TFTC: A Bitcoin Podcast - #623: Launching Bitcoin's First Native Trust Company with Jessy Gilger

Episode Date: May 24, 2025

Marty sits down with Jessy Gilger to discuss Bitcoin retirement planning as prices approach $110K, the launch of Gannett Trust as the first Bitcoin-native trust company, and the risks of derivative products like MSTY in the current bull market. Jessy Gilger on Twitter: https://x.com/idahohodl Gannett Trust: https://www.gannetttrust.com/ STACK SATS hat: https://tftcmerch.io/ Our newsletter: https://www.tftc.io/bitcoin-brief/ TFTC Elite (Ad-free & Discord): https://www.tftc.io/#/portal/signup/ Discord: https://discord.gg/VJ2dABShBz Shoutout to our sponsors: Coinkite https://coinkite.com Unchained https://unchained.com/tftc/ Join the TFTC Movement: Main YT Channel https://www.youtube.com/c/TFTC21/videos Clips YT Channel https://www.youtube.com/channel/UCUQcW3jxfQfEUS8kqR5pJtQ Website https://tftc.io/ Newsletter tftc.io/bitcoin-brief/ Twitter https://twitter.com/tftc21 Instagram https://www.instagram.com/tftc.io/ Nostr https://primal.net/tftc Follow Marty Bent: Twitter https://twitter.com/martybent Nostr https://primal.net/martybent Newsletter https://tftc.io/martys-bent/ Podcast https://www.tftc.io/tag/podcasts/

you've had a dynamic where money's become freer than free if you talk about a fed just gone nuts all all the central banks going nuts so it's all acting like safe haven i believe that in a world where central bankers are tripping over themselves to devalue their currency bitcoin wins in the world of fiat currencies bitcoin is the victor i mean that's part of the bull case for bitcoin if you're not paying attention you probably should be we're meeting on a day when we hit new all-time highs bitcoin approached 110 000 got jesse back on the show to talk about many things not just the price ripping

a lot of good things happening on the unchained unchained side of things watching gannett trust we'll get into it yeah lots of stuff happening i think um the price likes gannett i think that's the uh the mover what uh i mean that's been a big discussion in in the space right now is uh are we heading to new all-time highs how should bitcoiners be preparing how much bitcoin do people need to retire? How are you thinking about all this as we approach what seems to be another bull cycle? Yeah, that's a common question, right? How much Bitcoin do I need to retire? I get it a lot. And there's so many other questions I want to ask, like, well,

how much money are you spending, right? Do you need to be on a yacht every week? Or are you staying humble and keeping those stats? And so the amount of Bitcoin can vary because the spending pressure you're putting against your Bitcoin stack is the biggest factor, right? And age is probably in the second. A 30-year-old retiring on Bitcoin is different than a 75-year-old retiring on Bitcoin just because of the horizon. So, stacks vary. We've got people retiring with less than seven figures of Bitcoin because they have other assets. And then we have people retiring with hundreds of Bitcoin and putting very little pressure against that portfolio. So it can go in a lot of different ways.

But it is a question of the day. As you're poking new all-time highs, everyone's like, well, how high is it going to get? And then huge question is, do we have cycles again, right? If countries are buying, what would a downside look like? And that's the big question in the retiree's mind is, how do I protect and not ride that downside all the way down if we do have another 70%, 80% drawback? Yeah. No, and I think particularly for younger people having in their mind, like the perspective of 21 million Bitcoin, 8 billion people, what's the stat? 60 million millionaires in the world.

How much, how many sats do I need to get to feel comfortable that I have a sufficient slice of the Bitcoin pie? That feel comfortable concept is just so different, right? because Bitcoin is moving and shaking and all time highs are down 30% and that's still within a bull market. Is that comfortable? Can you actually hang it up and like, all right, not going into work and I'm just going to continue to ride these adoption cycles? I don't know if it ever gets comfortable. The most comfort comes from putting as little pressure as possible against that stack right that you're not pushing these withdrawal rates of like five ten twenty percent of my bitcoin stack i'm needing to live on every because then you're requiring bitcoin to do

something for you in the short term which is just not great at right what's bitcoin price going to be in a year far less reliable than what's bitcoin price going to be in 30 years yeah yeah well i i think one of the holdups too is the ability for people to get into bitcoin and know where to put it and not only have certainty of what it will be valued at in 30 years but will they have access to it that's one thing that you guys have been very much focused i know sound advisory is separate from unchained technically but within the unchained umbrella but unchained focused on helping secure individuals and business is and trust uh bitcoin and i think today's announcement of gannett trust is a massive step in a direction towards more certainty for

long-term holdings for particular entities yes the unchained umbrella or family of companies is growing and the intention will be for sound advisory to tuck under or be merged into folded into Gannett Trust Company as it gets stood up, but it is the most robust compliance offering that is out there in the fiduciary space. And so that, in my opinion, was the one thing missing as people want to live on a Bitcoin standard. Sometimes they're in an entity or an organization or have a structure that requires a fiduciary standard. And these two coming together is solved by Gannett trust company. So it's going to be the most robust way to hold Bitcoin and have like true inheritance that can be administered through generations. So how does this work mechanically

