Bitcoin advisor Jessy Gilger explains how to retire on Bitcoin and how Ganet Trust is changing long-term financial planning.
In this episode of TFTC, Jessy Gilger, Managing Partner at Sound Advisory and architect of Ganet Trust, unpacks the complexities of retiring on Bitcoin, emphasizing that the “right” amount depends on spending habits, age, and minimizing withdrawal pressure. He introduces Ganet Trust as a Bitcoin-native fiduciary solution that leverages multisig custody to meet institutional compliance standards without sacrificing decentralization. Jessy also critiques high-yield derivative products like MSTY, warning of systemic risks and advocating for safer alternatives like SMAs. The conversation broadens into the emotional pitfalls of financial decision-making, the importance of aligning wealth with values, and the evolving macro landscape where Bitcoin’s intersection with traditional finance and tax policy will shape how individuals and institutions protect and grow their holdings across generations.
"The most comfort comes from putting as little pressure as possible against that stack."
"Multisig is the upgrade from a honeypot to a distributed key setup."
"If a whale pees in the pool, everyone is affected."
"Everyone feels late to Bitcoin because they know someone who got in earlier."
"Stacking Saturdays is my new stack sats."
"Bitcoin doesn’t know about trust, it knows private keys."
"The money is there to serve your values—not the other way around."
"Some financial products will help, some will hurt, and some will fail. Our job is to help clients navigate them safely."
This episode offers a powerful blend of practical insight and philosophical reflection on long-term Bitcoin strategy, emphasizing the need for sound custody, inheritance planning, and emotional discipline in a volatile, financialized world. Jessy Gilger introduces Ganet Trust as a vital solution for secure, compliant Bitcoin ownership, while his “stacking Saturdays” mantra reframes wealth as a pursuit of time, freedom, and meaningful priorities. As Bitcoin moves further into the mainstream, the conversation urges listeners to stay grounded, think generationally, and build resilient systems for both assets and life.
00:00 - Intro
0:33 - Bitcoin Retirement Planning at New All-Time Highs
5:22 - How Gannett Trust Works
10:05 - High Net Worth Bitcoin Storage and Estate Planning Solutions
16:48 - MSTY Derivatives: Understanding MicroStrategy Product Risks
19:53 - Bitkey
20:56 - How MSTY Works and the Whale in the Pool Problem
30:16 - Unchained
30:37 - Bitcoin Financialization and Corporate Treasury Strategy
39:35 - Avoiding Ego-Driven Bitcoin Mistakes and Building Bridges
47:33 - Stack Saturdays
53:15 - Tax Policy Changes and Wild Times Ahead
57:18 - Where to Find Gannett Trust and Closing
(00:00) We have people retiring with hundreds of Bitcoin. Do you need to be on a yacht every week or are you staying humble and keeping those stats? 10 of the 12 ETFs are at Coinbase means all the keys are at Coinbase and with the news of the last week like, hey, there could be cracks. Micro Strategy is built on Bitcoin.
(00:18) It's got all of the risks of Bitcoin, right? But then it's got its own set of risks. Let's call them Sailor and Profitability. Then you have derivatives which are on top of Micro Strategy and they retain the risks of everything underneath. meeting on a on a day when we hit new all-time highs. Bitcoin approached $110,000.
(00:43) Got Jesse back on the show to talk about many things, not just the price ripping. A lot of good things happening on the unch unchained side of things. Watching Ganet Trust. We'll get into it. Yeah, lot lots of stuff happening. I think um the price likes Ganet. I 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 how are you thinking about all this as we approach what seems
(01:22) 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 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 the biggest factor, right? And age is probably the second.
(01:54) a 30-year-old retiring on Bitcoin is different than a 75year-old retiring on Bitcoin just because of the horizon. So, stacks vary. We've got people retiring with um less than seven figures of Bitcoin because they have other assets and then we have people retiring with hundreds of Bitcoin um and putting very little pressure against that portfolio.
(02:16) So, can go in a lot of different ways. Um 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 what would a downside look like and that's the big question in the retirees 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.
(02:42) 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. Mhm. How much how many stats do I need to get to 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 or down 30% and that's still within a bull market.
(03:15) Is that comfortable, right? 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 5 10 20% of my Bitcoin stack.
