BTC217: MicroStrategy 2025 w/ Jeff Walton (Bitcoin Podcast)
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Hey everyone, welcome to this Wednesday's release of the Bitcoin Fundamentals Podcast.

On this week's show, I bring back a very popular guest with Mr. Jeff Walton to talk about MicroStrategy and what we might expect to see in 2025. About a year ago, Jeff and I had a discussion about the company and what Michael Saylor was doing back then, and right now, maybe even more interesting than last year. Recently, MicroStrategy has announced an initiative to acquire 21 billion more Bitcoin through equity issuance and 21 billion more through fixed income for a total of $42 billion worth.

Not only this, but MicroStrategy is now a Bitcoin development company amongst many other initiatives that have it as one of the top common stocks on the planet, even outperforming Nvidia since he was focusing on Bitcoin back in 2020. This discussion is a whopper. So sit back, relax, and enjoy this chat with Mr. Jeff Walton.

You are listening to Bitcoin Fundamentals by the Investors Podcast Network. Now for your host, Preston Pysh.

Hey, everyone. Welcome to Bitcoin Fundamentals. I'm here with the one and only Jeff Walton, and welcome back to the show, man. Oh my goodness. It's been almost a year since we've chatted last. So welcome back. Thank you very much. Yeah. Excited to be here. Thanks for having me back. Some exciting things going on in the market right now. So Jeff, I was trying to prep for this discussion, and I went back and I looked at our last time we talked. Very well-received from everybody that was viewing it.

And there was tons of questions that I started looking through the comments. I hadn't looked at the comments on this interview since we did it.

And I was looking at these comments and it was interesting. There was a lot of people asking, what in the world does it mean when you guys are saying capture the spread? And so some of those things we'll talk about. One of the really funny things that I saw was you and I were having this conversation about, do you let this premium above the treasury blow out and then capture the spread? Or do you do it just as much as you possibly can?

And what's so fascinating is he was issuing some common stock. And I'm sorry, folks, we're just jumping right into this. We're just going right to the meat, right? Let's get in. When we first started talking, and I'd say the first six months after our conversation, he was doing just occasional common stock issuance. He was doing some more convertible debt and

And then, I don't know, when was it? October, November, it was like he made this 21 billion equity and 21 billion fixed income announcement. And then it was just basically exactly what I wanted from the beginning because also back in the show, I made the comment, I just want Michael to go out and issue 25% of his common stock outstanding and just start capturing the spread. Preston Pysh : Capture the spread.

And that's exactly what we've seen here in the last quarter. And as a shareholder, although the price is going sideways, and it's so funny because on Twitter, you see people just kind of losing their minds over like, "I can't believe it's flat and Bitcoin's up," or whatever. But as a shareholder, I'm looking at this and I'm just like, "Oh my God, pump this right into my veins." This is exactly what I wanted them to do because

at the end of the day, more Bitcoin he can keep putting on the balance sheet in a per share basis is what, in my opinion, the real shareholders of this company want to see. So what are your thoughts? What are your thoughts on him doing this in such, I mean, he is going after it and I'm curious what you think he's going to do after he gets to this 21 billion, 21 billion. So we'll start there, I guess.

Yeah. Yeah. I mean, you make a great point. I mean, this $21 billion, the $42 billion capital plan that was announced on October 30th in the Q3 earnings call was the largest capital plan ever, ever announced. There's never been a capital plan to such scale using at the market equity issuance and convertible debt ever. This is the biggest capital plan ever.

And just looking back in the Q4 performance, it's pretty incredible. I mean, they've raised $17.9 billion in like 50 days. The scale of that is astronomical, right? So for your listeners, I don't know if you know how hard it is to raise $100 million, let alone $17.9 billion. So $100 million, they've effectively raised $100 million 179 times, which is incredible.

And all of that capital that's been raised just has gone straight into purchasing Bitcoin and adding Bitcoin to the balance sheet. So, I mean, just, I've got some simple numbers here. They started the year, MicroStrategy started the year with 189,000 Bitcoin, and they ended the year with 446,400 Bitcoin. So, you know, they started with $8.3 billion of Bitcoin, and they finished the year with $42 billion of Bitcoin. And the price has gone up

astronomically over the entire year. Now- Preston Pysh : Jeff, do you know what that number is in a per share basis? And I'm not trying to nitpick, and I think this is really, really important for people to understand. When we talk about the total amount of Bitcoin that's being added to the company from an enterprise level, that's one metric, but for it to really be meaningful, in my humble opinion,

you'd have to own the entire company for that metric to be meaningful. When you look at it in a per share basis, that's how you can actually, because I don't know the whole company, I own so many shares, and if the Bitcoin per share isn't going up, then it's not meaningful. It is. I just don't know. I haven't done that math. It'd be pretty easy to do. We just take the common stock outstanding at the start, we take it at the end, and we take the numbers that you gave and we divide by it, and it would tell us that number. It has gone up. I just don't know percentage-wise

And this is another thing, his posts online on Twitter are always in an enterprise level percent, which I don't like. I would prefer to see it being posted as a MicroStrategy's Bitcoin yield has gone up by X amount in a per share basis, which would be a smaller, I think it'd be a smaller number, in a per share basis. So I think that's an important thing for everybody in the community to be using as the actual metric is in a per share basis. Preston Pysh :

I believe the Bitcoin yield is actually counted on a diluted basis. It's factoring in the dilution of the equity itself. The number that he's reporting. Yeah. Okay. Yeah. So to put it in perspective here, right? The Bitcoin held on balance sheet is up 136%. Yeah. And I think the Bitcoin yield figure at the end of the year was something like 86%. So that's the delta is the equity dilution. Yes. There you go. Yeah. I love it.

So that was what, a 40? What was the percent difference that you just said? Robert Leonard : 136% increase in Bitcoin held. And I want to say the Bitcoin yield was like 80%, something like that. Preston Pysh : So that's like a 60% difference just in the numbers, which is massive, but it's important for people, and they're both huge numbers here, folks. But it's important to know the difference because there is a big difference. So, okay.

