In this episode of Block and Order, hosts Kyle and Moish chat with Matt McClintock, founder of Bespoke Group, about estate planning, wealth preservation, and asset protection in the world of Bitcoin and digital assets. Drawing from his experience with ultra-high-net-worth clients, Matt offers a blend of practical insights and philosophical reflections on topics like digital custody, shifting regulations, and the evolution of generational wealth in the crypto space. As digital holdings become more valuable and complex, the conversation underscores the growing need for customized, mature strategies to manage and protect these assets effectively.

Follow Matt McClintock on LinkedIn: https://www.linkedin.com/in/mattmcclintock/
Learn more about The Bespoke Group here: https://bespokegroup.io/

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Chapter Markers:

00:00:00 Welcome to Block & Order
00:02:56 Welcome to Our Guest (Matt McClintock)
00:08:24 What in your background gave you the confidence and curiosity to take on a risky $150M bitcoin estate planning matter, despite the legal field’s cautious nature?
00:10:58 Had any other technologies or ventures sparked your interest before, or was bitcoin the first that made you say, ‘let’s go for it’?
00:16:10 Were you concerned that the Corporate Transparency Act marked the end of privacy protections?
00:22:10 Do clients come to you seeking education on Bitcoin and crypto, or are they usually already invested and informed?
00:23:56 Do clients still come to you with significant crypto holdings stored on platforms like Coinbase?
00:27:03 At what point does it make sense for someone with growing crypto wealth to shift from self-custody to more sophisticated estate and asset protection planning?
00:35:24 Beyond staying private about their holdings, what can Bitcoin holders do to protect themselves from threats like wrench attacks?
00:40:26 How do you view the role of leverage and lending in Bitcoin estate or treasury planning, especially as tools become more sophisticated?
00:49:05 Do you see a future where using Bitcoin for everyday payments becomes the norm in the U.S., like we’ve seen attempted in places like El Salvador?
00:53:47 What’s on your crypto regulation wish list—especially from a legal or RIA perspective—that isn’t getting enough attention?
00:57:59 For those new to this space, what’s the best starting point—what should they read first?
01:06:22 Thank You to Our Guest
01:08:50 Closing Remarks

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Transcript:

**This transcript has been prepared automatically by AI and may contain inaccuracies**

Kyle Lawrence [00:00:10]:
Welcome to Block and Order, the show that explores the legal issues facing the world of Web3 and beyond. I am a properly attired Kyle Lawrence, and with me all the way at the crack of dawn from the left coast, Mr. Moish Peltz.

Moish Peltz [00:00:22]:
Morning, Kyle.

Moish Peltz [00:00:23]:
From sunny San Diego.

Kyle Lawrence [00:00:26]:
San Diego.

Moish Peltz [00:00:28]:
San Diego, yeah I messed, I messed that up.

Kyle Lawrence [00:00:28]:
What brings you out there man ?

Moish Peltz [00:00:32]:
I am at the International Trademark Attorney Conference, the annual meeting in San Diego where there’s about 11,000 registered trademark attorneys all buzzing around the San Diego Conference center, and probably another 10,000 that haven’t registered.

Moish Peltz [00:00:47]:
That are like still there.

Moish Peltz [00:00:50]:
It’s the most insane conference. You can tell my voice is already shot. You know, it’s exciting, though. Related to Block and Order is, you know, I do a lot of blockchain work at this, at this conference as part of the IP practitioner community and actually had a panel on Saturday morning a few days ago for our audience that was talking about enforcement of Web3 on the blockchain, IP enforcement specifically, and how, you know, trademark attorneys around the world can use trademark laws, you know, effectively to prevent people from cracking their brands using blockchain stuff. So that is cool.

Moish Peltz [00:01:33]:
Yeah.

Kyle Lawrence [00:01:34]:
Look at you.

Moish Peltz [00:01:35]:
Well received.

Kyle Lawrence [00:01:36]:
Yeah, yeah, exactly.

Kyle Lawrence [00:01:39]:
Well, thank you for tuning in from the opposite coast. We have a very special episode coming up for our viewers and listeners out there. Matt McClintock, the founder of Bespoke Group. And it was a wonderful conversation that started off with me having a bit of a. Some technical and, if we’re being honest, spiritual difficulties at the very beginning. But Matt was just, what, a gamer, I mean, a rock star. He was a terrific guest. He was.

Kyle Lawrence [00:02:05]:
His insights were really incredible. Not just from a technical perspective of how people go about preserving their wealth and protecting their assets, whether it’s bitcoin or traditional assets, but just the philosophical approach that he had and his understanding of this ecosystem at its, its, you know, roots was something that I felt really impressive and, and, you know, important to me.

Moish Peltz [00:02:25]:
Yeah, almost philosophical, Zen like approach to this issue. And I thought his, his depth of understanding of the nuances of crypto and the issues that that face, you know, holders, you know, large and small, was really like unmatched. So blown away by the conversation. I’m sure the audience is going to love it.

Kyle Lawrence [00:02:49]:
And without further ado, here’s our conversation with Matt McClintock.

Moish Peltz [00:02:56]:
Joining us today on Block and Order is Matt McClintock. Matt, it is a pleasure to have you on board here today with us and would love to just ask you a bit about who you are, your background, and how you got into your current role.

Matt McClintock [00:03:12]:
Yeah, cool. Thanks. It’s great to be on your program, guys. Thanks a lot for hosting me. Yeah. Matt McClintock. I’m an attorney by background, spent 25 years in the trenches doing sophisticated estate planning for ultra affluent families primarily based in the United States. I’m just up, up in the mountains a little bit west of Denver.

Matt McClintock [00:03:33]:
You know, it’s kind of tough duty, but somebody’s got to do it. And you know, my. In 2017, you know, I was just minding my own business with my law practice, doing estate planning work. The way we do it, multi jurisdictional Alphabet soup of sophisticated planning. And along comes a young family with about $150 million worth of Bitcoin. And I didn’t know that’s in 2017. I was in 2017. That’s back when $150 million is a lot of money.

Matt McClintock [00:04:04]:
But, you know, they’re, they’re doing, they’re doing okay. Kids are going to make it. But, you know, I didn’t know anything about bitcoin. My business partner, my law partner didn’t either. And so we said, well, you know, he wanted to demur on this thing. And I said, you know, this is kind of an interesting thing. Let’s, let’s at least have the conversation figured out. So I met with these, with this family up in Boulder just north of me.

Matt McClintock [00:04:28]:
And I was just fascinated by the story, just how they got into Bitcoin around 2017. They were serial entrepreneurs in the space and the ideology around it and the hard money qualities. And I was just kind of psychologically hooked, right? Or like, you know, my interest was peaked, like, right on. But then as we were, as Jonathan, my business partner, and I were driving back, he said, yeah, we can’t touch this thing. It’s like we don’t understand it. I said, dude, I’m going to take the other side of that. It’s like, we have to take this because one, this is this family’s entire body of wealth. They’ve got a massive taxable estate.

Matt McClintock [00:05:04]:
They’ve got potential creditor concerns because, you know, they’re serial entrepreneurs. They’re just a business problem waiting for a place to happen. You know, we got to do this, and if we don’t do this, somebody else is going to do it anyway. So we might as well be on the leading edge of this. And so, you know, one thing led to the next, and we did a ton of estate planning for those people. At the end of 2017, first part of 2018, we kind of reached another Rubicon moment when they said, can we pay you guys in Bitcoin? And I mean, the answer had to be yes. We had to figure that out. Had to be yes.

Matt McClintock [00:05:32]:
Had to be yes. And along the way, they said, hey, these structures are great. You know, we did some stuff in Wyoming, some stuff in Alaska, some stuff in Neva, some stuff in the Cook Islands, whatever, for all the reasons that we can maybe get into, if you want to. But along the way, they said, this is great, but can you guys help us manage this stuff? Can you guys help us manage our real estate? And by just continuing stumbling forward and saying yes and yes and yes and yes, we accidentally became a fractional virtual family office for this client. This is before I even knew what a family office was. We were doing it. And we created Bespoke because it was tailor made for what these people wanted. That’s, you know, we were just doing it as we went.

Matt McClintock [00:06:09]:
And then through the, just the cycle of the practice, I did a lot more continuing education presentations. I did a lot of writing around what Bitcoin is, how it works in the estate planning context. Started to learn more about the deeper crypto space and Web3 and, you know, L1 protocols and start just getting more founders and more Bitcoin Wales. And almost to a person, you know, they would. Once we did their estate planning, they wanted us to do their family office too. And then the family office kind of took its own, took on its own life to the point where we restructured 2022, 2023, formed an SEC, registered RIA inside of Bespoke Group. So we’re now fully licensed, registered, all that kind of stuff. And we got to the point where we just, we couldn’t maintain the law practice and family office at the same time.