(03:38) 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 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. 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
(04:10) 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 businesses and trust uh Bitcoin and I think today's announcement of Ganet Trust is a massive step in a direction towards more certainty for long-term holdings for particular entities.
(04:36) Yes, the unchained umbrella or or family of companies is growing and the intention will be for sound advisory to tuck under or be merged into folded into Ganet Trust Company as it gets stood up. But it is the most robust uh compliance offering that um 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.
(05:04) 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 Ganet Trust Company. So it's going to be the most robust way to hold Bitcoin and have like true inheritance that can be um administered through generations. So how how does this work mechanically via Ganet? Mechanically.
(05:28) So as the first Bitcoin native trust company, other other trust companies do exist, right? but they don't build upon Bitcoin in the way that Unchained has. So Ganet in its um in its Unchained roots and using Unchained technology is going to be able to use multi-IG to achieve um trust company goals.
(05:50) And what that likely will mean is Ganet 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, right? 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?" Said, "I'm launching a new segment.
(06:15) I'm going to ask you a prediction of what what's out there that the uh the industry doesn't see eye to eye with you at." 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.
(06:37) 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 Ganet is going to offer to the custody space, it means that not all of the keys are going to be at any one entity.
(07:00) 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 the institutional and big money of the world, right? family offices, uh, Bitcoin treasury companies, they're going to need a structure that the CIO, the CFO can point to and say, "Yes, that is regulated.
(07:26) 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-IG like Bitcoin standard through onchain combining those two things.
(07:49) It's that that vin 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 the perfect use case.
(08:22) I've floated the idea internally. I think it might be too early to ask like a first week in business, but going for an ETF, right? How is a third, fourth, or fifth place AUM ETF keeping up with the Black Rockck and the Fidelity? They all just hold spot Bitcoin. That's that's what they have. And so I look at that space as maybe it's a Bitwise or an ARC or, you know, someone on that list might want to have a multi-IG secure Bitcoin ETF.
(08:54) Ganetic 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 Van Fidelity custodies their own keys and Van uses Gemini.
(09:15) 10 out of the 12 are at Coinbase and we just saw that they had an exposure last week, right? So that's it's kind of showing you there's 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-IG multi-institutional yet still uh regulated and compliant to fiduciary standards and moving for 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
(09:56) Bitcoiners feel comfortable has been pretty hard. Yeah. Uh 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 cuz if you die with too much money, there's the death tax.
(10:20) 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 to maybe change, 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.
(10:36) That's often a trust. sometimes an LLC, but in this case, we'll we'll use a trust that you that trust has to have separation from you. And so when you get into the the key management or who's the the trustee part of that, there's sometimes a 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. I keys above all else.
(11:05) Bitcoin doesn't know about trust. It doesn't care about trust. it cares about private keys, but trust company um 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.
(11:33) 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 trusts, that they are held legally to a fiduciary standard to effectuate that trust. If it says do this, that's what the trust company makes sure happens.
(11:57) So having one of those that gets Bitcoin, gets key management. That's the solution um 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 a herculean task for you guys to get this out there. So I'm pumped.
(12:18) And honestly, like looking at the history of trust companies within the ecosystem, they haven't been so trustworthy at 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 were anchoring into maybe perhaps similar to Coinbase, they would have been better focusing on Bitcoin, building on Bitcoin and got distracted by crypto.
(12:48) So there are other trust companies out there and they're very um amendable to like altcoins and you know how u 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 protection security that Bitcoiners kind of demand from a key control perspective um it was it was just missing. So yeah.
(13:20) So beyond the sort of multi-institution, multi-IG, 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 in inheritance side, um I'm 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.
(13:50) 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.
(14:13) 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 um from an administration and like relationship management side of things.
(14:48) So yeah, that would be on like the family side and the treasury side. You can look at um 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, right? 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 um some level of control in being able
(15:24) to make those like rebalancing or derivative decisions with and for your company then you can have more of an autopilot like volatility compression uh within your treasury. So there are lots of different applications and we're just now like standing up the basics. It'll roll out to unchained clients before the broader public.
(15:49) Um just because of the pentup demand and we'll see where it goes. Like the I think the sky's is the limit because we've seen over the last six months like Wall Street is here and it is headbutting Bitcoin head like head on, right? those worlds are colliding and navigating the middle and what's going to satisfy both sides.
