Matt McClintock (Founder & CEO of Bespoke Group) returns to the show alongside Alla Futterman (Associate Client Relationship Manager & Head of Philanthropy Operations) fresh off his main-stage talk at BTC Prague 2026 titled “Using Bitcoin to Change the World.”
In this deep dive, we explore how ultra-high-net-worth Bitcoiners and their families are moving beyond simple HODLing to become active stewards — deploying Bitcoin through sophisticated, values-aligned philanthropy to solve real problems (landmine clearance, human trafficking recovery, wildlife protection, cultural preservation, and more).
We unpack Bespoke Group’s “Wealth Operating System,” sovereign estate planning for bearer assets, tax-efficient giving structures, next-gen involvement, the mindset shift from ownership to “this wealth has been entrusted to me,” and practical advice for Bitcoiners at every level who want their capital to outlive them and actually improve the world.
If you’ve ever wondered how to turn Bitcoin conviction into lasting generational impact while keeping sovereignty and privacy intact, this is the episode.
Timestamps:
(00:00) – Introduction to Bitcoin Philanthropy
(06:38) – Tax-Efficient Philanthropy Strategies
(13:07) – Charitable Structures for Bitcoin
(20:22) – Mindset Shifts in Bitcoin Philanthropy
(27:22) – Wealth Stewardship and Bitcoin
(32:13) – Challenges in Bitcoin Philanthropy
(37:23) – Engaging the Next Generation in Philanthropy
(39:49) – Practical Tips for Everyday Bitcoiners
Links:
- Bespoke Group → https://bespokegroup.io/
- Matt’s article: “How Bitcoin Wealth is Changing the World” (June 2026)
- Alla’s article: “Philanthropy as Wealth in Motion”
- https://x.com/mcclintock_m
Stephan Livera links:
- Follow me on X: @stephanlivera
- Subscribe to the podcast
- Subscribe to Substack
Transcript:
Stephan (00:00.598)
Hi everyone and welcome back to Stephan Livera podcast. Today we’re gonna be talking about using Bitcoin to change the world.
For ultra high net worth philanthropy and stewardship. And rejoining me on the show today is Matt McClintock. He is founder and CEO of Bespoke Group. And also joining us today is Alla Futterman, also from Bespoke Group, focusing on philanthropy operations. And so yeah, welcome back to the show, Matt. it was great to catch up with you in Prague, just briefly. and Alla, great to meet you in Prague. let’s just start with you know some of these, you know, g I know obviously you gave your talk.
at the conference, Matt. In fact I was the one to intro you, but just for listeners who maybe haven’t caught that, give us a you know a bit of an overview there and what are some mindset shifts you see in these ultra high net worth Bitcoin families.
Matt McClintock (00:48.876)
Yeah, I mean first thanks for having me back. it’s it’s always great to chat with you, Stephan. So thank you for that. yeah, the talk was was really kind of a a different angle, I think, from what we see a lot in the Bitcoin space. and it really is a extension of a lot of the work that we get to do with the types of clients that we serve. I was challenged by the Bitcoin prog group to come up with a topic on using Bitcoin. The idea that was the theme, of course, of the conference. And
W in talking with Alla about this and with the rest of our team, we thought, you know, this is a really interesting opportunity for us to talk about what we’re doing in the philanthropy space for a lot of our clients. you know, the overwhelming majority of our clients have been profoundly enriched by Bitcoin. They’ve been in it for a long time. They’ve been in they’ve been in it deep. they were either early miners back when you could do that with a laptop, or in one case, there was literally a woman who mortgaged her home.
Alla (01:20.161)
Yeah.
Matt McClintock (01:46.454)
And bought Bitcoin with that back in 2012 or something like that. others were just early adopters because they were technology, they were in the technology space and they saw what Bitcoin could do that was so different. and along the way, they just they achieved a level of wealth that surpassed their desire for consumption. And we have had the opportunity. I mean, some of some of it has been driven by tax opportunities, tax.
Saving opportunities for sure. But but really more than that, it’s the sense of stewardship, the sense of responsibility, the sense of my wealth doesn’t just begin and end with me, but maybe there’s something else I can do that will make this world a better place. And I was able to kind of tell some of the stories about the work that our clients are doing, not just in the United States, but around the world, using Bitcoin and the wealth that they achieved with Bitcoin.
Alla (02:34.376)
Yeah.
Matt McClintock (02:43.201)
To change the world in tangible, dramatic, physical ways. You know, we talk a lot about change the money, change the world. and I think very often the conversation around Bitcoin is great, we’re changing the money, change the money, change the money, change the money. And that’s great. But that second piece, change the world, that was the the thrust of the talk and how people are changing the world with Bitcoin.
