The Breakdown - How Strategy Insiders Insulated Themselves From the Crash

Episode Date: June 26, 2026

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Welcome back to The Breakdown. I'm your host, David Tenless, as always. So, I mean, I think everyone is watching the price of Bitcoin right now and with good reason, because we ran an episode earlier this week that compared the similarities and differences between strategy and Stretch and Terra Luna in relation to the Bitcoin market. Since then, Stretch has crashed another 15%. It's now trading at 7380 in pre-market trade Friday, Friday.

morning. So since that episode stretches tanked another 15%. Bitcoin is also on its way down. It's now trading routinely underneath $60,000. Strategy is also on its way down as well, micro strategy stock, which means that indirectly you have gathered up a bunch of exposure just by holding crypto to the reality of what Sailor has cooked up and what strategy has done to Bitcoin and crypto over the past two or three years. And a lot of us has been super positive. Please don't get me wrong, it has, I mean, it's obvious. It has pumped Bitcoin way past 100K on multiple occasions, reaching everything 124K. And you have to admit that strategy was a big part of that. And I mean, it kicked off the dat boom. You have companies all around the world stacking sets,

trying to mimic what Sailor has done and trying to ride his coattails all the way to the moon and and so on. And that has done untold good. I can't deny that. So while holders and users and so on might be feeling the hurt right now, strategy insiders were able to really insulate themselves from the worst of the market, it seems, going by the amount of shares that they've sold throughout the past ball market with Bitcoin on its way up and strategy mimicking those moves. alongside it. So I'm just going to spend this episode. What we're going to do is we're going to look at the past few years of strategy inside of stock sales just to get a sense that those at the top of this of this plan, I don't think they have much to worry about, it seems, at least,

at least going by the data that we can see from the SEC disclosures over the past couple of years. So enough out of me. This is going to be the deal today. Let's take a look. This is the breakdown. Nothing said on the breakdown is a recommendation to buy of cell securities or tokens. This podcast is for informational purposes only and any views expressed by anyone on the show are opinions, not financial advice. Host and guests may hold positions in the company's funds or projects discussed. Okay, so first, I mean, I just want to preface this a little bit further. And that I am not really looking to demonize the idea that insiders at companies, the executives at public companies can't make money.

They absolutely can. I'm not anti-capitalist or what have you. I'm pro-transparency. And actually, I'm a big fan. of how much detail we can see in SEC disclosures about stock sales. And I want the same kind of transparency and disclosures for the crypto space. It would be really cool if we could see which insiders at which cryptocurrencies or token projects or whatever, which ones have sold and when.

It would be cool to also have pre-registered trading plans that can happen programmatically that aren't just, you know, actioned because you want to, the insider wants to sell at the top or what have you. I want this level of transparency and disclosures for crypto as well. But of course, you're going to see a bunch of numbers that you have insiders selling millions of dollars, tens of millions of dollars. In sailors' case, hundreds of millions of dollars worth of shares. And it's quite easy to try and spin that up into something that is quite negative.

What this is is just information for you to see that one great way to insulate yourself from the cyclical nature of the Bitcoin and crypto market is to apparently be an executive at a public crypto company and a publicly listed crypto company. And I suppose that goes without saying those those that are at the top of the industry who are on the frontier of all of this technological and financial innovation. They should be rewarded for it. So let's just take a look at the chart as well. I mean, we're also going to have a look at the chart.

So this is what's happening. The strategy is in blue. Bitcoin is in orange and stretch preferred stock is in green here. And you can see that over the past year, I mean, this is the whole bull market, the most recent ball market that I have on my screen. This is the view. And you can see that, of course, Bitcoin and strategy would share a very similar trajectory. but micro strategy just was amplified exponentially the moves of Bitcoin because everybody

piled into strategy because it was buying a bunch of Bitcoin. So, you know, we can see that strategy over the past, let's do a five-year view. Over the past five years, strategy at its most was up 700% across a five-year timeframe. Bitcoin at its most was up 250% over the same timeframe. So, yeah, that is what? three times, nearly two or three times, the returns on strategy compared to Bitcoin. What we are now seeing is that the two are flipped, actually. Now Bitcoin has outperformed strategy over the past five years by about double.

So all of the volatility, I mean, it's all being wrapped into strategy. But Bitcoin is really filling out right now. When it's at under 60K, that has effectively wiped out the second half of the Trump ball run. that that so it's back to its lowest point since around August 24 so yeah a little bit rough and I know there are a ton of other factors apart from strategy and so on but you have to admit that all of this that all of the stuff going on with stretch this idea that strategy might have to liquidate six billion dollars worth of Bitcoin to really make stretch shareholders confident that it's that it can continue dishing out dividend payments even if Bitcoin continues to slughey.

for a year or two. I mean, all those things are weighing on the Bitcoin space and the crypto market writ large. So that's what's happening with the prices right now. Let's take a look at the inside of stock sales at strategy and compare and plot those against micro strategy stock and the price of Bitcoin just to get a sense of what has been going on at strategy in terms of executive selling plans and so on. And again, Another disclaimer, most of these trades, and I haven't tracked every single trade, but the overwhelming majority of the trades are predetermined trading plans that are lodged in time with the SEC.

