In short
Whether Strategy/Stretch (STRC) is “trapped” below par and what it implies for Michael Saylor/Strategy’s digital-credit structure; also why STRC trades at a high effective yield and how capital raising works in a Bitcoin bear market.
Guest
Adam Livingston, a longtime Bitcoin/treasury-company investor and host guest; he discusses Strategy’s preferred/credit-like instruments and compares Strategy to Strive (SEDA/STRC vs STRC-like products). He also references his own MSTR ownership and daily Bitcoin buying.
Key claims
STRC isn’t a stablecoin; “par stability” comes from monthly dividend adjustments tied to VWAP and share issuance when stock trades above $100. The market is demanding slightly over 13% effective yield to compensate for risk. Strategy’s use of cash to retire $1.38B convertible debt was a misstep (timing hurt optics when Bitcoin fell from ~83K to ~60K), but credit quality remains strong and dividends have been paid. STRC’s drawdown reflects mispricing and retail yield-chasing, not existential failure.
Notable examples
Effective yield slightly >13%; $1.38B convertible debt payoff; debt puttable around Sept 2027; STRC around ~$89 vs $100 par; dividend guidance potentially to ~12% if VWAP < $95; Strategy raised $300M and is raising billions/year; comparison to Strive’s different cash runway; 2022 residual exposure for MSTR shareholders was negative (about -14,400 sats/share) yet MSTR didn’t go to zero.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOMarket Perspectives on Saylor
0:00 to 0:52
Exploring how Michael Saylor is viewed in different market conditions.
“I think that the market is trying to find a villain right now, and Saylor is that guy.”
Evaluating the Stretch Situation
1:34 to 4:00
Discussion on Stretch's trading value and potential existential threats.
“So I want to start with the stretch thing.”
Convertible Debt and Cash Reserves
4:00 to 5:48
Examining Stretch's financial decisions surrounding convertible debt and cash reserves.
“Yeah, I just look at the overall credit quality of the company.”
Comparison with Competitors
5:48 to 7:40
Analyzing how Stretch compares with competitors like Strive in the market.
“Yeah, so the soonest that the debt was puttable, where I believe that the bondholders could like ask strategy to repurchase them, I think it was in September of 2027.”
Understanding Shareholder Dynamics
7:40 to 9:48
Discussion on shareholder behavior and the risks involved with MSTR and Stretch.
“It must have been the filing after the USD reserve was announced, but they do talk about how they intended to use it.”
Market Influences on Retail Investments
9:48 to 12:12
Exploring the impact of retail investor behavior on Stretch and its dividends.
“So I am an MSTR shareholder for that reason.”
Performance Analysis of Stretch
12:12 to 14:00
Analyzing Stretch's performance and its implications for the digital credit narrative.
“And is that part of the reason we've had this drawdown?”
Evaluating STRC and Bitcoin Returns
14:00 to 18:59
Discussion on the performance of Stretch compared to Bitcoin and the implications of dividends.
“stretch holder that has made money at these prices, including the yield, including the dividend.”
Evaluating STRC and Bitcoin Returns
20:42 to 21:18
Discussion on the performance of Stretch compared to Bitcoin and the implications of dividends.
“Every SIM has a static ID and carriers, ad networks and bad actors all use it to track you.”
Capital Raising Options and Market Impact
21:32 to 28:00
Analysis of how companies like STRC can raise capital amid challenges in the Bitcoin market.
“Because it seems like they have a few options.”
Show all 26 chapters
Concerns Over Bitcoin Supply Control
28:00 to 29:10
Discussion on the implications of a single company controlling a significant portion of Bitcoin supply.
“I wouldn't say it's already won, but it's winning and I think it will continue to win.”
Institutional Investment Trends
29:10 to 31:08
Analysis of the ongoing trends of individuals selling Bitcoin to institutions and its impact on market perception.
“Like these are the sort of some of the concerns that I have around it.”
Market Dynamics and Bitcoin Valuation
31:08 to 32:59
Exploring how market dynamics influence the valuation of Bitcoin and MSTR shares.
“think it's impossible and so do you think that the market is looking at these liquidation levels and will potentially try and hunt them?”
Digital Credit vs. Bitcoin as Money
32:59 to 35:30
Debate on the validity of the digital credit narrative versus Bitcoin's role as money.
“They had minus 14 ,400 sats per share at the bottom in terms of Bitcoin exposure for MSTR shareholders.”
Market Recovery Predictions
35:30 to 37:30
Speculations on how long it might take for the market to recover and return to previous price levels.
“this is going to take a long time to get back to par, right?”
Market Recovery Predictions
41:38 to 42:09
Speculations on how long it might take for the market to recover and return to previous price levels.
“The thing that keeps me up at night with Bitcoin cold storage isn't Bitcoin failing, it's my setup failing.”
Analyzing Bitcoin's Price Bottoms
42:19 to 44:47
Discussion on indicators suggesting Bitcoin's price may have hit a bottom.
“Okay, so let's talk a little bit about Bitcoin price.”
Diminishing Returns in Bitcoin Investment
44:47 to 47:15
Exploration of the concept of diminishing returns in Bitcoin's price over time.
“Do you, what do you think is going to sort of play out over the next sort of Bitcoin cycles?”
Michael Saylor's Position in Bitcoin
47:15 to 50:14
Debate on whether Michael Saylor is trapped in his Bitcoin investment strategy.
“And maybe that means adding leverage, maybe like whatever it is, is he stuck and he has to just accelerate at this point?”
Current Market Sentiment and Its Implications
50:14 to 53:01
Analysis of current market sentiment and its predictive value for Bitcoin investments.
“Could MSTR one day command a huge premium because they own 6 million Bitcoin and they can issue more credit than everybody and Bitcoin is like the new foundation monetary base?”
Macro Economic Factors Affecting Bitcoin
53:01 to 56:03
Discussion of macroeconomic factors and their implications for Bitcoin's future.
“And it's one of those funny things in bear markets.”
Bitcoin's Reaction to Fed Actions
56:03 to 56:48
Learn about Bitcoin's responsiveness to changes in interest rates and media narratives.
“Anybody who knows shadowstats.com, the true government inflation.”
Inflation Manipulation and Its Impacts
56:48 to 57:59
Discuss how inflation statistics are manipulated and the implications for society and Bitcoin.
“When you immediately saw this war happen and the poly market, betting markets, price in, rate hikes for 2026.”
The Insanity of National Debt and Bitcoin's Value
58:01 to 59:35
Explore the staggering figures of national debt and the case for investing in Bitcoin.
“dollars by the time Trump leaves office?”
Equity Market Uncertainty vs. Bitcoin Stability
59:35 to 1:02:06
Examine the high multiples in equity markets and why Bitcoin is seen as a safer investment.
“totally orange pilled my orange pilling journey has been quite long but uh i have always thought that about equities.”
The Bitcoin Civil War and Future Outlook
1:02:06 to 1:03:01
Discuss the ongoing Bitcoin civil wars and optimistic views for the future of Bitcoin.
“It's people that are unfamiliar with Bitcoin and then they store their money and these things that are absorbing the money printer, essentially.”
Transcript
Automatic transcript. May contain errors.0:02I think that the market is trying to find a villain right now, and Saylor is that guy. Like, he'll be the hero in the bull markets, and then in the bear markets, you know, he'll be villainized by a lot of the community. I do think that they did make a misstep when they used that cash reserve to pay off that$1.38 billion of convertible debt. You have to think of how the market is pricing the risk of the instrument, and that's simply what it is. It's just the simple fact that right now, if you go to their transparent information, you can see that right now the effective yield is probably slightly over 13%.
