We Study Billionaires - The Investor’s Podcast Network - TIP284: Bitcoin - Law & Legal Implications w/ Caitlin Long (Bitcoin Podcast)

Starting point is 00:00:00 You're listening to TIP. Boy, it's discussions like this one that really make my job a lot of fun because on today's show, we have a total force in the Bitcoin movement to talk to us about the legal implications and potential government intervention into all things digital currency related. Caitlin Long is a graduate of Harvard Law School. She spent 22 years on Wall Street. She's started three successful businesses in pension and insurance. She's been the chairwoman and president.

Starting point is 00:00:30 president of the enterprise blockchain company Simbiant, which was named FinTech Company of the year in 2017. And today she's the gubernatorial appointee to lead the Wyoming blockchain task force. If you've ever wondered about the legal risks associated with Bitcoin and how everything is going to play out moving forward, you'll definitely want to listen to this conversation and you might even want to share it with some of your friends. Without further delay, here's the one and only Caitlin Long. Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected.

Starting point is 00:01:14 Hey, everyone. Welcome to the Investors podcast. I'm your host Preston Pish, and I'm usually accompanied by my co-host, Stig Broderson, but he was out an event in L.A. and was unable to join us for this conversation. But with that said, I'm here with the one and only, Caitlin Long, Caitlin, we are pumped to have you here with us. Welcome to the Investors podcast. Thanks. It's really awesome to be on your show. I've been an admirer from a distance for a while. It's nice to reconnect. Likewise, I mean, you're the go-to person when it comes to the laws and all this cool stuff happening around Bitcoin and just, holy mackerel. So I want to jump into this conversation just right off the top rope because I know we have thousands upon thousands of people that want to ask this question. And so I just want to put it right out there at the start

Starting point is 00:02:08 of the show. And it's a very simple narrative that I can't even tell you how many times I've heard people say this to me on Twitter or when I talk to somebody about Bitcoin. This is the narrative that they say. They say, well, you might be making a lot of money in the short term. But once it gets so big, the government is going to criminalize it or they're going to step in and they're going to ban an exchange, and then the value is going to go down in a tremendous way. How do you, Caitlin Long, respond to that simple narrative? Well, two ways. One is it's not possible for a government ban of Bitcoin to be effective.

Starting point is 00:02:47 That's been proven so many times over. And even though that there are some governments in the world who do try to ban it, if it were to happen in a major country such as the United States, what ultimately would happen is that it obviously would have an impact on the price, right? You know, the regulatory risk is definitely a part of, I think, why the price doesn't fully necessarily reflect fair value. But I think to Plan B's model, some of those risks are overestimated because Bitcoin would continue to operate. And the truth is, in the case of the U.S., if the government had wanted to ban it, the time to do it would have been 2012, maybe, 2013. But the network effects are so wide and strong at this point that even

Starting point is 00:03:35 having the United States ban it doesn't shut Bitcoin down. It just moves all of the activity elsewhere. And I really doubt the U.S. is going to ban it. What is more likely is that the tax situation will continue to be very frustrating for all of us. In other words, every time we use a crypto to pay for a cup of coffee, we've got to record it as a capital gain or a loss. And also the financial institutions that interact with crypto are going to obviously have to comply with some pretty strong regulations as well. That's the attack vector, I think, is regulation and tax as opposed to an outright ban. But I would just remind everybody who's listening that the internet, even if the internet,

Starting point is 00:04:17 even if all the ISPs in the world were shut down, there are nodes running on satellites, there are people who do Bitcoin transactions on ham radio. So there are definitely backups to the backups in the system. And it is really resilient. And I think it's at this point impossible to shut it down. I can't say I've had this much fun preparing for a podcast in a long time because this is really a field that is not my expertise when you step into the legal framework of a lot of things.

Starting point is 00:04:48 But one of the things that I discovered through the research was the definition of legal tender seem to be a really important definition to understand when you start trying to understand the risks associated with the laws and how the governments are going to start viewing this. And so I'm kind of curious if you see it the same way and more importantly, talk to us about this definition of legal tender. Well, legal tender is a legal concept. It's actually in the Constitution of the United States and in most countries' constitutions, where the government defines that the government's own issued currency is legal tender in payment of debts.

Starting point is 00:05:29 And so it must be accepted within the country. And interestingly, Trace has done a lot of this. Trace Mayor has done a lot of work on the legal tender definition in the United States Constitution, which actually makes reference to gold and silver. And interestingly, a couple of the states within the United States, Wyoming being one of them, have adopted a recognition of gold and silver. as legal tender because it is mentioned in the U.S. Constitution, Article 1, Section 10, I believe. So basically, that's where the government gives itself the power to tell everyone what money must be accepted within the borders. There's a concept, though, a much broader concept of money in commercial law in the United States. So that's where Wyoming, when we clarified the legal status of digital assets, which I'm sure we're going to get into in a little bit, we mapped virtual

Starting point is 00:06:20 currency to the same treatment as money. That's not the same thing as saying it's legal tender, to be clear, but it is treated the same as money under the law for the following purpose. When you take a dollar bill in the United States, you take it free and clear of all so-called adverse claims against it. That is, if somebody had a lien against it, as long as you were not knowingly defrauding the creditor who had a lien against that dollar, it gets what's called supernegotiability. Again, as long as you don't knowingly defraud someone, you take it free and clear even if it turns out there was a lien against it. You're deemed an innocent purchaser. We have that concept of supernegotiability, an innocent purchaser concept for securities that trade through securities intermediaries and for

Starting point is 00:07:05 money. Wyoming did was to say virtual currencies get that same treatment under the law in Wyoming. So we did the second best thing. We couldn't make virtual currencies legal tender because the U.S. Constitution says that only Congress has that power. And technically, it's actually only gold and silver in the Constitution that are legal tender, which is interesting because obviously the dollar is neither. But I digress. We weren't able to make virtual currency legal tender in Wyoming, but we did the next best thing, which is give it the same recognition under the law from a negotiability perspective. Yeah, you know, it's interesting when I was doing some research. There was a lot of debate, specifically going into the coinage versus fiat or paper money and the U.S.

