say is like, look, one, just let ’em know you have it, report it.

(12:20):

Get as close as you can, right? Add like 10% or so. If you get it back, great, but overpay, right? Just be safe, right? I’ve been telling our clients, look, just get as close as you can. Maybe send them a little more. You’re probably off. We track what we can and leave it up to them. Because what you don’t want to do is try to make it look like you’re hiding anything, like you haven’t given the best effort. Anything that you can find, track it, wallet, transactions, this, that, whatever, swaps, airdrops. And the other thing is NFTs is a whole separate thing. So it’s like now you got NFTs. And what a lot of advisors and CPAs don’t understand is when you use one of these block explorers or tax reporting things, if you put your stuff in there, they literally show it as net worth and it’s completely inaccurate. It’s completely inaccurate. And they basically go, oh, okay, well, we see a value here. We see a value here. Here you go. Maybe it’s $20,000. And it’s not pinpoint accurate. So it’s really important to understand moving forward, what are NFTs? Are there securities? Okay, well, what’s the tax treatment, everything else, royalties, all these other things. Yeah, I don’t envy you guys in a couple months here coming up. I think next year is going to be absolute disaster.

Commercial (13:50):

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(14:57):

Yeah, unfortunately, I don’t disagree. I mean, we’ve touched on a few of the different moving parts here, especially for those advisors who have been hesitant to be involved in crypto at all. You already said it, and it’s very true. It’s already happening

(15:07):

Whether you wanted to or not, whether you want to lead with it. You almost guaranteed any advisor listening to this has at least one client, if not many, who have some kind of digital currency, have some kind of crypto. It’s too common. Maybe it’s not a huge percentage of their portfolio, but geez, you can make a client real mad if they’re not getting any help on it. So the other thing we’ve got to keep in mind, we’re three or four years into the IRS having this sneaky little box on the tax return that just says, Hey, do you have any digital currency transactions? And when that box first came out, I saw so many people who were like, I just don’t fill it out. Wait, wait, did you just advocate for tax fraud because, and people think it was this innocent little data gathering thing? No, no, no. I try not to get tinfoil hat too often, but I think it was actually really smart on the IRS’s part. They basically said, we’re not sure what to do with this yet, but we want to keep our window open. And so they just said, why don’t we just put this box on here because the people who lie about it, great news, that’s now tax fraud. And there’s no statute of limitations to how far back they can go to hit you with this. Once they do figure it out.

Tyrone (16:12):

And to that point, you could probably correct me here, but I remember when they first did it, it was only virtual currency. And then they expanded the definition

(16:23):

That was, and I don’t know if that was two years ago or whatever, but they expanded the definition, right? Digital assets, all these other things, buy sold. That was the other thing was virtual currency. And if you just bought, but if you sold, if you swapped, they expanded that definition to make it very broad. And I remember posting about that and letting everybody know, listen, they’re catching on here. And to be very clear, I’ve been a part of, I’ve had multiple conversations with the SEC, Hester Percy’s office Commissioner Crenshaw, I’ve sat in on the SEC investment advisory committee. I’ve had a 1 0 1 closed door meeting with Corey Booker, all these other things to try to get the administration to understand what is happening here. And I’m letting people know, I know you think our government is old, stodgy or whatever, they’re onto this, they’re slow, but they’re catching up, right? So anyway, yeah, I think what you point out is really important is that if advisors do nothing else, just reminding a client report this. You did ’em a solid.

Steven (17:25):

Yeah, well, and you commented on it in there, make a good faith effort, make a best effort, show that you’ve done something. You might not get it perfectly right. Do something. It will work in your favor whenever they sort this out, even if you got it wrong, if you tried something as opposed to ignoring it altogether. And this might not feel related, but to me it does at least something to keep in mind. Look at what’s been going on with the Corporate Transparency Act and beneficial ownership interests.