0:35So really, at the end of the day, it's simply the market signaling to strategy, hey, in order to essentially by stretch, if we want to take our money, buy your equity, then we need to be compensated above 13 % right now to take on that added risk. All right, let's do it. Adam Livingston, thank you for coming on the show, man. This was a bit of a last minute one. Stretch has been having a real tough time for the last week or so. And I thought you were the right guy to get on the call and figure out if Saylor is trapped in this trade. But welcome to the show, man. Thank you, Danny. I've been a longtime fan of the show.
1:09So thank you so much for having me. You texted me last night at like close to midnight my time. I have a new kid at home. She's about seven weeks old. And I thought, will I get some sleep? Will I be sleep deprived? Can I even articulate my thoughts? But we're going to give it a go. So thanks for the invite, man. I'm a huge fan. No, thank you for pulling this out of the bag. That's impressive. With a seven-week-old at home, I don't know if I'd have said yes to that, but thank you for coming on the show. So I want to start with the stretch thing. It's trading at just under$89 right now, way below what's meant to be par.
1:44How big a deal is this? Is this an existential threat to stretch? It depends on how you define existential threat, of course. But in my opinion, no. Ultimately, it's an equity. It's a credit hybrid equity thing. It's a credit-like instrument and equity wrapper. So you have to think of how the market is pricing the risk of the instrument. And that's simply what it is. It's just the simple fact that right now, if you go to strategy.com and you go to their transparent information, you can see that right now the effective yield is probably slightly over 13%. So really at the end of the day, it's simply the market signaling to strategy, hey, in order to essentially by stretch, if we want to take our money, buy your equity, then we need to be compensated above 13 % right now to take on that added risk.
2:33So what a lot of people do fail to understand, though, is that there is no stable coin peg. I do see a lot of fun about this peg that's broken. And to be fair, I do think there is somewhat accuracy with the term because they have something that they call the par stability mechanic, I think is the actual phrase that they use. And at the end of the day, it's simply that, hey, we're going to raise the dividend based on a volume weighted average price guidance every single month. If there's too much volume, if the VWAP's below a certain price, then we'll be more than happy to raise the dividend. I expect that we'll see that.
3:07And then on top of that, once the stock actually trades at$100 or above, above that par value, on the other end, you have strategy there issuing more shares into the market. So I think a lot of people forget that if that ATM at the market facility wasn't in place, then the effective yield would actually be driven down a lot more because of the demand. So there is a par stability mechanic, but I do think there's a lot of people that don't understand whether or not it's like a stable coin Terra Luna peg. I think that there's lots of comparisons made. But no, I don't see anything wrong with it. It's just the market saying, hey, we want an additional percent to be compensated for holding this thing.
3:45So, I mean, it's not the first time that it's traded below that par value of$100. Like in, when was it? In sort of November last year, it traded way below. But this is definitely the furthest below. And it's not actually traded at par since, I think, mid-May. So it's been over a month now. Do you think it will get back to par? I do for sure. Yeah, I just look at the overall credit quality of the company. And I see they have decades of Bitcoin dividend coverage. They just raised$300 million last week. So if you look at their year-to-date capital raising, they are raising about 18 times what their daily dividend bill is or their monthly dividend bill.
4:23So the capital market's access remains open. They can continue stacking Bitcoin, stacking cash. I do think that they did make a misstep when they used that cash reserve to pay off that$1.38 billion of convertible debt. So there's been a few missteps that strategy has made in my time as a shareholder. But ultimately, I don't think there's anything existential. It's just the market wants an additional percentage point, the effective yields up, and then the overall credit quality, I do think, will win out. And it doesn't help when Bitcoin's down 50%. And timing didn't help either because Bitcoin dropped like$23 ,000 in no time.
4:59They paid off that debt and then Bitcoin went from 83K to 60K. So that's like, I don't know what the exact percentage is, but 20 % of your Bitcoin value just immediately going away. So that doesn't help the optics either. that um sort of retiring that convertible debt is something that i didn't understand at all like i i'm not sure what the thinking was behind that and i don't know if the company have sort of aired that and said why they did it but i thought that cash reserve was there so you had dividends for two years in cash there was no reason that strategy were going to sell bitcoin to pay the dividends like they had that as a buffer and then they got rid of almost all of that i actually i just saw before we started recording overnight my time i think they might have um hit the atm again and put a lot more cash in a reserve to do that.
5:42But it made no sense to me. Like that convertible debt wasn't due until I think 2029. Like why did they do that? Yeah, so the soonest that the debt was puttable, where I believe that the bondholders could like ask strategy to repurchase them, I think it was in September of 2027. So I agree with you, still a decent length of time away, right? So I agree that it was a misstep, But, you know, giving strategy the benefit of the doubt, I think, when you look at the way the equity was trading and you look at the true MNAV of strategy, there was a hefty premium on the common stock. And so if you're going to pull the lever on selling MSTR and if it's not accreted to the shareholders, I would have rather had them do that, to be honest with you.
6:31I think that, you know, probably tapping the USD reserve was not the right call. And what's really interesting is that when you compare the USD reserve strategy to that of Strive, it is really remarkable to see how the market is pricing both of these digital credit instruments. Because we both know that it's like competing for retail flows right now. Sailors coming out and saying, stretch is 80 % held by retail. And I'm not naive enough to think that Seda isn't competing for the same flows. But it's something like Strive has 43 times less Bitcoin than Strategy, or Strategy has 43 times more Bitcoin coverage.
7:09But because Strive has 11 more months in cash, or 8 months now, you're just seeing a huge discrepancy in how the things are trading. Now, obviously, because of the outstanding SEDA, the volume is a lot smaller. So you need a lot more liquidity to move STRC. But it's interesting to see how the things are trading. But yeah, I would tend to agree with you. I don't think that use of the reserve was a good move. If you look in the SEC filing, or maybe it was the STRC prospectus, I can't remember exactly. It must have been the filing after the USD reserve was announced, but they do talk about how they intended to use it.
7:47And then they also had the phrase, something along the lines of, we have total discretion to use it for whatever we want to. So the debate about whether or not they misled anybody, it's like, well, the language is in there that they have discretion. So but yeah, as an overall strategic move, I don't know if I agree. Yeah, like the misleading people is not something that I mean, I'm not a micro-contracting shareholder, so it doesn't concern me at all, really, that part of it. It's just whether it was the right move. I don't I don't understand it necessarily, but like I believe they've just raised or just hit the ATM to raise more money to have that sort of backup.
8:22So I think that's probably a good move. But the thing that I don't necessarily get, another thing I don't necessarily get is like, why would you be a MSTR shareholder when it seems like you're just going to get diluted at sort of every opportunity? Yeah, I think that if you look at history and you look at the overall total returns over a long time horizon, it's pretty apparent that MSTR has considerably outperformed Bitcoin in fiat terms. We were just talking before the show. As we get further into this Bitcoin bear, I become more convinced that holding the treasury companies definitely isn't for everybody because of the added volatility.
8:57And it requires a decent degree of understanding of Saylor's financial engineering. But overall, I do think, you know, you look to history, you look at the strategy. Can they continue to issue equity that's accreted to the shareholders? Can they amplify the Bitcoin exposure via the preferred stock issuance? And then if you think that they can pay those dividends, I mean, that's mechanically how the Bitcoin exposure is amplified. So, you know, it's added risk. You are taking the counterparty risk. You don't own the Bitcoin. You are economically exposed to the residual. But, you know, some people like that trade.