Starting point is 00:07:49 government's ability to print paper money because it doesn't specifically call that out in the Constitution. But there's been so much case law, it seems, that has occurred between then and now that has basically allowed that precedence to sit. I don't know that you're necessarily going to be able to argue any of that. But to be honest with you, I don't know that it even really matters because I don't think anybody's trying to claim that Bitcoin will ever be legal tender. Right.

Starting point is 00:08:16 And that's perfectly fine. And they can coexist with the dollar continuing to be legal tender and Bitcoin continuing to not be legal tender. And that still works, right? Yeah. In fact, actually, Dick Carter had a very interesting essay very recently about how the central banks don't necessarily need to be as afraid as they might seem of crypto. Because if you look at what the stable coins have done, it actually.

Starting point is 00:08:40 Actually, a lot of the stablecoin use, a lot of the tether use in particular overseas is to, like, for example, in Venezuela, to aid locals who are trying to get their hands on dollars. They do it through Bitcoin to get their hands on dollars by a tether. And so, you know, we're seeing some unusual paths, if you will, that actually are reinforcing counterintuitively the dollar as the world's reserve currency. And it was an interesting essay. I'd never thought of that angle before. But he's right.

Starting point is 00:09:08 We do not need Bitcoin to be deemed illegal tender in order for it to succeed. So how about the idea? Because I think the next angle that people would look at this, they'd say, well, in China, they banned the exchanges. So you got that whole discussion point around banned exchanges. And, well, if the government wants to shut down Bitcoin, all they got to do is go to the exchanges in the U.S. They could shut down the exchange.

Starting point is 00:09:32 Talk to us about this narrative and your opinions on it. Well, anything that restricts activity is going to have an impact on the price in the short term. Conversely, though, I really want to drive this point home. Anything that expands activity is likely to help the price because I do think that there are some things that can expand activity on the regulatory front. The U.S. is very restrictive, as we know, most other countries in the world, especially countries like Switzerland and Singapore, are very friendly to crypto assets. And And so the U.S. to the extent that its restrictions are lifted, that could be a positive. But back to your specific question, what if the exchanges are shut down?

Starting point is 00:10:12 Again, you know, most of the exchange activity in the U.S., mostly the exchange activity in the world is not in the U.S. So there are some pretty big exchanges that are based here, obviously, Coinbase, Krak, and BitTrex. But the biggest ones in the world aside from those are not in the U.S. So basically, the gist is that the vast majority of exchange volume is taking place, with companies that aren't even serving Americans right now because they're not licensed to do so. And so to the extent that that ever loosens up, there's an opportunity to really open up the markets even wider than it already is. So what you're effectively saying is if you're a lawmaker and you're trying to put a law like that in place,

Starting point is 00:10:52 you're going to be combated with just an army of experts that are saying, hey, listen, you're just going to shoot yourself in the foot because all this business is just going to go somewhere else. Is that really kind of your argument? Well, yeah, but, you know, I mean, a lot of us have been doing that with politicians for years, and in a lot of cases, of course, it falls on deaf ears. But it doesn't matter. You know, the market just goes right around these crazy restrictions that are put on by countries when they try to block their citizens from having access to services that are available to, to others outside of their country borders. So I just don't think it makes a difference, right? The exchanges are going to continue to operate. Would more restrictions on the exchanges generally,

Starting point is 00:11:32 have an impact on Americans' ability to use crypto, sure. But I think you're going in the opposite direction. I think we're actually seeing that you're seeing more companies actually become regulatory compliant, and that's where the activity is moving. And it's not that the U.S. is necessarily loosening up, although Hester Pers's proposal at the SEC was obviously a very big step to have a sitting SEC commissioner start talking about safe harbors for things that might actually be deemed securities. I doubt Bitcoin at inception would have been deemed a security, but there's certainly an argument that it could have been. It certainly isn't now, and the SEC has essentially admitted that, but there's still some question with ether as to whether it's a security, right? So it's nice that

Starting point is 00:12:17 the regulators are finally talking about safe harbors. There are things that I think are going to happen. I mean, that we've done in Wyoming is to create the first bank charter that is going to be allowed to touch crypto in the United States. The FDIC does not want. FDIC insured banks to touch crypto. So this is why we don't have banks actively involved in this market. If you look in Switzerland, for example, not only can they custody crypto through their trust powers, they can actually hold crypto on the bank's balance sheet. That is a lot farther than what Wyoming has done. But, you know, the move that Wyoming has made, which is to allow the state chartered banks to custody crypto through its trust department, that is a huge opening because no other

Starting point is 00:13:01 Bank in the United States is able to do that right now. And so I actually think that's all positive. We're going to be bringing more and more users into the market that heretofore haven't been able to because they didn't actually have a custodian available to them. That's a bank. Do you think that they're not allowing those FDIC insured banks to handle it because they understand how, I don't know, vulnerable is the right word, but how risky it is to actually take possession and not lose your private keys. Do you think that that's the reason why they've moved in that route to kind of keep them separated? Yeah, I mean, the banking industry in the U.S. is very conservative, and the regulators don't really

Starting point is 00:13:41 have an incentive to take risk, so they're definitely going to be slow movers. And no one's ever publicly said this, but my read of the tea leaves is that the regulators in Washington are watching very closely what's happening in Wyoming. And if it goes well, then that will actually pay the... way to a broader acceptance, but it's going to take time. So I think the vast majority of U.S. banks, in other words, every bank that's FDIC insured are going to face the FDIC restriction for several more years. And it's going to be the state chartered banks like the ones in Wyoming. They're really, the ones in Wyoming are the only ones that can exist right now. There will be