via Gannett? Mechanically. So as the first Bitcoin native trust company, other trust companies do exist, right? But they don't build upon Bitcoin in the way that Unchained has. So Gannett in its unchained roots and using unchained technology is going to be able to use multi-sig to achieve trust company goals. And what that likely will mean is Gannett holding a key, unchained holding a key, third party holding a key. Those three keys together ensure that the Bitcoin is not being held at any one spot. We could get into the Coinbase honeypot. We actually talked about this on our last episode like hey what do you think is the uh the risk out there that the industry might disagree with so i'm launching a new segment i'm going to ask

you a prediction what what's out there that the uh the industry doesn't see eye to eye with you and i was at conferences and they're saying hey coinbase is the best that's where we put all the cut that means all the keys are at coinbase and with the news of the last week like hey there could be cracks, right? If you've got exposure to Coinbase now, you could be questioning. I was on the list. I got the email. You were affected. That's not great. It doesn't feel good knowing that information. That information could have been a lot worse. That headline could have been private keys being mismanaged. When you overlay what Gannett is going to offer to the custody space, it means that not all of the keys are going to be at any one entity.

And so that gives the Bitcoiner who understands multisig the confidence that, okay, I'm upgrading from a honeypot to a distributed key setup. But it has to be done in a fiduciary and compliant way to satisfy the institutional and big money of the world, right? Family offices, Bitcoin treasury companies, they're going to need a structure that the CIO, the CFO can point to and say, yes, that is regulated. that meets all of our expectations, all of our standards, that's going to satisfy our board, our CPAs. There's a long list of industry professionals that have fiduciary obligations to clients, and they just need certain boxes checked. And that's what the trust company brings to the table. So trust company, think fiduciary standard, and then Bitcoin, multi-sig, like Bitcoin standard through Unchain, combining those two things. It's that Venn diagram overlap

that is going to be the true unlock and upgrade yeah this is desperately needed right now as coinbase via the emergence of etfs how popular their launches were obviously the bitcoin treasury companies which you mentioned micro strategy really leaning into that more and more and now a bunch of copycats coming to market and coinbase has taken a large part of that market in terms of securing those treasures perfect use case i've floated the idea internally i think it might be too early that's like a uh first week in business but going for an etf right how is a third fourth or fifth place aum etf keeping up with the blackrock and the fidelity they all just hold the spot bitcoin that's that's what they have and so i look at that space as maybe it's a bit

wise or an ARK or, you know, someone on that list might want to have a multi-sig secure Bitcoin ETF. Gannett can hold a key, Unchain holds a key, ETF provider potentially even hold a key, right? Now you've got three people securing that Bitcoin and it's not all at Coinbase. I think 10 of the 12 ETFs are at Coinbase, all but Fidelity and VanEck. Fidelity custodies their own keys. And VanEck uses Gemini. 10 out of the 12 are at Coinbase. And we just saw that they had an exposure last week. So that's kind of showing you those cracks. And again, it can be a structure and it can evolve into many different use cases of securing coins for large pools of capital with multi-sig multi-institutional yet still uh regulated and compliant to fiduciary

standards and moving from like the corporate and etf balance sheets but for high net worth individuals from what i understand the problem of holding bitcoin in a trust in a way that makes hardcore bitcoiners feel comfortable has been pretty hard yeah to date yeah as a precursor a lot of trust structures are pursued because you've got to get the money out of your name right it's got to get out of marty's name or out of jesse's name because if you die with too much money there's the death tax now that number fluctuates all around right now it's about 28 million for a married couple it's on the table in the trump tax bill that may be changed But the number fluctuates. But if you're over $28 million, you're in this world where you could be exposed to the death tax. And so there's estate planning where you get the money out of your name and into some other entity. That's often a trust, sometimes an LLC, but in this case, we'll use a trust.

that you that trust has to have separation from you and so when you get into the key management or who's the the trustee part of that there's sometimes a conflict between the bitcoiner and then the trust structures like bitcoin i want to hold keys right that's that's what bitcoiners mean by custody is like no keys no cheese keys above all else bitcoin doesn't know about trust it doesn't care about trust. It cares about private keys. But trust company can serve as a trustee on that trust, right? So having a trust company that understands Bitcoin, understands proper key management, that can be the overlapping solution that I need to get this money out of my name for significant death tax reasons. Now, it's in the structure. I'm happy with the rules.

But something professional needs to oversee that those rules are actually carried through. That's what trust companies or professional trustees do for trust. That they are held legally to fiduciary standard to effectuate that trust. If it says do this, that's what the trust company make sure happens so having one of those that gets bitcoin gets key management that's the solution that we saw was missing in the space and it's over a year ago a lot of hard work went into it it's live we're standing up and really excited about what that's going to be able to unlock yeah i know it's been a herculean task for you guys to get this out there so i'm pumped and honestly like looking at the history of trust companies within the ecosystem they haven't been

so trustworthy i get entities like prime trust and others and it seems like they were cutting corners to bring a product to market that many uh sort of white label exchanges were yeah we're anchoring into maybe perhaps similar to coinbase they would have been better focusing on bitcoin building on bitcoin and got distracted by crypto so there are other trust companies out there and they're very amenable to like altcoins and you know how broad trust companies can be with many different types of assets but what's going to be the one that starts to go deep into bitcoin right and having it be a serious focus and designing the operations procedures protections security that bitcoiners kind of demand from a key control perspective um it was just missing so yeah so beyond the