9:32I'm an MSTR shareholder myself. I buy Bitcoin every day. I don't own Stretch. But I do like with my risk capital. That's the way I think through it. I think of Bitcoin as saving and then Bitcoin is the hurdle rate in my mind. Like if I'm going to beat, I need to beat Bitcoin if I'm going to invest in an equity. So I am an MSTR shareholder for that reason. It's just getting back to the Sata versus Stretch thing. It's been interesting to see Sata do quite well. And I think one of the points you made before, I could be wrong on this, but like you said that Stretch is 80 % retail. And I'm purely guessing here.
10:08I would imagine Sator is not the same, even higher. Like they seem like very retail products at the moment. And it's part of the problem that if you play sort of retail games, you win retail prizes. And like this is part of it. Like I'm sure huge liquidations played a part in stretch dropping to like$83 or whatever it did. And I also think you said that the market is deciding that the cash reserves are sort of the thing that they care about more. I just think it's higher yield. I think people just chase higher yield. And so I don't know how you kind of balance those two things out. Yeah, I think that what we're witnessing right now in the market, Danny, I think you're spot on.
10:47I should have said that actually, because I agree 100%. I've talked a lot about this where I saw this study recently. I think Pierre Rochard tweeted it out or somebody else. I can't remember exactly, but it was essentially Bitcoin. Like how much of Bitcoin is explained by an efficient market hypothesis? Like just Bitcoin itself, not even like all of these crazy derivatives that, you know, these market participants continue to come up with, at least these issuers of the digital credit things. So, like, I continue to see pricings in my mind with the strategy preferreds that to me, in my opinion, like just totally don't make any sense at all, especially when you look at strike, for example, where you have an embedded call option on MSTR going up, which is essentially a call option on Bitcoin going up.
11:36and that thing will trade at the same yield as STRC. I see a lot of these weird mispricings. So I don't think that Bitcoin can be explained by the efficient market hypothesis. And it's almost like these things aren't either. But I agree with you 100 % when they're competing for retail flows. I don't think that a lot of people are doing the hard risk analysis of them, to be honest with you. I think that they're looking at a headline yield number and think, oh, I'll get paid daily and I'll get paid more money. They get that dopamine hit. So I agree with you. And did the daily dividends from Seta have an impact on Stretch?
12:12And is that part of the reason we've had this drawdown? Because I know that before Stretch were doing sort of bimonthly dividends and before Seta were doing the daily, people were swapping between the two, like getting in the lock-in date, getting the yield and then moving back. And that kind of got completely arbed out. The arbitrage was there. That's gone now because people have to hold Seta every day if you want to get the dividend. and has that meant that the retail has gone there parked their capital there and sata now has less inflows does that like sorry the stretch has now less inflows does that play any part in this yeah i think it has to like there's no way of getting around that for sure i think that we are so much in an echo chamber with number one bitcoin itself in terms of the broader world and then on top of people he even know what stretch and sata are um so ultimately like they've issued to 10 plus billion dollars of strc in a year i think that's been a success for them um they paid every single dividend on time so like it's going to take a while for the track record to really uh open up strategy only as a b minus credit rating right now so we're in this weird period where they have to prove themselves prove the credit quality of these instruments for a number of years maybe before you see larger institutional capital pools even think of this meeting mandates for example so um right now we're just in an infancy stage and there's highly little doubt in my mind that a lot of people didn't sell stretch to go to seda yeah it's it's been in i want to pull up a chart actually let me just grab this uh cool this is by my boy checkmate um can you see this yep so one of the interesting things this chart to me he wrote a newsletter piece on on stretch a couple days ago um is the number here at the end.
13:59So I believe, and someone can correct me if I'm wrong, but this shows that there is no stretch holder that has made money at these prices, including the yield, including the dividend. Like this is underwater in quite a big way. And I want to know sort of your opinion on this. And if this signifies anything about the digital credit narrative, maybe not playing out how people expected. Maybe like, is it still working? Is it real? Yeah. First thing I'd say, I don't know if I need to fact check this. The graph is really small, so I don't know exactly what it says. I see the price for the stocks. I'm assuming here.
14:37This stretch total return is at 99.795. But it was IPO'd at 89. So it's a positive return. So I actually just ran the math on this. It was IPO'd on, I believe, July 28th. And Stretch has an overall total return because it's only, like if it was IPO'd at$89 and it's around$89 today with every single successful dividend paid, then they're at about a plus 6 % total return. So ever since the Stretch IPO, Stretch is about plus 6 % total return while Bitcoin is minus 50. And so I've actually made this point where people say, Adam, like you're cherry picking data. And I'm like, well, I'm not really. I'm looking at the entirety of the data set.
15:23But I decided, OK, fine. I actually plugged it into AI just to number crunch everything. And I found out that of every single possible holding period between Bitcoin and STRC, Stretch has won out on 86 % of all possible time horizons since the Stretch IPO when you're comparing it to Bitcoin. So the stretch return is when you're including the dividends, it does go up into the right versus Bitcoin falling off 50%. So when you couple that with every dividend being paid successfully, and there are times of high volatility like now in February, for example, but overall, it's been a success. The dividends have been paid.
16:01It has stripped the volatility out of Bitcoin considerably, just showing that it's still a total return positive after a 50 % Bitcoin price correction. So 86 % of all possible time horizons since the IPO and at least total return since the IPO has been positive. Yeah, I'm in the same boat. I'd heard back from Checkmate. So the first chart that I showed you, which was the stretch returns, his point was that anyone who bought a par is underwater at this point. And the other prefs are below IPO on total return basis. so and like the question was that like i guess are these preferreds working as intended yeah uh me and checkmate must have different math because um i ran it today it's on my x account i have a totally different um number it was 89 or 90 at ipo and then we but he's saying anyone who bought at the$100 peg or$100 par basis is underwater.
17:05Yeah. Like, yeah. Like, uh, that is, well, I don't know. At any point in time. Yeah. Then probably. Yeah, definitely. Yeah. That's sorry. I was misunderstanding because his line was for like a month period. So now we're cleared up, but yeah. Yeah. A hundred percent. And then the other one that all the other prefs are below IPO price. Yeah. Yeah. On a total return. Yeah. He's correct about all that stuff. Yeah. When if you would have bought at a hundred, yeah, you'd be underwater right now, even after, uh, factoring in all the dividends paid. That's true. So what was your question? Well, and the other prefs being below IPO price, including like with total returns, are the prefs actually working as they were intended?
17:45Yeah, I do think so. I think that when you look at the amount of capital that's raised by them, like we are seeing some higher effective yields, but nothing that signals that the dividends can't be paid you look at the capital markets access they are just like they're having their most successful year of capital raising ever like 2026 with a bitcoin bear market they're still raising more money and buying more bitcoin at a faster pace than ever at least in a january through now year-to-date basis um so when it comes to the credit quality i think the risk is mispriced i think it's wild that they have to pay that high um ultimately they raised billions of dollars and they bought Bitcoin.
18:25So I think like that's a win for them. And then the people who bought them, I think, yeah, like just like with anything, if you would have bought Bitcoin in October, you would have been down 50 % right now. So buying stretch, you would have mitigated a lot of downside. That's just mathematically true. So yeah, I think that they're working just as intended. I don't think anything's broken. I think the credit quality is being questioned by a lot of retail shareholders. But overall, I think the credit quality is great. And I think when Bitcoin returns, you'll see them trade back up just like how they were last May.
18:57So I think that's what will happen. Do you want to pay less in taxes and stack more Bitcoin? Of course you do. Well, by mining Bitcoin with Blockway, you can. Under section 168K of the US tax code, Bitcoin mining servers qualify for 100 % bonus depreciation. This means every dollar you spend on miners can directly offset your income in a single year. and it's true for both business owners and W2 earners. So if you have$100 ,000 in ordinary income, you can purchase$100 ,000 in miners and potentially offset your tax liability entirely. Blockware's mining as a service does all the heavy lifting. They secure the rigs, they source the low-cost power and they handle all the day-to-day maintenance.