Stephan (03:11.776)
Yeah, Alla, I know you also work closely you know with with the team on this and with clients on this. What are some mindset shifts you see people make when they get into this mindset of thinking about philanthropy?
Alla (03:25.824)
Yeah, and great to be on the show. Thanks for having us. I think there’s a couple of things. I think primarily when you know Bitcoin is what, 17 years old. It’s I heard this mentioned at the conference that it’s now a teenager and I like thinking about it that way. because it’s all grown up and even some of the conversations that we were hearing at the conference are
somewhat more sophisticated. We’ve kind of grown up with the space and moved on to think about Bitcoin beyond just the Bitcoiner ecosystem, but to really think about it holistically and on a macro level, how it can impact every aspect of our lives. And I think some of the things that you know maybe hold us back is we’ve still kind of kept Bitcoin in its
Own speculative corner. We haven’t really integrated it with the full impact and legacy thinking that we give other asset classes. And I think Bitcoin belongs in the bigger picture with the same stewardship lens and the same, you know, things that you consider on your balance sheet. And so I think it’s that conceptual shift of bringing it in with.
the other more traditional asset classes and not kind of keeping it in the corner all by itself.
Stephan (04:53.984)
So Alla, can we can we just tap into that a little bit? Because what what would you say is like typical for p j wealth generated in other I mean, is it like land billionaires or, you know, just typical small to medium enterprise, you know, high net all very high net worth people? Like what was different about Bitcoin ultra high net worth people contrasted? Is it just that you know it took some time for Bitcoin to become, you know, to mature to the stage that there were a a decent cohort of
Alla (04:57.44)
Sure.
Alla (05:27.474)
Yeah, I think it’s a couple of things. I think one, there’s this almost feeling of barrier to entry, right? I think some people still believe that they have to liquidate their tokens right away in order to have impact or put their Bitcoin to use. And I I don’t think there’s that mental shift of finding
Creative solutions as bespoke has done for creative sh, you know, implementation, infrastructure, solutions for a client to kind of think outside the box and use that Bitcoin. So I think that’s a big one. I think also Bitcoiners tend to be very philanthropically inclined. It’s just the nature of the belief system that goes along with it.
but I do think that there’s still not complete clarity around what their options might be. There’s a lot of conversations, you know, previous to bespoke, I was with Digital Asset Hedge Fund, and there’s a lot of conversations around tax efficiency for you know, managing your assets while they grow, but there’s not a lot of conversations about tax efficiency when you’re giving your Bitcoin. So that disconnect I think is still there.
Stephan (06:43.446)
Interesting. So
Again, you guys are the experts, I’m just the the layman here, but I I the first things that came to my mind when you’re thinking about like ta obviously there’s a there’s many, many rabbit holes we could go down, but kind of a typical one would be tax loss harvesting, right? Like if Bitcoin is down, people might sell the high cost basis coins to rebuy lower, etc. And get a tax saving that they can use elsewhere. And then when it comes to like the philanthropic side of things, I guess it’s people are looking at, you know, five one C three because it’s like a tax free, you know, they’re getting something there or maybe they’re borrowing against coins.
Maybe you guys can spell that out a little bit for us. Like, what does that look like? A tax-efficient, you know, form of philanthropy?
Matt McClintock (07:23.191)
Sure, yeah. mean there’s there’s a couple that they’re kind of low hanging fruit here. one that ever that’s available to everybody is what’s called a donor advised fund. A donor advised fund is a 501c3 qualifying charitable fund within a charitable structure. So these are probably the most common form of charitable recipients. Now historically and and really even to this day, the vast majority of donor advised funds, even if they tell you that they accept Bitcoin.
They don’t actually they won’t actually hold the Bitcoin. They will go through some type of liquidation channel. And so you, Stephan, could could donate your Bitcoin to a donor advised fund, but then most donor advised funds will then liquidate that to fiat upon receipt because they don’t understand Bitcoin. They don’t have they don’t understand the technology. They don’t understand how Bitcoin behaves differently as an asset. And so and their investment committees just won’t hold the rate the the fluctuation risk.
