Saylor Just SOLD Bitcoin (Here's Why)

Added: 2026-06-03

[00:00:01]Michael Sailor spent four years telling everyone over and over never to sell your Bitcoin and then yesterday a filing hit the SEC showing that his company just sold Bitcoin. So which one is it?

[00:00:15]Did the most famous Bitcoin bull on the planet finally blank? Because the gap between I will never sell and here's a filing where I sold is where this entire storyline lives. And I'm going to tell you right now, by the time we're done today, the panic all of you are facing on the timeline will just be a moot point because here's what I'm going to show you. The actual filing line by line. Let's recall the reasons why he said he sold. The second one is the one that nobody's really covering. And then there's one thing underneath all of this noise that you can actually you actually should be watching because it's real and almost everyone's pointing at the wrong target. So between May 26 and 31st, Strategy, the company that you might know as Micro Strategy, sold just a measly 32 Bitcoin for almost about $2.5 million at an average price about 77,000 a coin. It's under 8K and it's a blunt reason. The money goes to the fund to dividend on something called STRC which I've covered in this channel before. So keep that word in your head because STRC that's the real reason and number one and we're going to come back to that.

[00:01:32]But the headline buries all of this.

[00:01:33]This is the first time Strategy has sold any Bitcoin in four years. The last time was December of 2022. So this is not a guy who's selling every other week. He sold twice. He sold Bitcoin twice in their entire history of this company.

[00:01:50]And everybody is acting like he's selling a ton more. I mean, but that doesn't beg the question, right? Why did sale sailor sell Bitcoin to sell a dividend? Because he's also sold $128 million in shares. So selling that 32 Bitcoin to get $2.5 million, he could have just maybe sold an additional $2.5 million worth of shares, right? Did he really need that? I mean, my friend George Gam is asking a valid question.

[00:02:19]And before anyone spirals, let's put that into context, right? Because Strategy now holds 843,76 Bitcoin. So they've just sold 32. 32 out of that 843,000.

[00:02:35]That's literally 0.0038% of the entire stack. So if you had a thousand dollars in your checking account, this would be about you spending 4 cents of that. So there's one that should really kill all of this panic. And in that same week, the company sold $128 million worth of its own stock through its ATM program.

[00:03:02]128 million of that, which is roughly 50 times bigger than their Bitcoin sale.

[00:03:07]And you need to notice something, right?

[00:03:09]Nobody made a scary thumbnail about the stock sale or anything like that.

[00:03:14]Nobody's tweeting in all caps about the equity raise. Their move was 50 times larger, but it all got completely ignored. And the tiny one becomes the full story. And that should tell you kind of how this is just running strictly on emotion and not really on the logic, right? I mean, you know, headlines right here all about strategy selling Bitcoin opposed to what they really did. But the thing that's almost funny is that he sold those coins around 77,000 and Bitcoin that week was trading down to near 72 to 74. So, he sold at a premium to where the market actually was. So, the guy who supposedly panic dumped sold higher than the market price. So, does this sound like panic to you? In my opinion, not really. But let's get back to the question at hand.

[00:04:04]Did he really break his promise? Did Mr. Never sell finally cave? Right? Because there's an honest answer here. And the promise was what people was never what people think it was. When Sailor said never sell, what he has clarified again and again is that he meant to be a net accumulator for every one Bitcoin company his company sells. The plan is to buy 10 to 20 more. So selling is allowed inside this strategy as long as the stock keeps growing over time. And the receipts back it up, right? because this is the same company that back in January bought 13,627 Bitcoin in a single purchase plus another 1,283 a week earlier. So in one month he brought close to 15,000 new Bitcoin this in a single month. Right? Five months later he just sold 32 to cover a dividend. And the internet is deciding that the thesis is dead. all these Bitcoin treasury companies are going to fail. But the answer to which is it, right? Never sell or just sold is that both are true and they were never actually in conflict. The contradiction only exists if you've never heard him explain what he meant by the word never.

[00:05:24]And that's the panic that everybody's facing. But let's talk about what he actually did because the real reasons are way more interesting than all of this drama and what all the headlines are saying. The real reason is to cover the STRC dividend machine. And STRC is the thing that money's going towards.

[00:05:44]And why does any forelling, you know, cause of it, right? Because Strategy doesn't just hold Bitcoin anymore. Over the last couple of years, they've built a whole stack of preferred dividend products. tickers like STRC, which they've nicknamed stretch, plus strk, strf, and strd, which are strike, strife, and stride. You don't need to memorize the alphabet soup for all of this, right? You just need to know that this is the part that matters. The preferred shares pay a dividend. They promise investors a yield and a promise to pay a yield, which means that the company needs to actually cash coming in in order to make these payments. So now, Bitcoin doesn't pay you anything, right?