Starting point is 00:14:19 other states, I think, who try to do what Wyoming did. But there are a lot of very specific reasons why it's very unlikely to work in other states. So, you know, I think the Wyoming banks are, are where everybody should be watching because there's an expansion of infrastructure that will solve problems that will be bringing solutions to the market that don't currently exist right now. And that one of the obvious ones is security token custody. There are custodians that provide security token services, but none of them are banks. And banks have special treatment under the securities laws. They can provide services that trust companies cannot, for example. And so for institutions who are required to deal with certain types of regulated financial institutions

Starting point is 00:15:05 that as of now can't provide those services, well, we're about to get some that can, and that's going to broaden the universe. So I'm less worried about a crackdown that closes off this market in the U.S. than I am optimistic that actually we're seeing improvements in regulation. And I happen to know what's coming down the pike in Wyoming. You know, stay tuned. I love it. So let me ask you this. If you personally owned an exchange in Wyoming, and let's say the federal government did do something crazy and they did say Bitcoin exchanges or crypto exchanges are banned, could they even enforce that based on the laws that exist in Wyoming? Oh, that's a good question. Because what's happening is crypto exchanges that are existing exchanges are looking to come into Wyoming. Could a de novo one start up?

Starting point is 00:15:56 up even if the SEC, yeah, see, again, I don't think they're going to be banned. I think what's going to happen is, is that the SEC is going to say, look, you're an unlicensed broker dealer, go get a broker dealer license. Or to be honest, the exchanges should be coming into Wyoming and getting a bank license because banks can handle securities and without having a broker-dealer license. Again, you know, that's why, that's why, again, stay tuned. Some of them are coming. And from what I see happening, there's not a movement to ban them. There's a movement to get them regulated. and bring them into the fold. And that's probably going to make some of the purists' heads explode.

Starting point is 00:16:33 I really felt for Eric Forhees when I saw the headline about what happened to ShapeShift, losing so many of its customers when it started to apply AML and KYC. But that's the price of being an operating financial institution in the United States. It just is. Whether we like it or not, it just is. And so to the extent that we're seeing some of the custodial exchanges, not ShapeShift, because it's non-custodial, but some of the custodial exchanges actually taking steps to become regulated, I think that's a positive for the market overall. And again, those that don't want to

Starting point is 00:17:04 deal with regulated exchanges, if you're not an American, you don't have to. There are plenty of alternatives that don't deal with U.S. customers. Let's take a quick break and hear from today's sponsors. All right. I want you guys to imagine spending three days in Oslo at the height of the summer. You've got long days of daylight, incredible food, floating saunas on the office. Oslo Fjord. In every conversation you have is with people who are actually shaping the future. That's what the Oslo Freedom Forum is. From June 1st through the 3rd, 2026, the Oslo Freedom Forum is entering its 18th year bringing together activists, technologists, journalists, investors, and builders from all over the world, many of them operating on the front lines of history.

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Starting point is 00:21:22 Back to the show. So recently, just in this past week, we saw that Treasury Secretary Manuchin had made the announcement that there's going to be some sweeping regulation. There's going to be some changes around how Bitcoin is handled. And from what I gathered from the article, it had to do with the mixing and the autonomy of basically mixing your coin so that no one knows where they came from and where they're going. Is that what your understanding of the sweeping regulations coming out of the treasury are addressing, or is there something else there that I'm missing?

Starting point is 00:21:56 Yeah, well, the sweeping regulations, by the way, aren't new. It's just the specifics that are going to be new, but they're not going to surprise anybody, I don't think, because if you've been watching this space, there's something called the travel rule, which essentially says that financial institutions within the United States, And frankly, it's happening pretty much across the world. Anybody who wants to be part of the regulated financial markets is going to have to comply with the travel rule, which means that you're not just knowing your customer. You're knowing where the customer's money came from and where it's going to.

Starting point is 00:22:26 And the crazy part about that, again, this is going to make people's heads explode. It certainly does mine is that financial institutions are now going to have to be sharing personally identifiable information with each other. And in the case of crypto, they have to share that information with each other before the crypto transaction, because there's no way to stop it after the transaction has taken place. So you've now just created, because of these crazy regulations, data honeypots that hackers obviously are going to be targeting. By the way, this is all happening within the banking sector today as well.

Starting point is 00:22:57 A lot of the big hacks of big financial institutions is people going after all this personally identifiable information that is not transmitted or stored in truly secure form. And the more of this personally identifiable information that the government requires financial institutions to collect and to share with each other, the less secure all of our personal information is. It's just a fact. But unfortunately, again, these laws are the laws. They're federal laws. I wish we could do something to change them. They have a tremendous cost. If you really understood how the Bank Secrecy Act worked, just the number of human beings who have to review financial transactions that are suspicious, They're required by law to have human review. It just adds a tremendous cost to being a regulated financial institution, but it is. There's no way around it. I personally don't think any of these laws are, well, not any. I think most of them are unconstitutional in their breadth and reach and that they will be struck

Starting point is 00:23:57 down probably over the next decade, but it's not likely that that's going to happen soon. So anybody who wants to deal with a regulated crypto financial institution in the U.S. has to comply with these laws. That's black and white. You can't stay in business in the U.S. if you don't comply with these laws. All that said, I think the U.S. crypto exchanges and the deal with U.S. customers are already complying with these laws. So to the extent they come into Wyoming and get a bank license, that just helps them broaden their customer base and become more legitimate. But there was one other thing in the question that you asked that I wanted to hit at, which is a lot of the companies in this industry passed missteps. And maybe they've,