sort of multi-institution multi-sig what does it mean going deeper in terms of giving those types of clients that that comfortability you know when you're operating at those levels um especially in like the family and inheritance side um sure you've heard the term trust fund kid right these structures can last generations and it is a way to to make money last beyond yourself but with your intentions and so when you're having conversations about well what did the trust say sometimes there can be an interpretation of like well how does that apply to the family so there is um if you're getting into the weeds in each specific family like trust officers um as they're carrying out the role of the trust they're like okay this

this kid or this beneficiary has this need does that meet the terms of the trust and there's a lot of um just administration and and you're kind of along with the family in that ride right everyone's kind of beholden to the trust structure and it can't always be changed and it just is what it is and you know trust fund kids now because of it how does the trust company navigate how money goes out of the trust and to beneficiaries and for what reasons they're just very involved from an administration and like relationship management side of things so yeah that would be on like the family side and the treasury side you can look at different strategies like i imagine where you've got bitcoin and a serious focus on bitcoin as a treasury company but you

want to reduce volatility within that because it's too much so designing other let's call them fiat components around maybe it's using derivatives or rebalancing to cash in an automated way if things get out of band when a trust company is involved and it has some level of control and being able to make those rebalancing or derivative decisions with and for your company, then you can have more of an autopilot volatility compression within your treasury. So there are lots of different applications. And we're just now standing up the basics. It'll roll out to unchained clients before the broader public, just because of the pent up demand. And we'll see where it goes like i think the sky is the limit because we've seen over the last six months like wall

street is here and it is head-butting bitcoin at like head-on right those worlds are colliding and navigating the middle and what's going to satisfy both sides um trust companies just a powerful swiss army knife that can unlock a lot of things yeah well on the topic of volatility suppression you had it in your pre-production notes that you want to talk about misty which is uh in all these different sort of derivatives and preferred offerings that strategy um has leaned into themselves with strike and strife and then products like misty and mstu which have sort of emerged as derivative plays on micro strategy strategy to get a different return profile yeah i think that's a good way to put it is like different return profile right it's all

built upon bitcoin you've got bitcoin as a base layer as money micro strategy is a company that is built on bitcoin it's got all of the risks of bitcoin right the volatility the political the technical but then it's got its own set of risks micro strategy risks let's call them sailor and key control and profitability and governance and all company then you have derivatives which are on top of microstrategy and they retain the risks of everything underneath they have all the microstrategy risks all the bitcoin and then their own set of derivative risks and so when i was asked the question a dozen times earlier in this year i was like okay this is where the question set is heading i better get into it and ended up releasing an article about

msty specifically because that was the the hot buzz of the day and like what are the risks some aren't so bad and then others i'd seen were catastrophic in the past and so i lived through uh covid the the march 2020 as an advisor and saw certain etf or derivative structures ETFs that use derivatives, they blew up during COVID, like just unrecoverable, down 95%, never came back. And these were gold mining ETFs. And I thought that that was a pretty good analogy because Bitcoiners are sympathetic to the gold bugs, right? To this day, gold is approaching all-time highs like Bitcoin, but that ETF that used derivatives on gold mining has never recovered. it never came back. And so a Bitcoiner could be right about the underlying thesis of Bitcoin

and Bitcoin could be successful. But if derivative based ETFs aren't managed well, or there's a rush for the exits and someone needs to sell and into a liquid market, it can blow everything up. It can affect everyone in the pool. And so the metaphor I started to tease out, which I didn't know if it was kosher or not, but I've landed on it and I'm comfortable with how edgy it is. If a whale pees in the pool, everyone is affected. If a large participant in an ETF structure wants out in size, and MSTY in particular is using derivatives to create a synthetic microstrategy position and then call options against that as well, that can be an illiquid market. If there's a rush to dollars, global crisis, correlation to one, everyone wants

dollars and a big whale wants out of msty they could sell those derivative positions into an illiquid market where there's no bid and it basically i mean that's my read on what happened with the gold mining etf that never recovered i've got clients asking questions i'm looking out for something like that like what is the risk and how do we avoid a 95 collapse that's unrecoverable because you could be right about Bitcoin. And if you had too much of your money in MSTY, you're down bad, never coming back. line so you keep your bitcoin secure if you have your bitcoin on exchanges and you're looking to get it off secure it in the best way possible pick up a cold card queue go to coin kite.com

find the cold card queue use the code tftc for five percent off if you're a power user of bitcoin like i am if you're running a business on a bitcoin standard if you're just a bitcoin or wants to secure your bitcoin get the most secure hardware wallet on the market go get the cold card queue it's a beautiful thing yeah so let's dive into sort of what msty does or how it's marketed the way i understand it and i i'll admit my understanding is cursory just at an arm's length from observing people talk about it on x for the last three months or whatever since the beginning of the year actually so from what i understand you put money into this etf that's your principle And then these derivatives and options sort of structures are layered into the ETF, which provide fixed income based off the principle that you're putting in.

