We Study Billionaires - The Investor’s Podcast Network - BTC227: Bitcoin, Taxes, and Smart Estate Planning w/ Jessy Gilger (Bitcoin Podcast)

Starting point is 00:00:00 You're listening to TIP. Hey, everyone, welcome to this Wednesday's release of the Bitcoin Fundamentals podcast. This week, I have special guest, Jesse Gilgur, on to talk about current events in Bitcoin, estate planning, and smart tax strategies for investors. As you'll see, Jesse is a wealth of information and someone that makes the topic exciting and accessible for the listeners. So with that, let's jump right into the interview with Jesse. Celebrating 10 years.

Starting point is 00:00:30 You are listening to Bitcoin Fundamentals. by the Investors Podcast Network. Now for your host, Preston Pish. Hey, everyone. Welcome to the show. I'm here with Jesse. And we've got a lot to talk about Jesse. We had a pretty fun experience together.

Starting point is 00:00:55 Out in Jackson, we were skiing. And we just happened to be fortunate enough to be out skiing with a couple of Olympians by chance. And I don't know how you felt after this. And we'll talk about this question. quickly and jump right into the content. But this is like too cool of an experience to not talk about. This was nuts to me. So I had skied as a kid and, you know, really haven't skied all that much as an adult. And, you know, we were at a conference. There were some people that were Olympic, like,

Starting point is 00:01:26 Olympic skiers and we just happened to be able to spend the day with them on the mountain. And I don't know about you, but like how I felt after I was done, I told my wife, I said, I feel like I played Russian roulette and won and like made it out of the day alive and didn't kill myself. I don't know how you felt, but I was pressing my comfort. Yeah. Before the record, I was on the Preston side of the keeping up with the Olympians. I was not, you know, one of the Olympians.

Starting point is 00:01:54 And the things these guys were doing were just completely humbling, right? Preston and I, I was pushing myself to my max and they were skiing the same mountain backwards, just relaxing, you know. It was quite an endeavor, try to keep up with them. And yeah, an experience I will remember for years to come. Forever. I remember I called my dad afterwards and it's like, you're not going to believe this experience I just had. But it was, it was miraculous.

Starting point is 00:02:18 I mean, we were moving out. Like how I didn't kill myself that day. I, wow. Yeah. It was crazy. It was crazy. And it's a tough mountain. Jackson is, we're talking to one of them.

Starting point is 00:02:29 They said, oh, favorite in the whole world. He'd seen essentially everything. And that was top of the list for them. So, yeah. Congratulations. We made it out. I can't look at over at you because I knew you were kind of at a similar skill level with me. But wow, that was crazy.

Starting point is 00:02:44 Hey, so you went to a traditional finance conference after this ski adventure we had. Talk to us about this. Like, what was your takeaway? Yeah. So I had a bit of back to back. I did the ski conference. And then I got to go to Austin for the South by Southwest Bitcoin takeover. which is a largely Bitcoin audience, lots of signal and probably names you've had on the show before.

Starting point is 00:03:08 And then right after that went to one of the more well-known Tradify conferences, and it was the complete opposite from a signal standpoint. So I got delayed in the flight, but as soon as I landed, got in the conference, I learned that Michael Saylor was speaking at it. I was like, oh, I've got to catch this. What does Michael Saylor have to say to a traditional finance audience? Got to the stage and seats were a third, maybe half a pack, right? Most people attending other events and Sailor is describing what he's up to with releasing

Starting point is 00:03:35 and arbitraging new products for essentially adding volatility to his stock. Right. And this is breaking the minds of traditional financial advisors. I got to have conversations with them afterwards and they're like, this is reckless. This is a complete scam. He's going to blow everyone up and we need to steer well clear of this. And I'd say the general consensus amongst traditional financial advisors is eight, nine out of 10, like do not go near Bitcoin.

Starting point is 00:04:00 Don't touch it. Don't talk about it. So, hopping from, go ahead. What was the general take at the conference with the current administration and everything that they're doing from like the Strategic Bitcoin Reserve? Is any of that being talked about or is it still just looked at as being this real novelty, weird, he's placating his voters kind of thing? If anything, it's the second.

Starting point is 00:04:23 I would say most people, it's not even on their radar. You brought up the Strategic Bitcoin Reserve. It's the what? And I'm just not, it didn't make it to their news feeds. And then if it did, it's like, oh, that's cute. He's probably placating to some audience and, you know, making some voting constituency happy with a promise, but not taking it as a serious asset. And we just maybe rewind a little bit to what I get to do day in and day out.

Starting point is 00:04:46 I help lead sound advisory, which is Unchained sister company, right? Unchained does Bitcoin products. Sound advisory does wealth management, financial planning for Bitcoiners. And so it's very common for me to see someone who is 50% of their net worth, 80, 90% plus of their net worth already in Bitcoin and using multi-sig key control before they ever even get to us. And then so hopping from that type of Bitcoiner to the traditional financial advisor, there is just a giant gap in knowledge between the two. And I got to see them back to back, like one conference to another and it made me realize like, we are still so early.

Starting point is 00:05:20 There were many conversations I had with advisors. They could not believe the type of, At least they're like the niche that we serve, right? I'm like, oh, that's very interesting. You've got people that are that crazy or, you know, off the deep end. And for us, it's a serious market that needs help. So, yeah, just the juxtaposition, it got me thinking like this is still very, very early. We're not even, used to say second inning. Like, I don't think we're even in the bleachers yet.

Starting point is 00:05:46 Yeah. Game hasn't even started. Yeah. Well, I'm curious, what are they talking about? So the conference is called Future Proof. It prides itself on being innovative, right? We're headed to the future. All of these new things are happening.

Starting point is 00:05:58 And I think the most innovative thing that they talked about was maybe adding AI to record their meeting notes, which is, you know, the Bitcoin content. I mean, Saylor was poking at it. He was very explicit. Like, hey, we are adding volatility to this situation. That makes a traditional 6040 stock bond advisor just cringe. Like, you're doing what? Their phones are ringing off the hook because of a 10% correction in the S&P 500.