19:33So you get to stack Bitcoin every single day while drastically shrinking your tax bill. Get started today at blockwaresolutions.com forward slash WBD and use code WBD for$100 off your first miner. That's blockquaresolutions.com forward slash WBD Bitcoiners, as you know, with fiat money constantly debasing Wealth preservation isn't optional That's why I recommend Swan Bitcoin A team of dedicated Bitcoiners who work with families and businesses To build and secure generational wealth with Bitcoin Strong relationships with clients are at the center of everything Swan does A dedicated Swan private wealth representative Which is a real person that you can text and call Will help you build a Bitcoin wealth strategy using Swan's comprehensive platform of Bitcoin services, including tax-advantaged retirement accounts, advanced Bitcoin cold storage using collaborative self-custody, inheritance planning with both trust and entity accounts, tax loss harvesting, asset-backed loans, and more.
20:26Swan have helped over 100 ,000 clients since 2020, and if you're serious about acquiring and securing Bitcoin, I recommend Swan. You can meet the team at swan.com forward slash WBD, which is S-W-A-N dot com forward slash WBD. You wouldn't reuse a Bitcoin address, so why does your phone broadcast the same identifier for life? Every SIM has a static ID and carriers, ad networks and bad actors all use it to track you. The big carriers have been caught selling that data over and over again. CAPE is America's privacy first mobile carrier. Their identifier rotation feature changes your ID every 24 hours so you look like a different subscriber every single day.
21:04And SIM swaps are off the table. Your number can't move without a 24-word phrase that only you hold. There's also no name at sign up, no social security number, and there's no profile to build on you. If you're a Bitcoiner in America, I honestly don't know why you'd use any other network. You can head over to cape.co forward slash WBD and use the code WBD for 33 % off your first six months. That's C-A-P-E dot co forward slash WBD. Okay, because the question I have is, how do they raise capital going forward? Because it seems like they have a few options. They can obviously sell the preferreds, but that then increases their dividend liabilities.
21:43They can raise more debt potentially, but again, that adds leverage. They can and have and probably will continue to dilute shareholders. Do you see that as the best option? Because the other option is sell Bitcoin. And as a strategy shareholder, is selling Bitcoin not the best thing for you? If they just start selling enough to pay the dividends, the Bitcoin market can easily absorb that amount of money. I think it's, is it around just under$2 billion a year or something like that? That they, is that right? That they owe? Yeah. The Bitcoin market can take$2 billion a year in sell side. Like, is that the best option?
22:19I don't think they'll do it, but is that the best option? Yeah. What's really cool is that they have so much optionality. As a Bitcoiner who like, I hate selling Bitcoin. I don't, that doesn't drive well with me, to be honest with you. It's maybe a personal preference where this idea of selling Bitcoin, the market absorbing, It's$1.7 billion is the annual dividend obligation. And do I think it can be done successfully? 100%. Like the total volume of Bitcoin is orders of magnitude higher. Like the market would absorb that no problem, as evidenced by the fact that he bought 48 times as much Bitcoin the next week after he sold.
22:52And the price probably went down. So like the market can absorb it no problem. But we really need to look at their total optionality with the true MNAV. people continue to look at the basic MNAV with the market cap in the numerator, the market cap, which is like the value of all the shares, you know, divided by the Bitcoin nav. That's not telling the entire story because that's not looking at the preferred stock and the outstanding preferred shares. And then so strategy does a better job with enterprise value where it incorporates the overall, just a more cohesive picture of the capital structure.
23:28But if you look at everything with the outstanding preferred stock and you essentially do like an algebraic look at the capital structure and find out what is the senior claim Bitcoin. So like when they issue stretch and they use those proceeds to buy Bitcoin, you have to think of the residual, what's left over economically for the MSTR shareholders. and what you'll find is that the residual value of balance sheet value that's backing the mstr shareholders it's not just the bitcoin it's also the cash because as an equity holder you are exposed economically to the total residual not just the bitcoin which is why bitcoin per share is incomplete but if you crunch that mnav number right now last time i ran the numbers was like a 1.2 x mnav right now and so sailor has come out and corrected people online about this where if you look at the total capital markets activity, it is accreted to MSTR shareholders.
24:25So in terms of a lever to pull, that would be my number one by far because the stock is still trading at a 15 to 20 % true premium. And I think that Bitcoin is close to a bottom. I could be wrong. Maybe it goes down to 50K or something, but I don't think that the premium will probably drop any more than it is now. And if it does, like if the true CEBEM nav goes down to one, they only have to dilute the shareholders 5 % per year to pay that annual dividend. And that's if they don't tap the Bitcoin or the cash. So to me, I'm like, the MSTR shareholders are seeing if all the premium evaporates to the residual, they would have to dilute the stock only 5 % per year.
25:08And in exchange, you get that 40 % Bitcoin amplification. So I think a lot of MSTR shareholders look at that trade-off and if they're bullish on Bitcoin from a pretty big overcorrection, the math makes sense for them. It's interesting because I was saying to you before we started the show, I get so much hate for trying to ask these questions about treasury companies. I've said a million times I'm skeptical of them. And honestly, I've come to the realization that the truth is I just don't really like them. My gut is just telling me I don't really like them. There's nothing wrong with that i don't like the narrative of digital credit like i don't like like all these sort of financial terms around bitcoin like bitcoin is just bitcoin like i i like the idea i like what strategy started as i like having a business that generates money and putting that money in bitcoin awesome like i love what block are doing i love what tesla and spacex doing like having just a cool business that makes money and that money goes into bitcoin is awesome what i i'm not a huge fan of and again like it's not that i think it's going to fail or i don't think it'll do well it might do amazingly well.
26:11I just don't like it. And I feel like there's a lot of the sort of, at least Twitter world that are kind of coming to that same conclusion. Like there's been a lot of hate on Saylor. And to be fair, I think probably that's bear market things. I'm sure Saylor will be fine. I'm sure he's not losing sleep over people like me complaining on Twitter. But like, why do you think this hate has sort of arisen? Yeah, that's a really good question. I think that there is a philosophical split in the Bitcoin community that's like really eating it away at kind of our previously at least better vibe that we had going on.
26:45I think that it's because people are defining Bitcoin's win condition differently. Like you just said, you don't like the treasury companies, and that's a very common viewpoint right now. I think a lot of people, they, you know, people come to Bitcoin through a variety of ways and they have their own win condition attached to it. Because to me, like Bitcoin is this monolith that's just this amazing, pristine, free, neutral monetary network. And then a lot of people like to attach their subjective, often political philosophy win conditions. What does it look like for Bitcoin to win? And I think a lot of people are finding disagreement about that.
27:23A lot of people, you know, they'll say Bitcoin doesn't win until government is abolished. And we live in an ANCAP society where we're all transacting equally. And then there's some of us that are saying, well, I don't know if that's necessarily a pragmatic thing. Like Bitcoin has improved so many people's lives and it's 16, 17 years since the Genesis block was mined. So I think it's really a philosophical disagreement about how Bitcoin will win. Like what does it mean for Bitcoin to win? So I don't know what your thoughts are on what it looks like for Bitcoin to win, but maybe that's the source of the disagreement.