(16:11) Um, Trust Compan is 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 Misti, 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 Misti and MSTU which have sort of emerged as derivative plays on Micro Strategy Strategy.
(16:47) 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 is 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 shed risks, let's call them sailor and you know key control and uh profitability and governance and all company.
(17:17) Then you have derivatives which are on top of micro strategy and they retain the risks of everything underneath. They have all the micro strategy 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.
(17:34) " 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 had seen were were catastrophic in the past. And so I lived through u co the the March 2020 as an adviser and saw certain ETF or derivative structures um ETF ETFs that use derivatives they blew up during COVID like just unreoverable down 95% never came back and these were gold mining ETFs and I thought that that was a pretty good analogy because Bitcoiners
(18:14) are sympathetic to the gold bugs right to this Hey, gold is approaching all-time highs like Bitcoin, but that ETF that used derivatives on gold miners 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 illquid market, it can blow everything up. It can affect everyone in the pool.
(18:44) And so the metaphor I started to tease out, which I didn't know if it was uh kosher or not, but I landed on it and I'm comfortable with how edgy it is, is if a whale pees in the pool, everyone is affected, right? If a large participant in an ETF structure wants out in size and MSTY in particular is using derivatives to create a synthetic micro strategy position and then call options against that as well that can be an illquid market right if there's a rush to dollars global crisis correlation to one everyone wants
(19:20) dollars and a big whale wants out of MSTY they could sell those derivative positions into an illquid 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.
(19:42) Like what is the risk and how do we avoid a 95% collapse that's unreoverable? 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. Sup freaks. This rip of TFTC was brought to you by our good friends at BitKey. Bitkey makes Bitcoin easy to use and hard to lose.
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(20:50) 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 arms length from observing people talk about it on X for the last 3 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 um sort of structures are layered into the ETF which provide fixed income based off the principle that you're putting in.
(21:24) 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 uh premiums that are received from the option, but it could also be return of capital.
(21:52) 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 hundred 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 Misti.
(22:16) 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 100 shares of Micro Strategy and you think it's going to the moon. You don't know when.
(22:37) 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 Micro Strategy 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? Micro strategy.
(23:00) 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 uh most harmless options strategies.
(23:24) It's not one of the more advanced, you know, levered. It's just trading your upside for income. Now, it's a more of a protective strategy and MSTY is doing that. They don't necessarily hold Micro Strategy underneath the hood. They don't they they've said they use synthetic derivatives to create what's similar to Micro Strategy, right? So, they might not even have the exact 100 shares that are called away at a certain price.
(23:54) adds a little bit of complexity in my opinion reduces some liquidity because you're dealing with more and more options and less uh micro strategy shares and so it's a risk doesn't mean it's right or wrong but it's there we need to understand what's happening I quoted a client what micro strategy yield is looking like at certain um price points this week and we came up with a range of you know what could be reasonable we we got an annualized yield between 16 and 22% that we were looking at for a particular client. MSTY's most recent distribution
(24:32) was annualized at like 120%. So I look at that like I'm seeing the same options market, right? We're looking at writing call options against Micro Strategy 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 and it's hot right now.
(25:08) 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 it's MSTY has been one of 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.
(25:33) 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.
(25:53) Nation states are adopting Bitcoin. All these corporate treasuries are adopting Bitcoin. It's up only from here. And so we're arbing this Mhm. information asymmetry that still exists in the market and we're in a super cycle. It does ring of that, right? Like 2017 is ICOs, 2021 is NFTTS, now we got MSTY. They always have letters.
(26:15) 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 in 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 saying you're what are the risks, right? Because if you go down 90% and you're never coming back, that can be a lifealtering.
(26:42) If you put all your money into something and lose 19 out of 20 eggs and it's never coming back, it's unreoverable. And that's I'm sure it happened with ICOs and NFTTS, 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.
(27:11) You can write the options yourself. You could stay in your you don't need to use MSTY to get income from Micro Strategy. 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.
(27:28) 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 W. 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 6 months, a year, whatever it may be, and then get out when they feel like they've sufficiently
(28:03) produced enough income. Mhm. And is MSTY aware of the narrative they've caught? Right. they've 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
(28:38) 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 to happen to Bitcoin which I don't think would happen and I hope doesn't that would affect everything above it MSTR and the derivatives.