Starting point is 00:06:20 Yeah. And so an average investor can't stomach a lot of volatility. And it's something that a lot of advisors shy away from. And so the most common question I got was, I hear all this talk from Bitcoin believers that it's a store of value. Not for me, not for my clients. They're nervous in a 10% correction. And that's a Tuesday in Bitcoin, right?

Starting point is 00:06:39 Yeah. And so I'm trying to help reframe some of those conversations educated by just like, okay, we store value, but it's over 20 years, right? It's not a tomorrow store of value. And I think often as Bitcoiners were so deep down the rabbit hole that we've like carved ourselves into a rut with our language and, things that we say that are just common to us. Most recent one I've been hearing is the Overton window.

Starting point is 00:07:00 No, like a regular person doesn't know. What kind of window are you talking about? Is it like a style or brand? We've got a lot of bridging to do to educate that. I mean, there's over a trillion dollars represented amongst those advisors and what they're managing, right? Billions and billions of dollars, one shop and 1,500 people at the conference. And they're thinking on, they're on the cutting edge of innovation, yet avoiding Bitcoin,

Starting point is 00:07:23 taking it seriously. or I did see a lot of this too. There's so much ego that goes into being an advisor. You have to be right, have a good knowledge and understanding about money. And if you change something fundamental, like, well, I think money is something different now, you're not only wrong to yourself. You have to go explain yourself to 100 plus clients. And so it's a hard, it's an ego death, right?

Starting point is 00:07:46 But if you're going to be an advisor who starts to take Bitcoin seriously, you have to not only change how you approach finance, but you're doing. doing that on behalf of your clients as well. And so I think we've got a long way to go. It's an industry that I think, thinks it's on the cutting edge of innovation, yet they're ignoring something that's often a cornerstone asset for at least my client's financial lives. Yeah. And you know what? If you go to business school or let's say you majored in finance or whatever, they truly define risk as volatility. So when you'd have a guy like sailor on stage saying, well, I'm basically taking Bitcoin's volatility and I'm bottling it up and

Starting point is 00:08:26 turning it into a product for fast money on Wall Street, I'm sure they're just looking at this and be like, this is a madman. What in the world's he doing? What's he talking about? And to even begin to understand it, you first have to understand the core thesis of Bitcoin, which I don't think any, I hate using the word any, but very few even understand that, let alone the building financialization on top of it. Yeah. On top of it, I think, is a great word. because the way I've tried to create a metaphor having this, it's like they have a financial belief structure, right? The way they view creating plans and talking about allocations.

Starting point is 00:08:59 And the base of that is the what is money question, right? It's like a janga tower. And if you start pulling for those low blocks, I'm going to change what is money in your mind and what it could be and how it might be broken, it just makes the whole structure crumbling. There's an instinctual reaction. No, don't touch that question. And you can tell them, look, Fed printed $3 trillion one night. There's the bottom, March 2020, right?

Starting point is 00:09:21 Watch it go straight up, everything, gas, beef, groceries, Bitcoin, gold. Did all those assets get better, March 21st? No. A Bitcoiner is very intuitive. Money's broken. Money is better now with Bitcoin. And a traditional financial advisor just struggles with that low janga piece. There's a cringe when you go for pulling at it, but not that one.

Starting point is 00:09:40 Yeah. It's so commonplace in our community, the Bitcoin community, to talk about how the real hurdle rate is basically like Global M2 that you should be trying to outperforming. form. But I think in traditional finance, I don't even think that that idea or that concept is something that they would, first of all, agree with. Second of all, they'd be like, where's this number that you're, this M2 number? Like, what are you talking about? It's not even. I would agree that. I'd say inflation to a bit pointer is the expansion of the money supply. Yeah. More currency units. Inflation to traditional financial advice is a CPI. Whatever the government tells you. Yeah. Yeah. Yeah. So that becomes their hurdle rate.

Starting point is 00:10:21 voted at three. We got outperform three. S&P does a good job. It's kind of like they're monetized. It's like a token, right? Like, okay, you're going to S&P as like a baseline to outperform CPI over the long term. Yeah. It's wild to me how far, like you said it. We're like still in the bleachers National Anthem hasn't even played yet kind of level of the ball game. And what helps people start figuring it out? Is it just pure price action? Is it, is it Bitcoin going to 500,000 and more people just questioning the narrative or what? Yeah. I've seen a lot of people start and continue their Bitcoin journeys on years and you can't

Starting point is 00:10:57 replace curiosity, right? And so sometimes, and Price does a very good job of instigating curiosity, right? You have a 10x on anything. It's like, whoa, why did that happen? And that can start the digging for some people and they land at different conclusions or they start like an bulk coin phase early in the journey, but it's got to be curiosity. And I've started to communicate with a different conclusion. advisors that are curious, I can't make you a believer in this or I can't make you understand

Starting point is 00:11:26 it. I can give you the information, but you have to, if it's going to be something that you believe, do the proof of work and get there yourself. And so, unfortunately, some advisors are like sitting on a golden goose of a 60-40 stock bond practice, have hundreds of millions of AUN, and they're just not interested in doing much more work. They're going to continue to ride that easy cruise control type of practice. And that's unfortunate. I think if I had a message to clients, you know, you've got an advisor like that, like what are you paying them for? Like what's going on there? So truly. Yeah. Yeah. Think curiosity is something you can't replace, can't teach, and it starts everyone's journey. Let's take a quick break and hear from today's sponsors.

Starting point is 00:12:07 All right. I want you guys to imagine spending three days in Oslo at the height of the summer. You've got long days of daylight, incredible food, floating, on the Oslo Fjord, and every conversation you have is with people who are actually shaping the future. That's what the Oslo Freedom Forum is. From June 1st through the 3rd, 2026, the Oslo Freedom Forum is entering its 18th year bringing together activists, technologists, journalists, investors, and builders from all over the world, many of them operating on the front lines of history. This is where you hear firsthand stories from people using Bitcoin to survive currency collapse, using AI to expose human rights abuses, and building technology under censorship

Starting point is 00:12:49 and authoritarian pressures. These aren't abstract ideas. These are tools real people are using right now. You'll be in the room with about 2,000 extraordinary individuals, dissidents, founders, philanthropists, policymakers, the kind of people you don't just listen to but end up having dinner with. Over three days, you'll experience powerful mainstage talks, hands-on workshops on freedom tech and financial sovereignty, immersive art installations, and conversations that continue long after

Starting point is 00:13:18 the sessions end. And it's all happening in Oslo in June. If this sounds like your kind of room, well, you're in luck because you can attend in person. Standard and patron passes are available at Osloof Freedom Forum.com with patron passes offering deep access, private events, and small group time with the speakers. The Oslo Freedom Forum isn't just a conference. It's a place where ideas meet reality and where the future is being built by people living it. If you run a business, you've probably had the same thought lately. How do we make AI useful in the real world? Because the upside is huge, but guessing your way into it is a risky move.