So what that means is that it's not like the executives are sitting there hitting dump when the price goes up. In many cases, it's like 30 days, 60 days, 90 days before they want to sell. They have to file with the SEC and notify them that we're going to see. sell it these times and it's all predetermined. So I know that I mean 30 days, sometimes they're 30 days. So it's like 30 days might as well be hitting the dump button. I mean, if we're being completely honest. But, you know, once you get to 60 days and 90 days, I mean, anything can really happen. And I mean, this is just how the stock market functions in terms of, in terms of this

disclosures for training plans. So so with that in mind, this is the chart that shows inside our purchases. and sales at strategy. And we can see it on my screen here. Everything in red is a sale. And that can either be a straight stock sale or an option or an options exercise. So options have been exercising and then they're sold at the same time. In green, the green triangles are buys because actually on occasion, strategy insiders do buy the stock.

But overwhelmingly, it is sales. So this chart goes back to 2021. So it's the last five-ish years. is worth of insider sales. And you can see that this big ramp up here is actually mostly Sailor, 99% Sailor. And you might remember that in 2024, Sailor had a bunch of, and it was $400,000 worth of options that would expire unless he optioned them and sold them, basically right away. And so he had opted not to sell. or not to exercise these options for basically a decade and then decided to sell them all at once

just as we're not decided to, but the timeline, the deadline to actually exercise them in sale was running out. And coincidentally, it was running out just as strategy stock was really ramping up while it was accumulating Bitcoin. And Bitcoin was obviously on its way up too. So huge sales here from Sailor in 2024, just as. as Bitcoin would reach, would surpass 60K for the first time. And these were the first sets of all-time highs in the start of the 2024 bull run.

Since then, he hasn't really sold much stock. But other insiders, like CEO Fongle, who was the CEO before, they've been selling on the way up as well. So a lot of red circles around the time that Bitcoin was peaking mid to late last year. And then again, they've been selling over the past few months as well. So a ton of, a ton of shares have been, have been liquidated at strategy, but a lot of, a lot of bought as well. So I have some stats here. I mean, the big burst of sales, those options exercise, the 400k shares sold by Sailor, he generated $411 million almost by selling those shares.

And interestingly, I figured, well, I mean, he really missed out on the biggest part of the Bitcoin Bull Run, if those options had expired only a year and a half later, so he could actually capture the October 2025 all-time high around Bitcoin, Saylor would have generated 903 million. So he would have doubled the amount of cash that he could have generated if those options had expired only just a year and a half later, which is a little bit rough. I mean, of course, micro strategy itself peaked a month or a month or two. to after Bitcoin did, if he was able to sell the shares around that, he would have generated nearly $1.5 billion on those shares. So that gives you just some context about how valuable

these options were. And I mean, when you read what Sailor's justification was, at the time he mentioned that he was only receiving a dollar annual salary from strategy and he had never really sold shares, which is true. So it was just a massive payday all at once for Sailor that coincidentally happened when the peak mania around strategy's plan was really was really taking off. Overall, strategy insiders have generated almost a billion dollars between them, with almost half of that going to Sailer himself. Now I have a chart for this too. So here we can see Sala with his $400 and almost $411 million.

Really he eclipses basically everyone else at strategy. But Fong Leda, the CEO, his soul. $130 million worth of shares since 2020. So not a very serious payday for the new micro strategy CEO. The GC, a general counsel at strategy, $117 million. Rickettson, a director, $70 million generated. Lang, the CTO, $61 million, patent a director, $46 million and so on. So life appears to be good for strategy executives, even in amongst all of this turmoil. Obviously, they really do want to maximize shareholder, holder value. I am sure of it.

But at least from a personal standpoint, you know, they've been well paid for their efforts to reinforce the health of the Bitcoin market to date. I will frame it like that. So what about the people who have bought? I mean, we've had Insiders buying over the past year pretty rough. rather steadily as well. So, you know, something to be said as well. I mean, I mean, more context as well, it's just so we don't overly demonize the idea that executives can make money. I mean, because these are trading plans, like 501 trading plans or whatever they're called, like, it implies that it is just standard stock executive compensation rather than just, oh, we really

think the company is trouble. We're just going to, we're just going to dump the stock. And it is normal for executives to be paid and compensated in shares and options and so on. And you have to, you have to liquidate them in order to, for them to be legitimate income. So it may, it also makes sense. But it is quite interesting that we also have people who are actively buying stock, strategy stock, basically as strategy and Bitcoin were on their way down. So that tells you something. Insiders liquidating their options as part of their compensation packages. That doesn't really tell us much.