Keep going. I'm sorry to interrupt you. That's just like a little bit of a pet peeve on my part when people aren't discussing it in per share basis, but go ahead. Yeah. It's a really good point. And we get to this term of accretion, right? Generally, when you issue shares, like any other equity in the market, when they're issuing shares and they're doing something that isn't Bitcoin related, it's dilutive. They're issuing shares and then doing something with it, it's dilutive. In this situation, it's accretive.

because you are capturing the spread of the premium on the balance sheet in order to add more Bitcoin on your balance sheet. So it's increasing the Bitcoin per share, as we just mentioned, by a significant amount. Now, the capital plan is really fascinating because there's two facets to it, right? So you've got this ATM component, which is an equity share issuance.

and you've got the convertible debt, which is a leverage tool. So what's been really interesting in watching over the last quarter is how much their leverage ratio has actually fallen because of the ATM equity issuance. So just to put it in perspective, MicroStrategy ended Q3 with 252,000 Bitcoin and a leverage ratio of 30%. So that means the debt that they had on their balance sheet relative to the assets that they had on their balance sheet, they had...

30% of their total assets was captured in liabilities. Now, fast forward to the end of Q4 with the significant increase in ATM issuance and the, I think it was a $3 billion convertible bond issuance.

The assets held on balance sheet are 42 billion and the liability held on balance sheet is 7.5 billion. So the leverage ratio went from 30% and dropped all the way down to 18% over Q4. So this is a part that- Insane, insane. Yes. It's crazy. Most of the bears and the traditional finance people aren't necessarily conceptualizing this or thinking about the leverage ratio. They're concerned about their like,

average Bitcoin price, and this is going to blow up and all of this stuff. When really in reality, their financial leverage is reducing. They're getting stronger. Yes. Healthier. They're getting healthier. Yeah. Stronger and healthier. And when you compare this to leverage ratios of standard equities, some other equities are 80, 90, 100% levered.

and some even 110%, 120% leveraged. And they have different financial structures depending on their cashflow and all these other components. Now, it makes sense to have a lower leverage ratio when you're investing in the most volatile asset in the entire market. That conceptually makes sense. However, as a shareholder looking forward here, I would say they're probably under leveraged

and they have capacity now to dip into this $21 billion convertible debt market, that $21 billion convertible debt plan, and add more leverage to the balance sheet to continue to increase Bitcoin per share and into the future. And one thing that I really love about this convertible debt is that

the convertible debt effectively reduces the volatility of Bitcoin to the buyer. So the pools of capital that are buying the convertible debt want Bitcoin exposure for a reason X, Y, and Z. We can get into that if you want. But what's happening is they're truncating the upside to the bondholder, and they're also truncating the downside to the bondholder. Now, that excess volatility to the upside and to the downside is

is return to the equity holders. The equity holders get the excess upside and the excess downside. And that is how this kind of Bitcoin yield is generated into perpetuity. So the people that hold MicroStrategy equity are generally very bullish Bitcoin and are willing to take on that excess volatility to the upside and excess volatility to the downside, particularly in the long term, four, six, eight, 10-year duration. Robert Leonard :

That's one of the most fascinating components to me is thinking about this excess volatility to the upside and excess volatility to the downside and that being transformed and delivered to the equity holders. Trey Lockerbie : This is what I think is going to be fascinating about the next time he does the convertible debt round. When we saw at last this coverage ratio or leverage ratio that you were talking about earlier, it being higher back when he did it

I think you said it was 30%-ish, somewhere in that ballpark. And now we're at one third of that because of what has played out in the past quarter. So when you look at the health of the company and you're issuing more converts moving forward, he should be able to get cheaper funding. He should get a cheaper funding rate. Well, the person would look at that and say, "Well, he's already getting 0%." Exactly. So

Where he's able to adjust this is on the strike of the convertibility of the converts, and he should be pushing the people buying the fixed income to an even higher strike, which is advantageous to the common shareholders because they're not losing as much equity, assuming they would decide to convert. Have you discussed this on your show as far as pushing the yields negative? I don't see that happening. I think it's just going to stay at zero and they're just going to push the strike higher. Is that what you also see playing out? I think this can go...

This can be the really cool part about convertible debt and really the future of additional financial products beyond convertible debt, whether that be preferred stock or anything else.

there's a lot of financial creativity that can happen here. And whether that be interest rates, and maybe it's not negative interest rates, but maybe it's a 1% interest rate, but you move the strike out 100%. Or maybe it's zero and you bring the strike down to 25%, but the payback at the end is 90% of the beginning. So let's say you get a billion dollars in the door to buy Bitcoin. The strike price is 25% higher, but at the end of the period, you only have to return 9%.

900 million. That could be a big future design. Let's take a quick break and hear from today's sponsors.

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All right, back to the show. Trey Lockerbie : At the end of the day, the fact that every one of these have been oversubscribed is telling me as an equity holder,

"Hey, maybe we could have done a little bit better on the terms and conditions of what we're bringing to the market because obviously there's appetite for the strike to be even higher than it was." Obviously, I'm very happy with the coupon-less instrument, which is amazing. But I think that on this next round, it's like, "Hey, let's see if we can just get it at subscribed or maybe even under subscribed to see what the market tolerance is." Preston Pysh : Where's it at? Jay Gould : Yeah, I guess that's where I'm at. It's like, "Hey, let's just see where it's at."

Let's see how good of a deal we can put into the market. I think who is ever buying this is still, at least from a fixed income standpoint, is going to do better than anything else out there because it's all trash. So,

Yeah, no, I guess that would be my last time we talked, I was like, hey, go out there and issue 25% of all your shares outstanding and let's seriously buy some Bitcoin. And now I think that that would be my next ask of MicroStrategy is like, hey, let's kind of test the waters and see what we can get away with on the T's and C's of the new issuance on the converts whenever they decide to do it.