Matt McClintock [00:06:54]:
So closed the law practice down last year and now just fully leaning into Bespoke Group as a global multifamily office. With just this unusual level of interest and expertise in bitcoin and the broader crypto space. We didn’t seek to become what we’ve become. It just kind of happened organically. And we crossed the billion dollar mark back in December. So we’re about one. Congratulations. Yeah, thank you.

Matt McClintock [00:07:21]:
It felt like a big milestone. And then we’re right around 1.4, 1.5 billion. And of that I always hear the.

Moish Peltz [00:07:29]:
First billions the hardest.

Matt McClintock [00:07:31]:
That’s what I hear. That’s what I hear.

Kyle Lawrence [00:07:33]:
Second one’s easy, takes six months, right.

Matt McClintock [00:07:36]:
Especially with bitcoin or, you know, then it could be down to 500 million. So it’s like there’s that too. But no, It’s. Of the 1.4-ish billion we support, probably 700 million is still bitcoin. And then, you know, helping clients diversify in intelligent ways through charitable planning and structured strategies and stuff like that. Coast to coast, we’ve got, I’ve got two partners in Europe. My head of asset management’s based in Lisbon. Our chief investment officer is based in Paris.

Matt McClintock [00:08:07]:
I got clients from Isle of Man or kind of places in the UK all the way to California. Don’t have anything in Asia yet. But we’ve got staff that span as far east as Zurich to as far west as San Diego and lots of points in between.

Moish Peltz [00:08:24]:
You said something really interesting there, which was you, you were an estate planning attorney for decades and then you got this case and you’re like, you and your partner are like, maybe, maybe not. And we, we deal with a lot of other attorneys and attorneys are known for being a little crotchety and conservative and not always taking on the newest kind of greatest. So what about your background or your work as an attorney? Do you think prime primed you to say, hey, like, let’s, let’s, let’s, let’s, let’s exercise some curiosity here and dive a little deeper and take on this thing that might be, you know, $150 million estate planning project, like that could go wrong and you could have issues that come up with that. So what, what, what led, what do you, what do you think led you to accepting the kind of risk and reward that comes with something like that?

Matt McClintock [00:09:12]:
To be quite honest, it’s probably because I’m not a very good attorney. I mean, it’s like, I mean, I’m a good strategist. You know, I’m an asymmetric thinker. I have a knack for connecting seemingly disconnected things in novel ways. And Jonathan, my co founding business partner, he’s an excellent attorney and he’s very linear thinking and very process oriented. And I’ve always been kind of the guy in the, you know, in the Wild west and the, you know, that the at the tip of the spear into the horizon type of thing. And I think it’s because, I mean, my upbringing is unusual, I think for a lot of lawyers. I don’t come from a family of attorneys.

Matt McClintock [00:09:55]:
I’m the first guy on my dad’s side of the family to have even gone to college, let alone get an advanced degree. So, you know, I kind of was raised as a scrappy guy. You know, my, that’s just my background, you know, originally from Oklahoma, you know, we kind of make stuff happen. And now I live here in Colorado in the wild west, and it’s just kind of the way I see the world. And I’ve, I’ve been fortunate. Just during the course of my career, I’ve just been exposed to a lot of different ideas. I read deeply, I read a lot of philosophical books, like a lot of philosophies, I read a lot of histories. I mean, I just try to read a lot of stuff and just consume a ton of information.

Matt McClintock [00:10:35]:
And then I try to give myself space to just make connections. And for me it’s like I probably because I just kind of yolo into stuff. It’s like I don’t, it’s like, you know, risks be damned. You know, we’re just going to figure this out and you know, we’ll plan, we’ll mitigate, but you know, we’re going to charge forward because somebody’s going to have to do this and it might as well be us.

Moish Peltz [00:10:58]:
Were there other technologies while you were estate planning attorney or other like business ventures, things like that that came along that made you have similar thoughts? Was it really like you saw bitcoin and like, let’s, let’s do this?

Matt McClintock [00:11:08]:
Yeah. It’s funny because during the course of a prior job I was in, before, before I opened the law practice that we since wound down, I was vice president of education for a national company that did continuing legal education and document assembly software for estate planning attorneys. And so to a certain degree I got to be like the, you know, the guy up on the mountaintop just kind of navel gazing and thinking about what’s interesting and all this kind of stuff. And so it got me to where I didn’t really have to worry about case matters and caseload and where the next client’s coming from. I had a paycheck, I had all this kind of stuff. And so I could just really think big. And so I got paid for 10 years just to think. And along that way, along that line, I got really interested in the role of trust protectors and this how, how to structure first directed trusts in different ways, you know, using trust advisors or trust directors or trust protectors, and how you can be really granular in how you give the powers and whether those powers are fiduciary or not fiduciary, whether fiduciary is binary or on the spectrum.

Matt McClintock [00:12:16]:
And then start doing to apply that beyond the trust space into the limited liability company space. And what Bespoke really started as was a failed project, Bespoke started as a company that was going to be a dedicated institutional trust protector company. I had created this model, I’d written some articles, I’d done some presentations called the Bespoke Trust Protector because, because my thought was, my theory was, and law is very clear that you can tailor, make the, the role of the trust protector, you can tailor the powers, you can even tailor the fiduciary exposure based on what you want, but you have to understand what you want first. And so I had done a lot of thought leadership around this. And when I left that other practice, when I left that other business, I was going to do two things. I was going to start the law practice, which was Evergreen Legacy Planning. And I also had started Bespoke Protector company thinking that would be trust protectors. And for the first, you know, eight months, 10 months of that Bespoke protector lived kind of in parallel to the law practice.

Matt McClintock [00:13:20]:
I said I don’t really see a path to revenue on this deal. It’s like nobody wants to pay me to do this stuff. It’s like they’re interested in it. Yeah, everyone loves it, everybody loves it, but nobody’s going to pay for it. So it’s like, well, that’s not that great. And so as I was mapping out the estate planning strategies for this very first bitcoiner in the middle of the schematic, I’m a very visual guy. And so I was creating a schematic on this big glass wall behind me and I there was a hole in the middle of the schematic which was who or what is going to serve as the manager of the limited liability company that’s going to own this luxury real estate? Because from a privacy perspective and from an asset protection perspective, we had the real estate owned by a limited liability company. It was a manager managed limited liability company, not member managed.

Matt McClintock [00:14:11]:
And the members were two Wyoming incomplete non grantor trusts. Because at the time Colorado’s income state income tax was high enough to justify a little bit of juice out of a non grantor trust. And so client set lore settles the two non grantor trusts. The two non grantor trusts form the limited liability company. But somebody’s got to manage the LLC, somebody’s got to go to closings, somebody’s name is going to appear in the chain of title as the manager of this LLC. And the client said, well, it ain’t me because I want this for privacy. This person’s well known. And so I said, this is the hole in the schematic.

Matt McClintock [00:14:48]:
I said, well, I was talking to Jonathan, my partner, and I said, what if we put Bespoke in the middle of that hole? And he said, yeah. He said, we’ll pitch it and see what happens. And so I said, look, you know, I. So I told the client, I said, look, you know, we’ve got this other company. It’s not doing anything. We could slot our Bespoke company in there. As the non member manager of your limited liability company, I, as the manager of the LL of Bespoke, serving in its capacity as the manager of your LLC. We’ll go to closings, we’ll sign the documents.

Matt McClintock [00:15:22]:
Fiduciary standard under the LLC act governed by the operating agreement. Great. Client said, great. What’s it going to cost me? And I said, I don’t know. I said, so let’s. Then I started doing some research about this kind of stuff and said, well, what probably makes sense is a percentage of the value of the property inside this thing. And so we figured out some kind of sliding scale of basis points. I didn’t know what basis points were.

Matt McClintock [00:15:45]:
I was so naive. And so it’s like. So I pitched at the client. He said, yeah, let’s do it. Cool. By the way, can I pay my invoices in bitcoin? Okay.

Kyle Lawrence [00:15:54]:
Just gets better and better.

Matt McClintock [00:15:55]:
Just gets better and better. So before long, before long, we’re stacking sats before I even know what stacking sats meant. That’s really the evolution of what? Of how Bespoke started. I mean, that. I mean, you guys have just heard the origin story.