(28:58) You could have something to have the micro strategy, right? something happened to Sailor or the company that would affect everything about 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.
(29:19) 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 um too much going along the with the herd for my comfort.
(29:43) So, who's issuing MSTY? Company called YieldMax. Uh or is that just the name of the You might have to double check on that one. Um I have the fact sheet posted in the article that would be a link to the the company's page. US Now has a strategic Bitcoin reserve. That's not clickbait. It's a policy directive. Unchained and the Bitcoin policy institute just dropped a new report and are hosting a live event to unpack it.
(30:06) It's called the strategic Bitcoin reserve era begins. We've got Congressman Nick Beich, Matthew Pines, and Joe Bernett breaking down how the first 100 days of the new administration flipped the policy script on Bitcoin. Go to unchained.com/tc to register and read the full report. That's unchained.comTFTC. And then obviously this is a derivative of Micro Strategy and what they're doing, but um how does it compare to something like Striker Strife? These two preferred preferred share offerings. Yeah.
(30:38) So the Strike and Strife wouldn't be derivatives. They're not um there's contracts on top of Micro Strike. They're actual offering from the company. Mhm. And those are let's just call them sailor's way to dampen the volatility, right? If you don't want all the volatility of Micro Strategy, but 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.
(31:04) Um, I do mix them up from time to time, but one is a 10% u preferred dividend. So, the dividend has a little bit better taxation than bond interest income. It's taxed at a qualified dividend rate. that can be nice and attractive 10% uh 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% in their world.
(31:43) And 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 10 to 11% yield. The other one is convertible, so it's a little bit less yield, but it can retain some upside if Micro Strategy truly runs and pops that you'll be able to participate in that.
(32:02) So, think of that one as more of like a hybrid between the fixed income and some of that uh upside or pop. Yeah, that's fascinating. What do you what are your thoughts on all this financialization of or the bitcoinization of finance to a certain degree with all these unique offerings. Um so lot a lot to keep up with. Um there are times where clients will ask me something that I have never heard of.
(32:29) I got one this week. Hey did you hear about micro strategies you know third offering str or something like I was like no I haven't. I went look it's fake. It wasn't even real. was some hypothetical that a uh a YouTuber made up like here's what I think Micro Strategy could do and I'm like oh goodness there's so much financialization and then so much um 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
(33:02) interact with its ruthless fairness and its like unchanging potential for how it improves 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 the institutions colliding with this protocol that doesn't seem to be moving.
(33:25) It's doing its tick tock 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 um 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.
(33:44) So, I think it's an interesting time to be a Bitcoin focused financial planner and adviser 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 my clients love Bitcoin. They they believe in the future and what it's but they're in their mid60s. They're approaching 70.
(34:06) 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 um 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
(34:42) pool options play is very smart. Yeah, I can't put my finger on or 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 um YouTubers who think they're trading savant. Um it's just like uh some of this seems too good to be true. Not all of it.
(35:08) Obviously, Bitcoin, nation state adoption, corporate treasury adoption in and of itself is not a bad thing. That's a very positive thing, but all these derivative plays around it with people trying to catch up scares me. I we 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.
(35:39) they 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.
(36:05) Every Bitcoiner I talk to feels like they were late because they know someone else who was 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, stay 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 respect and you're going to trade
(36:34) something that's more certain because you're feeling like you're lacking and that 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 time frame 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.
(36:56) Well, now you got Celsius. Uh, 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, right? 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're supposed to be this far into a having.
(37:15) It should be at this price. It's not doing that. This chop is boring. Let me And that there's the ego, the emotion, right? I'm going to 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.
(37:37) 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 catchup 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 cuz everyone knows what fear and greed feel like.
(38:03) Knows what like patience feels like. just it's neutral and it's it's hard and it's disciplined 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.
(38:31) 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.
(38:49) 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 uh 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.
(39:22) 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? That's the uh the whole Bitcoin corporate treasury thing.
(39:51) 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 going to have to look at yourself as a business, as an entity, and be like, okay, how do I actually produce Yeah.
(40:20) value? and turn that value into income and IBIDA that allows me to sustain my business. Yeah, the P&L will matter more as the balance sheet gets commoditized. Sailor was a pioneer in putting it on the balance sheet early mover in size found a lot of arbitrage opportunities whether it's the convertibles or the preferred when you're first.
(40:40) 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.