Yeah. I wish I was in their shoes. This is like, this is so cool. It's unreal, man. This is unreal. Yeah. I think what I'm fascinated about is all of 100% of the convertible debt that's been issued so far, private placement, unrated. Right. So get into that. Yeah. Get into this. Yeah. So they've been private placements and they've been 100% unrated bonds. So if you think about any money manager,

let's say you're a money manager underwriter, and you've got to go tell your boss that you want to buy bonds. And you've got two options. You've got a rated security and an unrated security, and you outline it to them. The unrated security looks sketchy. If you have just opportunity cost of capital, and you're viewing all of these different securities, unrated securities, there's less of a market that's willing and able to invest in unrated securities. Now, fast forward to the future, if we're going to look at tapping these larger pools of capital,

I can see this going many different directions where you start getting rated securities. They go through the process of having a public offering and having rated securities. Let's just say they're B-rated securities going through that entire process. Now, I think this is going to happen is because we've got FASB fair value accounting coming in 2025.

which I think is going to be monumental for really just the perception of MicroStrategy within the market, potentially getting added to the S&P 500, which would boost credit quality. Once the market cap starts to rise 250 billion, 500 billion, the credit quality of MicroStrategy increases drastically with that. So they have the ability to potentially offer rated products to the market, which taps a completely different pool of capital. There's a small pool of capital that can invest in unrated bonds

And the pool of capital that can invest in rated bonds increases dramatically. And in my world, from an insurance, my background thinking about reinsurance and insurance, most of the insurance market, they invest in bonds. The insurance market, they can't put Bitcoin on their balance sheet. They get zero regulatory credit for it. So that means you can't leverage against it. But you know what you can add to your balance sheet? Micro-strategy convertible debt. And you can get your Bitcoin exposure and leverage your portfolio against it.

And this is so huge because people don't understand how big the float is in all these insurance companies, Jeff. It's massive. It's out of this world. I mean, this is how Buffett made all of his money through Geico was reinvesting the float. We're talking trillions and trillions of dollars in the float of these insurance companies. This point you're making is so massive. So massive. Yes. It's massive.

It's an enormous pool of capital that wants these products. And just recently in the last couple of weeks as well, we've seen, what is it? Strive Capital that's created this kind of Bitcoin backed bond ETF, which I foreseen. I know this is going to take off and this is going to be totally huge. The pools of capital for this convertible debt are going to increase tremendously, especially if you have an ETF product.

that can diversify the Bitcoin-backed bonds. I can foresee over 2025, we're going to see 25, 30 companies adding Bitcoin to their balance sheet and running maybe a smaller reduced version of the MicroStrategy playbook where they're offering convertible debt. Maybe it's 25% of their balance sheet or 50% of their balance sheet, different sizes. And this Bitcoin-backed bond, convertible bond ETF can capture all of those. And you can have a diversified...

probably decently high credit rating ETF that you can hold on your balance sheet. And I can see that being very appealing to insurance companies, pension funds, I mean, even institutions that want this exposure. So-

Preston Pysh : It's really fascinating. Preston Pysh : Holy moly, dude. I even got to the first question. You and I are just catching up. Preston Pysh : We're cruising. Yeah. Preston Pysh : And by the way, it was nice seeing you in Miami, sir, for the first time in person. Preston Pysh : Absolutely. Preston Pysh : What I wanted to do was bring up a chart here. I actually brought it up very briefly while you were talking. This is just showing the comparison between Bitcoin and MicroStrategy in 2024. Preston Pysh : Yeah.

past performance isn't a predictor of future performance, all that fun stuff. But what I really want to look at is just the volatility difference here. I'm about to play a clip of Michael talking about his own discovery. This clip is one of my favorite clips I've ever watched of Michael in his interviews. And I think it's so demonstrative of

how MicroStrategy, they're trying to figure out what this even is, right? The clip is so good. But look at the chart. You can see the volatility. The orange there is Bitcoin. It was up 120% in the past year. And MicroStrategy,

And MicroStrategy is up approximately 357%, according to the really close approximation that I got to the start of the year and the end of the year on this chart that I'm showing. But look at that volatility difference. And we talked about this last year when we originally were talking, which was, it's almost like trying to get on a speedboat that's ripping past the dock, and you're trying to jump on the boat. And for a lot of people, they're looking at the volatility of Bitcoin, which is anywhere from 60% to 70% annualized, which is crazy.

And if you're trying to take a position, getting on something that has that much vol is totally nuts. And then you look at MicroStrategy and it's way more aggressive than even Bitcoin itself, over 100% annualized volatility. So before we start talking about what that is and what that means and whether people, how they should approach if they want to invest in this, how they should approach that, let's push that topic a little bit later in the conversation and what

And what I want to do is play this clip of Michael. Honestly, I think this is one of the best clips I've ever seen of Michael. And let me just make sure I give credit to the folks that were interviewing him here. This was Risk Reversal Media. There's a guy, his name is Adamy and Dan Nathan that were interviewing him on this. We'll have a link to the full interview if people want to check this out.

I highly recommend that you check this out because this clip is amazing. But we're going to play this in full form and then Jeff and I will probably have three hours worth of things to talk about after this clip. So let's go ahead and play the clip. Jeff Ross : We get to 2024 and then we discovered the value of volatility. I mean, really understand it. Because in January of 2024, Bitcoin isn't an asset class and in the second week, the SEC approves those ETFs.