[00:06:26]That's a big critique of the bears in the chat who I'm sure will be coming out saying that, "Oh, Bitcoin doesn't have an earnings. Bitcoin doesn't pay a dividend. Bitcoin has no real cash flow." Right? I mean, I'm sure we've all heard that from the bears before, right?

[00:06:41]But now, while we keep looking at all of this, right? Eventually, you have to turn a silver a sliver of that, excuse me, into cash. And that's all this is, right? 32 coins becomes $2.5 million. And that money services the stretch dividend. And here's the part that proves it, right? Because it wasn't a surprise. Back on the first quarter earnings call on May 6th, the company already said that this might happen. Sailors said on record that they were prepared to sell Bitcoin to fund the dividends. So, this wasn't a reversal and it wasn't a panic. It was a thing that they've announced almost a month ago before the filing even showed up. And there's even a clear number on that math. By the company's own logic, Bitcoin only needs to appreciate about 2.3% a year for the existing stack to cover these dividend obligations basically forever. So, that's without ever touching the common stock. And that's just 2.3%.

[00:07:44]And that's the bar, right? It's not a doomday's machine. It's a slow Tuesday for Bitcoin, right? Just 2.3%.

[00:07:52]And you know, other people like Adam Back came to his defense here saying that's tax loss harvesting and to send a message and recall before that there was drama about the ability to pay interest.

[00:08:05]So they sold some shares ATM at the market, right, and kept big cash reserves to stop that. And now I think trying for step two, get them to realize and accept that interest can also be paid with Bitcoin or shares. And even Lyn Alden tuned in and said that he she believes on recent earning calls that Sailor discussed selling some mainly to train the market that it's something that they can do to service the liabilities and such, right? It's not that Sailor is all of a sudden just dead in the water and fully away from, you know, his entire thesis, right? It's more to train the market and just say, "Hey, look, Bitcoin is a $1.5 trillion asset as it stands right now." Selling just a measly 32 coins and the market is absolutely panicking is just unreasonable at this point. It just doesn't make sense, right? So, even though, you know, we would all prefer to just never sell our Bitcoin, at the end of the day, Bitcoin is money, right? And and when it comes to these treasury companies, which I'll get to in a minute, it's looked at as more of an asset still right now. So, this clear math and clear reasoning is is out there and every reaction video is going to miss everything completely because there's a second reason a company like Strategy sells Bitcoin and it has nothing to do with fear and everything to do with taxes, right?

[00:09:30]Because back in December 2022, right, this is when strategy first sold Bitcoin, right? So, Bitcoin had been obliterated at that time and they were in a bare market. Bitcoin was in a bare market and strategy does something that looks insane on the surface, but they sold 704 Bitcoin at that time around 16,700 a coin. Then two days later, they bought 810 Bitcoin back at basically the same price. So, they sold and immediately rebought more than they sold. So, you got to ask yourself, why on earth, right, would anybody do that?

[00:10:10]And of course, it's because of taxes.

[00:10:12]They sold at a loss. They booked a capital loss and then the company said straight up in their filing that it planned to carry that loss against previous gains to generate a tax benefit. They lowered their tax bill and end up holding more Bitcoin than they started with. That's basically a tax cheat code, right? So, now here's what they can do. And you as a stock investor really can't, right? As an a stock investor, uh, and everything else, right? We just don't have access to these big capital markets because in the stock market, there's a wash sale rule.

[00:10:49]You sell a stock at a loss and you buy it back within 30 days. And the IRS says no, you can't do that. You don't get to claim that loss. But Bitcoin isn't a security. It's property according to the CFTC right now. And that's actually part of what the Clarity Act is going through. So this is all interconnected to what people in DC right now want to get passed. At least that's the thought, right? The only thing holding that back is is Brian Armstrong and uh Baldocks what he's fighting with over Jamie Diamond and the stable coin bill. But that's a completely different video, right? So strategy can sell at the loss and reby instantly, keep its exposure and still pocket the tax benefit. So it's a loophole that you know just a general stock investors are literally not allowed to touch. And that's the crazy part of all of this, right?

[00:11:44]Because this basically echoes what happened during that time in 2022. So connect the dots to today because on the same May 6th call which was just about a month ago now at this point Sailor signal that the company was ready to sell again and they brought up the 2022 tax logic and Sailor had and strategy have been buying for years non-stop basically which means somewhere in that stack of coins they've bought near the top. So they're underwater on some of those coins that they bought near 110 to 115 120,000. So if they sell those specific highost coins to fund the dividend, they pull off two things at once. They fund stretch and then they harvest a tax loss of nearly 50% on the coins that are down. So one one sale and they've got two wins. But that's not a man losing the faith in Bitcoin here.