Starting point is 00:13:57 With NetSuite by Oracle, you can put AI to work today. NetSuite is the number one AI Cloud ERP, trusted by over 43,000 businesses. It pulls your financials, inventory, commerce, HR, and CRM into one unified system. And that connected data is what makes your AI smarter. It can automate routine work, surface actionable insights, and help you cut costs while making fast AI-powered decisions with confidence. And now with the NetSuite AI connector, you can use the AI of your choice to connect directly to your real business data. This isn't some add-on, it's AI built into the system that runs your business. And whether your company does millions or even hundreds of millions, NetSuite helps you

Starting point is 00:14:40 stay ahead. If your revenues are at least in the seven figures, get their free business guide demystifying AI at net suite.com slash study. The guide is free to you at net suite.com slash study. NetSuite.com slash study. When I started my own side business, it suddenly felt like I had to become 10 different people overnight wearing many different hats. Starting something from scratch can feel exciting, but also incredibly overwhelming and lonely. That's why having the right tools matters. For millions of businesses, that tool is Shopify. Shopify is the commerce platform behind millions of businesses around the world and 10% of all

Starting point is 00:15:21 e-commerce in the U.S. from brands just getting started to household names. It gives you everything you need in one place, from inventory to payments to analytics. So you're not juggling a bunch of different platforms. You can build a beautiful online store with hundreds of ready-to-use templates, and Shopify is packed with helpful AI tools that write product descriptions and even enhance your product photography. Plus, if you ever get stuck, they've got award-winning 24-7 customer support. Start your business today with the industry's best business partner, Shopify, and start hearing sign up for your $1 per month trial today at Shopify.com slash WSB.

Starting point is 00:16:03 Go to Shopify.com slash WSB. That's Shopify.com. slash WSB. All right. Back to the show. The thing that continues to just boggle my mind, and it's boggled my mind for years and years is everybody that's gone to business school, everybody that's a financial manager, they know that you control the volatility, quote unquote, risk with position size. And so, right?

Starting point is 00:16:31 But it seems like when you look at Bitcoin and you look at its performance and you say, well, why don't you own one or two percent? You even have BlackRock now coming out and saying they think it's appropriate for a 2% position. This was literally in Bloomberg probably two months ago or I think before Christmas that there was a Bloomberg article that came out and BlackRock thinks that a 2% position size in Bitcoin is responsible. Has large cap financial companies like BlackRock saying these types of things, do you think that that's slowly starting to make an impact or is it still just kind of like. Yeah, few words slowly, right? Out of the 50, 60 advisors I talked to, I'd say like three are curious and starting to open the door in a reasonable way.

Starting point is 00:17:19 Let's put another 10 in, okay, I could consider that, but if I'm going to buy Bitcoin, which Bitcoin, right? Like, they still got the blockchain alt-coin, lack of understanding there and not, most advisors don't want to have to apologize for something, right? Yeah. And so if they stick their neck out for anything, even a 1, 2% idea and they got to explain to the client why they're putting it in portfolio. And then it goes down by half or to zero. They'd just rather not do it at all.

Starting point is 00:17:46 What I'm doing works well enough to keep the client happy and not calling. And I have to meet with them two times a year, continue to collect my 1%. That's the apathy that I think exists in too big of a chunk of the triad five. One of their current event topic that I would love to cover before we get into some of the top. questions you get as a retirement planning expert. Did you see this stuff with invidia that came out this week with all the robots and the AI and, oh, you haven't seen this? Oh, no, not the new cell. Oh, my God. What has they doing? Well, so Nvidia just comes out. And I mean, they are just going to town on providing GPUs and software interface for basically

Starting point is 00:18:29 pushing robotics at a pace that's like humanoid robots at a pace that I think is way, and then anybody's anticipating to the point where I'm hearing trials in factories this year, maybe even home testing, developmental testing this year, and maybe even by next year some initial prototypes going into homes, they're able to accelerate the learning through simulated environments, that 10x, the speed at which the robots can learn, the way that they're moving, the battery technology, like all of this stuff. And I'm just looking at it and I'm saying to myself,

Starting point is 00:19:04 I can't even imagine how deflationary this is going to be from a technology standpoint in the coming five years. And the amount of Fiat printing that's going to have to be conducted to offset the technological deflation that this is causing. And the dislocation and like all these other things. And I'm just like I'm watching all this in video. Maybe it's because I put a lot of this in my Twitter feed that I'm seeing a lot of it may be more prevalent. That makes sense and breaks my mind at the same time. Right, because if you imagine where we were at with chat GPT two years ago, yeah, it's like, okay, well, this is kind of cute in a tool and look what it can do.

Starting point is 00:19:39 And now I'm seeing regular people, like, use it as a necessary tool in their workflows now. You can't get rid of chat GPT that, you know, I'm reliant on it. And that was the software side. And now you're talking about hardware and, yeah. Yeah, mechanical engineering and like, okay, well, if you take the growth of what's happening in software and you showed me in Jackson, like, watch me speak Korean. I don't know how to speak Korean at all, but here, I'm going to have some Michael Saylor commentary,

Starting point is 00:20:06 and it's going to take all of that content, change how my lips move, and then you gave it to your friend who was fluent in Korean. He said, it's perfect, right? Yeah. And the software combining with the hardware, I can't even imagine how much the world's going to change. And he said, five, I've got to live 10, 20, hopefully 30 more years. Like, where does it all go? And it touches on that Jeff Booth idea.

Starting point is 00:20:29 Like, it's going to create so much productivity. which is going to cause deflation. And that's the kryptonite to the Fiat system, right? And so. Yes. This is what the trade fight, if I had a big gripe, this is the thing that I don't think all those people in the room that you were there at this conference understand is that the technological deflation is an exponential curve.