Is that correct? Pretty close. Only one word I'm going to pull out of that. It's not fixed. Not fixed income. And this is a misconception that was rampant on Twitter, calling it a dividend, right? Dividends come from profits. MSTY is not issuing a dividend. It's a distribution. similar but a big difference right because the distribution can be options or premiums that are received from the option but it can also be return of capital if you give me 100 bucks and i'm like thanks marty and i give you 20 bucks back you have no idea if that was from profit that i actually used in a business activity or a good investment or i just gave you 20 of your 100 back right

i distributed it back to you but it wasn't a dividend and so let i think it could be helpful to pause and just what is the income generating piece of Misty. They're writing call options against an underlying position. What that means and writing a call option, it's very simple. It's just trading your upside for income. You can imagine you have a hundred shares of micro strategy and you think it's going to the moon. You don't know when you're like, ah, I'd really like to live on some of it now, let me pick a date. Let's call it December. And if MicroStrategy goes to $600 a share, I'd be willing to part with it after that. You can have all the moon. I'm happy to let it go for 600. The person taking the other side of that trade is buying the call

option at 600, right? MicroStrategy. If it goes to 700, they're going to get it from you at 600. And so for giving them that promise of unlimited upside, you're getting income now today, you're going to get like a premium or a paycheck for giving them that promise. That is the writing a call option strategy. It's one of the most basic and one of the most harmless options strategies. strategies. It's not one of the more advanced levered. It's just trading your upside for income now. It's more of a protective strategy. And MSTY is doing that. They don't necessarily hold microstrategy underneath the hood. They've said they use synthetic derivatives to create what's similar to microstrategy. So they might not even have the exact 100 shares that are called away at a certain price. Adds a little bit of complexity, in my opinion, reduces some liquidity

because you're dealing with more and more options and less microstrategy shares. And so it's a risk. It doesn't mean it's right or wrong, but it's there. We need to understand what's happening. I quoted a client what microstrategy yield is looking like at certain price points this week. And we came up with a range of what could be reasonable. We got an annualized yield between 16% and 22% that we were looking at for a particular client. MSTY's most recent distribution was annualized at like 120%. So I look at that and I'm seeing

the same options market. We're looking at writing call options against MicroStrategy for a client. we think 16 to 22% is reasonable trading income for upside. Now, 120% is well beyond that 16 to 22, but it is happening. So the questions are, is some of that return of capital? Is some of that leverage? Is some of that just money rushing in and demanding and it's hot right now? I don't know, but I see risks and my main job for clients is just protecting them against risks that they might not see themselves so hopefully that's a little glimpse under the hood happy to click in deeper tease it out yeah well it's msty has been one of the like one of those things the last six months where it's it's reminding me a lot of like waves of altcoin pump and dumps in the past and

not saying that msty is a pump and dump i'm just saying the pattern recognition alarm bells are going off a little bit where you have people sharing screenshots of how much money they put in what the distribution looks like and they're calling people idiots for holding bitcoin and i'm just like it almost seems too good to be true but then you'll be like hey this we're at this inflection point nation states are adopting bitcoin all these corporate treasuries are adopting bitcoin it's up only from here and so we're arbing this information asymmetry that still exists in the market and we're in a super cycle it does a ring of that right like 2017 is icos 2021 is nfts now we got msty they always have letters people are piling into something

thinking it's a silver bullet and then the narrative can take off on its own i saw similar things like hey i was years away from retirement but i decided to yolo it all into msty now i retired both myself and my mom she's in 100 msty okay it's not a dividend so you just call it a dividend within that? What are the risks, right? Because if you go down 90% and you're never coming back, that can be a life altering. If you put all your money into something and lose 19 out of 20 eggs and it's never coming back, it's unrecoverable. And that's, I'm sure it happened with ICOs and NFTs, you know, FTXs. And if we're looking at something like MS2I, we just need to know the risk. Now, the same strategy can be done. And so what I saw as the biggest risk within that MSTY,

that whale in the pool moment, is that you can just have a private pool. You can do it yourself. You can write the options yourself. You don't need to use MSTY to get income from MicroStrategy. And so that's something that we started rolling out to our clients internally. They're called SMAs, Separately Managed Accounts. You can think of it as like a private pool that, hey, this is your own micro strategy. We will do your call option. If someone else wants out of MS2I, you wouldn't know. You're not in a part of that pool. You're in your own private way. So if and when it is right for clients, there's a better way to do it that removes some of the biggest risks. Yeah, that's what I wonder is how many individuals, entities that are piling into

MSTY understand the risk and view it as a game of hot potato where they're just going to juice the distributions for six months, a year, whatever it may be, and then get out when they feel like they've sufficiently produced enough income. And is MSTY aware of the narrative they've caught, right? They've caught this big pool and audience and they can juice their own distributions. They can return some capital. They can take on a little more leverage, get a little more aggressive. And can that cause an unsuspecting person to be like going along with the herd right if msty is successful and gathering all of this narrative and inflow because of it their incentives are aligned to to keep that

up right keep every distribution higher than the last and are you are you marching towards more and more risk thinking you're in something like a fixed income that's the big because it's not fixed it could dry up you could have you could have something that happened to bitcoin which i don't think would happen, and I hope doesn't, that would affect everything above it. MSTR and the derivatives. You could have something to have the micro strategy, right? Something happened to Saylor or the company that would affect everything about it. And then its own set of risks, like the fund management risk that you're in the pool with everyone else. And you've got the decision-making of that manager who's making a decision for all of the pool

participants. And so if it's right, I think the private pool is a better way to go. Just have the options managed according to you. You can dial it up, make it spicier. You can dial it down and make it more plain vanilla. It's your private pool. You can kind of control the temperature. MSTY is a little bit too much going along with the herd for my comfort. Who's issuing MSTY?