Read the full transcript
27:56I mean, that could be it. And like to me, Bitcoin is winning. Like I I wouldn't say it's already won, but it's winning and I think it will continue to win. But the problems that I have around it and the areas of concern that I have are like, I don't love that one company has 4 % of the Bitcoin supply. And again, there's nothing I can do about this. And then they can use Bitcoin however they want and they should. But I don't love that they have 4 % of the supply. I don't know where the sort of crucial number is where it's too much. But if it's 80, 90 % of the supply, clearly too much. is 4 % of the supply too much?
28:30Maybe. I just don't know. I don't love that. And like the other thing that I'm unclear on is whether this is now not actually attracting institutional investment, but dissuading institutional investment. Because like you said, Michael Saylor and Fong have come out and said like 80 % of the people buying stretch is retail. And to me, it's like, that's not a good thing. Like I thought this was meant to be aimed at institutional type investors. And are institutions looking at this and being like, let's wait and see how strategy shakes out? And is it actually putting people off? Are they concerned that strategy has too much Bitcoin can pretend like, you know, quote unquote, manipulate Bitcoin?
29:10Like these are the sort of some of the concerns that I have around it. Yeah, it's tough because obviously it's a question of like wealth inequality and the Gini coefficients. Like how much is too much? And like we know there's a finite amount and humans have never been face to face with true scarcity before. So I find it like psychologically fascinating how us humans are still absorbing it. I think we haven't even thought through the proper ramifications of Bitcoin yet. In terms of the institutional capital thing, I think that what you're seeing when you look objectively like over the past couple of years, a lot of people say that Bitcoin had its IPO moment.
29:47The OGs are selling like crazy. The individuals are selling their coins hand over fist to the institutions. like that has been the trend since the beginning of 2024. River does a great job where they'll post their graphic about this every quarter or so where it's like, you know, I don't know if it's 10 or eight consecutive quarters where like hand over fist individuals continue to sell to the institution. So I think that you raise an interesting point, like long term, will that be seen as a negative? But overall, when we look at the trend of this institutional monetization of Bitcoin, I think it's actually quite the opposite.
30:22we've seen a lot of inflows. The IBIT holders are surprisingly sticky, I think. So yeah, I think that you raise a very interesting question long-term, but like, to me, I'm like, I don't know if it's a cause for concern as of yet. If Saylor gets half of the network, maybe it will be. But yeah, thinking that hypothetical future is an interesting thought experiment. Yeah, I was reading Checkmate's recent piece on this and he raised a point that I think is super valid. It's like in a bear market, the market goes hunting for the most leveraged people and he liked they like to take him out to the woodshed and uh and chop him up and and he put a chart in there which i'm actually struggling to find but i'll put on the video so this shows like where the um where where the first impairments are for for strategy and it's around 25k um like i don't think we're going to go to 25k but i don't think it's impossible and so do you think that the market is looking at these liquidation levels and will potentially try and hunt them?
31:19Yeah, I think that it depends on what you mean by hunt exactly. When it looks like Checkmatey's math is spot on with mine, where it's$25 ,000 where the common equity is impaired, where I see a lot of people get what I see a lot of people get wrong is simply that this is calculating kind of that residual that I was just talking about, where the Bitcoin net asset value would equal the senior capital. So like the outstanding preferreds in the debt. So there's no room for the common equity. But when we look back in 2022, this exact thing happened. A lot of people don't realize this, but if you would calculate the residual exposure for the MSTR shareholders at the bottom in November of 2022, it was negative 14 ,000 sats per share.
32:05So it was in the negative and the market never valued MSTR at zero. So a lot of people run this math and they'll say, you know, MSTR goes to zero. And it's like, well, that's separating how the market values the residual versus how the residual is calculated. So essentially, it won't go to zero because there's kind of an embedded call option where, hey, maybe Bitcoin will go up again one day. And obviously, you know, price is sentiment and people will look for those opportunities. The stock was trading at a 0.7 XM nav that invites the opportunity for people to snipe that leverage Bitcoin at such a low price because your return is just higher.
32:47So it's impaired in the sense where the residual is calculated at zero. But like in terms of MSTR going to zero, I just don't see that happening at all. When you actually run the math, it's about 2022. They had minus 14 ,400 sats per share at the bottom in terms of Bitcoin exposure for MSTR shareholders. And now it's 145 ,000 today. So it's a huge gulf. like the capital structure is so much healthier. So like if we go to 25K, I don't think that it will. Like that's a crazy level of oversold. But yeah, MSTR doesn't go to zero when that happens. It's just the residual calculation. Okay. That's good nuance because I wasn't fully aware of that.
33:34And I actually didn't realize that it traded below that in 2022. That's interesting. Yeah. Yeah. 2022 is way worse for strategy, like crazy negative exposure. And I think the stock was bottom like$11. So yeah, it's quite a different story than today. What's your take on the whole digital credit narrative? Because to me, Bitcoin's just money. And I don't fully buy into the digital credit sort of narrative that's growing amongst the treasury companies. What's your take on that? Yeah, I don't mind the term digital credit. I think that you're evaluating the equities through a credit risk lens. This dictionary definition of provisioning money for the expectation of a return, like to me, it fits the dictionary Merriam-Webster definition.
34:20So a lot of people take issue with it. I don't take issue with that term. I agree with you. I don't like the digital money term either though. There was this clip, me and Jeff Walton, my friend from True North Jeff, with my recent appearance on True North, we kind of got clipped up where a lot of maxis were freaking out on us. I think that a lot of people miss the context of the entire situation where people were acting like I was advocating for digital money that's like tranched credit replacing Bitcoin as a medium of exchange. I view it as like, if some people want to do that as like an incremental improvement over traditional fiat, like if the capital goes to Bitcoin, I would view that as a net positive for the overall capitalization of the Bitcoin network.
35:08But yeah, I'm with you. I think the idea that you can like tranche out these risk tranches from a security and that's somehow money. I don't buy that narrative. So I don't like the digital money thing, but digital credit, I don't have an issue with. Okay, fair. With strategy, we're sorry, we're stretched now trading it like it's$88 post-market. this is going to take a long time to get back to par, right? I think last time it traded significantly below, it was a couple of months until it got back to$100. This is going to be sort of a prolonged stretch bear market, I imagine. Do you agree? It's tough to say because on February 5th, we saw the largest nominal Bitcoin crash in the history of the asset.
35:52And stretch rebounded in one day. So I'll be honest with you, I expected kind of the same thing where I was like, man, a rebound to 98, that should be expected. And we actually did briefly touch 97. Not after this Thursday, but with this recent overall price stress, we did see it like reach 97. I think that overall, they're going to follow the guidance that they've set forth with the volume weighted average price. If the VWAP is below$95, they will probably raise the dividend to 12%. That leads me to wonder how many of the people chasing that headline yield with SATA at 13. Like, is that enough to bring it back up to par?
36:33You saw Fong Lee today tweet that he bought a million dollars worth of STRC. So the CEO is doing his part, I guess. But yeah, I do think it'll go up to par just because I think that overall risk is mispriced with the strategy preferreds. I think the credit quality of the company is amazing. And I think that it's crazy that strategy even has to pay 11.5%. If I'm being honest with you, I think it's super wild that the dividend rate is as high as it is. It tells me that the overall broader market doesn't appreciate Bitcoin. And as a hardcore Bitcoiner, I hate that. I mean, that's something I do agree with.
37:09And if I was ever looking at buying Stretch, like this is, I imagine, one of the best buying opportunities you might ever get. Like, I don't think this is going to wipe to the right. I think it will get back to$100. Like, if you're into it, like, I get why you buy it at this point. Like, it seems very attractive. um the the interesting thing though is like bitcoin price is going to determine some of this and i i feel like it this works both ways where um strategy can have like a really good impact on the price and i think right now this is the big overhang we have like i think if we didn't have stretch trading trading way below i i imagine that bitcoin price would be doing better than it is i don't know if you agree with that yeah i might have misunderstood you are you saying that the Bitcoin price is being influenced by the stretch fiasco?