And then you start having this snide comments like, well, now we don't need MicroStrategy anymore. They're like just a proxy. They're like a clumsy ETF substitute. We'll just put our money into the ETFs. But what happened at the same time was the halving was coming and all of the investors, the vol traders went through a secular rotation

and they started selling the Bitcoin mining stocks and looking for something else to trade. So if you track the liquidity in the options market and in the equity market, there was a major shift in Q1 and early Q2 where

a lot of the volatility in the options traders and equity traders, they basically hopped off a dozen Bitcoin mining companies onto MicroStrategy because the Bitcoin miners were going to the halving where their revenues get cut in half. So when that happened, our options interest exploded and we became the number one options market. When the SEC approved the ETFs, they didn't approve options. Okay, so today our options market is like $95 billion. Our options market is the same size of our market cap.

And then we discovered that the real strategic opportunity we had was we can construct a balance sheet of permanent capital with leverage. And when you take Bitcoin and make it 100% of your stock, you're going to trade probably... If Bitcoin is trading with a 60 vol, you're going to trade with a 75 vol just because of the uncertainty of what the management team is going to do. Like I have the option to sell equity or not sell equity, or we might do something or not do something. I have the option to do debt or not do debt.

That option is going to move you from 60 vol to 70 or 80 vol. Then if you actually execute the option by selling equity at a premium or by issuing convertible bonds, you move to 90 or 100 vol. So all of a sudden, we had an equity trading with 100, I think today it's like 120 vol, basically double Bitcoin equity.

And now here's the big idea, right? The S&P is 15 ARR, 15 ball. Bitcoin is 60 ARR, 60 ball. It has been that way for four years. We take a company with permanent capital and we create something which is 100 or 120 ball, 100 to 120 ARR. Okay. Now that attracts all the options traders, all the arbitragers, all the Bitcoin maximalists. It becomes hot money. You know,

Now, the call rate, if you hold a dollar bill for 30 days, you're getting, so for 30, you're getting 480 basis points or something like that. If you hold a million dollars with the S&P index for 30 days, you can get like 15% interest by selling the 30-day calls at the market. If you hold Bitcoin, iBit, for 30 days, well, you couldn't sell the options until just recently, but now you can sell them in general at 100% interest. If you sell the MicroStrategy call option at the market,

It's 220% interest rate. Okay. Just hold the share. And so all of a sudden, what we've done is we've created a levered flywheel on top of a product, which is already four X's volatile and four X's performing as the S and P. The result is our liquidity explodes, our options interest explode. And we do a convert bond in Q1. A week later, we do another convert bond. That's the first time in history anybody ever did two convert bonds back to back, two

two consecutive weeks. Then we do another one in Q2. Then we do another one in Q3. Then we do a billion dollars of ATM in Q3. And then we start to get into a groove and we realize that at the end of the day, the market's going to rally around some leader. And you're either going to lead in a decisive way, or you're going to sneak around and apologetically be opportunistic, or you're going to hide and wait. Robert Leonard

And so we just decided we're going to lead. I mean, John D. Rockefeller decided to roll up the entire petrochemical industry and he bought out all of his competitors, all of his customers, all of his vendors. And first he did it for cash and they would say, okay, well pay me this. He'd go to the bank, he'd borrow the money and he'd give him the cash. And at some point people in the industry said, you know, standard oil stock is worth more money than the cash. And he just started issuing the stock. And Henry Flagler, of course, built Florida with standard oil stock.

And so there's this point in the market where the market decides it trusts you and it wants to rally behind you. And we got to the point in October 30th and we just said, look, we're going to put the question to our shareholders. Do you want us to basically build this business or not? And after 40 consecutive Bitcoin purchases, after laying the foundation of a Bitcoin, you know, development company, after actually rolling out the KPI of BTC yield, which is

We just sold a billion of equity. It was backed by 350 million in Bitcoin. We bought back the billion in Bitcoin. We captured 650 million in the arbitrage.

That works out to 4%. That 4% is like a Bitcoin dividend to the shareholders, but we're going to keep it on the balance sheet, roll it forward and reinvest it. Once we constructed that model, we just said, look, we're going to issue $21 billion of equity and we're going to issue $21 billion of fixed income, whether it's convertible bonds or preferred shares or corporate bonds. And we're going to do the fixed income to say levered. We're going to do the equity when it's at a maximization

massive premium to the underlying assets to capture the yield and to de-level. If you want to get behind us on that, that's the plan. We put it out there. The next day, stock trades up. We outperform every Magnificent 7 company. We outperform Bitcoin. We outperform every Bitcoin company. So the shareholders spoke. It's not a surprise to me. I was 95% certain they would like it because I meet with them and they were like, this is the most brilliant thing ever. Yeah, just keep doing this.

So after that, you know, we had a good week and then November 5th came and there's a red sweep. And all of a sudden you have a pro Bitcoin White House, a pro Bitcoin Senate, a pro Bitcoin Congress, pro Bitcoin cabinet. Bitcoin rages from 68,000 and 99,000. The short of it is we raised $10 billion in four years after our initial announcement. And that's like progressively work and learning. You know, we're learning and

And the market's learning to trust us, right? We're building a relation. My relationship's not just with my equity investors. It's with the convertible bond investors. You know, you meet with a convertible bond investor, say, I saw you last quarter. I saw you, you know, you yelled at me for this and this. I fixed this. I'll do this. We're partners together. I promise you, I will do this. I'm not going to mess with your opportunity. I'm not going to hedge it.