the v the volatility risk that the bitcoin has. but people can simply contribute Bitcoin to a donor advised fund. And we’ve been very successful with a growing number of donor advised fund sponsors here in the United States to not only be able to hold receive Bitcoin, but be able to hold Bitcoin long within the donor advised fund structure. So for people who have the Bitcoiner ethos and they’re not just contributing low basis coins
For the purpose of generating a tax deduction, but they say, I want to also share with the charity the values of Bitcoin, the low time preference of Bitcoin, the fixing the money side of Bitcoin. we can help them structure a special type of donor advised fund within an existing qualified charitable organization so that you can donate your five Bitcoins, 10 Bitcoins, 20 Bitcoins, whatever you want to b donate, and the donor advised fund can continue to hold.
those those assets long subject to the investment policy. But that’s that’s like the lowest hanging fruit when it comes to just making a charitable contribution of Bitcoin. One of the things I think is a lot more interesting than that is when people have especially and this is especially useful with low basis Bitcoin. People who have had Bitcoin for a long time, they’ve got a lot of unrealized appreciation that if they were to sell it, they would have a significant capital gains tax liability.
Matt McClintock (09:46.808)
There is a special type of charitable trust called a charitable remainder trust, which would allow me as the Bitcoiner to contribute Bitcoin to this charitable trust. I receive a tax deduction in the year in which I contribute to Bitcoin. Maybe I put 25 Bitcoins in this charitable remainder trust. And I designate some charity, maybe a donor-advised fund, maybe my own family foundation, maybe some other type of qualifying charity.
as as to receive that the the remainder of that trust sometime in the future. But depending on my age when I set up this trust, I can then retain an a an annuity off of this trust for a period of, in my case, up to 20 years for some people, their lifetimes. And so then when the Bitcoin is sold inside that charitable remainder trust, either all at once or incrementally, the event of the sale is non-taxable.
Because it is it’s a sale that takes place in a qualifying charitable trust. But then I receive an annuity stream from that trust for the duration of the trust. Twenty years, the remainder of my lifetime, maybe my life plus my wife’s life. And then at the end of that, it that what’s left in the trust goes to charity. Meanwhile, I got a charitable deduction in the year I set this thing up. Now it’s it’s it’s not an entirely tax exempt.
event because every time I take a distribution from that trust, I’m going to pay incremental capital gains tax on only the amount I I receive. So it’s really kind of a stretch of the tax recognition. But the idea is this charitable remainder trust can hold Bitcoin, it can reinvest in Bitcoin, it can start companies for me, it can invest in traditional investments for me within this charitable structure.
And every time something is sold, the sale the sale event is non-taxable. And I only receive I only have a tax recognition event when I take distributions. So if you kind of play this through in your mind, you’re ultra high net worth Bitcoiner, you you want to kind of harvest some gains that you’ve got. I mean, even at sixty-five thousand dollars or whatever today’s spot price is, you may still have a significant amount of of unrealized gain.
Matt McClintock (12:10.977)
Contribute the Bitcoin to something like a charitable remainder trust, get a tax deduction now for that, then designate your donor-advised fund to be the charitable recipient down the road. Meanwhile, the liquidation events that take place inside the trust take place in a much more tax-efficient framework. And so this is a way that you can kind of combine some of the traditional estate planning strategies that we’ve used with conventional assets for a generation.
We we can do the same thing with Bitcoin and we can hold that Bitcoin long within these structures, subject to what the Bitcoiner wants to do and when the Bitcoiner wants to make the exit points. So it’s kind of a it’s a way of of upgrading our thinking around treating Bitcoin as this really powerful asset for long term value accretion over time. Sometimes within cher within tax advantage structures, if
That is relevant for the family.
Stephan (13:10.207)
Interesting.
So let me just r summarize again, just make sure I’ve got it and probably for the listeners to make sure they’re following. Instead of, let’s say, selling your Bitcoin, paying capital gains on it, and then donating, the idea is, hey, if we restructure this into, as you mentioned, this like a donor advised fund or this other method, you could contribute coins in, take a tax deduction now and only pay and kind of stretch out, as you mentioned, this concept of not kind of taking
all the hit at once and you’re kind of stretching it out over the next whatever twenty years. And so I guess it’s kind of like there’s kind of double whammy benefits there, right? Because you’re instead of taking you’re just not taking the hit all at once, which I guess the naive approach would do that, right?
Matt McClintock (13:51.19)
It is.
Matt McClintock (13:56.972)
Yeah, for sure. And that’s and that’s really what we’re trying to do is bring an upgraded level of of thinking about wealth to the affluent Bitcoiner space because honestly normies with significantly appreciated assets have been doing this stuff forever. And so you you really nailed it, Stephan, when you said, you know, you you’ve got really at the at the end of the day, the key trade off is do I if I want to make a charitable contribution, do I sell this appreciated asset first?
Alla (13:59.305)
Mm.