Starting point is 00:24:36 been hacked before and never revealed it. We're recording this show on the day that Binance went down for several hours and it looks like there may have been a hack at Binance. We'll see if that indeed is the case, but that's what Coin Desk is reporting. And the F-coin exchange just imploded a couple of days ago. And that was not a hack. That was just pure mismanagement that caused insolvency. But here's where I'm going. There may be others of those that are hidden out there that we just don't know about. So I actually think the other interesting angle here is the new players that that are coming in with pristine balance sheets because they don't have any history and also pristine compliance record. So they don't have the risk of the SEC or Binson or CFTC going after

Starting point is 00:25:19 them for something they did a few years back. That's going to be interesting because also I think that that elevates to the extent that they are regulated, the ability for the institutional investors like pension funds and endowments and foundations, which are not investing in this space right now, they can start coming in once they have those regulated partners that they can do business with. So, Caitlin, talk to us about Kyle Bass and the way that he and some others that he worked with down there in Texas were able to prevent federal government from confiscating physical gold. So we all know the stories from the 1930s when gold became illegal and the federal government came in and basically usurped that gold out of the hands of the holders. Texas recently passed something that is preventing that from ever happening. Tell us the story and then tell us how this might relate to Bitcoin or the cryptocurrency space legally.

Starting point is 00:26:15 That's very interesting. And again, I think it's helpful to Texas that gold is mentioned as legal tender in the U.S. Constitution, Article 1, Section 10, that's all very interesting. That's another state that tends to have an independent streak, kind of like Wyoming, Texas does, that is asserting its rights. And because that's legal tender and that's property, they're saying, you know, the government can't come in and confiscate it. Wyoming actually did propose, and we passed through our blockchain task force, a bill that would prohibit the judges in law enforcement situations,

Starting point is 00:26:50 both civil and criminal, it was the original proposal, prohibit judges from compelling disclosure of private cryptographic keys. It didn't make it through the legislature this year. It's a budget session, and it needs. needed a 60% vote in order to be introduced because it's a non-budget bill. We're going to end up bringing it back next year in much stronger form. But that is essentially the same argument. It's saying that a court of law is not going to be allowed to compel disclosure of a private key. In other words, protecting someone's crypto as a result. The challenge, of course, is that you have

Starting point is 00:27:23 to be able to compel someone to use their private key in a divorce settlement or to give back stolen property and the like, those kinds of situations where the court system can compel you to disgorge assets, those are legitimate. I think even the hardest core libertarians would agree with that. And the distinction that Wyoming is making here is that you're not allowed to steal the asset. If you commit fraud, you're not allowed to keep it. But we are treating private keys as something different than the asset itself. And as a result, you can be compelled to turn over the asset. But you're not going to have to be compelled to turn over the private keys. We're distinguishing them as very different than, say, a password to an email account.

Starting point is 00:28:09 I'll come back at some point. It almost sounds to me like you're trying to redefine or upgrade the existing laws that specifically called out gold and silver, and you're effectively trying to redefine it for the modern era. Is that kind of what you're doing in the way that you're defining that? Oh, absolutely. That is what we're doing. And if you look at the 13 laws that we actually did pass that were enacted already, that's what we've done.

Starting point is 00:28:36 We've updated existing statutes. And in every case except for one, they were what I would call enabling to digital assets. We basically defined the legal status of digital assets. And we said they're not subject to taxes. We allowed a financial sandbox for vintech companies to come into Wyoming, et cetera, et cetera. We said utility tokens are not securities. therefore not subject to state securities laws, very much enabling in our approach to the laws that we passed.

Starting point is 00:29:06 And so it is very much, as you describe, it's designed to update the laws to reflect the fact that we have these new assets that don't fit within existing legal regimes. And that's part of the confusion in the United States. We've got this legal, in the tech world, people like to talk about tech debt. We've got this legacy cruft that's weighing us down

Starting point is 00:29:26 because it doesn't actually reflect the way the world works anymore. And Wyoming was the first to step up and modernize in a way that really reflects how cryptographic assets work. Now, from my vantage point, you guys just absolutely get it by not putting any type of tax on the gains there. And I mean, I just can't imagine the incentive that that's going to attract for businesses to any crypto-based business to step into the state of Wyoming. So where do you think we are at on a federal level? Have you had any conversations with

Starting point is 00:30:00 representatives that they're maybe viewing this from a similar optic that as we look with the United States competing globally in this space, are they trying to maybe adopt a similar point of view or a similar law that would at least minimize the tax burden for capital gains? Yeah, I sure wish that the federal government would be moving in the right direction. I don't have good news on that front and don't expect it to be. So Wyoming, we can only do from a tax perspective what applied within the state of Wyoming. Obviously, the federal government is different. So all Wyoming, I still do have to pay federal taxes.

Starting point is 00:30:36 They just don't have to pay state income property or sales taxes on crypto within the state of Wyoming. So, yeah, there's not much positive movement. I mean, Washington is just paralyzed. And it's really frustrating to me watching what President Trump has done in deregulating so many other industries, and yet in the financial sector, he's going in the opposite direction, going in the wrong direction. And I sure wish that he had someone that could bend his ear other than true Wall Streeters. And that's who he's got in his Treasury Department and economic team. So it's not obvious to me that anyone on his team really understands what's

Starting point is 00:31:15 going on here. You know, it appears like Germany's really kind of understanding what's going on, because I think they just, didn't they just implement something that didn't have any type of a tax burden for crypto in the whole country of Germany? You know, I don't know about that. I do know that they adopted a crypto custody rule, and apparently they had 40 companies within the first couple of weeks of January contact them to apply. I'm so not surprised, given what has happened in Wyoming, I'm so not surprised that that happened in Germany.

Starting point is 00:31:45 There's definitely huge level of interest. That doesn't mean that all the companies will make it through. And I don't know exactly what their licensing regime is. I suspect that it's easier than the Wyoming licensing regime to get a bank because banks are at the top of the hierarchy in the U.S. You've got money transmitters at the bottom, which in your state of Alabama, I think it only takes a $5,000 bond, get a money transmission license within the state of Alabama. So you're not putting up much capital. So money transmitters are the easiest and the lightest capital requirements. Then on top of that, you've got trust companies, which are more capital requirement, more regulation.