Starting point is 00:20:52 And it builds, and this goes that Jeff Booth's thesis that so many Bitcoiners talk about is like the 50th fold of the piece of paper gets you from the earth's surface to the sun because it's exponential. And when I'm just looking around at AI and I'm looking at robotics and I'm saying the amount of printing that they have to do to offset this is just miraculous. It's out of our comprehension just within five years. And I just want to be able to scream it to the rooftops of traditional finance. Like, wake up. You have to see this. Like, there's no way they're going to be able to mask this any other way than just printing like tons of more monetary units. But And that was really when I started taking Bitcoin seriously in clients' financial lives, right?

Starting point is 00:21:36 When they, in March 2020, created those new currency units to expand the system, you had something to point to, right? I was in a situation where I got a stimulus check at that time. Jove that puppy straight into Bitcoin. Encourage clients to do something. Which, by the way, is what amount now? It's like 20,000. Oh, geez, I haven't checked on it. It's like, I'll look it up while you're talking about it.

Starting point is 00:21:56 There was a $1,200 check and I want to say it. Yeah. I know mine was 1,400. So I don't know. 14. Okay. And maybe the point I was getting to within that is when they inject, they have to choose how and who.

Starting point is 00:22:09 And that's inherently an unfair process. In that month, they were buying Apple corporate bonds. There was the PPP loans for business owners. And then there were stimulus checks for, let's call them the place, right? The common folk. And it was just a whole set of rules that was created and then injected. And I think for the first time you saw when the new money units are in, injected into the lower socioeconomic ends of the population, that's where you're getting the

Starting point is 00:22:35 grocery store inflation, right? If you just injected into banks and Apple bonds, you're not going to see beef be affected as much as capital assets, right? And so I was paying attention to injection site, like, okay, they got to print new money. Where's it going to go? And that can't an effect is not a straight line, right? It filters and flows through the kind of over years, and it has ripple effects. And so the printing that got done was still under a Trump one administration. But then all this price inflation is like trickling through into the Biden administration and people like, oh, it's Biden's inflation. It's just not intuitive to people that, okay, money gets injected, three trillion one night. People didn't change the list price on their

Starting point is 00:23:18 house the next morning, right? It takes years to trickle through. And it's not fair. You can't choose how it happens. And it is going to happen again. And so I guess the, But that's a question. I kind of want to ask you, like, how big do you think the next Federal Reserve balance sheet expansion is going to be? Yeah. Your point on the frequency or the lag factor of the input versus the output is so on point and so important and so lost on so many. By the way, the stimulus, if you got a $1,200 stimulus, it's now worth $12,000. It's 10x in value since they mailed those out if you would have taken all of it and put it into Bitcoin. My answer to that, I'm sorry, help me remember the...

Starting point is 00:24:01 Oh, it was a cheap shot question. How big is the next print? Oh, yeah, yeah. The way I would go about answering this would just be, you know, look at the growth rate of the global M2 and the U.S. is printing at about 8 to 10 percent annualized and it's been very flat for three or four years. This is another point on how much do they got to print. It depends on how much of that deflation of the credit.

Starting point is 00:24:25 How much of that credit do they allow to be soaked up or to go poof, all the promises? How much of that do they allow to go poof? And for how deep do they allow that to go? Also plays into how much they've got to print in the immediate term to get it back on track with that 8 to 10% growth rate. So if they don't ever allow that impairment to really kind of play out in the credit markets and they just continue to like juice it, then the print is just going to continue to take, you know, whatever 8 to 10% of the current nominal growth rate is, and just figure that out. But if it contracts, like what we saw in 2020, like, that was really a sharp reaction to COVID.

Starting point is 00:25:03 And so the amount that they put into the system was, I would say, a little bit extra than what they probably needed to. But I think that if you're looking at it from that, the speed at which they're able to bring. Yeah, the speed, their response has become quicker. So tarp was what, wait, and tarp was three months. COVID was like three weeks. Yeah. And then the bank's breaking.

Starting point is 00:25:22 You know, I think they did that over a weekend, right? like Silicon Valley Bank and, you know, over it was broke on Friday and made whole on Monday. That's a perfect example of why it's so hard to predict the next amount that's going to be printed is because look at Silicon Valley Bank. Perfect example. Died on a Friday, was reinvigorated before the market open on Monday, and everything just kept chugging along. Yeah, it's like nothing to see that weekend. But if they would have let that play out for, let's say they didn't do anything and they took their hands off the controls for two weeks. could you imagine the amount of the dominoes would just start the impairment would have just cascaded through the entire global economy and then they would have had to have printed a lot more to offset that versus how they responded to it. So it's a little bit of a fool's errand to answer

Starting point is 00:26:08 a question like that because you just don't know how long they're going to allow the impairment to play out. But I think that if you're looking at it on a net long term basis like over how much are they going to print in the next five years, I think you can actually figure that out pretty closely to by just looking at the chart and just kind of doing the math of that growth rate. Now, whether this robotic stuff will accelerate the technology deflation, I don't know, but AI, I don't know, but yeah. And it's that it's feedback for too, right? The more they do, the more they have to do. Yeah, big time. Yeah. It's crazy. All right, so here's my question for you. Okay. What's the number one question that you hear? Because, you know,

Starting point is 00:26:48 with like ego death, we, when I'm talking to an LP, I can tell you the number one question I hear like, how do you outperform Bitcoin? That is the question. That is the question. So what's your number one question? You hear. You nailed that, by the way.