Matt McClintock (14:25.525)
recognize the capital gains tax at that point and then donate the after tax fiat to receive to t to a charity. I mean that’s a very inefficient way to make a charitable contribution.
Stephan (14:36.171)
Right. Which could be like what, just as a off the top of your head number, that could be like twenty or thirty percent that you pay in long term capital gains tax for an American, plus some plus some state capital gains tax depending on where you are and this, that and the other.
Matt McClintock (14:44.521)
Easily. Easily.
Yeah, you’re paying you’re paying almost twenty-five percent long-term rates for federal, cause it’s twenty percent plus three point eight. So you’re playing twenty-four percent federal, and then whatever state you happen to be in, if you happen to be in California, it’s thirteen point three. If you happen to be in New York, it’s something comparable. So it could be upwards of, you know, thirty-five, forty percent, which then means you you’ve got this massive tax liability. And then you’re turning around and donating the net fiat.
just to try to wipe out some of this tax liability you just recognized, you can avoid the tax liability altogether by and and level up your giving by say by finding or structuring a donor advised fund, first of all, just to receive the Bitcoin. If what you want to do is make an outright gift. if if you want to make a deferred gift and you want to actually receive some economic benefit yourself in a tax optimized way, you can use this charitable remainder trust.
Set up the charitable remainder trust that designates your donor advised fund on the back end to receive the remainder at the end. But when you take the you you contribute your Bitcoin to the trust, take a deduction now. Then when you later sell the Bitcoin inside this trust, the sale event is tax exempt. And then as you’re taking distributions each year, your distribution carries with it a portion of the capital gains tax. So the charitable remainder trust.
Is a tax deferral, it stretches out the recognition of of gain. A donor advised fund is a single year lump sum contribution with no returning economic benefit back to you. And again, the worst case scenario is you just sell the Bitcoin, pay the tax, and then make an offsetting gift of cash.
Stephan (16:31.167)
Yeah, okay. So yeah, sorry, I I was a slightly off when I said donor advise fund, because what you’re talking about is charitable remainder trust. Got it. Okay. And so let’s I guess also just to clarify, because are we only in the American context here or is is this concept of a charitable remainder trust applicable outside America also?
Matt McClintock (16:48.001)
There are analogs in other jurisdictions, but this th this specific strategy is relevant mostly for US bet US taxpayers, regardless of where they are in the world. And one of the things I know you and I have talked about previously is you know, if if you are a United States citizen, but you live in Dubai, you live in El Salvador, you live anywhere else in the world, if you’re still a US citizen, you’re still subject to worldwide tax on your worldwide income, or US tax on your worldwide income. And when you die
You’re subject to US estate tax on your worldwide assets. Doesn’t matter if you’ve not lived in the United States for fifty years, if you’re still a citizen, that tax exposure follows you. The same thing is true if you are a green card holder. And the same thing is true if you ever were a green card holder. If you you know, if you came to the United States after going to London School of Economics or wherever you happen to be, you were maybe you’re from Sri Lanka originally, and you
at some point received a green card and then you left the United States, didn’t renew your green card. Well, guess what? Your tax attachment follows you wherever you are. so the the universe of people that are US taxpayers is much bigger than a lot of people realize. But even if you’re not a US taxpayer, if you happen to be a you know resident less citizen of the UK, France, Germany, any of any of these other taxing jurisdictions,
There are analogues to this that would be comparable.
Stephan (18:19.393)
Yeah, it’s a good it’s a fair point about
not only American citizenship, but American taxpayer, which is a broader set and a broader category. And maybe some listeners might even be aware there was kind of a famous case maybe five or maybe ten years ago. Boris Johnson, once the UK Prime Minister, I think he was I think he’s maybe he was born in America, but he had lived he had grown up in the UK and when he sold a property or something, I think the RS went after him for that because he was technically an American citizen and I I I don’t know exactly what how that story you know, the end of that story, but
It can happen to people where maybe unknowingly, or maybe they knew, but they thought they would get away with it, but no, they’re, you know? Yeah.
Matt McClintock (18:57.483)
Well, y and honestly, Stephan, I mean you’re you’re kind of you’re kind of nailing something interesting here because it’s possible to be a taxpayer of one jurisdiction and not even realize it. I I realize I I learned about a month ago, I learned that I’m a Canadian citizen. I was never born in Can I was never born in Canada, but I had a great grandmother born in Canada and Canada had pretty draconian laws at the time. If my great grandmother
She was born in Quebec. She married a dude who lived in the United States. And just that act severed her citizenship at that time. But then Canada recently opened up its citizenship laws such that if you happen to be in this category, you are automatically a Canadian citizen. You just have to go and substantiate it. So it turns out me, my kids, my sister.