Starting point is 00:32:21 And then at the top of the hierarchy, you've got banks. And actually, a subset of the banks is what we call the primary dealers. These are people who actually deal directly with the Fed and distribute U.S. Treasury. So that's the city groups, the Bank of Americas of the world. But yeah, in that hierarchy, banks obviously have the higher capital requirement and regulatory burden, but they can do a lot more things than trust companies and money transmitters. I don't know in Germany whether that hierarchy, is the same. I suspect it is, but I just don't know about the new custody law, whether that's

Starting point is 00:32:58 more equivalent to a trust company or a bank. So I assume you share the same opinion that I have, but correct me if I'm wrong, that the stock to flow model is valid. And that moving forward in the next two years, we can expect a pretty aggressive price move due to the halving that's about to happen here in May. If that would play out, I think you've got these primary dealers that are sitting at the top of that food chain that are, they're making money because they're pretty much assured to make money based on the model that they have with the Federal Reserve. But they're going to be looking at what's happening in this market, and you're going to probably see this thing go well above a trillion dollar market cap, and it's less than 200 today in Bitcoin specifically.

Starting point is 00:33:43 So with such an aggressive move and such smaller banks participating or smaller entities participating in this and making ridiculous amounts of money in transactions and just the sheer price movement of the underlying securities or the underlying commodities or however you want to call it, at what point do you suspect that they're going to say, hey, we want a piece of this and then that starts coming into the full scale legal framework because they're wanting a piece of the pie and they're there, they're being forced to buy these, in real terms, negative yielding bonds. Yeah, see, I actually, you know, this is interesting.

Starting point is 00:34:20 This goes back to when I was at Morgan Stanley still debating how this is all going to play out. At the time I thought that the mainstream financial sector was going to adopt this technology eventually. And I did, I like how Jimmy Song describes it, his detour through enterprise blockchain when he was at it bit for a little while. I was at an enterprise blockchain company for a little while as well. And I watched how hard it is to get the traditional financial sector to adopt these technologies,

Starting point is 00:34:49 whether they have a token associated with them or whether they're these sort of private or federated blockchains that so many of the enterprise companies are working on, their result is the same. That mainstream sector is still shunning this. And I actually think that the biggest issue is that the settlement systems are so different. They do not have the technology. They do not have the technological capabilities in-house to handle cryptographic assets. And so they're, I think, going to stay pretty separate from where we are in the crypto sector.

Starting point is 00:35:22 So when I pivoted, I concluded that the real adoption is actually happening in the decentralized systems and we're building a whole new financial sector in parallel to the traditional financial sector. And the interesting question is how many bridges are going to be built between the two. And, you know, the more bridges that get built, frankly, the better off both of them are. But I think they'll stay pretty separate. I just, you know, you see J.P. Morgan the announcement a couple weeks ago, that they're spinning off quorum to consensus. So you see the big banks actually going the other way. And I'm not shocked based on my experience. It's just such a different world for them. And they don't have the the core skill set on their technology teams to handle it.

Starting point is 00:36:09 Yeah, it'd be interesting to see how the equity ownership of those big banks would be potentially shifting or distributing their equity across both of those two camps, if you will, and to kind of see how much of that is changing over time. Because for me, I think in the past, the market cap had never been to a point that really anyone took it serious. But on this next move, I mean, if you start going over $500 billion, you go over a trillion, I think at that point when it starts going over a trillion and you're, I mean, you're already hearing this being discussed every single day on CNBC with the price of Bitcoin.

Starting point is 00:36:48 And I mean, four years ago, this was, you'd have a conversation with somebody. They'd just straight laugh at you like, yeah, right, there's no way this is going to be at a level where globally this could be a settlement currency. But I think you start getting up into those prices. all of a sudden this really becomes a hot topic conversation. And now it's not just, oh, I knew a guy who owned a Bitcoin and they made a bunch of money to pretty much, you could talk to anybody in an office and everyone knows what you're talking about at that point.

Starting point is 00:37:17 And probably there's a couple people that had 100 or 1,000 percent or 10,000 percent return. Oh, yeah, yeah. Stay tuned. There's definitely a lot more institutional interest. And the issue they're all running into is custody. There's a reason why the big custodians that handle institutional investors are banks. So this gets back to what we talked about previously, that we don't have any banks that are

Starting point is 00:37:41 allowed to custody crypto because the FDIC is standing in the way. And so you've got to have a non-FDIC insured bank that is providing crypto custody. And that's the Wyoming law. It's a non-FDIC insured state chartered bank that still has access to the Fed. and actually I would argue that it's even safer than a traditional bank because the Wyoming banks, since they're not FDSC insured, are required to hold 100% reserves. And so you don't have the classic counterparty credit risk. Banks go bust generally because they either have bad loans or they mismanage their interest rate risk. In a 100% reserve bank, they can't do either because they can't

Starting point is 00:38:20 lend and they can't play the yield curve. They can't mismatch their assets and liabilities, in other words. So I would argue as a counterparty fees are actually going to be safer. It's going to be very interesting to see how institutions handle this. But I alluded to this earlier, there are things these banks can do that the market doesn't have available right now. For example, one, you know, I'm going to go into the weeds now, but there's something called a good control location that the SEC requires a custodian to have. And the SEC and FINRA has not clarified what good control location is for a digital asset. Now, they only have jurisdiction over security. So we're talking about security tokens here.

Starting point is 00:38:55 It's a pretty small, pretty small market by market value, but pretty big opportunity over time. And one of the log jams that has kept that market pretty small by market value is that there isn't a bank that can be a custodian. Why? Why are banks special? Because they have a safe harbor for good control location. So until the SEC and FINRA define what good control location is, that means only a bank can provide it, but no banks can provide it except for one. Wyoming banks. So you see where I'm going. We've really found some very interesting angles to solve regulatory problems with the Wyoming law. And there are people stepping up and using them.