I believe it's a company called YieldMax. Or is that just the name of them? I might have to double check on that one. I have the fact sheet posted in the article. That would be a link to the company's page. read it now at unchained.com slash tftc that's unchained.com slash tftc and then obviously this is a derivative of microstrategy and what they're doing but um how does it compare to something like strike or strife these two preferred preferred share offerings yeah so the strike and strife wouldn't be derivatives they're not um there's contracts on top of

MicroStrategy, they're an actual offering from the company. And those are, let's just call them sailor's way to dampen the volatility. And if you don't want all the volatility of MicroStrategy, but you want to use the power of what it's doing with Bitcoin in some different flavors, that's what Strike and Strife are for. I do mix them up from time to time, but one is a 10% preferred dividend. So the dividend has a little bit better taxation than bond interest incomes taxed at a qualified dividend rate. So that can be nice and attractive 10%. And depending on where it's trading, you can get higher than 10% if you're buying it below par, but it is attractive to the fixed income market because they're not being offered 10 or 11 percent in their world

so in that way you're taking that nuclear reactor that sailors talked about with bitcoin and like shoving it into a fixed income product there you go you got a 10 to 11 yield the other one is convertible so it's a little bit less yield but it can retain some upside if microstrategy truly runs and pops that you'll be able to participate in that so think of that one as more of like a hybrid between the fixed income and some of that upside or pop yeah it's fascinating what are your thoughts on all this financialization of or the bitcoinization of finance to a certain degree with all these unique offerings it's a lot a lot to keep up with um there are times where clients will ask me something that i have never heard of i got one this week hey did you hear about

microstrategy's third offering strd or something i was like no i haven't i wouldn't look it's fake it wasn't even real it's some hypothetical that a uh a youtuber made up like here's what i think microstrategy could do and i'm like oh goodness there's so much financialization and then so much social media momentum that can just it can get overwhelming but it was inevitable right that as Bitcoin collides with the world and Wall Street specifically, they're going to have to interact with its ruthless fairness and its like unchanging potential for how it improves people's finances. And they're going to create products around it. Some will be helpful. Some will fail. Some will hurt people. And it's, it's the humans and the institutions colliding with

this protocol that doesn't seem to be moving. It's doing its TikTok next block thing. And Wall Street doesn't operate with that level of patience or consistency. They're going to buzz around it and create a lot of... Usually a lot of selling, right? That's where their interests are aligned. If we can create products and people buy those over Bitcoin, that's how we make money. So I think it's an interesting time to be a Bitcoin-focused financial planner and advisor because you have to help clients navigate that space when we're at the top of the call talking about retirees they love bitcoin my clients love bitcoin they they believe in the future and what it's but they're in their mid-60s they're approaching 70 they're they need to retire now

and they they they're wanting to pull some of that forward because they've got more bitcoin than time often right and so a financialized product can can sometimes be a solution but we don't want to approach it without understanding the risks and having balance around it so very interesting time to be navigating case by case what are all these products coming out and how could i interpret and apply them in a way that my clients are still safe and meeting their goals um yeah i think the private pool options play is very smart yeah i can't put my finger on her i don't know if i can articulate it exactly but again pattern recognition alarm bells going off the animal spirits of ex-community groups and youtubers who think they're trading

savants um it's just like some of this seems too good to be true not all but obviously bitcoin nation state adoption corporate treasury adoption in and of itself is not a bad thing it's a very positive thing but all these derivative plays around it with people trying to catch up scares me i recorded a podcast yesterday that'll come out on friday with the 1031 guys and um john arnold had a really good point like people try to use leverage to become an og they have fomo and they feel like they need to play catch up and accumulate um enough bitcoin to be on the level of who they perceive to be ogs and the way they typically try to do that is leverage and historically in bitcoin it's never worked out too well for people yes

over the years whether it's just at unchained or sound advisory the two biggest things that wreck people are the ego and the emotion right that's they're almost combined into the same thing every bitcoin i talked to feels like they were late because they know someone else who's in before them they know someone who got a price lower than they did and it can feel it can be a shot to the ego that you're not as smart as you think you are right bitcoin humbles all of us and there's a reason why that saying exists like stay humble stack because the emotion and the ego can lead you to do something, whether it's fear or greed driving you there, that you're going out on the risk spectrum and you're going to trade something that's more certain because you're