My whole family are also citizens of Canada, had no idea.
Stephan (19:57.954)
Yeah, there’s all these like weird rules with this sort of thing. I know I know you guys in America have this thing called the substantial presence test also. That’s like another way that people can kind of if they spend enough time in America, now you’re part of the American tax, you know, payer situation and you know, this kind of thing. So what is it? Thirty nine trillion in debt, the US government? So, you know, yeah. so Alla, let’s go to you,
Matt McClintock (20:04.449)
Mm-hmm. Yeah.
Matt McClintock (20:10.989)
Right. Stephan, we need the money, man. I mean we we need we need the money. So it’s like we’re gonna get every every chance we can.
Stephan (20:24.801)
We we were touching a little bit, I mean, maybe we we kind of shifted off the topic a little bit. I wanted to get on onto this idea of like just any mindset shifts that happen when people actually start doing this, right? Because obviously you’re working with the families who are doing this. What are some mindset shifts you see them make once they actually kind of realize, wait, I can actually I can do this philanthropy thing now?
Alla (20:46.3)
Yeah, I just you know, maybe bouncing off of what Matt just described with the CRTs and the DAFs, I think it might be helpful for your audience to hear some examples of how those were actually used, especially if you don’t come from necessarily that world. and you know obviously we’re all familiar with the wild volatility swings of Bitcoin. we had a client who
Stephan (20:59.597)
Що
Alla (21:15.442)
approached us and they had come into bitcoin through the tech space initially and they were working on a really huge project that they were very passionate about. the family made a $300 million dollar endowment I believe 60% of which was in Bitcoin and they were able to
you know, manage that volatility by holding within these structures that Matt described. So if you think about you know 60% in bulk in Bitcoin on 300 million, what kind of implication that could have with a 60% correction, that’s huge. you know, just some other examples, we had you know, a family that came to us and they really didn’t know how to
manifest their vision. They were really you know interested in vulnerable helping vulnerable women, women of color, and they they basically landed on an initiative around human trafficking. But they really didn’t have this whole model planned out. And so thinking through these creative structures on how we can take somebody’s passion, take somebody’s vision and what they really care about.
when they are holding significant Bitcoin wealth, and then translate them into some of these structures are some of the creative things that I think, again, going back to your question, Stephan, is you know, how is somebody thinking differently, or what are some of the challenges around it? Is really stepping outside and taking a bird’s eye view to say, okay.
what is possible and how do I not restrict myself to only thinking about you know the the structures that I know about or that are the traditional structures. So really kind of zooming out. I think that’s a really big one.
Matt McClintock (23:24.023)
Yeah. Stephani, I let I let me just jump in real quick too, because that there’s something that Alla is pulling on here that that is an echo of one of the questions that you asked earlier. And that is what makes Bitcoin different maybe than some of the other assets, like if you if you made wealth and land or if you’ve been a serial entrepreneur. I think my take on this, I’ve I’ve been working with clients in this space for almost nine years now. in the case of Bitcoin.
as opposed to other assets, if you’re a serial entrepreneur, you are working day to day in the business. Your life is consumed by that business. If you’re working in the land industry, or in commercial real estate or whatever, your life is entirely consumed by by something that is known. This is a this is a conventional industry. There are clearly defined pathways to significant economic success. In the case of Bitcoin.
The economic success just kind of happened along the way. Yes, I mean some of our clients were serial entrepreneurs building in the Bitcoin space, but most of our clients receive or kind of develop this outsized wealth almost passively by holding this asset because they have a low time preference. They they understand that they’re going to make their wealth in other ways. They were not going to make their wealth in Bitcoin.
They’re gonna make their wealth in the practice of medicine, or they’re gonna make their wealth in other things. And the Bitcoin wealth just kind of happened, and it happened in a very outsized way. It 10x on them, it 20x’d on them, or whatever it did. And so now they they say, Well, this isn’t really what I this is not the reason I got into Bitcoin. I got into Bitcoin because I have a low time preference. This is a better form of money. This is a sense of responsibility manifest in code. This is stewardship in code.
We have a dec we have a decaying supply rate. We have fixed and finite supply. We have a superior form of money in that that form of money is an expression of responsibility and stewardship. And now, because of what it has done for me in my life with my wealth, I’m not going to consume that. I don’t want to set up my kids to where they’re going to consume all of that. My kids don’t need yachts. My kids don’t need all this kind of stuff. What does stewardship then look like in the next phase?