Starting point is 00:39:35 And by the time this podcast is out, there will be news based on what I know is in the pipeline in Wyoming. There's something else. You and I talked about before a lot of people are looking, a lot of crypto companies are looking. The Wyoming Banking Division has said they've had well over 100 inquiries. And there haven't been that many that are going through the process. The interesting question for the crypto industry becomes why. We alluded to this earlier. We don't know if the crypto counterparties we're dealing with are solvent. There is no audit in most cases. There's no proof of reserves. There's no transparency. There's commingling of assets. So I was looking at one of the largest stable coins, one that is targeting the institutional market. And there is absolutely

Starting point is 00:40:20 no ring fencing of the cash backing the stable coin on that company's balance sheet. There are some regulatory questions surrounding that company because of, again, the history that it has. So it's an interesting question. What happens if the regulators go after that cash? What happens to that stable coin? Because the cash is commingled. And it's not bankruptcy remote.

Starting point is 00:40:41 So if one of those companies ever went bankrupt, how do the crypto holders get that cash? Read their terms of service. Their terms of service allow the stable coin issue. sure to use your cash in any reasonable manner it sees fit or just some language to that effect. When an institution reads this kind of stuff, they look at it and say, I can't touch that with a 10-foot pole. So as I was talking to one of my friends in the industry, the ability to, the opportunity to professionalize this industry and to bring in the true big money institutional investors that aren't here yet is like shooting fish in a barrel. There's going to be so much

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Starting point is 00:44:06 asset class in the last few years. Visit fundrise.com slash WSB to invest in the fundrise income fund in just minutes. The fund's total return in 2025 was 8%, and the average annual total return since inception is 7.8%. Past performance does not guarantee future results, current distribution rate as of 1231, 2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the income fund fund's prospectus at fundrise.com slash income. This is a paid advertisement. All right, back to the show. You know, when you say all that, it's just, I'm just here smiling and shaking my head. The technology is moving so insanely fast that the

Starting point is 00:44:55 regulatory side of it just cannot even keep up that. And I mean, really, that's how you're getting the entrenchment that you have, because I mean, I'm with you. There is just total, absolute entrenchment. I mean, you got derivatives stood up around this. You got, I mean, it's just, it's kind of mind-boggling to think how much infrastructure is set up around all these payment rails that I don't know how anyone could think that they could possibly shut this down at this point. Oh, they can't. There's just, there's just no way.

Starting point is 00:45:26 Yeah, they can try. But where I'm going is that the ones that come into Wyoming and voluntarily become regulated under Wyoming's law, that separates the proverbial men from the boys because Wyoming's law requires 100% reserves under cash. and prohibits re-hypification. So a lot of the crypto lenders outright disclose to you that they're re-ap-officating your assets. Okay, that means they're fractionally reserved. You know that up front.

Starting point is 00:45:53 And so your plan, you're rolling the dice, if you have a counterparty exposure to them and they go down, your loss severity is going to be pretty close to 100%, I would guess. Yeah. So they're not at the I see in short. Of course not. Right. So those firms are obviously doing, in some cases, extremely well. And the interesting question is, will they ever be able to break into the institutional market?

Starting point is 00:46:16 As someone who used to be an ERISA fiduciary, ERISA is the highest standard of institutional asset management. ERISA fiduciaries have personal liability. I've been personally sued twice as an ERISA fiduciary for Morgan Stanley's pension plan, just because everybody on the committee got sued. But we have personal liability under ERISA, right? So if you're in ERISA fiduciary, boy, you dot eyes and cross-tees. you're going to start looking at the credit risk analysis of these institutions and you're going to look at

Starting point is 00:46:41 their terms of service and you're going to say, I'm staying away from this. I'm never touching this. Another example, fork policy. I was looking at one of the institutional players on their fork policy and it said that they may or may not support forks, if any. So I read that and I'm like, what is this institution promising you? Exactly. There is nothing legally enforceable in your contract with them. And again, an institutional lawyer is going to just, it's going to laugh the way you did. And I hope some of your listeners actually take the time to go look at the terms of service of their of their counterparties because you're going to see this stuff. Another one, one of another major quote unquote institutional player. Do you know how they define Bitcoin?

Starting point is 00:47:24 They serve Bitcoin only. In their contract, they define Bitcoin as quote, a digital asset. Okay, again, you can drive a Mac truck through that. What is it? They are promising you nothing. And in Wyoming, in the terms of service, you are required to, for example, define the asset that you are handling by reference to the source code version on GitHub. And so if the asset forks, like the old ETH Classic, ETH fork, where the new fork became the accepted asset, in that instance, if somebody was actually custodying EVE Classic, they are not allowed to just change the asset to the new ETH without getting express approval from the customer because the customer had a property right in that original ETH classic. They're not obligated to continue to service it

Starting point is 00:48:17 if they don't want to so they can give it back to the customer, but they cannot just magically say, oh, well, ETH is now new ETH, not old ETH, and just change the terms on you because that is actually theft of property if they do that. The problem is, you're dealing. You're dealing with with an institution that defines Bitcoin as, quote, a digital asset, you're never going to win a lawsuit against them. Ever. Because they're not promising you anything enforceable. Yeah.