Kyle Lawrence [00:16:10]:
That’s really interesting. You must have been sweating the Corporate Transparent Transparency Act. That was you putting a nail in the coffin of privacy protections for everybody out there.

Matt McClintock [00:16:20]:
Yes and no. Because we found a wrinkle in the Corporate Transparency Act. Again, we can go on this. Look, I don’t have a hard stop, so I can just go all day, so. Yes and no. I wasn’t sweating it because we could always comply. No big deal. It’s fine.

Matt McClintock [00:16:38]:
I mean, I was very early to be pissed off about the CTA. I mean, I thought it was a profound. I thought it is a profound invasion of privacy. I think.

Moish Peltz [00:16:49]:
I’m with you.

Matt McClintock [00:16:49]:
I think it’s a profound violation of the rights of due process. I just. I think the Supreme Court got it wrong. You know, they. I mean, there are nine guys. There are nine people in Washington who disagree with me. But I mean, it. The way it was enacted, the way it was, the way it was piggybacked onto the Defense Authorization Act, I mean, the thing died in committee until it got tacked on to must pass legislation.

Matt McClintock [00:17:14]:
Because who’s going to be the member of Congress who’s going to go back on an election year and say, yeah, I voted against the Defense Authorization act because of some type of esoteric little thing called the Corporate Transparency Act. Nobody cares. And so, and then it got, you know, back and forth and back and forth, as we all know. And then Supreme Court finally signed off on it. Yep, it’s, it passes constitutional muster again. I think they’re wrong about that, but they don’t. I’m not the one in the robe. And then, then we see now a new constitutional crisis arises when you have the executive branch refusing to enforce law enacted by Congress.

Matt McClintock [00:17:53]:
That’s been reinforced by, I believe it was a unanimous decision at the Supreme Court. It’s like, I kind of remember Marbury versus Madison during my, during my Constitutional Law 1L class. But, you know, here we are kind of in this hiatus. So, yeah, I think the Corporate Transparency act sucks. I think it’s terrible. I’ve been unapologetic and unabashed in my resistance to it. I’ve also done a little bit of presentations on the wrinkle that was, it’s right there. It’s in the black.

Matt McClintock [00:18:26]:
It’s in the black letter of the law. And it’s also addressed in the comment period, which was, remember, remember, there are two definitions that are pivotal. One is the domestic reporting company and one is the foreign reporting company. Domestic reporting company is pretty much everything that matters in the wealth transfer and wealth structuring space. The foreign, the foreign one is the wrinkle because the foreign LLC, the foreign reporting company has a two pronged test. One, it’s an entity that is formed under a Secretary of State or comparable regulator in the jurisdiction where the entity was formed. And the critical word is and not or, and the LLC, the entity must also register in the United States with a Secretary of State, tribal authority or something similar. So then the opportunity becomes, if you can thread the needle between a company established outside the United States that is exempt from filing with a domestic entity, you have a foreign non reporting company.

Matt McClintock [00:19:42]:
That very issue was raised in the comments during the regulatory period. They didn’t change it, they didn’t close it. So it’s like, is it a loophole? That’s what the law, it’s what the law says and that’s what lawyers say. It’s like that’s, you know, that’s what the law says. If Congress wants to change the law, change the law. During the rulemaking period, Treasury could have closed it, they didn’t. It’s again, it’s in the comments. I’ve read the entire thing, the conjunction and is the pivotal point.

Moish Peltz [00:20:12]:
So it’s interesting because then the, the enforcement leaves the door open for foreign reporting companies. But then it sounds like now there’s a loophole for some of them.

Matt McClintock [00:20:21]:
So, well, you can create a foreign non reporting company that remains exempt even under the, even if they, even if the executive branch decided that they would enforce the law. This, this loophole or this gap remains until they change the rules, until they change the regulations. So I think we kind of have two things working in our favor. One is the Constitutional Crisis of Marbury vs Madison too, which may or may not ever come. And even if that does come, they will have to change the law, which may give us, which may give all of us rebels an opportunity to, you know, raise a ruckus again and you know, maybe get a different outcome.

Kyle Lawrence [00:21:05]:
Right.

Kyle Lawrence [00:21:05]:
I think we’d be happy with some crypto regulation, but we’ll start small and we’ll go from there up to constitutional crises.

Matt McClintock [00:21:14]:
So that was a bit of a diatribe. But I mean, my point remains that in the family wealth structuring space we have been during the pendency of the Corporate Transparency act, back and forth we’ve been helping clients kind of thinking through the, the structure of foreign non reporting companies. And the secret is using a non US jurisdiction and then bifurcating the management regime so that the client can serve. Again, kind of back to this idea of tailoring powers, letting the client serve as the investment manager. They’ve got kind of like an investment trust advisor. They make the decisions. You get a non discretionary mandate and then having an independent third party general manager in a jurisdiction that doesn’t require reporting and filing with the Secretary of State. And so that’s a lot of the work that we continue to do.

Matt McClintock [00:22:03]:
Even in this, you know, like murky non enforcement zone for CTA.

Kyle Lawrence [00:22:10]:
Do you have clients to shift, you know, to pivot a little bit? Do you have clients who come to you and they have, you know, aggregated wealth, family wealth, you know, earned in their career, whatever it may be, and they want exposure to Bitcoin and other cryptocurrencies. Is there an educational component to what you do? Or are most of the people who come to you, they already have it and don’t need to be taught?

Matt McClintock [00:22:29]:
We’re seeing a shift in that, Kyle. I mean we, we started around Bitcoin And I would say that the overwhelming majority of the clients that we see are clients who made their wealth in Bitcoin or in digital assets. But even, even in the digital asset space, probably 90% of our clients were bitcoiners. But we are seeing a lot of single family offices for ultra high net worth families and just other ultra high net worth people who have come out of an exit or whatever. And they know that we’re a multifamily office. We’re in this space. We’re now Bitcoin native. We’ve been in the bitcoin space since 2017.

Matt McClintock [00:23:05]:
And so they say, yeah, how do we think about this? How do I get exposure? We’ve had some conversations with people who bought $50 million worth of an ETP, they bought BlackRock or whatever, and they said, now, how do I think about getting out of the ETP and into Bitcoin into a custodial framework? And this idea of custody is going to maybe tie into a conversation that Moish and I were having a little bit earlier, which is, how do you think about maintaining private key material once you own the underlying asset? Whether you started with the underlying asset, now you need the structure for it, or whether you started with ETP exposure, or you’re just like bitcoin curious and now you want to actually acquire the asset. How do you think about ownership? How do you think about custody, how do you think about tax consequences? And those are all decisions that we help people think through.

Kyle Lawrence [00:23:55]:
Very important. And the custodial angle to it is something that’s very important to not just us, but to all our clients and really should be top of mind to everybody out there. You know how you store your assets. Do you still get people who come to you and say, oh, I made 40 million of Bitcoin, it’s all sitting on Coinbase. I mean, after this morning, I can’t even say that out loud.

Matt McClintock [00:24:14]:
But, dude, I had that conversation yesterday. Yeah, I had that conversation yesterday with a dude out of San Francisco. He’s in his 60s, he’s serial real estate entrepreneur. And now he’s got. I don’t think it’s 40 million. I think he’s got. I think he said around 10, sitting at about 10 million sitting at Coinbase. That’s not great.

Kyle Lawrence [00:24:36]:
Danger Will Robinson.

Matt McClintock [00:24:38]:
Danger Will Robinson. And here’s the one I get more often than that, Kyle. It’s like, these are my clients. It’s like, yeah, I mined Bitcoin back in 2010 on a laptop when I was in college. Mind about 5,000. Okay, that’s a little over half a billion dollars by my count. And so, I mean, I’m not great at math, but I can do that. And he, these, this is, this again, this is my prototypical client.

Matt McClintock [00:25:06]:
And they said, you know, I just, I, you know, I just feel good about having my, my key material. I said, that’s, that’s great. What happens next? You know, it’s like, I’m an estate planning attorney. I’m always going to be thinking about, you know, I’ve always got to be thinking, second order effect, third order effect. What happens when you die? What happens when you have a stroke? What happens when you have a massive federally taxable estate? What happens in a state where you have state level estate tax? Right. What happens when you want to liquidate this stuff? Because if you’ve got a lot of the clients I see are 90 plus percent of their total wealth is in bitcoin or in crypto. Low basis bitcoin, low basis crypto, whatever. And so it’s like, okay, well, you ever want to buy something? I mean, yeah, you want to buy a house, you know, you want to start a business, you want to capitalize something else, how are you going to do that? How do you think about that? And this whole idea of not your keys, not your coins, all that stuff that we’ve heard for years and years and years, it’s like, that’s great.