Matt McClintock (25:44.054)
Stewardship, first of all, was understanding Bitcoin as a superior form of money and why it’s a superior form of money. And now it’s money that I will never consume in my lifetime. How can I then share what Bitcoin has done for me with the rest of the world that doesn’t understand Bitcoin? And so for us, what I’ve seen is that the clients who are most active in philanthropy in this space are clients who were were frankly that were shocked.
By the amount of wealth that they built over the period of 17 years. That just was not, it was just not on the bingo card for them that that was that it was gonna do this, and yet it did. And so now they say, you know, I could I could give my family all the economic stuff in the world, but that’s fiat thinking. How can I then apply my stewardship mindset, apply my low-time preference mindset, and consider that maybe part of an inheritance I can leave behind?
Isn’t just measured in economic terms, but it’s actually making the world a better place in very physical, very tangible, very real ways for people who don’t otherwise have the same type of thing I have. And this was the story in Prague. This was the story about landmine recovery. This is the story about human trafficking. This is the story about preserving arts and antiquities and religious ruins around the world. It’s because we have clients who say,
as a result of what Bitcoin has done for me economically, and as a result of the fact that I understood Bitcoin as a superior form of stewardship manifest in code, how do I then live that forward? And that that becomes part of the philanthropy conversation with clients.
Stephan (27:27.224)
Fantastic. And on a related note, is there like so we talked about the clients who built who built wealth, you know, in Bitcoin, even though they had wealth from other means, let’s say. I’m also curious, what did Bitcoin change anything in the way they actually executed the philanthropy compared to fiat wealth? Like was there a you know i yeah, was there something different about the way it was done? maybe you guys can elaborate on that.
Matt McClintock (27:47.798)
It had to.
Matt McClintock (27:53.304)
Yeah, I mean it it had to because charitable planning requires structure and if you if you want to get tax benefits, you have to use legally recognized, like fiat world, normy world recognized strategies. And so for Bitcoiners who kind of come from this this mindset of unilateral key control, self-sovereignty, it’s like this kind of breaks their brain a little bit to think that
I I want to use this Bitcoin wealth, but I want to use it in ways that actually I can benefit from economically in ways that are legally recognized. We have to help them think through how do you structure key control? How do you get legally recognized outcomes? I mean, if you just want to give your Bitcoin away, give your Bitcoin away. That’s fine. But if you want the legally recognized benefits of doing that, which you can do through proper structure, that then means you have to adopt.
fiat recognized or normie world recognized structures and custodial control in order to get those outcomes. And so the conversation that we have with clients along this road is okay, this the heuristic that you have in unilateral key control breaks down under the weight of these objectives that you want that you say are important to you. So you you you can’t really have it both ways. You can’t have unilateral key control and get these outcomes.
So it’s a matter of kind of sizing what you want to accomplish and then structuring your key controls accordingly. And this is also part of the sovereignty paradox that you and I talked about previously.
Stephan (29:22.318)
Of course. But I I presume even this is not really all or nothing, right? Like they could keep some of their coins in self custody and some of their coins in the, you know, legally recognized structure, right? So it’s kind of, you know, yeah.
Matt McClintock (29:27.799)
Totally. Absolutely. That is absolutely what they have to do. And this is this is the sovereignty paradox you and I have talked about previously. This is the white paper that I that I wrote last year. It’s like it’s not an all or nothing proposition. It cannot be an all or nothing proposition. We have to mature our thinking to realize that the transactional Bitcoin that I want to free spend freely, that absolutely unilateral key control, no friction, nobody standing in my way. If I’m talking about succession,
Protocols. Now I want to transfer my wealth to my family members who may or may not understand Bitcoin as well as I do. Then maybe I need to have something like a multi-sig type of framework with all the great multi-sig facilitators that are out there in the marketplace right now. And then when I have so much wealth in this asset that I need to be thinking about, maybe it is tax optimized structures. Maybe more than tax optimized structures, it’s a a maturing framework so that the people who ultimately receive the the wealth.
That this Bitcoin can produce for them actually has scaffolding around them so that as they grow and mature, they can start making better decisions. That requires a much more elaborate type of structure and it requires me to get to give up my unilateral control f in exchange for those legally recognized benefits. But it’s it’s absolutely it it happens on a spectrum.
Alla (30:51.902)
Well, and I I would add to that, Matt, that, you know, we talk a lot about the transfer of wealth being a process, not a single event. I think as you described, how some Bitcoiners came into their Bitcoin wealth was sort of sometimes overnight, right, when there’s a huge rally. and it’s the challenge of transferring the meaning of their wealth along with the actual asset itself. the challenge I think on the philanthropy side also is.