Starting point is 00:48:44 Exactly. So, I mean, again, as my friend said, it's like shooting fish in a barrel to professionalize this industry. I am wildly optimistic about the opportunities for the companies that are going to come in and step up and comply with those standards. And there will be some. There have been some publicly named as hanging around it. I actually met one last night that's not been publicly named. It's a huge company in this industry

Starting point is 00:49:08 looking at coming into Wyoming. There will be some existing players as we were chatting before we started the podcast. I think a lot of the incumbents can't comply with those rules because they've done so much fast and loose because they didn't have to comply with any rules in the early days to try to actually backfill and comply with strict rules like that. They just can't. And so we look back three to five years or now, we're going to see truly that the best companies in the industry are in Wyoming complying with those very strict rules. And it just simply means that they're solvent. They're not allowed to become insolvent and play fast and loose. Like everybody else, frankly, is. And we just don't know who's insolvent and who's not. We don't know where the next

Starting point is 00:49:52 F-coin is or, you know, the next finance hack. So one of the things that I really took away from a conversation that I listened with you and Trace and Tyler out there in Wyoming was just this idea of states rights versus federal law and how this interchange between both of them really kind of take place and where Trace was mentioning how he feels like there's so much power down at the state level. And I think an example that so many people can understand so easily right now is for years there was no legalization of marijuana. And then out of nowhere, it's seemed like the states were starting to bump their chest and saying, hey, we're declaring that marijuana is legal in the state of Colorado. It's legal in California. Do you feel like there's

Starting point is 00:50:40 something similar kind of taking place with respect to how Bitcoin and crypto assets are being viewed from a state's rights standpoint in the face of the federal government? Oh, yeah. And if you look at the Rocky Mountain states, they're the ones that are actually taking the lead on this. It's not the coastal states. I think we've had now 12 states past the utility token bill that Wyoming originally passed. And it's basically Wyoming and pretty much all the states surrounding it have passed it, which is awesome. It's not one political party or the other. At Heath Denver, we had a very conservative Wyoming governor with a very liberal Colorado governor on the same panel vehemently agreeing that we should be attracting crypto. Your earlier question,

Starting point is 00:51:21 the United States is a republic. We are not actually a democracy. We are a republic in which the states are the sovereign unit within the government. We tend to forget that a lot, but the U.S. Constitution defines the powers for the federal government and all other powers are reserved to the states. Now, that concept has been eroded substantially by the Supreme Court in a lot of cases that I think were wrongly decided, but the concept is still there. The states actually have the vast majority of the political power in the United States. And the biggest piece of that is what's called the Uniform Commercial Code, all commerce is governed by state law. There may be portions of federal law where federal regulations preempt for various reasons, but the basic commerce that

Starting point is 00:52:10 governs every transaction that every one of us does every day is actually state law. And so the states have enormous power. And that's what we stepped up and recognized in part with what Wyoming did with its regulations. So with that said, I think this is under Article 1. section 8 of the Constitution, there's a very specific portion that calls out the regulation of interstate commerce. Do you see any vulnerabilities with interstate commerce and how the federal government could come down and start regulating things inside of, let's call it, Wyoming due to that clause being in the Constitution?

Starting point is 00:52:46 Yeah, that's the truck that's been driven through the federalism concept in the U.S. Constitution is the interstate commerce clause. it has been a kitchen sink of federal powers that have been implied into that. And again, I was specifically alluding to that when I said a lot of those Supreme Court cases, I think, were wrongly decided. But that said, in the crypto industry, it's clear that the federal government has jurisdiction over securities. That is settled law. But it doesn't have jurisdiction over property. And so if you try to figure out where does, where do the digital assets fit, digital securities are clearly securities. That's obvious. Virtual currencies are not. So what are they?

Starting point is 00:53:29 This is where we mapped it to money. And then utility tokens that are not securities, we created a new class of property called digital consumer assets. So these things don't fit very clearly within the law. And it's also true that there's going to be a skirmish over where these assets are quote unquote located. Again, only lawyers would dance on the head of a pin and argue where is data located? But actually, the accountants are doing the same thing. They're settling on the location of the private key is where the asset is located. But frankly, you could memorize your scene phrase and walk across a border and the asset literally moves.

Starting point is 00:54:09 So it's going to be interesting to see if that remains the case or not. I saw Drew Hinkas tonight tweeting about a very interesting case where the argument, the argument was about local bitcoins. And because the servers are all over the world, is that considered interstate commerce? Or because it was a peer-to-peer transaction that took place where two people were physically present in the same place, is that the jurisdiction? In which case, there was no interstate commerce because they were literally in the same place. This is going to be an area that's going to be fought out among judges and Wyoming's done everything we can to broadly define how you locate an asset in Wyoming for commercial law purposes, but it also is worth stating that the

Starting point is 00:54:53 answer may be different for criminal law purposes. So we may actually have broader federal jurisdiction under criminal laws than we do under commercial laws where the laws will ultimately be controlled by the states. And two people can memorize a private key. Absolutely. You betcha. You betcha. Yeah, these are thorny issues. In fact, actually, I was invited to participate in a group called the Uniform Law Commission. They originally attacked Wyoming for what we were doing. And actually, surprisingly, they've come full circle to recognizing that Wyoming actually was getting this right. We may not have gotten it perfect, but I think the 50 state group that is moving, that is rethinking all this is moving

Starting point is 00:55:37 in the right direction. They're moving toward Wyoming. But there's going to be a specific working group session in May to discuss this whole question of where our digital assets located. The accountants are definitely moving, at least in an enterprise context, to the question of where's the HSM, the hardware security module, you know, or where's your flash drive that has your private keys on it? If it's located in some place, then that's where the asset's located. And if it's multi-sig and it's located all over the place, then where is the decision authority around the asset? And that's how they define where it's located. The reason why that has to be, that question even has to be answered is when you're dealing with enterprises, they have to

Starting point is 00:56:19 disclose where their assets are and their auditors have to know where they are and they have to pay taxes in those jurisdictions. So as much as that may make you uncomfortable, on the flip side, you can actually optimize for where those assets are located. You can and everyone does look for welcoming regulatory regimes to make sure that the business that they're doing is wherever they are is actually lawful. It's not difficult to make sure that your service are in a particular place if you want them to be, for example. So real fast on the mixing discussion, how do you see this playing out as the most likely form moving forward? I mean, I just look at it from a tax implication standpoint, and I can