Matt McClintock [00:26:04]:
When bitcoin is a few hundred bucks, maybe a few thousand bucks, and the grand total of what’s in your bank, if you were going to be your own bank, if the total of what’s in the bank is 50,000 bucks, fine, knock yourself out. End of the day, probably not going to be that material to your family’s wealth. But now in the world of bitcoin being worth tens of thousands and now six figures, it’s like, you got to grow up. You got to grow up. This is now a real asset. You got to treat it like a real asset. This is not just bitcoin. This is not just like Internet funny money anymore.

Matt McClintock [00:26:37]:
This is like massive generational wealth that you have built. You have to create generational architecture around that wealth. You know, if you ever, if you want to get the kinds of outcomes that you want, if you want to mitigate your tax, if you want to pass this on intelligently to the next generation, if you want to provide for your spouse or partner, if you want to run wealth into charities and there’s, you got to grow up and treat this right.

Moish Peltz [00:27:03]:
Yeah. So I guess how do you. This is what you were talking about before is you’ve got these people, you know, people, us, I think, on this call included, who feel very strongly that self custody and the purpose of Bitcoin is reinforced by that. And there is this feeling that you need to have, not your keys, not your coin, need to own the Bitcoin outright. But then that intersects with what you’re exactly talking about is once, once you get to a certain level of wealth, and especially if you ask an attorney what’s the proper legal way to prepare for and plan for some of these intergenerational questions, tax questions like, you know, growing up and putting on the suit. There’s. It does seem to be, yes, there’s a spectrum where you go from I fully self custody and that’s all I’m doing to everything’s behind a trust and there’s a trust protector and et cetera and maybe. But like, how do you even have that conversation? At what point in the trajectory of, you know, someone having some of that wealth or that wealth growing doesn’t even make sense to start asking those questions like, where does this conversation start? How did it start? Perhaps when you were, you know, maybe like that early stage? And how is that conversation mature is as we know, like we’re now having much more sophisticated conversations about asset protection, wealth planning, involving crypto that I don’t think anyone at least was having publicly, you know, three or four years ago.

Moish Peltz [00:28:26]:
But it seems like that’s, that’s a lot of where the conversation is now and certainly is going to become much more mainstream as bitcoin continues to, you know, we think, increase in value. Even if it doesn’t, it’s already at six figures. It’s a pretty big deal where it wasn’t when it was $3,000.

Matt McClintock [00:28:40]:
Yeah, no, for sure. Well, the conversation, I mean, it’s. The conversation is very gradual, very iterative, and it argues in favor of what we’ve created at Bespoke, which is a family office, so we can kind of walk along that journey with clients. Because when we were just in the law practice space, even though we wanted to be a relational estate planning law practice, there is still a transactional nature to it. And so now we can be more objective, I think, and more agnostic to what a client ultimately does with their Bitcoin because we, you know, we end up with relationships that are based off of a total value of the wealth that we are supporting you, you know, stra. Strategically. And so you bring into us whatever you want us to be thinking about for you. And then we can, whether we’re supporting the custody through qualified custodial relationships or whether we’re just helping you think through your multi sigs or helping you think through your self custody solutions, we just, we slow down the conversation and we, we get philosophical about this stuff and, and I, I think we have some credibility to say, look, you know, we’ve, we’ve only been in the bitcoin space since 2017, but in the, you know, that’s kind of a long time now.

Matt McClintock [00:29:52]:
I mean, it’s. So we’re not just like the newcomers here. So we, we get it. We’ve not been chasing the crypto stuff. We’ve not been doing all the DeFi stuff. It’s like we’re, you know, we’re kind of bitcoiners. We do support people with crypto beyond bitcoin and that’s, that’s fine. But I mean, ideologically we’re probably bitcoiners.

Matt McClintock [00:30:11]:
I say, look, we get it. But if you rewind the clock to when you were mining bitcoin or when you were buying bitcoin out of a sense of sovereignty and ideological kind of values and this kind of stuff, what was the price of bitcoin back then and what was the percentage of your total family wealth that was comprised of that bitcoin? Odds are the value of your bitcoin has grown at a pace that is far faster than anything else you’ve ever had. You know, so it’s like, so your level of sophisticated thinking around this asset also has to keep up. And it, and it hasn’t. It’s like if you’re still sitting on the not your keys, not your coins mantra as the, as the end all, then you got to evolve your thinking. We’re not saying you have to give up all of your control. It’s like, because it’s like you don’t just have like one bitcoin, you have.

Moish Peltz [00:31:05]:
Well, even if you do, they’re divisible.

Matt McClintock [00:31:07]:
Yeah, exactly, exactly, exactly. So it’s like, so I said, look, you know, and I said, look, I do the same thing for myself in a size appropriate way. The vast majority of my bitcoin is in qualified custody, owned by a limited liability company which is owned by an offshore trust that’s outside of my estate. From an estate tax perspective, it’s beyond the reach of my creditors. That’s a high friction type of environment. And so when I want access to that, there’s a lot of friction between me and those assets. But with that friction comes protection, comes tax efficiency. You know, it creates this multi generational vehicle through which I can provide for my family maybe for generations, depending on what happens.

Matt McClintock [00:31:55]:
And so it’s like, okay, well that’s, that’s not all of my bitcoin. Then I have what I would consider more of a moderate friction type of environment where I’ve got a, I’ve got a vault set up at a qualified custodian. That’s just the name of my revocable living trust. And it’s got a few bitcoins in there. It’s like I can access that anytime I want to. But if I, if I step off the curb and get, you know, hit by a bus or here in the mountains, more likely like run over by a moose, then then, okay, there’s at least a framework for that part. But then I’ve got like, I’ve got like beer money bitcoin. If I, if I go to a pub and somebody says they’re bitcoin curious or whatever, I can say, hey, download this.

Matt McClintock [00:32:38]:
Download to your. There you go, moon wallet or your ex’s wallet or whatever you want to. And next round’s on. Next round’s on me. And so I’ll just, I’ll send them some SATs. It’s like, fine. Now, from a tax accounting perspective, it’s a pain in the butt, but it allows me to kind of share the orange pill journey in a very low friction or no friction type of environment. But the way I’ve sized that is the no friction bitcoin.

Matt McClintock [00:33:04]:
That’s the bitcoin that if I get stamped, you know, stomped to death by a moose, okay, that’s not great for a lot of reasons, but the amount of bitcoin that gets lost, kind of immaterial. The stuff that’s in the moderate friction, it’s still within the. It’s still includable in my estate because it’s in my revocable trust. It’s in a qualified custodian with layers of multi sig built in. But you know, when something ultimately happens to me, my spouse, my kids, my trustees, they can access that, no problem. Includable in my estate, within the reach of my creditors. If I were to get sued for whatever reason, my wife divorces me or something else, fine. The high friction environment, that’s for the most important part of my wealth.

Matt McClintock [00:33:46]:
And so that’s where my, that’s where my equity in Bespoke Group sits. And that’s where the vast majority of my bitcoin Sits. So it’s, you know, I tell clients, look, this is the journey I’ve been on. And I don’t have hundreds of millions of dollars worth of bitcoin. I can’t afford to be my own client. But I size my. I size my solutions in ways that are appropriate for me. You’ve got a whole lot more to deal with.

Matt McClintock [00:34:10]:
And so let’s start thinking about that journey for you. And as I mentioned, because we’re not a transactional type of shop, if it takes you five years to figure this out, that’s fine. I mean, I don’t really care. And if you. I don’t care who you hire to do your estate planning work, you know, we can help you strategize, we can help map it for you. We can track the values. We can make recommendations. When you want to rotate out of bitcoin into something else, we can help you think about how you rotate out.

Matt McClintock [00:34:34]:
When you want to diversify globally across your investments, you want to get. You want to get access to markets that are ordinarily not available to US Depositors. When you want access to Swiss banking as a US Client, we’re your guys. But, you know, whenever you want to have your Dynasty Trust, your sale transactions, your Gratz, your Slats, your Alphabet soup, we can help you think through that. We can explain it to you. We’re not on the clock, so it’s like we’re getting paid either way. So we can just help you understand that. And then when you find an estate planning attorney, or if you want us to help you find one, we’ll help you find that.

Matt McClintock [00:35:09]:
We’ll project manage it for you. We’ll provide some perspectives if the attorney’s open to our perspectives on that deal. And then once it’s done, we’ll just bring that in and kind of shepherd it for you as things go. And so that’s just the way we’ve been able to establish our relationships.