37:58I wouldn't be surprised if it was because people are then baking in like the Michael Saylor risk of Bitcoin. Yeah, I think that I'm not so sure if I agree with that, like as being a huge because I do like going back to what I said earlier, I think that we are in a super niche of a niche of a niche. Like, I don't think people know what digital credit or STRC particularly are. Even amongst Bitcoiners, I see so much misunderstanding about it. But I don't think that... But I don't know if they have to understand it to look at this. In fact, maybe it actually works because they don't understand it, because they might look at strategy being like, this looks like it's at risk of blowing up, therefore Bitcoin's going to go down.
38:36I think it can be that simple. Yeah, I just don't think that Bitcoiners who are orange-pilled, they're going to be dissuaded from buying Bitcoin because of Saylor's preferred equity. I'm not saying it doesn't have a portion of the influence on the price of Bitcoin. Of course, like if you understand Austrian economics and human action praxeology, it's the price is the reflection of an endless, uncountable number of variables. But like in terms of an overall driver, I don't think that that's sizable. I'd be interested to see like research on on the sentiment behind Bitcoin and stretch or something to maybe explore that further.
39:14But on its face value, I'm not so sure if I agree. But I think you're right. Like, I don't think orange pill Bitcoiners who are just stuck in Sats care. and I think like they'll still be buying consistently but it's the big money that I wonder if this is putting off. Yeah, I think it's definitely a possibility. I just don't know. It's difficult to say to the extent that it is. It's like an unfalsifiable thing right now. I just wish that we had more market data to tell us that but I think that it's an interesting theory. If you hold Bitcoin for long enough, there's probably gonna come a time when you need some dollars.
39:47Maybe it's for a business expense, a tax bill, a property purchase but whatever it is, you might not want to sell your Bitcoin. That's where Ledin comes in. Ledin lets you borrow against your Bitcoin so you can access cash without selling your stack. They've originated over$10 billion of loans since 2018 and they've operated through multiple Bitcoin cycles. And Ledin has now introduced new tiered rates so there's no negotiation, no guesswork. It's just the larger the loan, the lower the rate and you can see all the rates up front before you apply. The important part for me though is the custody.
40:16With Ledin's custodied loans, your Bitcoin collateral is never lent out to generate interest. You also get all the tools to properly manage the loan, including LTV alerts, auto top-ups, and the ability to repay whenever you want with no penalties. I've used Ledin myself. The application has taken me less than 15 minutes and you get dollars in your account within hours. So you don't need to choose between getting liquidity and sticking to your long-term Bitcoin plan. With Ledin, you can do both. Check your rate using the loan calculator at ledin.io and use the code WBD for 0.25 % off your first loan.
40:48That's L-E-D-N dot I-O and use the code WBD. If you're already self-custody Bitcoin, you know the deal with hardware wallets. Complex setups, clumsy interfaces and a seed phrase that can be lost, stolen or forgotten. BitKey fixes that. BitKey is self-custody built for real life. It gives you an intuitive, easy to use wallet with no seed phrase to sweat over. And it has a strong recovery system and built inheritance for long-term peace of mind. And BitKey's just had a massive upgrade. The new device now has a screen. So before you approve something, you can check it on the BitKey itself. The transaction, the address, or any account changes.
41:21It's a big difference. You're not just trusting what's on your phone, you're seeing it for yourself on the device. It's simple, secure self-custody without the stress. Go to bitkey.world today and use the code WBD to get 10 % off the new BitKey. That's bitkey.world and use the code WBD. The thing that keeps me up at night with Bitcoin cold storage isn't Bitcoin failing, it's my setup failing. And this is where Anchor Watch comes in. With Anchor Watch, your Bitcoin's insured with your own A-plus rated Lloyds of London insurance policy. And all Bitcoins held in their time-locked multi-sig vaults.
41:52So you have the peace of mind knowing your Bitcoin's insured while not giving up custody. So whether you're worried about inheritance planning, wrench attacks, natural disasters, or just your own silly mistakes, you're protected by Anchor Watch. Rates for fully insured custody start as low as 0.55 % and are available for individual and commercial customers in the US. You can speak to Anchor Watch for a quote and for more details about your security options and coverage, visit anchorwatch.com today. That's anchorwatch.com. Okay, so let's talk a little bit about Bitcoin price. This is when we hit 60 the first time, I thought that was the bottom.
42:26When we hit 60 this time, I think it's the bottom. Do you think this is the bottom? That's so tough, man. I'm not like a technical analysis astrology for man chart squiggler guy. But when you look at so many indicators that mark bottoms, you look at the deviation from the four-year moving average, which to me is like the most bullish indicator ever, how that line just continues to compound at over 20 % per year. We're like in the single-digit percentile with a deviation from the four-year moving average. Bitcoin priced in gold is like cheapest since 2010 level of percentile. I don't know if you're a power log guy, but the same thing there.
43:09Like we're seeing so many indicators, relative strength index, where we're just seeing the same levels as 2022. It's flashing November, 2022 FTX levels. So I don't think a wick down to 50K or even 30K is impossible. Nothing is impossible. But I think a lot of people are freaking out because that's what happens when you are in like a single digit percentile of Bitcoin's oversold price. So yeah, I think that given Bitcoin's volatility, a lot of people don't realize this, but Bitcoin's volatility has almost been cut in half since 2022, which is a wild stat. Like the volatility has been crushed for Bitcoin.
43:51And a lot of people don't realize that the moves necessary on a daily basis to get you below like a 40k Bitcoin number or like a FTX black swan after black swan type situation, it is so much more statistically unlikely given the amount of capital that has to move now. Like, so I think that, you know, who knows if we're in the exact bottom, but it has to be close. I don't know if you agree with me, but it seems like we're right there. Sentiment, I think is the worst it's ever been. So I don't know. And sentiments always like that. That's kind of the counter trade, right? When sentiment's the worst ever been, you're probably close to the bottom.
44:28And I don't go off anything but vibes at this point. Like I've been in Bitcoin long enough that I sometimes get feels and it feels like the bottom. I don't know if it is, but like I've certainly been any spare cash that I could possibly get my hands on has been going into Bitcoin recently. And that's not always the case. Like it just, it feels like we must be close. Do you, what do you think is going to sort of play out over the next sort of Bitcoin cycles? Do you think we have sort of diminishing returns? Because again, Saylor obviously talks about he has his CAGA targets and he thinks Bitcoin is going to continue to pull them in the way it has in the past, at least somewhat.
45:03Do you think that's true? Yeah. As of now, I think when you look at the actual price data and the price performance of Bitcoin, it's tough to argue that diminishing returns aren't a thing. And a lot of people do this super cringe thing where they'll draw a line from the 2021 top and they'll do a horizontal line to now and they'll say, look, it's been flat, dead capital. But what I like to look at is the year over year, four year moving average compound annual growth rate where you smooth out the volatility. And you are seeing that, you know, 10 years ago when it was going up 54 % per year, year over year, now it's 30, then 29, then 28.
45:43I might be making some numbers up there, but that's essentially what it is. You are seeing a decrease in the CAGR of the four-year moving average. So the people that say diminishing returns aren't a thing, well, we just saw a huge muted upside with the October 2025 bull run, where we were trading at the power law trend, which is way less than previous bull markets. So it's tough. I think that we're going to see muted downside volatility as well. I think that's the most realistic scenario. I think the people calling for 30k Bitcoin like it's some certainty are smoking crack. To be frank, I think it's totally insane when you actually go to AI and crunch in like the statistical likelihood of moves like that with how big Bitcoin is now.