Starting point is 00:56:59 understand why pretty much any sovereign nation state would have a real issue with the mixing of coins so that you don't know where who owns the public address at that point. How do you see it playing out moving forward? I think we'll have two markets. I think we'll have mixed markets and I think we'll have the regulated markets. And I think that they're not going to clash enough that coins become non-fundable. But again, this travel rule, it makes it very difficult for the regulated financial institutions to deal with mixers unless they're mixing themselves. And so I'm not an expert on this. I need to dig into it. And it's going to be playing out in the next couple of as we as we see these new regulations, but we generally know what's going to happen. You have to know

Starting point is 00:57:46 who the counterparties are. That doesn't mean that you can't use mixers to ensure that the transactions remain private. There's an enormous amount of privacy around Wall Street firms trading strategies, and yet their financial institutions know exactly who they are. There's a difference between privacy and anonymity. So I think you will always have the sort of dark markets that stay out, of the regulated financial institutions. And Godspeed that those exist, I was reading recently, something like on the order of 20 to 25% of both Bitcoin and Ether are self-custodied. And so they're not actually held on financial institutions books.

Starting point is 00:58:29 So people are heeding the not your keys, not your coins advice. I love that there is a parallel market. We have a choice to take our assets off these counterparties balance sheets and put them on our own and be self-sovereign. But if we choose, we can keep them at an intermediary. If you're at an intermediary, that means you're in the regulated market almost certainly, especially in the U.S., because even the exchanges that don't have, you know, a bank license or a broker-dealer license, they all have to comply with FinCEN. And it's frustrating. I saw a Twitter argument over, I think it was Paxos, who was flagging that transactions were being

Starting point is 00:59:07 sent to a wasabi wallet and they were asking for more information from the customer. And the customer was getting upset. I would advise that when an exchange has to do something like that to talk to a customer like that, they should explain that it's not their choice. They have to apply the law in order to remain in business. And it's their obligation that, you know, don't be angry at the company, be angry at the government for putting that law in place in the first place. It's like everyone gets mad at the airlines for all the crazy policies in almost all circumstances that those policies were not the airline's choice.

Starting point is 00:59:43 So we've definitely got that situation. But you should expect that if you're dealing with an institution, that you're not going to be able to coin join and that the institutions are going to have to do all of that, know your customer and anti-money laundering and counterterrorism financing analysis. So if I was a person that was listening to this conversation and I had no idea who you were before. for listening to this, I'd be asking myself, all right, where can I follow this person on Twitter immediately? And so I guess my question for you is, who are two or three other people that you look at with that same lens of, holy moly, have to follow this person from a legal standpoint with respect to crypto assets that you think is at the top of the game is really kind of understanding where the direction of all this is going? And that is somebody that you just

Starting point is 01:00:33 couldn't stand without having in your roll of decks of people that you follow. Oh, I'm going to end up leaving people off. So I'll start with an apology for, because there are so many that are really terrific. But I will say one who I check regularly is Drew Hinkas. He just is so on top of breaking with the breaking news related to crypto litigation and also related to new proposed laws, both at the federal and state level. He's just got a great thread. Actually, I'm going to stop there. Well, I would add Catherine Wu just because every time some, you know, regulations come out, her annotations are just amazing. She's just an absolute star, and they're just for their entertainment value, much less the explanation, they're spectacular.

Starting point is 01:01:21 I'm going to end up making so many people mad if I keep going. So I'll just highlight those too. I think most people in the legal community would concur that calling them out for their analysis in each of those respective ways. Everybody's following them for those reasons. Okay, so this is my last question. What do you think a lot of people in this space or even people that aren't in this space are missing right now?

Starting point is 01:01:44 I think it's the counterparty risk in the institutions and we are going to see a big separation. There's a push towards proof of reserves. I've been a lot of conversations about that, crypto Twitter and Reddit forums, that customers are starting to get upset that there's no transparency into their crypto exchanges. Some of these companies are now five, six years old and they're not audited.

Starting point is 01:02:07 Why? Why aren't they publishing audited financial statements? Why don't we have proof of reserves in at least Bitcoin? I recognize that in some points it's difficult to do. But we have no idea how to do counterparty credit risk analysis on these exchanges and lenders and custodians. And all of them, if they've been in business for a while, have a history. And again, the ones that actually do get licensed by coming into Wyoming and voluntarily submitting to the regulation that they have 100% reserves, it's not as high in at least the developer's minds, not as valuable as actually having proof of reserves, but it's not nothing. It's going to be quite a statement, I think. So stay tuned. You'll see who comes into Wyoming. And I think once they voluntarily comply with those regulations, that's separating the proverbial.

Starting point is 01:02:57 men from the boys. Caitlin, I cannot thank you enough for this conversation. I have learned so much. I am such a big fan of yours. If people that are listening to this want to learn more about you, where can they find you? On Twitter at Caitlin Long underscore. I also publish pretty regularly on LinkedIn and on Forbes.com. Okay.

Starting point is 01:03:18 Well, we'll have links to all those locations for people if they want to check it out. And thanks for coming on the Investors podcast. Yeah, thank you. Great to talk to you. I really enjoyed it too. All right, everybody, thanks for listening to the show. If you guys enjoyed this one, make sure you share it with your friends. And with that, we'll see everyone next week. Thank you for listening to TIP. To access our show notes, courses, or forums, go to theinvestorspodcast.com.

Starting point is 01:03:44 This show is for entertainment purposes only. Before making any decisions, consult a professional. This show is copyrighted by the Investors Podcast Network. Written permissions must be granted before syndication or rebroadcasting. I'll know.

We Study Billionaires - The Investor’s Podcast Network - TIP284: Bitcoin - Law & Legal Implications w/ Caitlin Long (Bitcoin Podcast)

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