Moish Peltz [00:35:24]:
It’s fantastic. I’m curious, you said something getting stepped on by the moose. But I’ve been hearing a lot, a lot in the news lately about the Wrench attacks. In fact, there’s a list of all the different. So I’m curious how if any component of this, this is about, you know, personal security and safety. And I think it’s just important. I’m curious, like what? Besides just not disclosing your worth and how much bitcoin you have, which I think people generally shouldn’t do, is there. Is there more proactive things people can do to be mindful of those kinds of attacks and what we think about that issue.

Matt McClintock [00:36:01]:
Yeah, I mean, the, the attack with something that’s definitely in our minds a lot and you know, as much for us as it is for our clients, frankly, because mostly because, you know, we’re.

Moish Peltz [00:36:12]:
Getting, we also accept bitcoin and firm has on our balance sheet and yeah.

Matt McClintock [00:36:18]:
We’re unapologetic about the fact that we’re in this space and I do a lot of presentations and stuff like that. So I’m, I’m a bit, I’m a bit of a known quantity, which does concern me personally from a client perspective. You’re right. I mean, a lot of it is opsec. Don’t tell people you got bitcoin. Don’t be that sorry. Sorry, guys. Don’t be that douchebag.

Matt McClintock [00:36:38]:
Driving around the bitcoin license plate, it’s like, sorry, I mean, sorry if that’s a bit too risque, but it’s like, don’t be that guy conversation we just.

Kyle Lawrence [00:36:46]:
Had the other day.

Matt McClintock [00:36:47]:
Yeah, it’s like, it’s like, don’t, don’t be the guy with the, you know, with the wrapped Tesla that’s like bright orange and it says like to the moon or whatever.

Kyle Lawrence [00:36:54]:
It’s like got the bitcoin sunglasses right here.

Matt McClintock [00:36:57]:
Like. Yeah, yeah, I’ve got, I’ve got all kinds of bitcoin chotchkis on my, on the bitcoin.

Moish Peltz [00:37:04]:
Yo, yo, imagine.

Matt McClintock [00:37:06]:
Yeah, exactly. It’s like, okay, if you’re going to be in the space, be in the space and that’s fine, but, you know, but be smart about it. And back to this idea of protecting stacks. It’s like you could be worth hundreds of millions of dollars or tens of millions of dollars, whatever’s, whatever the wealth is. And size your size, your sovereignty appropriately. You know, it’s like, by which I mean sovereignty in the bitcoiners sense, this, you know, self sovereign key custody thing, it’s like, feel free to maintain a stack. Let that be the stack that you’re willing to lose and then structure for the rest of it. So then if you do happen to get doxxed, you do happen to get subject to a $5 wrench attack, or somebody wants your thumbs more than you do or whatever it is, then you can give up some bitcoin.

Matt McClintock [00:37:57]:
It could even be a meaningful amount to whoever wants to give you a hard time, but it’s not the entire thing. In fact, maybe it’s only like 5% of what you’ve got. But I want to touch on this sovereignty argument too, because this is. I mean, I’m a sovereignty maximalist, but I, I have kind of a nuanced way of thinking about it, which again, probably, occupational hazard. We’re all a bunch of lawyers on here. It’s like, you know, it isn’t, it’s not. But the, I think a lot of times in the Bitcoin space, the conversation around sovereignty is overwrought or, or is just seen as a binary type of thing. I think of sovereignty as taking control of the totality of your situation.

Matt McClintock [00:38:38]:
And it’s not just like having sovereign key material. It is to it, again, to a point, but it’s also seizing the greatest opportunity that the law and regulations will allow to make sure that you structure your family wealth according to your rules, which should mean privacy, which you don’t get once you die. You got probate, you got guardianship or conservatorship if you get hit by a bus or, or the moose doesn’t finish its job. And, you know, it’s subject to the claims of your creditor. So unless you want to be the guy who’s going to commit fraud and then go to jail for that, ultimately, then you got a structure for this type of stuff. And so then how do you structure that exercise in structuring intelligently the exercise in opportunistically selecting the right strategies and the right jurisdictions, that is sovereignty. That is controlling the family situation. Sovereignty.

Matt McClintock [00:39:33]:
Back when Bitcoin was 10 bucks, 100 bucks, thousand bucks, 10,000 bucks. That’s, you know, that’s key sovereignty. That’s great. You can still have key sovereignty over a small portion of your wealth, but then you have to think more expansively about what sovereignty means. And then back to our prior part of this conversation. Grow up. I have been so, I have been so on the nose with potential clients and with presentations to say there are only two, only two people who don’t need to do any kind of structured planning, and that’s Peter Pan or Deadpool. It’s like, if you were never going to grow up, or if you literally cannot die, then fine, do whatever you want to do.

Matt McClintock [00:40:20]:
But if you’re not Peter Pan, and if you’re not Deadpool, you better do something more intelligently about your wealth. Grow up.

Moish Peltz [00:40:26]:
How do you think about leverage? I. I hear a lot about, oh, man, you know, you’ve got, you got strategy, you know, formerly microstrategy, talking about, you know, Bitcoin, treasury and leverage. Now people are talking about private kind of treasury companies. More companies are holding Bitcoin on their balance sheet. More people are now have access to tools, you know, whether it’s centralized exchanges or increasingly more sophisticated like quasi custodial arrangements that also allow for lending and kind of leverage type. So like how does that fit into. I mean obviously there’s tons of benefits where if you have a ton of bitcoin and you have zero basis and you don’t want a huge taxable event as you start to utilize some of that, like it makes sense that you would take a loan and use that to. I think there’s, there’s probably use for that.

Moish Peltz [00:41:16]:
But then again, is that, is that just part of that spectrum? Is there, is there more or less sophisticated ways to think about that? How does it fit in?

Matt McClintock [00:41:23]:
The way I think about that, Moish is. I think they’re two different things. What Microstrategy and these companies that are doing, I mean, I can’t argue with what they’re doing. I mean they’re taking an asset that is, you know, like company debt or even company equity that they largely can control the value of and then buying a pristine asset with that, they’re issuing debt and they’re buying Bitcoin. I think that’s pretty freaking brilliant. I mean, I think that’s great. When you’re talking about individuals, I think the conversation shifts and if you’ve been, if you’ve been in the crypto world for more than a hot second, you’ve seen all the car, you’ve seen all the carnage of like Three Arrows Capital and Celsius and blockfi and FTX and all of its, you know, there’s so much radioactive fallout that arose from this pursuit of Alpha, this excess return above just Bitcoin’s ordinary performance.

Moish Peltz [00:42:27]:
Which on its own is the best performing financial asset certainly in our lifetimes, maybe ever.

Matt McClintock [00:42:32]:
I mean, nothing, there is no other one. I mean that’s it. I mean Michael Saylor is right about that. It’s like there is no second best. It’s like it’s it. But I also understand that. I understand the allure of people who are in the digital asset space and they say, hey, all these proof of stake tokens can generate a staking return for me. You know, I can do what I want to do in DeFi.

Matt McClintock [00:42:56]:
I can roll this through protocols and lend and borrow and all this kind of stuff. And we don’t and can’t and wouldn’t support that anyway because we’re SEC registered. So we, you know, we’re under the custody rule we can’t do any of that stuff anyway. We’re also risk managers and we think that that is really in the thin branches of risk. So we don’t. If clients want to do that, it’s their money, they do whatever they want to with it. But the stuff that we manage for them, we don’t even engage in that at all. And our philosophy about this idea of seeking additional alpha on top of the world’s best performing asset is it’s like, okay, let’s think about, let’s think about the mechanisms that are involved in doing that.

Matt McClintock [00:43:38]:
The borrow is not great against Bitcoin. If you’re going to use a qualified lender for this, you’re not getting the kind of borrow rates that you would get. If you’re borrowing it’s real estate or borrowing against gold or some other type of long term store of value asset. It doesn’t make sense for those of us who understand Bitcoin. But Bitcoin’s volume just kind of. The lending market is not deep enough yet to give interesting interest rates.

Moish Peltz [00:44:03]:
You would expect that over time that that market will become more mature and those will narrow and.

Matt McClintock [00:44:08]:
Yeah, absolutely, absolutely. And the other side of this is so much of what we see passing for Bitcoin Alpha is either running option strategies on the bitcoin. And I’ve seen that go far more wrong than right. I mean, I’ve seen, man, I’ve seen people become forced sellers and they become forced sellers at the wrong time on a zero basis or low basis asset. So now you’ve lost the underlying asset and you just triggered a massive capital gains tax liability. What are you going to do to satisfy that? You’re going to sell more Bitcoin. That’s going to create this spiraling effect of capital gains tax liability, terrible outcome. Okay, so then what happens if I want alpha through a fund? Okay, so if we take, so let’s think about this.