(40:59) 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 sheet, all this money is going to flow to me.
(41:13) You're still pretty early, right? 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 of Bitcoin. Just having Bitcoin on the balance sheet is not a sustainable unlock because that's where most companies are are going to be headed over the coming decades.
(41:35) Yeah. And Yeah. I I can already hear people like, "Marty, you're so bearish. you don't understand is going on. I just want to say, hey, been around the block few times, few cycles, and just be careful out there. Be careful out there. Stay humble stacks exist for a reason. And then for anybody who doesn't understand, like the stay humble stacks meme started, Matt started it.
(42:05) This is like six or seven years ago now at this point. And it's basically like just don't go lever long. Don't margin trade. Don't shitcoin during the bull market because that's how you get blown up. Yeah. And end up with less Bitcoin 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 sacks.
(42:33) 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 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 patience.
(42:53) " 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've 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.
(43:14) And I believe I have enough and I'm 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 is I want to have that those meaningful experiences along the way?" And I think that when people find that value and what connects them to their
(43:44) 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.
(44:05) And so, I don't know if anyone had ever brought up that pun or double on Tandra to you, but that's what I'm hearing. If you guys close out your podcast, stay humble, stacks, and I think y'all record on like a Thursday or Friday, depending on Saturday. Okay. Saturday's coming. And I'm like, "All right, well, I I don't know how many Saturdays I have left in this life.
(44:24) We know there's 21 billion Bitcoin. I've only got some time with a six and sevenyear-old, and I need to make today count." And so, that's my own personal rabbit trail. Uh, I love that that you 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.
(44:42) It's that fix the world, you know, fix Jesse side of okay, if the money is 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 antandra. No, it reminded like last night we had an event here at Bitcoin Park Austin with Adam backster Parker, bunch of others speaking and everybody's like, "Oh, you want to go grab dinner?" I was like, "You know what? I'm going to go home.
(45:09) " I was able to make it home in time for bedtime. And yeah, read stories. And you probably feel that working in Bitcoin like you're surrounded by all the questions, all the news, all the products and people and personalities and drama and did you see who did this and that and you're talking about Trump did something crazy.
(45:27) 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 have 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 60s and 70s, and they have money, they have resources, and they're their retirement's locked.
(45:49) 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.
(46:08) 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. Mhm. 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 a I didn't have to do this and then I get home the kids are asleep and I'm like oh I missed I
(46:44) missed a bedtime tonight. That wasn't fun. Much would have much rather done a bedtime then. 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 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.
(47:12) Um, you know, I know you've got a story. It'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 and its greed, those aren't the emotions that you want in your life.
(47:32) 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.
(47:50) 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 soap box, but I I think so much of my job like I thought I was going to be a financial adviser, but it gets so psychological.
(48:09) so quickly cuz the saying is personal finance is 80% personal and only 20% finance and it's even more powerful in the Bitcoin world because it's Bitcoin is such a powerful tool. Yeah, really is. It really is. No, no, I'm happy you hopped on that soap box because especially right now as we're we passed alltime 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.
(48:38) 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 like this is what he says, right? Just don't dance.
(49:06) 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 are yet to transition and haven't found Bitcoin yet. Yeah.
(49:40) Get uh get so distracted at T-ball games that you don't even think to dance. Just losing your mind and throwing peanuts. Yeah. Yeah. the 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 of their yield curve.
(49:59) Looks like we're losing control of our yield curve here in the United States. Um yes, Japan losing the their bond market to Met Planet. Yeah, I mean it seems like it could that's very possible. Will the bond market of Japan just float into a hotel company? That's why I tweeted that out yesterday. is like is are the Japanese using Metaplanet as a Bitcoin proxy flight.
(50:21) They're like the micro strategy of their country, right? Like you know just the skate patch is tiny and so it can easily blow out when the the the flood comes. No, for those who 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 Metanet. Yeah.
(50:47) I think if I could segue it a little bit. Mhm. 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 um it's the number one friction in people's lives, right? The CPAs are in business because tax is there.
(51:11) 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. IRA, uh, gains, losses. Bitcoin's trying to be money, but it's not tax like money. It's tax like property. And I had used, um, Sailor and Jack Mullers like had different opinions on this.