Starting point is 00:27:02 It's a twofold set of problems. So typically, I'll just tell you the tip of it was a husband and wife coming in. This isn't always, but the husband is more the technical bitcoiner and very curious on if there's tax savings to be had. So tax is number one. That one's typically the primary technical bitcoiner in the family wants to save money

Starting point is 00:27:21 so they can buy more Bitcoin, the less technical spouse is looking at that guy and saying, well, what if I do if he smokes out, right? Like, I'm on board with the Bitcoin. I'm not involved in the finite, but if something happens to him, health, you know, or otherwise, God forbid, I'm not confident that I know what to do or if I also want to talk to. So it's twofold. It's like a tax and inheritance one, two punch. And then maybe a third as a backup is like, well, if we're right about Bitcoin,

Starting point is 00:27:47 then I'm going to have a new set of opportunities or choices. So how do I like dial back maybe the work I'm doing or pivoted to something else? So can you save me money on taxes? Probably the number one question and that's a deep and customized question. Inheritance is pretty standard, especially in couples. I believe in my spouse and I'm on board with Bitcoin, but I'm not as technically confident or no, I don't know I'm going to be okay if something happens. And then once those two are solved, we start looking at the future and what transition scenarios

Starting point is 00:28:17 might look like. So I'd say that's the most classic. Let's talk the tax piece because I know that you said this gets very nuanced to the individual. But if you would take, let's say you have a person, their net worth is $500,000, how would you walk them through the tax implications and how to think about it? Yeah. So there's a couple different components to tax. And I'd say the two big ones that are just highly dependent on who you are in your financial situation is going to be income tax. I make money every year and have to pay taxes on it, and then estate tax, which is kind of the net worth one that you are poking at. I've got this much money. And the way the tax law is currently structured, if you die with too much, that's the death tax, right? Government comes in and takes a quick,

Starting point is 00:29:01 it kicks into 40% really quickly. And so if death tax is in play, that's a huge needle mover. We're often, we're looking at hundreds of thousands, if not millions of dollars taxated. Bitcoiners are unique because even the person that's at a $500,000 net worth, thinks they might be in some measure of time, like, oh, yeah, well, I'm going to the moon. And so I might have the death tax as a problem. So it's something we're always paying attention to regardless of net worth. Right now, those numbers are about $14 million per person. So $28 million net worth for a couple.

Starting point is 00:29:37 That's part of the Trump tax bill. That sunsets this year. If they don't change any rules, gets cut in half to $7 million per person. So coming down from 28 for a couple down to 14. Yeah. And just depending on the uniqueness of your situation, if you see a net worth and like those two, that perfect storm collides, like, well, I might be over 14. And if this sun sets, it's nuanced. It's a little bit complicated. And we're talking about two different structures that we can move the needle in. So when you present net worth, that makes me think, which tax are we talking

Starting point is 00:30:06 about, right? Is it I pass away and I had too much money. So now I'm taxed and pay half to the government. That's a big one to avoid. The more common one, I think, that applies. to everyone is income tax, right? I've got a rental properties or W2 or sold a business. And that tax is experienced every year. You're not having the death tax every year, hopefully. And the income tax, that's a different one, a little more unique. I would say if I could answer the question quickly for you and then kick it back to any follow up, the three biggest needle movers we have as bitcointers within the income tax are going to be a good understanding of your basis to do both gains and loss harvesting, right? In a pullback, you can do lost harvesting, but there's also gains harvesting. There's a

Starting point is 00:30:48 zero percent capital gains tax bracket. Some people live in zero percent tax states. So if you can go get and sell a Bitcoin and pay no tax, sometimes you can do that and just buy it right back and give yourself a higher basis. Help us understand where that would apply. So we'll take someone who is at $100,000 a year of income as a couple, right? Husband wife make $100,000 a year and they don't have any other complexity in their tax situation, the 0% capital gains rate goes up to about $130,000 for this year, 2025. I'm using round numbers here. It's a little more specific.

Starting point is 00:31:25 But there is a situation. If that couple lives in one of the nine states that have 0% tax, they can sell $30,000 worth of gain in Bitcoin and then buy that Bitcoin right back in the very next second. That is a capital gains harvest. And they're not going to pick up any tax for doing that. They're still within the 0% federal window, 0% state. What they can do is sell where are we at today, 85,000. So let's pick, they bought Bitcoin at $55,000, $85,000 today.

Starting point is 00:31:55 I'm going to sell the $55,000, buy it back for $85,000. And I just improved my basis and future tax situation by that much for free. So that's one to pay attention to do. That's outstanding. Just quickly the other. Yeah, I love that. No, I love that. That's outstanding.

Starting point is 00:32:11 The other two are going to be donor-advised funds. So we have a lot of clients who are charitable. It's kind of just fix the money, fix the world idea, and we're often identifying their lowest basis Bitcoin and using that within their tax situation to get write-offs, right? You can front-load that. And they can continue to hold the Bitcoin. It doesn't have to go straight to charity.

Starting point is 00:32:33 They just leave it in a structure where they can continue to hold it, let it grow, give it to charity one day. We've saved hundreds of thousands, if not millions of dollars by doing that for folks. And then the third one is going to be Roth conversions. Roth IRAs being tax-free. Bitcoiners love the idea of tax-free. And so if we can get Bitcoin into a structure that without tax law changes, by the time they want to use it, they can do it without having to pay taxes,

Starting point is 00:32:58 that's a big one. So that is pretty nuanced in looking at the current bracket and how much can we get from traditional to Roth IRAs or we build a Roth IRA from scratch. But in general, those are the three quick answers of like real needle movers. There's other more peripheral ones, but tax gain, tax loss, donor advised funds, and charitable gifting, and then Roth conversion. Let's take a quick break and hear from today's sponsors. No, it's not your imagination.

Starting point is 00:33:23 Risk and regulation are ramping up, and customers now expect proof of security just to do business. That's why VANTA is a game changer. VANTA automates your compliance process and brings compliance, risk, and customer trust together on one AI-powered platform. So whether you're prepping for a SOC 2 or running an enterprise GRC program, VANTA keeps you secure and keeps your deals moving. Instead of chasing spreadsheets and screenshots, VANTA gives you continuous automation across more than 35 security and privacy frameworks.