If you have next gen heirs who don’t understand why their family was holding Bitcoin to begin with, or they don’t understand the asset itself, they’re statistically more likely to liquidate it. So I think it’s something like three to five years. if they’re not prepared, they will if they or if they don’t understand the why, they’re very likely to just get rid of it or spend it, or you know, do what they will with it. And so
I think also crafting the very sensitive conversations and the education. I’m glad we heard a lot of that at Bitcoin Prague. There were so many conversations about educating the next generation of what it means to hold the asset. that is also, you know, the stewardship process of it it’s not just spending it or, you know, watching it go up. It’s it’s really what does it mean?
Stephan (32:19.124)
what are some typical challenges, pitfalls, failure modes that you have seen in Bitcoin philanthropy that people maybe they don’t talk about it? What are some lessons that we can learn out of that?
Matt McClintock (32:33.291)
Yeah, I think from my perspective, a lot of it i happens i either in
To your first point, selling the Bitcoin and then giving the net dollar amount after you’ve recognized the tax. I mean, that’s that’s probably failure mode number one, which is not unique to Bitcoin. And it’s people make this mistake all the time with highly appreciated stock or anything else like that. So just thinking, I need to make a deduction, I need a deduction this year. I’m just gonna give it or I’m just gonna liquidate it and then give the cash. That’s just not thinking.
that there are other options out there. Another one is
Probably just not being super thoughtful about the downstream effects of the charitable gift. And by which I mean you giving it to just some huge charitable organization because you’ve heard about them, but you don’t but you have no idea how how efficient they are with their giving or how effective they are with their with their charitable work. It’s like, well, I’m just gonna give it to such and such charitable organization because everybody’s heard about them. They may actually be terrible from an administrative perspective.
and then when they g when they give Bitcoin thinking that they’re that the recipient is gonna hold Bitcoin, not realizing that they won’t. and that I’d say probably the final thing that I see is people not understanding the fees involved in transacting with Bitcoin. I mean I I’ve seen I’ve seen fees that are as high as one and a half to two percent on the transaction that this that the middle intermediary that’s taking the Bitcoin and converting that to fiat for the charitable fund is like
Matt McClintock (34:13.835)
You you just taking a two percent haircut or a one and a half percent haircut, yeah, that you just don’t that you don’t have to have.
Stephan (34:15.938)
Getting rinsed on a bad fee, yeah.
Alla (34:21.172)
Well and I think there there’s a lot of you know, existing great organizations and and structures that will take Bitcoin charity. And I think there’s a distinction between charity and philanthropy. With charity, you’re just you know, what Matt described, you’re just giving it and passing it on and maybe don’t understand the full scope of the impact. Philanth philanthropy is really thinking through what the long term
implication will be and really being involved in the process. And I think there there should be a distinction made there too because yeah.
Stephan (34:57.802)
I see. So you see that as like more like an active process that you’re kind of actively managing you know, instead of just like a one shot gift, you’re seeing it more like a ongoing process?
Alla (35:07.52)
Well, and you I I think the other distinction is that philanthropists really care about getting at the root cause of really major issues. certainly anyone can be a philanthropist. You don’t need, you know, hundreds of millions of dollars. But I think people sometimes conflate the two with charity just being, you know, I made a donation to
Stephan (35:25.174)
A gazillion dollars, yeah. Yeah.
Alla (35:34.11)
my church and then I’ve moved on rather than I volunteered, I got involved, I joined the board, I really took part in understanding the trail of money and what the implication is for the community that I’m seeking to impact.
Matt McClintock (35:49.39)
And I I don’t I don’t really think our clients are these huge outliers. I mean, they they’ve got a lot of wealth in this space, but I do think that this is I think that this is emblematic of the broader Bitcoiner mindset. people who have been in Bitcoin for a long time, I mean, we become ideological about it. And you and I have talked about this a lot. I mean, we we get ideological about this. and because we’ve become ideological about our form of money, it then makes us, I think, become ideological about a lot of other things in our lives.
Stephan (35:50.198)
yeah.
Matt McClintock (36:16.223)
It makes us want to be more involved in how we train our kids about what is money. How does money work? Why does money work the way it’s supposed to work? What how do how does why does government exist? And where does it break down and why does it break down over and over again? And then th the charity versus philanthropy point that Alla is talking about is to my mind, that’s like the Bitcoiner step change. It’s like a f normie mindset just says, give it away and give me the tax deduction.