46:30But yeah, I think that's overall I'm bullish. The money printer has to print man and the feds in an interesting situation where they're being triple squeezed with oil inflation and do you cut rates in this environment? Maybe we don't see that for another half year or a year. Overall, I'm bullish on Bitcoin because monetary fiscal repression is going to be what happens. There's no getting around that. Fiat has no bottom. So long term, I'm super bullish on Bitcoin, but I cannot be speaking with any degree of certainty right now. That's for sure. I do want to ask a question I did allude to earlier, which is something that I can't get out of my head in that is Saylor stuck in this trade, whether he likes it or not.
47:10And this idea that he does have to just keep his foot on the accelerator, keep coming up with new things. And maybe that means adding leverage, maybe like whatever it is, is he stuck and he has to just accelerate at this point? No, I don't think he's stuck at all because I think that everything they're doing is working. If you look at their KPIs, I don't like Bitcoin per share, Bitcoin yield, but that's up considerably year to date. They're raising money at a faster pace that they ever have before. They're buying more Bitcoin faster than they have before. So what they're doing is working. It's an amplified expression of Bitcoin.
47:45The amplification ratio is about 40 % right now. So I think that when you saw that crazy blow off top where MSTR went to a 3.4 XM nav in November of 2024, when you have that, and then on top of leverage on the way down with Jim Chano shorting the stock and a lot of people taking advantage of that frothy premium on the way down. I think the price performance is largely explainable. And then, of course, man, getting kicked in the teeth with a 50 % Bitcoin price correction, that doesn't help an amplification story. So yeah, I don't think anything's broken. I think it's largely explainable by those market forces.
48:22And with the, like you said, it got to 3.4 XM NAV. Are those days gone? Do you think it can ever get back there again as an MSTR shareholder yourself? Do you think anything over two now is kind of out of the question? That's a good question. It's really hard for me to think of that happening again, I'll be honest with you. I see this critique a lot. There's some MSTR maxis out there that are losing their mind, I'll be honest with you. I'm like the biggest strategy bull, but I think it's going to be the most valuable company in the world. I'm like, Bitcoin's going to$3 million a coin. they're going to have trillions of dollars of assets.
48:58That said, some people are losing their minds. They will say, Sailor and Fong, stop selling MSTR. Wait for the MNAB to go to a 2.5. And I'm like, you think that the company, like the market's going to give them$80 billion in premium just because? Like, they're too big now, man. Like, I think that me and you probably are in agreement there where like a 3.4X MNAB, you got to think of when that happened. That was when And there weren't so many Bitcoin derivatives in the market that you could access with a brokerage account. That was when Trump just won the election where we were talking about a strategic Bitcoin reserve.
49:33You saw Bitcoin move from, I don't remember exactly, 55K in September to 90K. Like that was like lightning in a bottle, everything going right to hit 3.4 at that time. And that's why Saylor was selling stock hand over fist because you don't squander that opportunity. Like go get the Bitcoin when the stock is that expensive. So I think MNAP will always oscillate just because the price is in the numerator, the price of the company and price is a reflection of market sentiment. So I don't think that like we go to one and stay there forever. I think that's insane. But also, I don't think like we just go back to a 3.4 either.
50:11It's tough because we're thinking of these like long term hypotheticals. Could MSTR one day command a huge premium because they own 6 million Bitcoin and they can issue more credit than everybody and Bitcoin is like the new foundation monetary base? That's an interesting question, but it's all like hypothetical. At least in the next five years, I would be shocked if we ever saw an MNAV explosion like that again. Yeah, me too. Okay, I want to get back into sentiment because you mentioned before, like this feels FTX level sentiment. And I totally agree, if not even worse. And I've said this before on the podcast, but I think it's true in that when FTX blew up, if you were a Bitcoiner in Bitcoin land, you could look over there and be like, huge fraud, scams.
50:54Like, of course, the market's going to dump. Makes sense. Nothing's changed for Bitcoin. Therefore, like sentiment surely was bad because the price was way down. But everyone knew why. And whereas this time, like price is down a lot. We didn't really get the sort of highs that we expected last cycle. and there's nothing to point to directly and be like, that's why. And I feel like that's adding to the sort of negative sentiment within Bitcoin world. And obviously, Saylor is now bearing the brunt of that in a lot of ways because people are just mad about something and trying to find someone to blame it on.
51:28Is that a bullish sign, though, that we are at these levels and there isn't some like out and out fraud blow up that you can point out and be like, this is why? Yeah, I agree with you 100%. I think that the market is trying to find a villain right now. And Sailor is that guy. Like he'll be the hero in the bull markets. And then in the bear markets, you know, he'll be villainized by a lot of the community. I think that it is a buy signal. I think that, and it's not even a question of opinion almost. It's almost like a mathematical reality. Just going back to what we talked about, people often forget that like your statistical likelihood of higher returns skyrockets when you buy at this level of oversold versus these indicators.
52:13And nobody has a crystal ball. You can't predict the future. But it's so fun to like load up Bitcoin's entire price data for every single day since January 3rd, 2009, or at least the exchange data in July 2010. And just ask it like, what are the forward six month, 12 month, 18 month, 24 month returns of Bitcoin whenever we've been at this level of oversold? And you could do it for like the fear and greed index if you wanted to. And all of the numbers throughout all of history are like triple digit returns where sometimes I'm seeing them thinking, man, like I want to like take out a second mortgage to buy Bitcoin right now because like it's seriously, that's what it is.
52:50Your statistical likelihood of higher returns skyrockets when you buy when we're this oversold. And the sentiment is an indicator. It is a buy signal. It like literally just is like the people who bought mstr call options in 2022 and made 10 million dollars like they literally bought the most leveraged possible bitcoin at the worst ever sentiment in history and they made out like bandits so like are we 2022 levels of oversold it's pretty close but um yeah i think i agree with you man like the the negative sentiment is it's a buy signal for me i'm like i've never been more bullish because I understand the mathematical reality of to make money and to go up NGU, you need to be buying right now.
53:33100%. And it's one of those funny things in bear markets. I kind of perversely enjoy when price is crashing. It's always exciting. There's always stuff to talk about. I don't like the just dragging out. This bit's boring. And I just can't wait for the tide to turn again. I'm ready for us to go up again. The time pain is awful. Yeah. Yeah, I but i'm it's weird i'm i'm sort of i have this turbo bullishness around bitcoin and if i was to trade it would get me in big trouble it's like the big reason i don't trade but i i can't see bitcoin staying at these levels for long i i hope not anyway um do you follow what's going on like on macro side with everything that's happened in the fed recently yeah i do to a degree i don't have a total technical understanding like a lot of these macro experts do but like i do a lot of analysis on my own channel and then on the Swan channel as well.
54:24I have a two day a week show over there where I talk about this a decent amount. But yeah, following the macro side a little bit, I kind of alluded to it earlier, but like the Fed's being triple squeezed right now, man. Like it seems like, like how do you explain away potential monetary easing or rate cutting? Like that, that seems like the battle they've got right now. Yeah. Because when you talk about headwinds in Bitcoin. We don't really have one that's necessarily intrinsic to Bitcoin this time, but the macro side is the thing. And they seem totally trapped. Inflation's higher than they want it.
54:58Jobs are pretty good, but they need to cut rates. And how do they do it? But this is very interesting. If people have been paying attention to what Warsh has said leading up to his appointment and recently, he's mentioning things like, we need to recalculate how inflation is calculated. And then with his last statement after this latest Fed meeting, Warsh is saying that like, we're going to be giving less future guidance or like less commentary essentially. So that's very interesting. Like, what does that tell you? To me, it's almost like you need to play your cards closer with any like obvious moves you're going to be making.