(17:48):

And the reason I bring that up is because you have this area where fencing, where the treasury department has basically said, Hey, we want more information on this topic. So here you go. Here’s how it’s going to work. And I don’t know how that one’s going to sort its way through the Supreme Court. In fact, we’re recording this in January. The episode will air in February. It’ll probably change three times between now and then it’ll change three more times. But people who are sitting there saying, ah, crypto tax isn’t a big deal. You are in for some nasty surprises when they decide to take action on this because they’re going to suddenly go from feeling like there’s a lot of inaction to, in classic government fashion, they’ll probably weigh overreach or way too broadly reach, and it’s going to impact a lot of us.

Tyrone (18:27):

Yeah, no, I agree. And I think that’s the interesting thing here is clarity. Moving forward with this administration on the recent IRS guidance on crypto taxes and the end of year, everyone was running and scrambling to do a safe harbor with universal wallet accounting ending. Then right before the end of the year, they’re like, no, you don’t have to worry about that anymore. So now you have another year where you have to keep your own personal books and records. Why are they doing that? I’ve been telling people for years, the custodians are not yet set up to handle anything more than ffo.

(19:04):

So they got to figure out specific ID and everything else. And now after that, they’re going to start issuing 1099s or whatever. But you’re still going to have to go in and let them know what you were choosing and why. So these are all things that are important. But that small change that they made, I think on a random Friday right before the holidays, and then the headlines are like, I saw all these incorrect headlines. Crypto IRS delays crypto tax reporting. No, that’s not what happened at all. So it’s like you get that type of stuff, but now again, you got another year where folks are having to do it themselves, which is why I’m saying in this coming year, it’s just going to be a mess. And you look at everything that has happened leading up to this point with the meme, coin explosion, ordinals on Bitcoin, all these other things. So there’s a lot of people who made a lot of money, got to track all this different stuff, they’re going to fall short and the IRS is going to make a ton at everyone else’s expense.

Steven (20:06):

The other thing I think is important to remember, let’s set aside digital currencies for a second and just look at tax reporting on the more traditional stuff. That’s stuff already gets messed up. The number of amended 1099s every year, the number of just incorrect forms that we see, the lack of clear reporting on 1099 Rs tax reporting is already not exactly a clear cut arena. So even if at the end of this year the IRS says, yep, the new reporting requirements are X, Y, Z, and let’s move forward, it’s still going to be a hot mess for a while. And so I think what you’re getting at there, and I’ll just say it bluntly, if you have this stuff or your clients have this stuff, you have to take responsibility for your own investments. Whatever those are, don’t assume even as this gets streamlined over the next couple of years, which I will look forward to, don’t assume it’s going to be right the first time. You need to keep track of this stuff. As an advisor, you may be asking those questions of, Hey, do you have any digital currencies? Do you have any digital assets?

(21:02):

Start providing some of that education, even if it’s super high level, even if you are devoutly of the opinion that crypto disappears in a year. I don’t know how you come up with that opinion, but let’s assume you are for a second. There are still tax implications. You can’t just ignore this.

Tyrone (21:16):

Yep, absolutely. Couldn’t agree more. Couldn’t agree more. That is the table. I’ve been pounding for 11 years, my friend.

Steven (21:23):

I’m certainly with you on that. We can’t just ignore this and pretend its going to be simple.

Tyrone (21:27):

It’s not going away. It’s not going away.

Steven (21:29):

So Tyrone, how are you helping people dip their toe into the education piece of this? It can feel like a lot. I mean, we’re kind of nerding out on this. We spend more time on it. Where’s the starting point as people want to learn more about the tax implications of all this stuff?

Tyrone (21:41):

So specifically what we’re doing at 4 0 1 or just generally,

Steven (21:44):

Let’s start with what you’re doing at four. What are you doing with 4 0 1? And then, I mean, you have a pretty big voice in the advisor community, so I would love to hear what you’re doing to help other people too.