[00:12:46]This is a former software CEO running a boring and a smart accounting play to say the very least. Right. So now before the scary part, I want to show you something that will make you a little calmer the next time you see a sailor [snorts] going for a forced cell as these headlines may try to portray because we just lived through one of those and it completely fizzled, right?

[00:13:15]because block had this camp exclusion for unrealized crypto profits. Right? So this is what that tax called the corporate alternative minimum tax. Right? That's what CMT is. So the short version is that it's a 15% minimum tax on the income of giant corporations. And because of the accounting rule change, strategy had to mark its Bitcoin to market value on its books, which meant huge unre unrealized gains on paper. The fear was that the government would tax those paper gains, the money that they hadn't even cashed in. But strategy itself warned in a filing that this tax could force them to sell Bitcoin starting in 2026 to pay the bill. So the whole market freaked out. Sound familiar yet? I mean, this is basically what's happening right now. But then what happened, right? In October last year, the Treasury and the IRS issued guidance saying that companies could disregard unrealized crypto gains for that tax.

[00:14:23]And Strategy turned around and said it no longer expects to be subject to it.

[00:14:28]So then the stock jumped on that news.

[00:14:31]The multi-billion dollar tax bomb that was supposedly going to force Sailor to dump was diffused. So this is a pattern because it's more than anything else I'll say today. The last giant that sailor said is going to be forced to sell, right? That story quietly died with barely anyone covering it towards the end. And the panic always travels faster than the resolution. So keep that in your back pocket because we're going to get back to what is going on with Sailor and his sale. But if you are watching this and you do not want to sell like Michael Sailor just did, I've got a solution for you. You guys at Greencandle can go to saltlanding.com/green-ash candle or the link down below in the description and get an exclusive offer.

[00:15:19]They're going to give you guys some of the best rates in the industry as well as giving you guys access to keep your Bitcoin and keep stacking your liquidity. And if you're worried about a lot of this volatility that we're seeing in the market, if Sailor sells Bitcoin, the price dumps and you're going to not be set up properly for retirement, you can go to strongwealth.net, visit my friends over there. Mitch is absolutely amazing. I've got a podcast coming out with him here in the near future. So, be sure to be tuned in for that. you can go visit them and you can see that hey even though some of these treasury companies might be blowing up they'll get you set up right so you don't have to worry about that Bitcoin sale because with all of this right the one real thing worth watching past this and I'm not going to try to sugar quote this because if I sat here telling you that everything is perfect uh I'd be doing you a deal real disservice right the real risk in this corner of the market is not just stress strategy selling the 32 coins. I at the end of the day the difference between a behemoth like strategy with 843,76 coins and you know Mac house with 125 coins is 88 80 80 8 what 843,000 Bitcoin plus folks. So the games that sailors are playing is significantly different than the games that these other potential Bitcoin treasury companies are playing, right? Because the MNAV, right, it measures how much investors will pay for $1 of a company in Bitcoin. MNAVs means, you know, these investors can pay $3 for every dollar. Let's say if the MNAV is three and that premium is magic. It's what let these companies sell their stock higher, buy more Bitcoin, and grow their stack without hurting shareholders.

[00:17:14]And at its peak, Strategy traded around seven times premium, $7 for every $1 Bitcoin. But today, that trades at a slight discount. It's below its own Bitcoin value. And Strategy is not alone in all of this, right? I mean, if you look at their overall Bitcoin price, right, and all of the metrics that they report themselves, Strategies MNAV is now, you know, sitting around uh just one, right? Their BTC yield is at 9.9%.

[00:17:51]Right? Let me see if I can find Yeah, their MNAV is just at around one 1.22%.

[00:17:56]Or 1.22, 22 excuse me not percent but you guys get what I'm saying right so it'll get dangerous when Bitcoin falls for sure and that premium is going to continue to shrink and as it shrinks towards nothing because you know as James Czech friend of the program and a lot of people have come out and said these companies can't raise money the easy way anymore and a lot of the newer ones didn't just sell the stock they borrowed money they took on debt to buy Bitcoin and so picture a leveraged treasury company with no premium let and debt coming due. There's honestly no way to raise fresh cash right now unless the Fed goes and lowers rates. So what's the only lever left? Well, it's to sell Bitcoin. And when a forced seller dumps into an already falling market, the price is going to drop more, which shrinks everyone else's premium, which pushes the next company towards selling.

[00:18:51]So one four seller will then become two which become five and then that's a potential spiral out of control. Right?

[00:18:58]So this is where we do have to worry about you know the potential of a death spiral when it comes to these Bitcoin treasury companies. But you know other analysts are coming out and saying that this sale is now immaterial right because even though strategy sold right the death spiral that could take place to these Bitcoin treasury companies is not theoretical late last year roughly one uh in three of the more than 100 track treasury companies were already trading below their own Bitcoin Treasury strategy. So, their MNAs were already lower than one, right? So, that's literally a third of them, 33%.