55:34I'm not quite on the level of like the conspiracy tinfoil hat. Like he's Trump's puppet and he's going to do the bidding of cutting rates. But those two things are very interesting. I think like they're already being open about talking about how you recalculate it. And we've seen this game happen time and time again. The government lies to us about CPI. They literally replace ribeye steak with 7327 ground beef. They lie to us and they manipulate the basket. Anybody who knows shadowstats.com, the true government inflation. I know I'm preaching to the choir here, but like we're seeing the same language happening.
56:11They continue to change the lingo. And this is very interesting. I saw this recently. There was a meta analysis of Bitcoin price action relating to not only the Fed's actual actions in terms of rate cutting, but the market perception in terms of how the media was reporting about it. And the finding was that Bitcoin is the most reactionary asset by far to even the perception of rates being cut or rates being hiked. So like a 25 study meta analysis of that, to me, that's a big explainer of the Bitcoin price action. When you immediately saw this war happen and the poly market, betting markets, price in, rate hikes for 2026.
56:55To me, that's like a large explainer. If you look at that meta analysis, that was interesting. I 100 % agree. And the interesting thing is like, it seems like Walsh is trying to be sort of somewhat covert in what he's trying to do. Like he said, no forward guidance, but it's so obvious. Like it's so overt, like he's going to redefine what inflation is. He'll come out with like a new CPI adjusted number. It'll give us a lower inflation print. And I'm sure he'll go to cut rates or do like monetary easing in some way. That's what these central banking snakes do. This is what these snakes do. These people manipulate the fiat money supply.
57:32This is the case that it's been for over 100 years. This should be so obvious to everybody by now. I know I'm preaching to the choir. We're Bitcoiners, but it's literally the same playbook. Change the name of this. We'll change the inflation statistic. It's wild, man. It's literally another page out of their playbook. Call it something else and then repress the society monetarily. It's a sad state of affairs. Like, dude, did you know that the United States debt is like on pace to be over 50 trillion dollars by the time Trump leaves office? It's insane. It's just it's just numbers that like I can't even understand.
58:11Like, I don't know what 50 trillion is. I just know it's absolute insanity. Yeah, it's just crazy. Like, wait, Elon just became a trillionaire. That's one thousand billion dollars. And that 50 times over it's it boggles the mind. It's just ridiculous. It's crazy. And honestly, Bitcoin's at$64 ,000 right now. With all this happening, there is literally... I don't understand why more people don't know this is the best place to put your money and move into a Bitcoin world. It's crazy to me. And the other interesting thing that I think Walsh has to battle with is he's got rid of forward guidance. And like you say, markets move on what they say, not even what they do.
58:52And so without the forward guidance, do markets just get even more confused as everyone tries to read the thieves and they don't really have anything to go off apart from vibes? Like everything's vibes. Yeah, I was going to ask you, like, do you feel like that this has been the most uncertain market in history? Like versus when you first started investing? To me, I can't imagine being in anything else but Bitcoin. like literally 100 % of my family's future and my the success of my bloodline it is 100 % reliant on the success of the bitcoin network uh because i look at equity multiples and i can't like square that in my head on how to how these things are investable and what's funny even before i was totally orange pilled my orange pilling journey has been quite long but uh i have always thought that about equities.
59:43And I've always been able to perceive certain valuations being ridiculous. And I continue to see that get more crazy as my life goes on and I get older. And it just, the uncertainty is wild. We have people debating on whether or not MSTR should trade at a 10 % premium to their Bitcoin holdings versus DoorDash stock trading at a 70X earnings. it's like what like to me i'm like guys like the answer is probably somewhere in the middle here so to me that's why i love bitcoin and i actually do like the treasury companies because in terms of like a risk reward calculus it's so much easier of a tell to me like do i buy costco at a 60 pe is that overvalued or undervalued will costco exist in 2100 when robots have replaced humanity.
1:00:34There's never been more uncertainty, yet equity multiples are at the highest they've ever been. I believe that the composite price to earnings multiple for the S &P 500 is a 29. I think that's crazy. I would rather just buy Bitcoin. JBB, just buy Bitcoin, stack sats and call it good. That's absolutely nuts. I didn't realize it across the S &P was 29 times. That's insane. And like people might think that's silly that because you said before that Bitcoin trades off what the Fed says more than almost anything. Like, so sure, it could have a really negative effect, but we're just playing a different game.
1:01:12Like this is a much longer term, like I'll take the short term volatility to own Bitcoin for the long term. Like that's an easy bet for me. I can't possibly imagine having my wealth stored in anything else but Bitcoin and then like with some risk capital buying like a an equity that's reliant on bitcoin like i cannot even fathom honestly like buying the s &p 500 to me like i want to like i don't want to say vomit but i get like nauseated about this it's just like it feels gross like to me it's like this latest stock market crazy rush it's like the last big boomer hurrah where we've seen real estate and And equity is just at the mercy of the money printer getting inflated.
1:01:58And we have all of this old boomer capital. I don't say boomer disrespectfully for anybody older listening to this, but like that's what it is. It's people that are unfamiliar with Bitcoin and then they store their money and these things that are absorbing the money printer, essentially. And it's a really sad state of affairs. And, you know, as well as I do, like, you know, the capital is going to hunt scarcity at the end of the day. So I can't buy anything but Bitcoin. Let's go. Adam, this has been awesome. The takeaway is you think strategy is going to be fine. Buying Bitcoin is always the way.
1:02:34I'm excited for the next few years, man. I think we're going to have good times are coming back. Yeah, I think so. I think there's a lot of this Bitcoin civil war is super interesting. People throw and shade at each other. There's multiple civil wars. There are. Yeah, the core and knots thing. That's for sure. We didn't even talk about that. So maybe another episode or something. But yeah, like crazy stuff, man. It was a great talking to you. I'm bullish on Bitcoin. Sounds like you are too. And at the end of the day, that's how we win. Adam, where do people go to find more of your work? Yeah, I do a daily YouTube show at Adam Livingston BTC.
1:03:09And then I have an X account where I post analysis on Bitcoin and a lot of MSTR stuff as well at Adam B. Live. So those are my two platforms. Let's go. So, all right. Thank you so much, Adam. We'll have to do this again. That was awesome. Thanks, Danny. Appreciate it. Appreciate your time, man. Have a good one.
From the publisher
“The market is trying to find a villain right now—and Saylor is that guy.”
Adam Livingston explains the pressure building around Michael Saylor, MicroStrategy and STRC as the preferred stock trades at $88, well below its $100 par value.
Is STRC broken, or is the market mispricing Strategy’s credit risk? Adam explains how STRC works, why its yield has climbed above 13%, whether it can recover to par, and what Strategy’s capital structure means for MSTR shareholders. We also get into dilution, dividend coverage, Strategy’s use of its cash reserve and whether Saylor is now forced to keep accelerating his Bitcoin strategy.
We also get into the Bitcoin bear market, the possibility of a market bottom and why Adam believes the current environment is presenting a major buying opportunity.
In this episode:
- Why STRC is trading below par
- Whether Michael Saylor is trapped
- The risks facing MSTR shareholders
- Bitcoin treasury companies and “digital credit”
- Bitcoin’s potential market bottom
- The Fed, inflation and monetary repression
THANKS TO OUR SPONSORS:
FOLLOW:
Danny Knowles: https://x.com/\_DannyKnowles or https://primal.net/danny
Adam Livingston: https://x.com/AdamBLiv