feeling like you're lacking. And that is what wrecks people. I think it was the underlying thing under Celsius, BlockFi, FTA, that when Bitcoin's not doing something on your timeframe and you want income or you want the yield, oh, I'll just put it with them and I'll get 5% more Bitcoin. Okay. Okay. Well now you've got Celsius. Oh, I'm just going to do this with it so I can have it. And you're kind of like bartering with Bitcoin because it's not meeting your expectations. I've got a timeline. I want to do X, Y, and Z. And here's my ego. I want to impose it on Bitcoin. We were supposed to be this far into having, it should be at this price. It's not doing that. This chop is boring. Let me, there's the ego, the emotion, right? I'm going

of take a different risk level with my bitcoin to try and do something with it and i think people are blinded to the risk by the greed or the the fear or the uh yeah it's um the underlying cause of a lot of bad decisions yeah no i think the the right move what i've learned over the years is that when you feel that urge to lever up and try to play catch up instead of expressing that by levering up your bitcoin go try to be more productive and produce more income so that you can buy more it's very real because everyone knows what fear and greed feel like who knows what like patience feels like just it's neutral and it's it's hard and it's discipline and it's continuing to work and build uh or or have a disciplined investing strategy if you're if

you're no longer working and building and you're retiring like sometimes people are having to settle for the ultimate enemy of just like i should have some dollars right if i have enough dollars to ride through a cycle then i know i never need to sell bitcoin this cycle and that's that's the unfortunate trade-off that the hyper bitcoinizing generations have to live through because we're not at full unit of account medium of exchange yet and if we're headed there it's going to be volatile and we'll have this transition period where we live in the dollar and the bitcoin at the same time and in my opinion that's what all the best companies are solving for right how do we navigate between dollars and bitcoin as things are volatile whether it's unchained strike river

they're creating these dollar and bitcoin services and products secure um and and really designed to be a bridge right they're trying to build a strong secure bridge where you can hop back and forth between those two worlds dollar and bitcoin as your needs change and i think that's where the majority of bitcoin companies value is being built yeah it can only be built if you're focused right which is very important yeah it's easy to buy a ticker symbol it's hard to build something that hasn't existed before right let's see uh the whole bitcoin corporate treasury thing again in and of itself i think it's a good thing but i think there is information asymmetry a potential financial arbitrage that is being exploited right now but at some point in the future when bitcoin

reaches a particular liquidity profile that game sort of has marginal diminishing returns and yes you're gonna have to look at yourself as a business as an entity and be like okay how do i actually produce yeah value and turn that value into income and ebony that allows me to sustain my business yeah the pnl will matter more as the balance sheet gets commoditized sailor is a pioneer in putting it on the balance sheet, early mover, in size, found a lot of arbitrage opportunities, whether it's the convertible or the preferred. When you're first, you don't even have to be the best because you're the only. But now there's more and more participants. You're getting Bitcoin treasury companies that understand that it's powerful to put Bitcoin on a balance

sheet. And at the end state, many, many companies will have Bitcoin on their balance sheet. it's table stakes at that point and so how are you going to differentiate and provide value on top of bitcoin that's the building right and so in my opinion there are some treasury companies that are doing the equivalent of buying that ticker symbol oh if i just switch to bitcoin balance all this money is going to flow to me still pretty early right you're probably still within the group of pioneers and that may happen but it's not sustainable if you don't have a thesis or a value proposition of how you build value on top of bitcoin just having bitcoin on the balance sheet is not a sustainable unlock because that's where most companies are going

to be headed over the coming decades yeah and yeah now i can already hear people like marty you're so bearish you don't understand what's going on i just want to say hey been around the block a few times a few cycles just be careful out there be careful out there stay humble stack stats exist for a reason and then for anybody who doesn't understand like the stay humble stack stats meme started matt started it this is like six or seven years ago now at this point and it's basically just don't go levered long don't margin trade don't shit coin during the bull market because that's how you get blown up yeah and end up with less than you otherwise would have had yeah if i can fanboy for a little bit i listen to you and matt all the time and i

i love that quote and i've started to uh personalize it for myself the meme of stay humble sack sats and i i see within the social media sometimes where people ask well how much bitcoin do you have not enough i never have enough bitcoin i've gotten to a point within in my own personal life, I'm like, I feel like I have enough. If I can just stay humble, stack the sats that my bullishness, I'm trying to express through my patients. And so I'm changing that sats to Saturdays. I don't work on Saturdays and I want to stack those because if I've got enough Bitcoin, what don't I have enough of is time with my family. I got a boy who's about to be seven. I'm like, man, he's getting into T-ball and I need to stack

saturdays now because the bitcoin is i'm confident that it'll be there in the long term and i believe i have enough and i'm trying to build and be patient and do the things um that i think will make bitcoiners proud and see this industry flourish let's stack some saturdays too right and start to get some time and like it helps connect me to like what is the bitcoin all for if i die and leave my family a stack and they're like okay well what i want to have the those meaningful experiences along the way. And I think that when people find that value and what connects them to their money, that can pull you out of the fear and greed. You're no longer comparing to, oh, so-and-so got in before me. They were class of 20, whatever. I've found a way that Bitcoin

is a powerful tool in my life and it's helping me stack some Saturdays, right? I get to live for now because I feel more confident in my future. And so, I don't know if anyone that ever brought up that pun or double entendre to you, but that's what I'm hearing. You guys close out your podcast, stay humble, stack stats, and I think y'all record on like a Thursday or Friday. Depending. Saturdays. Okay. Saturdays come in. I'm like, all right, well, I don't know how many Saturdays I have left in this life. We know there's 21 billion Bitcoin. I've only got some time with a six and seven year old and I need to make today count. And so that's my own personal rabbit trail.