I'm not going to steal your trading opportunity. I will do this and this and this. The guy goes, well, and I'm looking forward to this future. The guy goes, thank you for your candor, $500 billion order. Like if you have trust and people understand you, they'll give you your money. So what happened next is we raised 13 and a half billion dollars in four weeks and

And if you look at my tweet, my tweet this morning is basically, yeah, we generated about a $9 billion plus gain for our shareholders in those four weeks. We're making hundreds of millions of dollars a day. It's tricky for conventional investors to understand it because you're not capturing shareholder value creation via gap accounting because for two reasons. One, Bitcoin's indefinite and tangible, but two, in the history of 50 years of the capital markets, everything's

everybody's been on the US dollar standard, which is zero vol, zero ARR against the dollar. And this is the Bitcoin standard, 60 vol, 60 ARR against the dollar. We don't have the math, the accounting to keep up with that in a traditional system. And that's why we have to put forward things like a BTC yield, a BTC spread, a BTC gain,

And those that understand BTC, they get it and they're long and they love it. And those that don't understand BTC or don't understand this, or just aren't really interested in putting in the work, they just think it's sham crazy and they're just going to short it or

or they're just going to whatever. So that's where we are today is from desperation to opportunistic, to strategic, to identity. At this point, we're a Bitcoin treasury company. I'm on a mission. My mission is I'd like to see the entire world recapitalize on Bitcoin. Every company, every family, every individual, every government. I think it's an economic protocol for prosperity. I think it's as important as English or fire or electricity or steel. I

I just think it's good technology. It's a good idea. We're reaching the fun stage. The next four years, I think are kind of fun. We get to, we get to do a lot of interesting things to help people. There's so much there. There is so much there. I don't know if you can see me laughing as I'm watching this. Okay.

So, I want to start off… Where do we start? Where do we start? So, people might have heard Michael, and I think for some, they hear him saying things and they're just like, "This guy's off his rocker," because he's using… He's an engineer, first and foremost, right?

He goes out and he's saying, the vol that we're seeing at MicroStrategy, it's like we've figured out a way to tap. It's like a nuclear reactor. And instead of running from the volatility, we're going in there and we're literally harnessing the volatility for our own benefit. And so he's basically created a crypto nuclear reactor. So what in the world does he mean by that?

And sorry to just jump in here. I'm just like, this gets me so excited, Jeff. I swear to God. I'm like, I'm ready to jump through the roof. So when we think about a nuclear reactor, you have your plutonium rods, you push them down, they create all this heat that's coming off. And then you put just water around it and it heats it up and you get all this violent volatility through the water molecules. It creates the heat and you pump it out to people that need the energy.

So very simply, what he's doing through all of these financial instruments, whether it's the convertible debts issuance, or he's going out there and just issuing more common stock into the market, and then he's raising cash and he's going and buying Bitcoin with it. These two things, this interplay between these two things is creating this violent amount of volatility in the marketplace. And what it's doing is it's attracting speculators.

It's attracting people that are going long and short simultaneously to capture yield in the market. This is sometimes referred to as fast money on Wall Street. And he's just sitting back and he's harnessing this energy and just pumping it more to become more and more Bitcoin on the balance sheet is what he's doing. And this is nuts. I think most people are looking at him and they're saying, "Oh, this is so dangerous. He must be in debt up to his eyeballs. He's going to lose all of his Bitcoin because he's borrowing so much money."

But think back to what Jeff and I were talking about at the start of this show. From a health standpoint, from a financial health standpoint, the assets versus the liabilities, it has improved tremendously in this past, like a lot. And not just in percentages, but in nominal terms as well, the numbers are crazy. They're in the billions and billions. So I would start there. I want to hear what your take is, Jeff, of that clip. Jeff Booth :

Yeah. A lot of people don't recognize or understand that the Bitcoin itself that they're raising is permanent capital. The exit strategy is buying Bitcoin. Bitcoin is the best collateral the planet has ever seen. Intangible too, which he highlighted very clearly in there, which means he doesn't have operational sustainment costs associated with this permanent capital. But keep going. I'm sorry to interrupt. Yeah. Yeah, absolutely.

And I'm incredibly bullish for the future of Bitcoin as collateral. Like the next decade for Bitcoin as collateral is going to be incredibly exciting. We're going to see that infiltrate in many different ways where people are going to be wanting to...

post their Bitcoin as collateral and return a yield or effectively yield it. I mean, we've seen that go poorly in past situations, but I think that's very appealing for many different reasons. In thinking about MicroStrategy stock and the volatility, a couple of things have been really interesting to me as well. In the last 30 days, MicroStrategy has been one of the top 10 publicly traded equities in the entire market for the last 30 days in a row. They're

the 110th largest equity company, but they're trading in the top 10 for the last 30 days in a row. That's really appealing to me. They're trading effectively with the Mag7 in terms of daily total traded volume. Why is that? It's because there are so many players in this game that are leveraging that volatility in both directions. And that's the derivatives market. He mentioned the options market was...

just as big as their entire market cap. And there's so many people that are playing in the options market, whether that be the convertible debt arbitrageurs, long options players, hedge funds that are managing exposure in any one direction. And some other things that are particularly appealing, and he kind of hit it there, is if you hold a large amount of micro strategy stock, you can use the derivatives market, the options market to generate a yield on your equity holdings into the future.

There's not a really good robust system for that yet for Bitcoin. And just to put this in perspective, back in November, you could sell covered call options. So a covered call is, let's say you have 100 shares, you could sell a covered call option that represents 100 shares, and you could sell it 100% out of the money and return a 2.5% yield in 30 days.

So if the price of the stock goes up another 100%, you get your shares called away, or somebody is buying the stock from you at that price. If it doesn't go up another 100%, you collect two and a half percent yield, and you could run that 12 times throughout the year and make 50% yield running a derivative option strategy strategically. Now,

doing this in different perspectives. Everybody's trying to figure out exactly how they want to strategize and use this derivative options structure to facilitate cashflow. One, to either add Bitcoin to cold storage or facilitate their life so they could build on Bitcoin or whatever that may be. And it's a fascinating design. There's so many people that are using these other different products in different directions and different ways to do whatever they want to do. And it's really appealing. So I

I think we're also seeing some people come into MicroStrategy with the idea that if there is a bear market, which I think there will be a bear market at some point in the future, who knows exactly what that looks like. But if there is a bear market, you can use your MicroStrategy stock and generate a yield, a cashflow in the interim.

if you have an understanding of what's going on in the market and how things are moving. The other thing that's really appealing is I feel like if you look at MicroStrategy stock and you zoom out and you think about, okay, it's trading at the top 10 publicly traded equities, and you look at the volatility it's had just in the last three months in Q4, right? We saw a huge run up. It broke 200, went up to 550, came back down to 300. But