Tyrone (21:51):

So a lot actually beside, I mean there’s a few media interviews and things there. So always media always reached out and ask for my feedback there. So that’s one area. But personally with clients, we’re just obviously going through clients one by one. And I always tell advisors a couple of things. You want to find out what do they own, where do they own it? Is it in exchange or is it on chain? And then lastly, do they have the passwords and private keys?

(22:22):

Every client we go through that make sure that they’re backed up, so on and so forth. But also we have obviously CPAs and centers of influence that we work with in that regard. We have estate planners that are crypto savvy lawyers that are crypto savvy, and we kind of make sure we bundle all of that with what they’re doing. We’ve even had to get introduced to international tax laws. We have a client rolls a ton of cryptos in Portugal, so we do that as well. So anything involving crypto, we’ve touched it. So it’s an ongoing thing for us. And then we have this internal social media type of platform for our clients where we’re constantly knowledge sharing with them. As far as other advisors and firms, we have a consulting arm of what we do. So actually this morning I was on with an advisor, an RIA, that has an advisor who has a young client. It’s a gamer, is getting paid in crypto, has millions in crypto, get paid a crypto tax implications.

(23:16):

Everything else they want to be concerned about, but they don’t know anything at all, right? So I’m trying to walk them through it and there’s strategies from a one to make sure that you’re paying taxes, but also make sure that things are trackable. And little nugget here for anybody watching, if you have a client that whether they’re getting paid in crypto or not, if they are moving, especially with these new rules coming, if they are moving to an exchange to sell, right? Or even move into an exchange to sell from self custody or they’re selling from an exchange, convert that crypto to a stable coin first, then sell. As opposed to just selling out of that actual, just selling the Bitcoin and then going into something else makes it easy to track these things. And specifically identifying everything else. Because what the IRS has not specified yet, and you are going to learn this and you probably have learned it and other advisors will. There’s still this, what is an account and what is a wallet? So right now to the IRS, if I was to write all of that piece of paper here, but if I was to write all of my seed phrases on a piece of paper to them, that’s a wallet.

(24:35):

And that’s an important distinction as opposed to, alright, well I have this account at Fidelity that has my stuff and that’s an account,

Steven (24:45):

Right?

Tyrone (24:45):

They’re considering that a wallet or an account. But what if this is my wallet and I have multisignature, which is basically more than one signature is needed to sign a transaction to move asset.

Steven (24:58):

Which

Tyrone (24:58):

One is the account? So the IRS hasn’t specified this yet.

(25:04):

So that’s what I’m saying. So if you do these things in this manner, you’ll be able to show these and these, this is separated by this wallet, is the wallet that I use for signing transactions. This is the wallet that I use for making transactions. This is the wallet that I use for storage. The IRS is going to have to catch up with this treasury, all CPAs, everything. It’s important. And to be honest, that’s great hygiene that CPAs should be encouraging if their clients to do. And advisors should be encouraging CPAs that share clients to do, right? It makes it cleaner for everybody. So those are the kind of things and conversations that we’re having with firms as well. Another example, very large RIA out there, I think top three in the country. There was a client that they had that she’s an investor of one of my companies, and it took them a very long time to do her taxes. They couldn’t get her crypto taxes done. We helicoptered in, we calculated and got them done in an hour and a half.

(26:11):

They were going to lose her 40,000. We made her 250,000 and gave them projections for the next year. So it’s different when you’re really in it and you’re doing it every day. And we just have tools that they don’t have. So advisors are working with Warren old out tools. There’s no good crypto data reporting at all, right? So how do you help long story list long? So what we do is we have a consulting arm where advisors will reach out, we’ll sit with them and their client, we’ll engage with the firm. They love us because we don’t fight them over the assets. We don’t want the assets. We’re advice only pay for our advice. We’ll leave, right? Similar to a CPA, right? You pay us, we come in, we fix it, we leave. So that’s kind of how we do the education piece right now.