[00:19:42]Meanwhile, the well-run ones are fine, right? Metaplanet over in Japan was still trading at a healthy premium, well above one, while leveraged copycats are the ones that were underwater. So, the fear you're feeling about strategy today actually belongs to those other companies in my opinion because all of this is getting pointed at the wrong target. So, the obvious question is, is is strategy one of these companies that you should be worried about? And could Sailor get stuck into a spiral and be forced to dump a big stock? The answer to that, and I'm using the company's own words, because they've literally spelled out their own kill switch with all of this, right? Sailor admits, right, that it's possible.

[00:20:28]and the kill switch and Fong Lee who's now the CEO of strategy laid out these exact conditions for a force Bitcoin stale. Two things have to be true at the same time. One, the stock has to trade at below one times that line. So that below that 1.22 number that we looked at earlier. It's got to be below that that MV valv MN nav line, excuse me. Two, the company has to be unable to raise new capital.

[00:20:59]Now, look at it this week, right? The stocks near that discounted line. So, the condition is arguably in play, but condition two, they just raised $128 million from their stock sale this week.

[00:21:14]So, the capital markets are wide open for them. Condition two is not even close to being met. So, the 32 coin sale was a choice. a company with the markets wide open choosing to sell a rounding error to fund a dividend and probably book a tax loss while doing it. So this is the opposite of a forced sale that maybe a lot of these headlines might try to get you to believe, right? So a more flexible and more active strategy. See what I did there? Rather than one guy who buys and never touches it. That debate whether the philosophy is shifting is what I'll say not even worth giving the time of day because not the 32 coins the mindset is behind them right so zoom all the way out because four years the for years the strategy play was simple for the past five years six years right since they started buying Bitcoin it was simple right sailor buys Bitcoin swears he'll never sell ever no matter what and that was the whole brand but what we're watching is now a developing story because now Sailor has all of these preferred strike, strife, stride, and stride and stretch. Um, so they've moved from never selling at all to actively managing a giant balance sheet and trimming just a sliver of that to fund dividend while potentially harvesting a tax loss during this time period while still buying far more than they would ever sell.

[00:22:43]So this is not the thesis breaking, it's the thesis maturing over time, right?

[00:22:48]Because through all of this, Sailor has now been developing, like I said, all of these div dividends, these preferred, right? If Sailor just had MSTR, he wouldn't have ever had to sell Bitcoin.

[00:23:01]But the fact of the matter is, if he wanted to now get more access to capital to buy Bitcoin, well, he had to turn off that faucet a little bit, right? He couldn't just keep buying. he had to sell some in order to pay dividends. He had to get retail back on board in order to, you know, really come in and uh help fund more of Strategy's buys. And that's what we've seen from Stretch. And so, sure, it was a Bitcoin sale, but the real question isn't did Sailor sell because of course he did. But it barely matters. The real question is whether this is just normal housekeeping or the first quiet sign that even the most committed Bitcoin bull alive is starting to treat his stack like something managed instead of something worth being woripped. And you know I've got my read on it and I want to hear what you guys in the chat have to say right because now loan uh flare is saying sailor is a chillcoin artist. he should be working on lightning infrastructure but instead hawking out securities and doing financial engineering. I mean at this point like I don't know if Sailor really like has the desire to do that. I mean he has a software company. He was very successful before. So I think his complete mindset around all of this is just simply you know hawk out and get as much Bitcoin as possible. So I don't really foresee him doing anything like that. Right. I mean, in my opinion, I think like he's just looking at basically this old system, this old fiat system, using as much of that old fiat system to get into the new system because he's seen the light. Um, you know, I agree that we need to support the builders to say the very least. But, you know, it changes that thesis just oh so slightly here with what we've seen.

[00:24:51]And the biggest fear that I have is not Sailor dumping all 843,000.

[00:24:57]It's look who's now gotten into number two, right? We've seen Marathon Digital for a while. Uh for those of you guys who've been following my channel for a minute, make sure you're subscribed. But Marathon Digital used to be number two here with over 50,000 coins. Now that's 21 Capital with 43,000, right? So Marathon Digital sold 15,000 coins. A lot of these Bitcoin miners are going into Bitcoin uh Bitcoin mining plus AI and they're doing a little bit of a pivot themselves. So, in my opinion, this is not something to freak out about because, you know, Sailor is one company. Of course, they are a giant whale, but when you look at it in the grand scheme of the numbers, 32 Bitcoin out of this 843,000 Bitcoin is is seemingly immaterial. So, I'm going to be breaking this all down and tracking this as well. So, make sure you guys are subscribed. Smoke the like like Chichin Chong. Tell a friend to tell a friend.