Who knows where it goes from here? But it appears like it's moving like a trillion dollar company, yet it's only just a hundred billion dollar company right now. It's like it's gaining steam and getting bigger. And I have a feeling that two years from now, this Q4 moment in time where it dropped from 550 down to 300 will look like a blip. So it'll be

It'll be interesting to see. Preston Pysh : These numbers that you're saying, I think it's important if somebody would go back and listen to our conversation from last year, you have to make sure you take into account the stock split for some of the numbers that we were saying. We were saying $160 and some of these types of numbers.

which would be the equivalent of $16 because they had a 10 for one stock split. So that's also important for people that are maybe listening to the previous conversation in concert with this one. So there was a really good point that he made in here to talk to this idea of capture the spread, this terminology that we keep talking about. Michael said in that clip, he said, "We did a billion dollars of equity. It was backed by $350 million of Bitcoin. And then we added $650 million of more Bitcoin after we did this race."

So what in the world does all this mean? I'm going to try to make this as simple as possible for people with this capture of the spread. His company, if you add up all the shares out there, trades for, and we're going to use very simple numbers here, we're just going to say a billion dollars. If you took all the shares and you looked at how much Bitcoin he had on the balance sheet, there's a billion dollars worth of Bitcoin. The common stock that represents this Bitcoin and the operations and everything else on the company, the shares sell for $3 billion.

Okay? So that's a three to one ratio. So the amount of Bitcoin is a billion, the company's trading for 3 billion for a three to one ratio. So now if you're Michael, you can just say, let's say he wants to go out there, however many shares there are, and he says, "I want to add 10% more shares into the market." Okay? He just basically creates more stock certificates. He goes out into the market, he sells the stock certificates.

And he sells them approximately for this $3 billion price. You take the 3 billion, you divide it up by the 10% more shares that are added. And what he's doing is he's just raising cash. He's selling more shares to raise cash. In this scenario, he would have raised $300 million because he approximately, most of the time we were saying it's a dilutive activity where that $3 billion would be diluted in a per share basis.

This, because he's raising this, call it $300 million in this scenario, he goes out in the market, he buys Bitcoin with the $300 million of cash he just raised from issuing the new stocks. And now he has an additional, now how much Bitcoin does he have on the balance sheet? He has $1.3 billion worth of Bitcoin on the balance sheet because he took the $300 million, he bought Bitcoin, he put it on the balance sheet. So now when you look at the ratio, if it was trading at a three to one before, you would think that it would then...

Let's say the multiple is the same. You'd take $1.3 billion, you'd multiply it by three, and that would be the new market cap. What are we at? $3.9 billion, somewhere in that ballpark. And you can see what he's effectively doing is he's taking something that is, let's say the Bitcoin is $100,000.

If he does this activity, he's effectively kind of buying the Bitcoin for $33,000 when he's doing this, because he's able to issue shares that are worth three times the amount of Bitcoin on his balance sheet. This is what we call when people say he's tapping the ATM.

This is what he's doing. When I'm yelling, "Capture the spread," what I'm saying is your shares are worth three times the amount of Bitcoin on your treasury, so issue more common stock and go buy more Bitcoin with it. Because if the common stock and the Bitcoin were at parity, let's say they're both a billion each, it's not as big of a value capture for him to go out and issue more common stock and buy more Bitcoin because he's getting it. It's 100,000 per coin and he's going out and buying $100,000 price. But if you got this multiple blown out at 3X, the treasury,

He's effectively buying it for $33,000. So you want them to do that all day long, folks. This is what we mean, capture the spread. This is what we mean by ATM. And so I don't know what else. Preston Pysh : Where this gets even more fascinating is that if the price of Bitcoin goes up, the leverage ratio drops.

So you're talking on the convertible debt side. Yeah. I'm just talking period. Health-wise. Yeah. Just health-wise. And so they've raised, what is it? 200,000 Bitcoin in Q4. Yeah. And so that's now base permanent capital. Okay. Base permanent capital. If we see increased Bitcoin price from, let's say, strategic Bitcoin reserve or any other company that are adopting a micro strategy playbook, continue to buy

Bitcoin, and we see a bull market where the price of Bitcoin goes up another 25%, 50%, 100%, all of a sudden that leverage ratio drops drastically really quick, exponential. As the price of Bitcoin goes up, the leverage ratio drops exponentially. And that provides more capacity to adding convertible debt to the balance sheet and leveraging up the balance sheet even more, which is

Also incredibly appealing because it's accretive, right? You're selling your stock even further out of the money. Instead of issuing it, you know, an ATM, you're issuing it at the market, whatever the market price is that day. The convertible debt effectively issues it at a future price that's greater, 55% higher than what today's trading price is. At least that's what the last piece of convertible debt was offered at. So it provides even more Bitcoin per share by taking that leverage on the balance sheet.

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All right, back to the show. What are your thoughts on the NASDAQ news? The QQQ? Yeah. The NASDAQ 100? Yeah. The NASDAQ 100, I thought that was an incredibly exciting moment for MicroStrategy. So for those that are unaware, MicroStrategy was added to QQQ, which is the NASDAQ 100. This is the fifth largest index ETF in the world, and it represents the top 100 globally NASDAQ listed non-financial ETFs.

companies. And so this is incredibly appealing to me because one, they qualified for the NASDAQ 100 before S&P 500, which is very rare. It's very rare that you see a company have a $100 billion market cap without the financial underlying base support from an index ETF like the S&P 500. So it's very rare that you see a company go into the top 100 before getting S&P 500 inclusion. So-

There's a couple of reasons this is incredibly appealing. One, because it adds a constant bid to microstrategy in perpetuity. So any person or pension fund that's buying QQQ, when they put a dollar into QQQ, that dollar is split and spread between the 100 equities that's represented in the QQQ index. So those buyers, when they buy QQQ, they don't care about any of these metrics that we're talking about.