Starting point is 00:33:56 Companies like Ramp and Ryder spend 82% less time on audits with VANTA. That's not just faster compliance, it's more time for growth. If I were running a startup or scaling a team today, this is exactly the type of platform I'd won in place. Get started at Vanta.com slash billionaires. That's Vanta.com slash billionaires. Ever wanted to explore the world of online trading but haven't dared try? The futures market is more active now than ever before, and plus 500 futures is the perfect

Starting point is 00:34:30 place to start. Plus 500 gives you access to a wide range of instruments. S&P 500, NASDAQ, Bitcoin, gas, and much more. Explore equity indices, energy, metals, 4x, crypto, and beyond. With a simple and intuitive platform, you can trade from anywhere, right from your phone. Deposit with a minimum of $100 and experience the fast, accessible futures trading you've been waiting for. See a trading opportunity, you'll be able to trade it in just two clicks once your account

Starting point is 00:35:01 is open. Not sure if you're ready, not a problem. Plus 500 gives you an unlimited risk-free demo account with charts and analytic tools for you to practice on. With over 20 years of experience, Plus 500 is your gateway to the markets. Visit plus500.com to learn more. Trading in futures involves risk of loss and is not suitable for everyone. Not all applicants will qualify. Plus 500, it's trading with a plus.

Starting point is 00:35:30 Billion dollar investors don't typically park their cash in high-yield savings account. Instead, they often use one of the premier passive income strategies for institutional investors, private credit. Now, the same passive income strategy is available to investors of all sizes thanks to the Fundrise Income Fund, which has more than $600 million invested in a 7.97% distribution rate. With traditional savings yields falling, it's no wonder private credit has grown to be a trillion dollar asset class in the last few years. Visit fundrise.com slash WSB to invest in the Fundrise Income Fund in just minutes.

Starting point is 00:36:11 The fund's total return in 2025 was 8%, and the average annual total return since inception is 7.8%. Past performance does not guarantee future results, current distribution rate as of 1231, 2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the income fund's prospectus at fundrise.com slash income. This is a paid advertisement. All right. Back to the show. If a person was a lot of people hear about having their own trust, at what point would you start recommending this for somebody, a self-directed trust or self-directed

Starting point is 00:36:50 IRA through a trust? Help us understand how you think through some of these mechanics. Yeah. So there's a couple of nuances within there. And I want to be clear on what you're asking about trusts, which are typically more for like asset protection and don't necessarily need to be IRAs. And then there's IRAs, a subcategory of IRAs is like the self-directed where a lot of early Bitcoiners had to use that structure to hold Bitcoin in an IRA. So which one you pull? Both of those.

Starting point is 00:37:20 Sorry. Okay. Yeah. Yeah. Okay. So I think we'll do the IRAs one first because early on in Bitcoin, there wasn't a great way to like hold your own keys for a Bitcoin. and have it be tax-advanged.

Starting point is 00:37:32 And so what happened is you'd set up what's called a checkbook IRA, right? It ends up being IRA owns this LLC, and then the LLC is a business, and they can go hold Bitcoin on its balance sheet. And so people or Bitcoiners to have key control, they do this checkbook IRA structure. Or, hey, I'm going to have the IRA. It's going to own the LLC. The LLC is going to go buy Bitcoin, and I'll hold my keys in that. And I would say that's probably one of the earliest ways you saw Bitcoin in IRAs.

Starting point is 00:38:00 Now there's far more products and options, right? Whether you would just want to be the ETF on Schwab or Fidelity, I helped develop when I was at Unchained for a few years. They have a two of three multi-sig IRA, right? Where clients still holding two keys. Unchained holds the third. They use their third to keep you compliant from a reporting perspective. So because they have a key in the setup, they can watch if the Bitcoin ever leaves.

Starting point is 00:38:25 That's the mechanism they use to keep you compliant as an IRA. And so there's far more options now. And I think it's rare for me to see a checkbook IRA, but they still do exist like anything. There's trade-offs, the structure. So I don't want to rabbit trail too much on that. And then how about just the trust in general? Yeah. This is more of an estate planning and inheritance question.

Starting point is 00:38:47 Trust can hold assets, wills cannot. So when you look at doing your estate planning, say, hey, I want my kids to be taken care of by, you know, Grandma Suzy and I want the dog to be taken care of by someone else because She does, you know, you can do everything you want within a will, but a will can't hold Bitcoin for you. When assets are transferring to inheritors, you often want to trust. And this is a 50 statewide question. I'm not an attorney. Attorneys have to write trust.

Starting point is 00:39:16 But I'll brainstorm this with clients because the three big things that Bitcoiners don't like when they hear what I'm about to say is the state can be involved with how your assets are transferring to your errors. You don't have that set up. So if you've got Bitcoin and you bought it in Preston's name, right? I'm Preston. I bought Bitcoin. Something happens to Preston and that Bitcoin is supposed to go to your wife, depending on how you're set up, the state you live in could be involved. That is a process called probate.

Starting point is 00:39:42 It's often very slow, can be expensive. And the big one that Bitcoiners don't like is it's public record. Hey, Preston's wife got this many Bitcoin on this day. That's an avoidable situation. And so a trust is that mechanism that can hold assets. I'm Preston. I'm going to set up a trust. My wife is going to be a co-trustee to that trust.

Starting point is 00:40:04 And we are going to put the Bitcoin from my Preston name into the trust. That is a non-taxable event, like going left pocket to right pocket. Now the trust owns the Bitcoin and there's still key control structures available to do that. Then if something happens to you, your wife is just the co-trustee the next day. Not going through the state. No one needs to know. It's next day access and it really keeps her above board, right? She doesn't have to document, well, how'd you get this Bitcoin?

Starting point is 00:40:31 She's able to find your keys like in a single signature setup, hey, it's unfortunate, pressed and passed, but I got the keys. She's going to bring that into a financial service at one point to sell it or take a loan against it and they might ask, well, how did you get this? And you can save a lot of that pain up front by just, hey, let's title this correctly. We don't have to make sacrifices in our key control setup. We just need a good legal wrapper around us to avoid really the state getting involved in having their say.

Starting point is 00:41:02 Yeah. And what net worth or like what would be the metrics that you would tell somebody that that that's common? I don't think that one's tied to net worth at all. So that situation we described is called like revocable living trust. Yeah. Revocable meaning I can take it back as long as I'm living. Right.