I love that. never asked for but it is it's deeply meaningful to me and helps me remember that bitcoin is a tool that should be empowering our lives it's that fix the world you know fix jesse side of okay if the money's fixed it can help be a tool in my life here and now no i love that and i've never heard it so it's the first time i'm hearing a double entendre no it reminded like last night we had an event here at bitcoin park austin with adam back turdemeester parker a bunch of others speaking and everybody's like oh you want to go grab dinner i was like you know what i'm gonna go home i was able to make it home in time for bedtime and you know read stories and

you feel that working in bitcoin like you're surrounded by it all the questions all the news all the products and people and personalities and drama and did you see who did this and that talking about trump did something crazy it can be so much that it's overwhelming and to to shrink down and be like, I'm just dad. I get to read a book. Might've read it eight or 10 times before, but I'm never getting these moments back. And I am so fortunate that I get to work with clients in their sixties and seventies and they have money, they have resources and their, their retirement's locked. What do they want? A lot of them want to go back to when their kids were six and seven, right? They want that time back with their kids. And that, and I'm fortunate

that they share that with me and it had brought tears to my eyes a couple times because i'm like okay well i get to live like that client their wish is to go back to where i am right now and i get to live it right and i don't need to be stacking sets right now i need to be stacking a saturday and like really um making the most of this moment so yeah yeah no it's really important to put those things into perspective it's the most important thing and i i've had i don't want to say regrets but there's been times where i've like committed to something in the industry gone wasn't it was like i didn't have to do this and then i get home the kids are asleep i'm like i missed yeah missed a bedtime tonight that wasn't fun much yeah i would have much rather done a

that time it's that it's that double-edged sword of success right when things are taking off and bitcoin's winning and your company's healthy and the people around you are excited and want to talk to you it can take you from the people that are the most patient with you right my wife my kid my dad um i know you've got a story that's like that that time is so precious and remembering it and anchoring to it is a powerful draw against the negative emotions that Bitcoin can easily sweep you up into, right? Whether we have a bear in its fear or a bull in its greed, those aren't the emotions that you want in your life. You need to find something deeper than the tool, deeper than Bitcoin. Like what are your values? For a lot of people, it's family and

time. There can be others, you know, hobbies, just things that really connect you and make you feel alive that's what the money's there for that's what's going to fix the world and that's once you know that the money can serve that and you're not just thinking only as deep as the money you've got a deeper base layer of what it's all there for yeah it's very probably yeah i can hop off the soapbox but i think so much of my job like i thought i was going to be a financial advisor but it gets so psychological so quickly because the saying is personal finance is 80 personal and only 20 finance and it's even more powerful in the bitcoin world because bitcoin is such a powerful tool yeah it really is it really is no no i'm happy you hopped on

that soapbox because especially right now as we're we passed all-time highs earlier we're a little below it but who knows could continue and things are going to get crazy and it's important to have this perspective in mind as things are getting crazy yeah um and as they get crazy and you feel right and your thesis was proved just remember that you being right about this is also simultaneously painful for the rest of the world who doesn't see it as early as you like it's that just don't dance from the uh the big short right is it that's what he says right just don't dance like this is this is not a good thing we're going through it's good that we have a solution but you understand the solution far more than 99 of the world and 99 of the world

going through pain is not it's probably what's happening i prefer it happens slower than all at once but just don't dance because um so yeah connecting to the things that are deeper than money will help you from help you from dancing as others are yet to transition and haven't found bitcoin yet yeah get uh get so distracted at t-ball games that you don't even think to dance just losing your mind throwing peanuts yeah yeah um but speaking of like things do seem to be getting out of whack in the traditional financial system it seems like japan's completely lost control their yield curve looks like we're losing control of our yield curve here in the united states uh is japan losing the their bond market to meta planet yeah i mean it seems like it's

very possible market in japan just flowed into a hotel company that's why i tweeted that out yesterday i was like is are the japanese using meta planet as a bitcoin proxy yeah they're like the micro strategy of their country right like yeah you know just uh the escape hatch is tiny and so it can easily blow out when the the flood comes none for those are unaware i think japan's tax situation is such where it's a massive tax benefit to buy stocks over spot bitcoin as well so um it makes sense that people would flow in the meta planet yeah i think if i could segue weighed a little bit. It's that every country's got that different tax, right? Japan, I'm not familiar with their tax regime, but pretty familiar with America's. And that is what drives so much.