They don't care about NAV premium. They don't care about PE ratio. They don't care about anything. These are buyers that are agnostic to price and are buying equity at any price, which is incredibly appealing for the future of being able to issue at the market equity issuances or having increased credit quality for raising federal debt. Preston Pysh : But Jeff, so I totally agree with what you're saying, but I think it's important to also highlight this can cut both ways.

let's say they take up a lot of market share in one of these indices, let's say Bitcoin starts really selling off, like we've seen it sell off 70%, 80% in previous cycles, that sell pressure is going to come along with being in these indices as well as they would potentially be dropping in those indices. So I think that's also an important highlight. Robert Leonard : Yeah, it is an important highlight. It definitely can go both ways. I think QQQ

once a year and S&P 500, for example, rebalances four times a year. So you see maybe different rebalances. Yeah.

But regardless, it's a new buying pressure that wasn't previously there. And even if the price falls at some point in the future, let's say you go into a bear market, as long as they don't fall out of the top 100, you're not going to see a drastic, probably market noticeable movement in my perspective going forward. It kind of depends on the macro environment and all these separate things. But thinking about micro strategy, that's something that Bitcoin doesn't have, right? Bitcoin doesn't have this kind of

I mean, there are Bitcoin ETFs and we've got passive buyers that are buying the Bitcoin ETFs, but MicroStrategy is an equity, Bitcoin is a commodity. And the fundamental design of those markets are different and they're different products

that serve different solutions or reasons for holding in a portfolio. Preston Pysh : I read a tweet a little bit back that was like, "It's hard enough to understand Bitcoin." Then you- Preston Pysh : That's so true. Preston Pysh : Over here, right? It's so hard to understand that and wrap your head around it. And then you also look at how hard it is just to understand security analysis. And what you have with MicroStrategy is the overlapping of these two things.

of deep security analysis, especially because it's not even the income statement is typically how you're doing security analysis. This is all balance sheet based, which is also very strange and weird. And then you're just overlapping. You have to understand Bitcoin in the first place to even wrap your head around this.

it's very obvious why so many people are very confused by this company. They're looking at the performance over the last four years and it's outperformed Nvidia. And they're saying, how in the world is this guy's buying imaginary Mario coins? How in the world is this outperforming AI chips? And I don't know how to cover it in a way that...

Because I'm sure people are listening to this conversation and they're like, "What in the world are these guys even talking about right now?" I'm sure. Because there's a lot of financial jargon and you have to really understand the financial jargon to begin to get your head around a lot of this. But I say all of this because I think it's really, really important for anybody that's hearing this conversation and saying, "I feel like they know what they're talking about, therefore I'm going to buy some of this," to just caution this person.

Because buying the S&P 500 is basically like driving a Volkswagen Jetta. I would argue Bitcoin's like hopping in a Ferrari, and I would argue micro strategies like climbing in an F22 and trying to fly it. The technical competence and what you're going to experience from a volatility standpoint is such a quantum leap from each one of these types of investments.

that if you don't understand it, there's a good chance you're going to buy it at the exact wrong moment. You're going to see the price move away from you. You're going to get scared to death. You're going to say, "I never understood it from the beginning," and sell it. You're way worse off than you ever were by not participating in the first place.

That's my word of caution and that's my concern for listeners that are listening to you and I talk about this. I just want to throw that out there that you really do need to know, you need to understand what you're buying, you need to do the homework. Now, with all that said, if a person is going to buy, this is the real question I have for you. If a person is going to buy this, what's the best way for them to buy it if they actually want to participate in this? Preston Pysh : So that's a great question and I'm going to double tap everything you just said.

one, I think this is the most interesting story in all of corporate finance ever, ever. Robert Leonard : Amen. Robert Leonard : Two, it's incredibly complicated. I mean, you have to have understanding of so many different market components to understand what's going on with the MicroStrategy stock. So it's incredibly confusing. And it's interesting, and you mentioned this, right? You've got like two camps, right? You've got the Bitcoiners who understand Bitcoin,

And then you have traditional finance who understands leverage, but they don't understand Bitcoin. So you've got these two camps that are both confused, but they're confused for different reasons. And they're kind of merging and getting close to each other. So it's a fascinating interplay. And I think with where we're at right now with the microstrategy equity, anybody who's understood Bitcoin probably owns some microstrategy. Just understanding where the power of Bitcoin and where it can go into the future. And I

And I think anybody coming into the scene new now, they've probably heard about it on the news or they're just dipping their toe into Bitcoin. And I think there's so much to learn from understanding the foundation of Bitcoin and the power of what Bitcoin can do and how transformative it can be before you understand what microstrategy is. I think Michael Saylor has even said this. It takes like, first you're a denier, then you're a skeptic, then you're a trader, then

then you're like a bull, and then you're a maximalist. And that's, you know, it takes 10 hours, 100 hours, 1,000 hours, 10,000 hours. And once you go through that kind of character arc, then you start to get into the micro strategy character arc. And I would say it's almost exactly the same. First, you're a denier and a skeptic, and then you start to trade it, think you know what you're doing. And then you start thinking long-term about like, whoa, this might be the most powerful financial company that's ever existed.

And it just, it takes time to research and understand both of those things. So, I mean, the way I view it is you have to have a fundamental understanding of Bitcoin, have done a cold storage transaction before you can even begin to conceptualize the power of where MicroStrategy can go. And ultimately, there are so many products out there that are incredibly appealing to people that want to make a ton of money.

There's these leveraged products. You can get two times MicroStrategy returns, which if you were new and you're listening to this, I would caution against jumping into these products that are leveraged equities or feeling like you missed something. I think the safest way to participate in this entire trade is really just taking the same fundamental view of Bitcoin, just buy and holding common stock into perpetuity.