The Bitcoiner mindset says, wait a second, as a result of my low time preference and the way I view the world, I want to make sure that my that my charitable dollars, my charitable Bitcoin, my goes actually does what I want it to do. It’s not just to give me a deduction and then move on down the road. It’s to actually change the world. And to change the world in a meaningful way. And if I just give it away and take my hands off of it, I have no assurances that
that the recipient of this is gonna do what I want them to do with this. So therefore I attach my I attach my my energy to this and say, Okay, well now even though I don’t own it anymore, this is still a creative act of my giving and therefore I am going to steward my giving forward through these organizations.
Stephan (37:36.601)
What does good management look like? Is it like as you mentioned, Alla, is it taking a a board seat on an organization? Is it you know sort of rolling your hands up, proverbially rolling your sleeves up and getting into into it yourself as you know, into the involved in that operation? What are some of some of the things you’ve seen people do here?
Alla (37:58.463)
Yeah, I I think there are many ways that people can be impactful and it doesn’t look the same for any one situation. I think it also depends how early people are educating their children or the next generation or bringing in other family members into their philanthropy. so y you know, we’ve seen a lot of really creative things. For example, Matt talked about the donor advised fund.
sometimes a younger family member can be brought in into a sub-DAF. So there’s a family donor advice fund, and for example, an heir or child or someone could be given a small portion of those assets to craft and define their own values. What am I really passionate about? maybe it’s different from mom and dad. and to really learn through action in that sense.
Certainly there are committees and boards and ways to be more involved from an administrative side. there are giving circles or pools where people can share ideas if they’re passionate about the same sort of core issues. and those are other ways that you know maybe even fellow Bitcoiners can get together and align on their values.
so there really are is no one size fits all. There is certainly a lot out there. I think the important thing is starting as early as possible and being very transparent and candid about what wealth means to you. again, I think this is the Bitcoin ethos, right? We’re all about transparency and you know being able to to do it yourself and trust and verify yourself.
that is the only way to learn how to be the best philanthropist that you hope to be, is to just get as involved as possible yourself.
Stephan (40:03.542)
Now, let’s say for a obviously most of this conversation has been around ultra high net worth philanthropy. Let’s talk about just a an everyday regular Bitcoiner who is not an ultra high net worth person or family. Do you have any practical tips or takeaways for them on what they should think about, you know, going forward? Obviously, if we all think we’re all bullish on Bitcoin, we think it’s going to, you millions of dollars a coin or whatever. What do you have a tip or a a takeaway for them?
Matt McClintock (40:30.527)
My perspective would be that
For them to start thinking about their their wealth as something that they are entrusted with. It’s this is not really a religious thing, but just like something that I’m entrusted with instead of just something that I’m here to consume. I I think again this is part of the low prime pri low time preference mindset. and so I think it’s just a matter of realizing that hopefully you’re not just in Bitcoin because it’s going to make you wealthy in fiat denominated terms.
It’s actually changing how you see the world and it’s changing how you see your family and your family’s place in the world. and again, so w whether it’s based on some type of spiritual notion or just a philosophy that there’s something bigger than me and something bigger than my family that I want to be a part of. whether you d whether you use your Bitcoin wealth to do to use that or use your fiat wealth to do that, it’s like talking to your family about what money
means? What is money? Why why why do we have this mindset? and how then does that express itself beyond just what school we’re gonna go to or what car we’re gonna drive or what house we get to live in or or how we’re going to measure our wealth in normy fiat terms. It’s like is there something w what does fix the money, fix the world really mean? What does the fix the world side of that
equation really look like? Is it just fixing the money? Or are we actually fixing the money so that we can fix the world?
Stephan (42:11.84)
Excellent. Alla, any closing thought from yourself?
Alla (42:14.868)
Yeah, I just to add on to that, you know, every dollar has impact, it’s pointed somewhere. It’s doing something, whether you are thinking consciously about it or not. and so having the most thoughtful process around that so that you can direct every dollar to what aligns with your values is really important. And that wealth, whether it’s you know
a little bit or a lot, it should enrich every aspect of your life. and so really, you know, being being thoughtful about where do you want your money to go? How do you want every s dollar to have value in the world?
Stephan (43:00.888)
Great. Well, I think we’ll leave it there. So listeners, my guests today have been Matt McClintock and Ola Fatiman from Bespoke Group. You can find them at bespokegroup.io. and of course, listeners, if you found this interesting, make sure you share this episode. and I think we’ll leave it there. Matt and Ola, thank you for joining me today.
Alla (43:16.673)
Thank you so much.
Matt McClintock (43:16.696)
Great, thanks so much, Stephan. We’ll see you soon.