Starting point is 00:41:17 And so revocable living trust often called a family trust. You can put assets into it, take it back out. That is something that everyone should consider currently, regardless of net worth. I would say some of the more automated legal zoom type options can be a few hundred bucks, meeting with an attorney's probably between $3,000 and $10,000 to get it done. And you're getting your basic set of documents taken care of that you can still make changes to. And so that one, in my opinion, doesn't have a net worth trigger like some of the more advanced trust. to the more advanced trusts are called irrevocable, which means no takebacks. And the big reason

Starting point is 00:41:55 you're doing that is for asset protection or to avoid that death tax that we talked about earlier. Okay, I'm over that 14 or 28 million. Let me use that number now and get the Bitcoin out of my estate into this trust that I no longer control. And so you set up that type of trust with a lot more intentionality and due diligence. And you're usually not exploring that until you're on the the 14 or 28 or whatever it decides to be next year. Yeah. Let's talk the technical risks that you say come up in, you know, these initial meet and greets that you have,

Starting point is 00:42:31 that one of the two bring up that they have concerns if the other one passes to be able to manage the keys. How do you go through this? I mean, when I'm thinking about this, I think about on one extreme you have like my grandmother, there's no way she could ever do anything with Bitcoin keys without having somebody do all of it on her behalf. So buying something like an ETF or somebody of that technical competence seems to make more sense.

Starting point is 00:42:59 And I know that that's not a popular thing to say in the space. How do you go about talking about it? It might not be popular, but I think it's right. Take everyone for where they're at and try to get them the best thing that fits them. So unfortunately, we had a client passed last year in its 80s and surviving spouses in her 70s. He was holding his own keys. She doesn't want to have anything to do with that. And so in some ways, we have to ask the question like, is, quote unquote, going backwards

Starting point is 00:43:27 the rest of the right? We were holding keys and now, but she's very nervous and it's tough for her to feel comfortable with, she likes Bitcoin. Her husband believed in it. She feels almost this urge to carry on, you know, in his name with the asset, but maybe the ETF is a better fit for now or at least we can choose a little bit of each, right? And we just have those discussions and figure out what might be right. As far as ETFs go, it's common for us to divide amongst the custodians, Coinbase Honeypot.

Starting point is 00:43:56 I think they're helping out eight or nine of the ETF. Spide already runs their own custody and then a Gemini runs Van Eck. So if we use ETF, like, hey, let's maybe spread across these custodians to diversify against the hack a little bit. Yeah, what are your thoughts on the Coinbase honey, quote unquote, honeypot? Oh, they hold a lot of ETF coins. Yeah. I think there are a lot of micro-stratities coins. I don't know where America is going to hold its coins.

Starting point is 00:44:22 Within that summit that we went to in Jackson, I heard them called the gold standard for Bitcoin custody. And what I see with, we'll just call them Bitcoiners on the street, it's like, it's not the gold standard of how many Bitcoin maximalists would trust Brian Armstrong with their private key? Yeah. I don't know. Not a high percentage.

Starting point is 00:44:43 Yeah. And so that looks like a big risk. to me. And I have Bitcoiners, don't say that. Don't jinx it. We saw Mount Gox. We've seen the Xx. We're looking at what a honeypot could be. They're holding between those three entities, it's over a million and a half Bitcoin somewhere around there. The ETF's my strategy in potentially America. I don't know. And so I'd like to see coins leave Coinbase slowly rather than all at once, right? Yeah. If a million Bitcoin leave in a night, that's a bad year, potentially decade for Bitcoin, if we can have better custody options develop and be adopted

Starting point is 00:45:21 over 10 years and Coinbase doesn't have to have a catastrophic event, that would be a preferable outcome. I think the SAB-121 and this request for in-kind redemption is all a positive direction to remedy some of this, what you're talking about. I just don't know the pace at which it would play out. Yeah, because that would allow banks to be like, hey, we're going to redeem the ETF at Coinbase but then they still have to come up with their key control model, right? What does Chase Bank running cold storage multi-sig look like?

Starting point is 00:45:51 I don't know. I don't know. How much work have they done from that perspective to make sure that that's secure? So, yeah, I'd like to see maturity in the industry. Competitors develop Sab 121 and or in-kind redemptions would help make it easy to transfer some of the ETCF coins at both square. Yeah, no doubt. You had mentioned that the third thing that sometimes comes up is this.

Starting point is 00:46:14 discussion around like, well, what do we do if we're right? I don't know. No, it seems more like a philosophical discussion with purpose. And I'm just kind of curious to hear your thoughts on some of that. Like, hey, we're 10, 15, 20 years into the future. Let's say you're very right about all of this. And it changes your life. Like, you know, for some people that-

Starting point is 00:46:38 I get to see it, right? I work with clients who started in 2012, 2013. Yeah. And exactly that happened, right? This used to be a nominal amount and now it's grown into a life changing amount. Yeah, life changing amount. And what if that happens again. So what I've already seen if it compounds, right, we're folding the paper and you're going

Starting point is 00:46:56 to be presented with opportunities that you've never seen before and simultaneously problems that you've never encountered before. For a lot of people, I didn't know what death tax kicks in at $28 million. So I encourage them, hey, do your moon math and figure out when this matters. I've seen some Bitcoiners, like, well, my answer is to just go underground. I'm going to do the no KYC thing and I'll make my family go dark for generations. Okay. Or with some planning and intentionality, you can choose to stay above board and just have

Starting point is 00:47:28 good structures and a strategy in place. So it being exponential, and if you're right, in 10, 15, 20 years, you're presented all this new opportunity from a time and energy perspective, like how you make work optional and what you focus on, what matters to you. I do see a trend of fix the money, fix the world. As Bitcoin has happened to people, it unlocks that fixed the world side of them. And they start caring about causes and want to use their Bitcoin for that. So that's exciting to partner with.

Starting point is 00:47:56 And then, yeah, just the problems that wealth brings. I've got to meet, in my opinion, some very, very wealthy people on this journey. And they are not problem free. I just have a different money problem. Yeah. So it's a fun job getting to see the whole spectrum, right? It goes early in the journey and ones that it's already happened to. What would be the strokes for different folks?