If this is your first time thinking about this or learning about what's going on, because it is so volatile, if you're taking a longer horizon, four, eight year horizon, you'll have no stress and you'll be able to sleep at night. But if you're taking positions on leveraged products or options, you better have some fundamental understanding of what's going on and be willing to pay attention and be actively trading within the marketplace.

If you don't have the time or the space or the capacity to do that, I would really caution against any of these little leveraged products or even options. Preston Pysh : Jeff, on this topic, so what people often don't understand is when you're dealing with something that has a ton of volatility on the underlying of any 2X product, you

you better be performing to absurd levels if it has a lot of volatility. I have a chart I'm going to pull up here and show people what I mean by this. So I made this and I made it for the ETFs, not for MicroStrategy. Whatever I'm showing you right here, just amplify it for MicroStrategy because it's so much more volatile. It's almost double the volatility of Bitcoin. So the way to read this chart on the left rail, if you go down the left column there, it says Bitcoin annual return.

So if Bitcoin, and I'm just going to pluck out a number here, let's just say 30%. Let's say in this coming year, for the whole year, Bitcoin does 30% on the underlying of Bitcoin. A 2X levered ETF-

Okay? If we're assuming that the daily volatility on Bitcoin is, let's just say 3%, and that would be the top row, you see where I have ETF return at 3% daily volume. You come down, you look at the 30% on the underlying on the left rail, and you come up with 36.32% is what you would expect to see out of a 2X levered product. Okay? What I want to really show people here.

is if you get more volatile on the underlying, instead of it being 3% daily volume, let's go to 5%. So let's move over. The underlying of Bitcoin still did 30%, but we had 5% daily volume. Look at your return that you would get on the 2X product. It would be negative 4%, even though Bitcoin, the underlying was up 30% on the year. Let's go over to 6% daily volume. Now you're at a negative 31% return on the 2X product.

And go down and you can see where in the last, at the very bottom there, if you look at the row, the very bottom row, it'll show you what the break even return has to be on the underlying for each one of those corresponding daily volatility levels. And you can see as the volatility goes higher and higher, it is extremely difficult to make money in these 2X lever products because the churn of what they're having to do in the derivatives market is so massive.

It's Herculean effort to keep this under control. And so I see these people buying like a 2X levered microstrategy product, and I'm thinking, oh my dear God, what's the vol on microstrategy on a daily basis? 6%, 7%? It's totally, it's out of this world how high the vol is.

So if you're trying to do a 2X levered product on this and you're really trying to get ahead of the underlying, honestly, good luck. I don't think people really understand the amount of risk they're assuming by doing something like this. I still own the calls that we talked about last year. They don't mature until December of 2025.

And I haven't sold them. I'm continuing to squat on them. And those are way different than a 2X levered ETF product. Let me tell you, folks, like way different. So word of caution, I'm not saying to do it. I'm not saying to not do it. I'm just showing you the risk profile and how heavily levered it is to the daily volatility because it's just chopping up the returns because they have to be able to balance it all out. Preston Pyshenko Yeah.

Yeah, if the price falls 50% in one day, if the price falls 50%, let's just say the price falls 50%, let's just say in a week,

It has to go up 100% in order to just break even. And that's the challenge with those products is timing could be your worst enemy. And the pros, the people that are actually holding onto this, they're generally trading it quickly. Not to be rude, but yeah. Yeah. Well, I mean, with the Twitter crowd, definitely amateurs. But there are pros that are using this as a tool, as part of their...

trading strategy and they're in and out of it. They're moving in, they're moving out. They've got way more information and they're trading on tons of data that maybe the amateur trader isn't- Preston Pysh : Good luck. Nick Huber : Taking into consideration. Yeah. Good luck. Preston Pysh : You better have some type of crazy, who's the Paul Simon? You better be like Paul Simon level mathematical genius if you're playing those games in my humble opinion. But-

Absolutely. Preston Pysh : Jeff, we could go on and on, man. We need to do another one, not a year from now, but probably in six months or something. Jeff Booth : Yeah, absolutely. It's going to be exciting. Preston Pysh : I do want exciting six months. Jeff Booth : It is going to be so exciting. And going back to the one question, this is the one thing I would say, if a person is wanting to take a position, I think the best way to go about this is to just slowly dollar cost average and not try to market time anything.

dip your toe in the water this thing is violent this thing is violent it's a bullet train yeah like it's jumping on a bullet train right like you can get your face ripped off in both directions and like i mean good yeah hang on hang on for your life

Hang on, for sure. All right. You have a podcast. Tell us about that. Tell us about anything else that you want to highlight and we'll wrap this up. Yeah, absolutely. If you want to find me, I am on ex-Twitter. My handle is punterjeff, or you can search Jeff Walton. You can find me there. We have a super group investment club and we do videos every Wednesday. And

And it's called MSTR True North. And it's a group of guys. We've been at the front edge, the knife's edge of this trade for the last year. And we're staying up to date on everything that's happening within the market, convertible debt, ATM issuance, SEC filings, earnings reports, all of those things. And we digest them and jump into them. None of it's financial advice, but we love to talk about how we view the trade and what's happening in the marketplace. So feel free

Feel free to join us there. There's a ton of different groups that you can check out. There's Irresponsibly Long Micro Strategy on Twitter. There's a Discord called the MSTR Den where you go talk to other like-minded people in different groups over there. And there's so much content out there. And yeah, please follow along. This is what I love about you, Jeff. You make it fun, man. You do.

You do. You guys make it fun. Yeah, it's a lot of fun. And I've really enjoyed following what you've done this past year. And I really appreciate you making time to come back on the show. Yeah, absolutely. Thanks for having me. Look forward to the next one. Yep, for sure. Thank you for listening to TIP. Make sure to follow Bitcoin Fundamentals on your favorite podcast app and never miss out on episodes. To access our show notes, transcripts, or courses, go to theinvestorspodcast.com.

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