Matt McClintock [00:44:51]:
We have Bitcoin, the native underlying asset. We have Bitcoin sitting hopefully in some type of qualified custody if it’s economically material to your family. But you, even if you have key material sovereignty over that, you own the asset and then you pledge that into a fund or you exchange that into a fund. Now you don’t own the underlying. You own a minority interest in the limited partnership agreement. You’re on somebody else’s ledger as an unsecured creditor. If they fail, you have no visibility as to how the partnership is custodying its underlying assets. You have no price discovery because you’re lucky to get a quarterly report that has any kind of meaningful value and you have no liquidity when you want to sell, you can’t sell when you want to redeem.

Matt McClintock [00:45:42]:
You’re probably subject to at least a 12 month lockup initially and then you might have like quarterly redemptions. So guys, this is, understand what you are giving up in pursuit of a few additional basis points or even consequential potential upside. Look at the risk of the downside. And then the way we think about alpha is much more comprehensive than that. We think about seeking alpha in the context of tax mitigation, asset protection, liability insulation, long term family wealth governance, and then preserving flexibility and optionality. You don’t get that in most of the strategies through which you’re seeking alpha. And then if you’re playing in the DeFi liquidity pools, you’ve got all kinds of protocol risk. You’re trying to take a non stackable asset and turn it into some type of version of a staking asset.

Matt McClintock [00:46:35]:
It’s like, if it works for you, great, but don’t come crying to us when these things unwind. And all you have to do is have a modicum of understanding about the recent history of crypto to realize that that seems to work, that seems to, that seems to fail more often than not.

Moish Peltz [00:46:55]:
I think that’s really powerful and I think gets back to the Peter Pan analogy of once you’ve worked through all this low hanging fruit of tax optimization and custody optimization, all these things like, okay, maybe then we could talk about it when you’ve kind of run through all those roadblocks. But there really is just, there’s so much of the basics that people forget to even start with and they just jump to okay, let’s, let’s do all of that. Right?

Matt McClintock [00:47:21]:
Well, it’s because bitcoin starts as mad money for these guys.

Kyle Lawrence [00:47:24]:
It’s like, it’s like it was just exactly right.

Matt McClintock [00:47:26]:
It was immaterial. It was immaterial for them. It’s like even if they, even if it was somewhat material, like my very first client kind of somewhat famously spent their last 10,000 bucks on Bitcoin back when that would buy you a lot of bitcoin. And so it’s like he was kind of YOLO. Okay, fine, just YOLO, that’s great. Continue to YOLO with $10,000 and if you want to be crazy, adjust that for inflation. Okay, so lose your mind or, or size it, or size it proportionally to what your risk is. Maybe it should be 5% mad money, go crazy maybe it’s 10% of your mad money or whatever, but just understand, go crazy with the amount.

Matt McClintock [00:48:05]:
That doesn’t matter. And if you. If it moons on you, that is so. That’s so great. Congratulations. You just won at the casino. But if it goes to zero, don’t create this spiraling unwind that then decimates your entire stack. Don’t get cute playing a place short and running.

Matt McClintock [00:48:23]:
All these per. These perpetual options. It’s like, cap your losses. Yeah, I’m not a big gambler. I go, I’ve been to Vegas a couple of times. But my rule has always been gamble with what you’re willing to lose. And then once you’ve recovered that, only play with house money. And then just keep playing with house money.

Matt McClintock [00:48:43]:
And if you want to keep scraping, keep scraping. That’s great. But don’t lose. Don’t lose the kitty.

Kyle Lawrence [00:48:48]:
Yeah. No. 100%. It’s a mistake a lot of people make. I. I’ve, you know, been guilty of it. When I was a younger man, you see people all the time. It’s.

Kyle Lawrence [00:48:54]:
Don’t chase losses. Don’t euphoria, trade. And above all else, pigs get slaughtered. You gotta. You gotta stick to those three and you’ll be okay.

Matt McClintock [00:49:01]:
100%. 100%. Dude, man. Absolutely. Absolutely.

Kyle Lawrence [00:49:05]:
You mentioned before if I could pivot a little bit. You were talking before about using bitcoin as tender to pay for things. And before I asked the question. Moish, what’s the name of that bar in the city that takes.

Matt McClintock [00:49:17]:
Nice.

Moish Peltz [00:49:18]:
Have you been there, Matt?

Matt McClintock [00:49:19]:
No, I haven’t.

Moish Peltz [00:49:20]:
It’s a really. I was just describing it to someone. It’s like the cheers of bitcoin.

Matt McClintock [00:49:25]:
Sweet.

Moish Peltz [00:49:26]:
Where you walk in, everyone, in there’s a bitcoiner. There’s always an event going on. It’s like people that you know or that company you know is like, doing something. It’s awesome. Go check it out. I was. I was like. I was just in a.

Moish Peltz [00:49:37]:
I was going to an event in the neighborhood a couple weeks ago. I was like, oh, I have half an hour to kill. Let me walk in. I walked in. I, like, knew two people. I knew the company that was holding an event. I, like, met someone new that was, like, super interesting. It’s like, definitely check it out when you’re in New York next.

Matt McClintock [00:49:50]:
Yeah, I’ll. I’m actually coming to the city sometime late July, I think, so I have to come check it out. I’ll get some more information from you guys.

Kyle Lawrence [00:49:55]:
Yeah, well, we’ll definitely meet up there. But do you see a World. Do you envision a world where that becomes the norm? You’ve seen countries in certain areas in Africa and Asia, you know, El Salvador, somewhat notably, where they’ve tried to let people use crypto, Bitcoin or whatever it may be to pay for things. Do you see a world in which that kind of takes over, at least in the United States?

Matt McClintock [00:50:18]:
I, I go back and forth on that, Kyle. I think, I think, yes, at some point. I think Bitcoin has been on a really interesting journey, which. It follows the course of all kinds of stores of money that we’ve talked about. I mean, it has multiple qualities. It could be a medium of exchange, it could be a unit of account, it could be a store of value. The answer is probably to some degree it’s all at the same time. And the US Dollar has historically been that way, although its use as a store of value is diminishing somewhat rapidly, especially compared to stronger currencies like the, you know, like the Frank and, you know, Singapore dollar and others like that.

Matt McClintock [00:51:02]:
But I, I am optimistic that within the next, I don’t know, I always hate to put a date on something, but I’d say within the next decade, I hope we see some reasonable legislation and regulation around the use of digital assets more broadly and beyond just stablecoins. I mean, stablecoins are great for that kind of stuff. But yeah, I’d love to see a world where there is a meaningful de minimis value exception for the use of Bitcoin or Ether or Solana or anything like that that’s readily tradable. I mean, we’ve all read the white paper. I mean, Bitcoin was floated not as a peer to peer store of value system. It was marketed as a peer to peer electronic cash system. That’s what it was designed for. To create a medium exchange between parties who have no reason to trust each other and never even meet.

Matt McClintock [00:52:00]:
And that’s what that was its, that was its purpose. But by the nature of its algorithm, it just is designed to go up in value against inflationary assets. So yes, I hope to see meaningful de minimis, like value exceptions either on a per transaction basis or on a per quarter or per year basis. To say, like, look, you can spend up to 10,000 bucks of your bitcoin each year and it’s not going to be a taxable event. Now if once you go above that, then maybe it’s still subject to the capital gains tax rules, because I think that’s kind of fine. But this whole idea of like a de minimis of $50 or $600 or whatever. It’s like that’s, I mean, I could not buy us a round of beers in New York City for 50 bucks. I mean, it’s like, yeah, I mean, seriously, so give a reasonable de minimis value exception, you know, below which basis tracking doesn’t matter.

Matt McClintock [00:52:55]:
And then once we’re doing like tens of thousands of dollars worth of transactions or much, much more, maybe that’s a different conversation. I just, I think that, I think that it’s going to take a couple of things. I think one, it’s going to take a turnover in the gerontocracy that governs most states and certainly Washington. I think it’s going to take a turn. I think it’s going to take a generational secular shift around with, around regulation and legislation. I think we will ultimately get there. The question to my mind is timeline. And I think it’s, you know, trying to pin a time on something is I think is a fool’s errand.