Starting point is 00:48:17 What would you say is the one bit of advice you'd like to leave with the listener as they think through some of these things? I think the biggest piece of advice is your situation is not like anybody else's. And I'll bring Saylor back into this. Another common question, I guess, I'm told to never sell my Bitcoin, right? Michael Saylor said to never sell my Bitcoin. Well, Michael Saylor is getting zero percent debt and arbitrage of a convertible bond market that we have no access to, right? And so he's playing a different game and his needs are going to be

Starting point is 00:48:46 met incidentally. Like they're a rounding error of his life, right? He's operating in a different threshold. So don't play somebody else's game. Yeah. You go on Twitter and to see all this advice, do this, this, and this. Often someone's speaking from like, hey, here's the game I'm playing and how I want, you know, I'm a revolutionary. I'm going to die on the fill and I'm never selling my Bitcoin. Yeah. Talk to a 62 year old couple. They're retiring. And are they in that same spot, right? Are they a revolutionary? No, they're not going to work. They want to have a calmer experience than what Bitcoin's volatility has traditionally brought most folks. So it can be tough, especially within, if we are in an echo chamber, right? We're saying those words to ourselves,

Starting point is 00:49:25 you can get caught up playing somebody else's game. And you think you're making good financial decisions because that's what a community or a signal could be telling you, but they're not playing your game. They don't know who you are. They don't know if you have a wife or kids or what your job looks like and or that you just sold your business and you've got to pay a bunch of taxes. They don't know any of that. And so only you are in your shoes. You can reach out to people that work on this. Like, that's why we built sound advisory. I got the question. Before sound advisory launched, I got that question all the time at Unchained. He said, what should I do? Oh, I can't say should, right? You hear it all the time in every podcast. Not financial advice. Go talk to your guy. There weren't

Starting point is 00:50:01 many good guys or people in the space that could answer that question for folks. And so that's what we look to do is just be a sounding board, understand Bitcoin deeply, and try to give advice that makes sense for Bitcoiners and like be a partner with them in the game that they're playing. Love this advice. Love this advice. Because you do. You see it on Twitter X all the time where people are actually like getting in fights and arguments over.

Starting point is 00:50:27 No, that's not. And it's like, no, everybody has a different like life circumstance that they're dealing with. And I just really like that point a lot. You mined a little bit for three years and I'm curious what your takeaway, like looking back at the experience, what was your takeaway with mining for three years on your own? So I mine out of my garage and heat my house. So in the winter, I think we kick it on around October and I just above the fridge, popped a vent through the garage and then just pump it out into the entryway.

Starting point is 00:51:00 I live in Idaho, so it's cold, right? Often be like single digits or the teens. And so we just keep it on all winter. It's not an advanced setup, but it was heating the house for about $8 a day in electricity, and at the time, maybe making $6 to $7 a day in Bitcoin. So more of a nerd hobby, but fun. And I see the conversation starting around heat reuse, right? Yeah.

Starting point is 00:51:23 For so many of these mega-scale miners, they're looking for cheap electricity costs and then doing just massive scale, right? And a lot of heat is the output and it's valuable. And I saw that just personally. I'm like, I could either run the heat pump, which is really expensive and doesn't make Bitcoin, or can run the miner and like get some Bitcoin alongside. And so it's just completely on grid. We weren't getting any sort of special rate or anything.

Starting point is 00:51:48 But I'm very encouraged to see, you've seen the prototypes of like the hot tub, right? We're going to heat the hot tub with Bitcoin and talking to another Idaho locally. He's like, I want to keep my driveway and I want to eat my pool. And if it makes Bitcoin all the better. And I just think that's energy that's changed from electricity into heat is often being wasted by miners. And it could be injected into so many homes, right? Water heaters, there's just a deep need for heat. I was chatting with someone on a plane who did get, it got Bitcoin a little bit.

Starting point is 00:52:21 I'm like, very curious to see miners migrate in winter. Like, they go from North America to South America for the winter just because that's where the heat is needed. I don't know if that'll happen, but yeah, there was a joke there with chicken. and eggs six. And it was a good joke, right? Like, maybe we'll see minor migration if he becomes more valuable. If you could look at it objectively from the typical person that's wanting to do this at their house and the technical competence required and the operational and maintenance,

Starting point is 00:52:50 like you just told me before we started recording that you were on quite a few trips in the past three weeks and being away from that, how likely do you think something like this coming into the home is? And like, what kind of timeline do you think something like that? that might occur. Oh, goodness. If they built, so I've seen like the heat bits and there's an industry that's poking at the user interface of it all, like making that easier.

Starting point is 00:53:13 It wasn't too difficult. Like I am not an electrician or an engineer. I don't know how to code at all. And I just opened up my panel, ran a wire over, plugged it in, and I was able to jerry rig it. I'm confident that others could, but I think the industry making it plug in play is just a very, that's a curiosity. I think I have that.

Starting point is 00:53:33 Okay, well, what if you could just buy a water heater at Home Depot that has A6 using to heat the water? Yeah. Have it all point to an address or a wallet and it's not too difficult and your water heater goes out. It's like, are you going to buy the one that mine's Bitcoin or doesn't? They cost the same. You're going to choose the one.

Starting point is 00:53:49 And I think that'll just start to infect the need or heat market. Yeah. It's exciting to just see the potential. Yeah. Jesse, if people want to learn more about you or Sound Advisory, give them a handoff. Yep. So we can be found at the Soundadvisory.com. That's T.H.E. Sound advisory.

Starting point is 00:54:10 You can book an intro with our team. We're three advisors, two CPAs doing taxes in-house for folks. I'm at Idaho Hoddle on Twitter. And then other folks on the team. So Bonn, Kellerman, Malcolm, I'm sure any of them would be happy to have a follow. So reach out, say hi. If you've got questions, that's what we're here for. All right. We'll have links to all this in the show notes.

Starting point is 00:54:30 And until next time, hopefully we can be as lucky as we were this past time in Jackson, not killing ourselves on the slopes. Boy, I had a blast with you, sir. So thank you for making time and coming on the show. Yeah, thank you for having. It's a real good honor. Thank you for listening to TIP. Make sure to follow Bitcoin Fundamentals on your favorite podcast app and never miss out on episodes.

Starting point is 00:54:56 To access our show notes, transcripts or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only, before making any decision consult a professional. This show is copyrighted by the Investors Podcast Network. Written permission must be granted before syndication or rebroadcasting.

We Study Billionaires - The Investor’s Podcast Network - BTC227: Bitcoin, Taxes, and Smart Estate Planning w/ Jessy Gilger (Bitcoin Podcast)

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.