(26:52):

And the last point on that where I think where folks can learn and should start learning, obviously there are a lot of great folks in the space to put out. There’s a crypto, CPA, Patrick Camuso who does a really good job. You should have him on as well. He’s really sharp and he’s on LinkedIn. He comments on my posts sometimes and him and I have been going back and forth, follow CPAs that are getting it and really putting out really good content. I read that stuff a ton. And then there are some really good publications that are staying on top of it as well. CoinDesk has done some really good stuff. There’s a few publications out there that are kind of staying on top of it, but that’s really it. So I think it’s tough right now. I’m slow to recommend people to go look at stuff. There’s very

Steven (27:36):

Few

Tyrone (27:37):

Credible resources on crypto right now, and if I’m being completely honest, chat GPT, an advisor reached out to me and he’s like, oh, I found this information from chat GPT. I’m like, chat GPTs, crypto information is not good. Garbage

Steven (27:49):

Reliable. It’s garbage. Yeah,

Tyrone (27:50):

Right?

Steven (27:50):

Yeah.

Tyrone (27:51):

So that’s the thing. It’s like it’s rare to go to somewhere now that really has good resources. Going back to what I was saying a minute ago is . And unfortunately right now there’s not too many good venues for solid advice.

Steven (28:09):

It certainly is evolving. Hopefully it’ll continue to evolve rapidly. There’ll be more people like you who are so dedicated to making that reporting better and make this more accessible to people. Because again, for advisors listening, wherever you are on this spectrum of your personal beliefs on crypto, I really don’t care. I want you to help your clients get this sorted out. And I mean, at a minimum, you talked about those questions that everybody should be asking and the first two questions, what do they own? Where do they own it? I mean that’s what you would ask about anything, not just crypto. So don’t make this a crypto issue. Make this a client service issue. You should understand what your clients have, where they have it, and at least be having these intro conversations. So where you’re at on the spectrum, are your clients strictly playing around on Coinbase and it’s not as big of a deal, but you should still be aware of it. Or do you have people getting compensated in crypto? So many other things for an advisor, you don’t have to be the crypto expert, you don’t have to be the tax expert. No, you do have to take responsibility for finding great resources. So Tyrone, on that note, if there are people listening who are like, you know what, I need help on this. I mean, how would somebody reach out and engage with you who need some of that advice?

Tyrone (29:11):

Advice, yeah. So before I get to that, I think you said something which is really important and it’s probably the most important thing said in this podcast. And I’m the same way. Now I am a punch drunk crypto hippie. I am not going to hide on that, but I don’t care whether advisors like it or not anymore. I’m fast trying to convince them. I’m just, we are in the client service business

Steven (29:33):

A hundred percent.

Tyrone (29:34):

Help your clients a hundred percent. All this stuff help ’em. That’s it.

Steven (29:39):

Yeah.

Tyrone (29:39):

No matter how you feel about it, right? Bite your tongue, help ’em with it. Do your job. Go home, right? And throw tomato cans of Bitcoin. Great.

Steven (29:49):

Yeah.

Tyrone (29:49):

So a couple ways folks could reach out. Obviously LinkedIn, Tyrone v Ross Jr. Look me up on LinkedIn. A lot of folks DM me happy to be a resource there. I’m also on X. For those that are X, I still call it Twitter, but XT at TR four one is my handle there. You can follow me there. And then my company email, which is tyrone@fouronefinancial.co. Happy to again at any moment. Again, I do this 24/7, 365 for 11 years. I’ve never turned it off. So happy to help be a resource, answer any questions can sit with you and your client can do webinars, can whatever you need. We got it all. Happy to help. And again, appreciate you having me. This was an awesome conversation that I think will be very valuable for folks that are listening.

Steven (30:34):

Oh, a hundred percent. Yeah, really appreciate your time. Appreciate the generous offers of being a resource for everyone listening, just really want to reinforce, you’ve got to be taking action on this depending on where your clients are at. It might look like a lot of different things, but inaction is not acceptable on this and so many other topics. So thanks for being here. Until next time, good luck out there. And remember to tip your server, not the IRS.