(51:30) Or I think even Odell had one that what is Bitcoin? Sailor will say property maybe and Odell would say something like money. Yes, technologically Bitcoin's trying to be money. money's prop, but the where they disagree is like that tax component. It's so powerful to just hodddle or hold Bitcoin because of the tax friction.
(51:48) And so the thing I pay most attention to is which countries are easing up the 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 um reduce frictions in and out of certain structures. I think that's where all of the as the flood's coming and Bitcoin is hitting the global world, it the water is going to find its sweet spot, right, in the jurisdictions that carve the trench for it.
(52:27) 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 bitcoiner's 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 can do this or that or metanetan or micros they might do this those are
(52:59) 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 ful um sometimes boring, right? People don't like tax, but that is a needle mover in uh Bitcoiners financial lives. And so what can we expect with this big beautiful tax bill? Oh goodness.
(53:19) I've heard they're going to eliminate the IRS. Uh 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 it or what's not.
(53:43) I imagine it's something like the TCJA bill we've had for the last 7 years with maybe some new caveats. Um things that Bitcoiners could pay attention to, bonus depreciation if mining is um on your radar, right? Being able to depreciate those mining machines. um 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.
(54:18) 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.
(54:43) 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, talked to some clients that think the IRS will go away. There's a potential strategy of sell your $100 Bitcoin and buy the $110,000 Bitcoin if there's no IRS. Reset your basis and floor. You could do Roth conversions.
(55:03) There's so many whatifs 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 table? That' 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.
(55:29) 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 10% chance. Nothing zero these days.
(55:52) 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, "Okay, 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.
(56:17) Thank you for coming on, particularly welcome helping people gain perspective on how to approach this. Things are going to get weird both in the Bitcoin world and the fiat world. Try to keep your head on straight. Stay humble. Don't be become beholden to the whims of FOMO and animal spirits and have a plan and stick to it. Yeah.
(56:44) I think uh I've heard you say is this peak clown world like is it peak like 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 so it's going up going up forever Laura hyper bullish on peak clown world clown world is going up forever Jesse the uh yeah where can people ticker cn can I invest in peak clown world not yet just wait that'll come the treasury company You going to spack it out? That'll come. That'll come.
(57:16) Um, where can people find out more about Ganet? Ganet is at ganuttrust.com. They are operationalizing, standing it up as we speak. So, chartered uh 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 um others.
(57:38) So ganetrust.com if you're interested in learning what that roll out looks like. You can request an introduction there. Sound Advisory, which I help run, is going to be tucking up and under Ganet Trust over the next few months and will be the the wealth advisory arm of the trust company. And then um that can currently be found at theoundadvisory.
(58:00) com, but it'll tuck under Ganon eventually. And as always, Unchained, uh, the parent company and Umbrella, uh, the leader of the Umbrella family is Unchained.com, um, for their products and services. Check it out. Think about using Unchained.com/TFTC if you want to engage in anything they're doing there. Check it out, Jesse. Thank you.
(58:26) Um, I know and congrats on on getting Ganet 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.
(58:48) 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 product, 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 the team that launched it and we'll see what we can do with that Swiss Army knife here in the the coming years. All right.
(59:14) Well, I'm looking forward to to seeing it flourish. All right. Well, thank you, sir. Thanks for the time. Thank you. Peace of love, Freaks. Freaks. Thank you for listening to the show. I hope you liked it. If you did like it, please make sure you subscribe, rate, review the show. It helps us out a lot. And also, if you like these conversations, I've come to realize that many people listen to the podcast.
(59:33) They don't know we have another sort of layer of this media company. We have the newsletter, the Bitcoin Brief. Go to TFTC.io. Make sure you subscribe there. A lot of the topics that are discussed on this podcast, I write about 5 days a week in the newsletter. We also have the TFTC elite tier.
(59:53) If you sign up for that, become a member. We have a private Discord server for the elite freaks out there where we're dropping adree versions of this show and having discussions about everything we talk about a day early. Logan wanted me to make sure if you want to get the show a day early, become a TFTC Elite member. You will get that. We have our Discord server right now.
(1:00:17) conversation between myself and TFTC elite tier members, but we're going to expand that. We'll probably do close Q&As with people in the industry. Uh I may be doing macro Mondays. So, join us. Go to tftc.io, subscribe, find the button in the top right corner of the website, become a TFTC Elite member.
(1:00:39) Thank you for joining us. Okay.