It's the number one friction in people's lives, right? The CPAs are in business because tax is there. It's a powerful reason why loans exist. I don't want to sell my Bitcoin and pay tax, I'd rather take a loan against it. IRAs, gains, losses. Bitcoin's trying to be money, but it's not tax-like money. It's tax-like property. And I had used... Saylor and Jack Mauler had different opinions on this. Or I think even Odell had one that, what is Bitcoin? Saylor will say property. Maybe an Odell would say something like money. Yes, technologically, Bitcoin's trying to be money and money is property. But where they disagree is like that tax component. It's so powerful to just hodl or hold Bitcoin because of

the tax friction. And so the thing I pay most attention to is which countries are easing up the friction on people. El Salvador being a great example, but you see other countries or even states in America where they're trying to do something with cap gains or reduce frictions in and out of certain structures. I think that's where all of the, as the floods coming and Bitcoin is hitting the global world, the water is going to find its sweet spot, right? In the jurisdictions that carve the trench for it. And so the number one thing I'm paying attention to for my clients is what's coming in this big, beautiful tax bill, right? Trump has called it big and beautiful great i'm sure it's beautiful what's in it and how does that tax

affect the bitcoiners or maybe even other parts of that you know bitcoiners financial life but that's once they change the game of the friction that's what you navigate for people because it's not an opinion of price price can do this or that or meta planet or microsoft they might do this those are just crystal ball and opinion taxes here and now and if you say if you do x y and z you're going to save this much money. Very, very powerful. Sometimes boring, right? People don't like tax, but that is a needle mover in Bitcoiners' financial lives. And so what can we expect with this big, beautiful tax bill? Oh, goodness. I've heard they're going to eliminate the IRS. Doesn't sound like it

would need to be a big, beautiful tax bill to do that. So if it's big and beautiful, it's probably got a lot of different bells and whistles that are likely an extension of the TCJA. So I know I see there's jockeying between the Senate and the House and like what's going to be in or what's not. I imagine it's something like the TCJA bill we've had for the last seven years with maybe some new caveats. Things that Bitcoiners could pay attention to, bonus depreciation. If mining is on your radar, right, being able to depreciate those mining machines could look at, like, and this is just a side note, that the public miners aren't able to pass through losses or that bonus depreciation, but the privates sometimes can. And so that could be a benefit. Bonus depreciation comes back.

I'd be looking at if you're exposed to the mining space, like, well, now do we buy rigs because we can write it all off? Um, social security, if that's a part of your now or your future, there might be no tax on that. No tax on tips. If you're in the service industry, there could be others. Um, they do end up getting rid of the IRS. There's some strategies for that too. You know, maybe it's selling all your Bitcoin and buying it right back to lock in a new basis. Uh, talk to some clients that think the IRS will go away. There's a potential strategy of sell your a hundred dollar bitcoin and buy the 110 000 bitcoin if there's no irs reset your basis and floor you could do roth conversions there's so many what-ifs that i'm just telling many many clients let's pause

let's see what the rules are and then i'll help you play the game after that do you think no capital gains on bitcoin is on that'd be nice yeah on whose table i don't know about i mean america needs money uh even if they got rid of the irs like where's the money going to come from there's probably a large they did that that's a tariff regime right they're going to have to get the money from somewhere else cap gains would be internal they're losing a big chunk of revenue for not taxing that is it only to bitcoin would it be to stocks and real estate as well i think it's pretty far-fetched i would give it a five ten percent chance nothing zero these days lots of craziness but not a base case um if there's no cap gains i'm

personally probably waiting till december 31st of the year so they don't change their mind and say and then i'll sell the bitcoin and buy it right back to lock in a higher basis yeah wild times jesse wild times wild times yes thank you for coming on particularly helping people gain perspective on how to approach this thing's gonna get weird both in the bitcoin world in the fiat world trying to keep your head on straight stay humble don't become beholden to the whims of fomo and animal spirits and have a plan and stick to it yeah i think uh i've heard you say is this peak clown world like is it peak maybe the peak is uh correlated with m2 money supply like it's more the more they print the

more the peaks just keep coming it's going up going up forever laura hyper bullish on peak clown world clown world is going up forever jesse yeah yeah where can people ticker c c l w n can i invest in peak clown world not yet just wait that'll come treasury company you're gonna spack it out that'll come that'll come um where can people find out more about gannett gannett is at gannett trust.com they are operationalizing standing it up as we speak So chartered Wyoming Trust Company getting installed and rolling out to Unchained clients first, probably in the second half of the year, that'll be made more broadly available to others. So GannettTrust.com. If you're interested in learning what that rollout looks like, you can request an introduction there. sound advisory which i help run is going to be tucking up and under gannett trust over the next

few months and will be the the wealth advisory arm of the trust company and then that can currently be found at the sound advisory.com but it'll tuck under gannett eventually and as always unchained the parent company and umbrella the leader of the umbrella family is unchained.com for their products and services check it out think about using unchained.com slash tftc if you want to engage in anything they're doing there yeah check it out jesse thank you um i know and congrats on on getting ganon out there because i know it's been a a long haul it's very important very important to do it correctly and for anybody out there high net worth individual somebody managing a corporate balance sheet or a pension fund whatever it may be looking for say for

fiduciaries families founders so if you're in that world we'd love to start a conversation with you and yeah as the the world gets crazier and develops and there's more products we are doing our part to try and build and solve what we think is needed in the space and again it was a lot of proof of work and, um, proud of the team that launched it. And we'll see what we can do with that Swiss army knife here in the coming years. All right. Well, I'm looking forward to, to seeing it flourish. All right. Well, thank you, sir. Thanks for the time.

Thank you. Peace and love freaks.