Kyle Lawrence [00:53:36]:
Yeah, yeah, I think that’s, I think that’s fair. But we’ll see. You heard it here first. You heard it here first. 10 years from now it’s going to happen.

Matt McClintock [00:53:43]:
That’s right. We’ll be doing it anyway.

Moish Peltz [00:53:47]:
In terms of regulation or is there anything else from your perspective do you think should be spoken more about in terms of a wish list for regulation impacting crypto? I know especially from like the, the RIA and like legal adjacent space, there’s probably not a lot of, as far as I know, like spoken about in that context. I mean, one of the things that I especially, like, I want 401k to have like the bitcoin fund. And like those are things that are kind of in this kind of gray off limit zone right now. Is there anything else on that list that you would want to see that the regulators or that industry talks about in terms of regulation that should happen?

Matt McClintock [00:54:24]:
Yeah, I think there are a couple that come to mind. It’s a great question. I would like to see the ability to have bitcoin or crypto natively in a tax deferred account without having to go the route of like self directed.

Moish Peltz [00:54:41]:
Yeah, self directed with an LLC that takes cash and puts it into.

Matt McClintock [00:54:45]:
I’ve had that since 2018. And it’s, it’s a, it’s fine. It’s a hassle, but it’s fine. I’d like to see that more natural in this, you know, and more readily available for people. And the other one that really is a hot button issue, which you kind of alluded to in the lending space. I want to see very clear legislation come out of Congress with very clear rulemaking by treasury that doesn’t just open the doors to banking for people who operate, who operate with crypto. But I’d like to see strong penalties against banks that debank bitcoiners and people in crypto. It’s like, I would, I would love to see that flip because, you know, this is the whole choke point 2.0 type of thing.

Matt McClintock [00:55:30]:
We saw it. You know, I, I try to be about as agnostic politically as possible, but we saw this during the Obama administration during choke point 1.0, when regulators went after ammunition, firearms companies, porn companies, other companies like that, that were perfectly legal but just deemed to be unsavory by the administration at the time. Then we saw during the Biden administration the resurgence of choke point 2.0, primarily focused around gambling, you know, online gaming and crypto. And in both cases that seemed like profound overreach and it was, you know, outside the bounds of legislation. They got, you know, Obama’s administration got their hand slapped on choke 1.0 and then Biden resurrected it. And I’m not a Trump fan, it’s like, that’s not me. But at least the, the executive order that effectively prohibits, in a way, this idea of choke point 2.0. That’s a step in the right direction.

Matt McClintock [00:56:35]:
But executive orders are only as resilient as we know as whoever’s sitting in the White House. And so unless and until Congress enacts meaningful legislation and treasury enacts meaningful regulations in support of the enforcement of that legislation that will financially penalize banks that otherwise debank perfectly legitimate law abiding citizens who simply are acting in the crypto space. That would be the biggest regulatory shift I could imagine. And then now all the banks jump in and say, oh, wait a second, we want a piece of this crypto action. Well, now you’re going to get reasonable lending rates and then we’re going to see a lot more velocity, I think, on the movement towards what Kyle was asking, which is saying, okay, well what else can we be thinking about from a crypto regulation perspective? Maybe we do start allowing transactions on the blockchain with tokenized assets with de minimis, with reasonable de minimis exceptions from reporting perspective, that kind of stuff.

Moish Peltz [00:57:41]:
Yeah, the other point that ties to what you were saying before, I think that should fit in with that. And you’re seeing it now with the new proposed stablecoin bill, which I think was released earlier this morning. Is the. Is the creditor protections and making clear that, like, if you’re doing a stablecoin, you can’t be Celsius, because those are two different things. Right.

Kyle Lawrence [00:57:59]:
Well, one last question. I want to be mindful of your time, Matt, and thank you so much just for all the insight. You know, Moish and I are really excited to have you on. You mentioned you’re an avid reader, as am I. And one of the books that I’ve read, I mean, it was years ago, it’s called Sacred Economics by Charles Eisenstein. But it’s something that I think. Do you have it right there? No way.

Matt McClintock [00:58:17]:
No, I don’t. I’m gonna write it down.

Kyle Lawrence [00:58:18]:
Yeah, it was.

Moish Peltz [00:58:20]:
It’s.

Kyle Lawrence [00:58:20]:
I was going to be amazed. It’s a great book about, you know, what does value come from? Where do we derive, you know, what do we want? You know, is. Is it money? Is it things? Is it tangible goods as barters, all that kind of stuff. And little did I know how important that would be as I began my crypto journey. So for our viewers and listeners out there who are not necessarily keen to these things, what would be the starting point for them? What should they read first?

Matt McClintock [00:58:46]:
Oh, geez.

Kyle Lawrence [00:58:48]:
Put you on the spot.

Matt McClintock [00:58:49]:
Yeah. I would have them start with Epictetus and then proceed on to Letters from a Stoic by Seneca. Okay. And then. Then Marcus Aurelius and spend some time with that and starting to really zoom out. Take. Take assets out of the equation for a second and just zoom out. What.

Matt McClintock [00:59:10]:
What matters. Read the Dao de, read the Dao de Ching. It’s like, just zoom out and realize that this. This journey that we’re on is a lifespan. It is a lifespan. It’s not a moment in time. And a lot of what I see in the crypto space is just like, chase the money, chase the money, number, go up, all that kind of stuff. And that’s what got a lot of people into bitcoin as it rallied.

Matt McClintock [00:59:37]:
And I think people are still aping into bitcoin that way. But then the longer you’re in this space, at least for my journey and the journey that I’ve seen through some clients, is when you overlay a deeper philosophical perspective. It’s like you say, wait a second, everything slows down, and you. You’re less concerned about the spot price at any given time. I still check the spot price multiple times a day. I mean, I’m sorry, you know, it’s an occupational hazard. Old habits die hard, you know, it’s like, is it, is it above 3,000 today? It’s like, oh, yeah. So.

Matt McClintock [01:00:08]:
Because it’s like I’ve been around that long, but it’s like we’re best friends. So I would start, I would start with that and then I would also. I mean, I’m a big fan of the sovereign individual. And whether it is good reading or not, some of us argue about this internally within Bespoke group. I mean my, my head of, my head of geopolitical macro analysis and my CIO hate this book. I love this book. And it is the fourth turning. And the, you know, this, this idea, whether it’s.

Matt McClintock [01:00:42]:
They, they can’t. My guys kind of hang up on the fact that William Howe and Neil Strauss just, they got so many facts wrong. It’s like, okay, okay, zoom out. You know, zoom out. Do the philosophical reading. What is fundamentally wrong about this idea that generations operating together create a cocktail that, that generates a tone of an age? And it’s like, no, history doesn’t repeat, but maybe sometimes it has an echo, maybe sometimes it has a rhyme. And again, this idea that if we realize that our lives are probably 70, 80, maybe 90 years or longer as, as we progress, the returns that we chase quarter to quarter, kind of immaterial. And so zoom out.

Matt McClintock [01:01:23]:
And the journey that I would have people explore is, is a journey of meaning. You know, what, what is it about? You know what if you’re, you’re building this great wealth? Why? What’s it for? What’s it for? It’s like there’s probably not a wrong answer to the question, but you have to at least sit with a question. Are you driven by it? And that’s all you know how to do? Great, okay, why is that? And then are you going to leave anything behind? The answer is probably, yeah. Okay, then to whom are you going to leave that? What do you want them to know about you and what drove you to build this wealth? And then what do you want them to think about as they learn how to become stewards of this wealth that is found money to them? You know, if you’re going to create a windfall, which is what most of my clients have done, if you’re going to create a windfall, what goes into that part of that is, yes, economically enriching the lives of the people that you care about, your children, grandchildren, whatever. But is it possible that part of the inheritance that you’ll also leave behind is a deeper sense of meaning, A deeper sense of their humanity, a thrive, this desire to really Flourish as a well rounded human and maybe part of the inheritance is a better world for your children and your grandchildren to grow up in. And then that might manifest in some impact oriented investing that certainly should, should manifest in some intelligent philanthropy and really active thinking about philanthropy, not just a testamentary CLAT to wipe out your estate tax when you die. That’s fine, but, but what about now? It’s like what, you know, I’m working on a charitable remainder trust model for some clients right now. They happen to live in the east coast in a high income tax jurisdiction, zero basis Bitcoin.

Matt McClintock [01:03:25]:
And so that’s the vast majority of their wealth. They’re deeply, deeply, authentically philanthropic. But they’ve been just donating Bitcoin to a donor advised fund that we’ve helped manage for them. And as you guys know, then when you donate property to a donor advised fund, you can only deduct up to 30% of your AGI against that property deduction. But if you donate cash, then you can deduct up to 60% of your AGI. So part of what we’re recommending to them and part of what I’m going to be modeling the rest of this day and tomorrow is various forms of charitable remainder trusts, annuity trusts, unit trusts, to then make a contribution of Bitcoin to this charitable remainder trust. They’ve got cash needs anyway, they’ve got capital calls, they’ve got other investments they want to make. Okay, so then sell the Bitcoin through the charitable remainder trust.

Matt McClintock [01:04:15]:
Yes. You got a deduction when you funded the CRT. And then you sell the Bitcoin inside the CRT. You’re going to take back an income stream, either an annuity or a fixed percentage of the underlying value. Yeah. That’s going to be subject to income tax to you, that’s fine. But you don’t have a massive income tax recognition event. In one year you got a deduction that’s again, it’s a 30% deduction.

Matt McClintock [01:04:37]:
But now guess what you can do with the cash flow. You can take that cash flow and, and now you can augment your charitable giving with cash that’s deductible at 60% up to 60% of your AGI.

Kyle Lawrence [01:04:49]:
Oh, wow.

Matt McClintock [01:04:49]:
So you can get, you can really kind of start thinking more deeply about what your wealth means. And this gets to a certain degree. This is back to the sovereignty conversation and the friction conversation. These are high friction types of strategies. You can’t just do this by, you know, just, you have to go through a lot of steps to make this stuff happen. But when you do, the juice that you get from a tax perspective, from an asset protection perspective, from a family governance and family wealth transfer perspective, that is massive. Massive. And these are people who, when we met them, had engaged in some of the alpha chasing strategies and ended up getting, becoming forced sellers.

Matt McClintock [01:05:32]:
They were borrowing, they were borrowing fiat against their bitcoin at like 15% interest rates.

Kyle Lawrence [01:05:37]:
Yeah.

Matt McClintock [01:05:38]:
That when they, when they’d get called for collateral, they’d have to top up or then they’d be forced sellers. The forced sale causes a capital gains tax hit. Now they have capital gains tax liability. They sell bitcoin to pay the capital gains tax liability and it creates the circular effect. It’s like now it’s like, wait a second, guys, slow, you know, slow it down. Yeah, let’s start slowing it down.

Moish Peltz [01:05:56]:
I love that idea.

Matt McClintock [01:05:56]:
Think, think more, think more. Long term and so very long winded answer to your very succinct question, Kyle. But it’s like this, this notion of take in more information. Slow it down. You don’t have to make this decision right now. Slow it down. And you’ve got many, many bites at the apple. If you do this right, you don’t have to do this whole thing at once.

Kyle Lawrence [01:06:22]:
That’s great stuff, Matt. Really, thank you for just a wonderful, spirited conversation. Sorry I was a couple of minutes late, but Moish and I were really excited to have you on and you did not, you did not, not meet our expectations. This was fantastic and we hope to have you on again soon.

Matt McClintock [01:06:37]:
I’d love to be on, really. Thank you guys for the opportunity to just chat. I mean, I enjoyed meeting you guys the very first time and I’ve been thrilled for this conversation. So thank you for hosting me.

Moish Peltz [01:06:48]:
Where else can our audience, if they want to learn more about you and Bespoke, where can they find you?

Matt McClintock [01:06:53]:
Yeah, the company’s website is just Bespokegroup.IO you can find me on LinkedIn. I’m still one of the old guys knocking around on LinkedIn, just under Matt McClintock. If you, if you index Matt McClintock against Bespoke Group, you’re going to find me. I am intermittently on Twitter. I’m so old. I call it Twitter.

Kyle Lawrence [01:07:11]:
That’s what it’s called.

Moish Peltz [01:07:12]:
We do too.

Matt McClintock [01:07:13]:
Yeah, it’s like, I mean, X is X is a letter. It’s just dumb. absurd, come on.

Moish Peltz [01:07:18]:
Yeah, look, if hbo, if Max can go back to hbo. Max. I still am holding out hope that.

Matt McClintock [01:07:25]:
Yeah, Twitter for the win, man. So, yeah, I’m. I’m on Twitter episodically @McClintock, so it’s M, C, C, L, I, N, T, O, C, K, underscore M, McClintock, underscore M. Not super active there because there’s, you know, I think it’s kind of a cesspool of bad ideas generally.

Moish Peltz [01:07:43]:
It’s not the place where you slow it down, I’ll say that.

Matt McClintock [01:07:45]:
No, it’s not. And it’s. And it’s. It’s like, guys, it’s like there’s. Again, there’s no room for nuance.

Kyle Lawrence [01:07:50]:
Yeah.

Matt McClintock [01:07:50]:
There’s no room for meaningful conversation. But I’m. I’m there every once in a while when people want to kind of dig in a little bit deeper. So I’ve got a couple of pieces I’ll be dropping pretty soon. I also have a substack, so I’m told my team has set one up for me. But I don’t know. It’s like, I guess that’s what the cool kids are doing these days. I don’t know.

Matt McClintock [01:08:08]:
Yeah, so it’s like, yeah, fine. But I’ll be dropping some content fairly soon, so people can kind of stay tuned to that. We also do a quarterly newsletter through our company, so people want to update our. Our.

Moish Peltz [01:08:19]:
Our show notes to include the content. So please send us a link and.

Matt McClintock [01:08:22]:
Yeah, for sure.

Moish Peltz [01:08:22]:
Thank you so much for coming on and for the meaningful conversation.

Matt McClintock [01:08:25]:
Thanks, guys. Really appreciate it.

Kyle Lawrence [01:08:27]:
Thanks, Matt.

Kyle Lawrence [01:08:32]:
Well, that was our conversation with Matt McClintock from the Bespoke Group. And in watching it again, Moish, I’m just reminded just how great of a speaker he is and how insightful he was. Really special. Thank you to Matt. His time is very important, and. And frankly, I can’t wait to have him on again in six months when the world is upside down again and.

Kyle Lawrence [01:08:50]:
Bitcoin is doing God knows what.

Moish Peltz [01:08:54]:
I thought you were gonna say you can’t wait to hire him when you have 100 million.

Kyle Lawrence [01:08:56]:
That goes without saying, but, yeah, let’s go. What do you think of Matt’s just.

Kyle Lawrence [01:09:05]:
You know, what he brings to the.

Kyle Lawrence [01:09:06]:
Table is unique because we approach everything from a legal perspective, but to hear his thoughts is not. I don’t think we’ve really had a guest on with his sort of specific background before.

Moish Peltz [01:09:17]:
Yeah, it’s very unique to be a asset manager, financial planner for people in this space. And really, I mean, you talk to a lot of financial advisors who don’t really deal with crypto, and they’re very hesitant and they say, yeah, you can put 1, 2, 3, 5% into crypto, but anything more than that’s kind of crazy. And to hear, to hear Matt’s take on that, obviously is a breath of fresh air. So. And it’s not like he’s just saying, hey, yolo, everyone should be crypto. I think he’s taking a very measured, personalized approach, which I think is exactly.

Kyle Lawrence [01:09:48]:
What it’s the kind of maturity and measured approach that the space needs. Because you’re right there, there, there’s still a lot of, you know, YOLO out there. Even in. When things are not as, you know, as firing as they are in bull markets, even during bear markets, it’s important to have that. That type of measured approach. It’s a perfect word to use to describe him. So very special thank you to Matt. Thank you for again for your time and hopefully we can see him again.

Kyle Lawrence [01:10:13]:
That’s it for another episode of Block and Order. A very special thank you to producer Shaun. Without him, the show would not be possible. Don’t forget to like and subscribe to all our socials. Links are down below in the show notes. Don’t forget that Block and Order is intended to be informational and for entertainment purposes only. We do not dispense legal advice here. Please consult your own attorney or advisor if you going to take the plunge.

Kyle Lawrence [01:10:33]:
Any assets that we may discuss on this show is not an indication of an endorsement of any type of those assets, even if we own them. So on behalf of Moish Peltz, I’m Kyle Lawrence. Take care, everybody.

Moish Peltz [01:10:44]:
See you next time.

Please note that this show is meant for informational and entertainment purposes only. This is not legal advice. Please hire your own attorney. The hosts or guests appearing on Block and Order may hold cryptocurrency, NFTs, or other digital assets from companies mentioned during our programming. This possession of digital assets does not constitute a professional endorsement, legal advice, or financial advice. Listeners are encouraged to consult with their own legal and financial advisors for personalized guidance in the blockchain and cryptocurrency space.