It just tells us that executives are being paid for their work. But actively buying, that tells us something. With that in mind, there's been about 20, about two dozen instances of Insiders buying stock over the past year or two. It's the equivalent of 343,000 shares for a total of about $31.6 million. dollars. And on average, those shares have been bought for about $92. The strategy share price right now is currently 85. So actually, insiders are down on their purchases to date. And the unrealized loss is about $2.32 million. So those confidence bets in strategy have not exactly paid off yet. And it would be interesting to see if those insiders do unwind those positions over the

coming months as it becomes apparent that perhaps this turmoil is going to drag on for quite some time with strategy and Bitcoin. The worst percentage loss is Carl Rickinson, who bought 5,000 shares at $156 almost in January of this year, is now down 45% on those shares on those shares to date. So a little bit brutal, but it just goes to show that I guess it can go both ways. And I guess if you've already liquidated a bunch of shares and you're down a little bit on some bind, a dip that you've done, I suppose it's not the worst thing in the world. So, I mean, what does the Coinbase chart look like? Because we can also do this for Coinbase and we can also do this for Circle.

So let's just take a look super quickly. What we got here. So for Coinbase, we can see a ton of sales constantly, but there were a lot of buyers in 2020. particularly Tobias Lutke, who's a board member, the Shopify CEO. He was buying a bunch of stocks, Coinbase stock in 2022. And obviously we are way up still on those prices. But, you know, and just something particular about Coinbase, it was a direct listing. So during direct listings and afterwards, like Insiders kind of have to sell stock in order to put shares out into the market.

So it makes sense that the insiders would have a ton of stock to sell. But again, it is just a function. that public companies pay their executives in stock compensation, in stock options. And so we can see this routine selling from Coinbase Insiders, pretty much constant as it goes on. Over at Circle, we've also had sales basically all the way down. I mean, Circle Stock is kind of struggling at the moment. It's down 17.5% over the year to date. And 67%, nearly 68% over the past year.

So, you know, and I mean, it just also makes sense that executives can have, have shares and sell. But, I mean, the most interesting thing to me is this strategy chart. Just because we do have this, a lot of insiders buying while the stock was low, and also just this idea that Sailor was forced into not being able to time the top in any sort of way. And these stock options kind of ticked over and forced his hand before basically the, massive Bitcoin bull run throughout 2025 last year. So I mean, should we be pouring one out for strategy and strategy insiders right now with all the turmoil going on? I'm not too sure, but I will say that there is a clear discrepancy in the pain being felt by the market at large

and what pain the strategy insiders might be feeling considering they've effectively been able to insulate themselves with a ton of stock sales throughout the bull run. But I suppose that's their prerogative. Pioneers need to be rewarded. And the whole reason that any of this really exists is to inspire people to push things forward as far as they can. And in the case of crypto, it's usually, you know, as wild as they can. That is what this market rewards.

So it makes perfect sense that, that, you know, you can be rewarded monetarily for, I mean, I don't want to say brave, but just having the nows and so on to go and put yourself out there and do something that really kind of shifts not just this market, but the world in general. I mean, what strategy has done, we can't be overstated the impact of strategy and so I have had on Bitcoin. But unfortunately, we are right now seeing that influence unwind. And if you scroll through the XStrecht, you scroll through the feeds if you scroll through wherever you're looking at Bitcoin content or crypto content. It right now feels pretty bleak in terms of sentiment towards Sailor and strategy.

You know, it's wild to see, you know, the tide turn against Sailor so much. And perhaps it's just the loudest, most negative voices are the ones that I'm seeing. But I don't know how strategy and Sailor come back from this, especially if the pain gets significantly worse from here. If Sailor makes the option to just rip the band-aid off, sell $6 billion or so worth of Bitcoin OTC so it doesn't impact spot prices, and reinforces the strategy balance sheet and writes the ship again. Stretchholders are happy. Money starts flowing in and he can start buying again. Then okay, cool. We haven't seen him making those decisions yet. And perhaps we're going to see that today or early next week. And you can effectively ignore

everything that I'm rambling about right now. But any misstep from here is going to have exponential ramifications for sailors standing in the Bitcoin space. And the crypto space in general, perhaps the Bitcoin space is so sold on the idea that strategy can stack forever and be the holder of last resort or however you want to style it for Bitcoin. And perhaps he can do no wrong in certain. Bitcoin maxi circles, but I think the patience is wearing thing in the wider crypto space for these types of flywheel schemes to pump prices. I feel like this could be the last that we see of this for

Bitcoin and crypto for a while. That said, again, not trying to demonize insiders for being paid in the way that they should be paid or the way that their companies have deemed appropriate for them to be paid. I want this level of transparency and disclosure for the crypto space and I would love to make similar charts for other cryptocurrencies just to get a sense of, you know, who has the risk here, who is punished when the stock, when the prices go down and how easy is it for your regular retail investor to insulate themselves against the cyclical nature of crypto markets compared to the insiders at the teams and so on that are building the space that's where i'm where's where i find the most interest in analysis like this so hopefully this has been interesting for you too

please reach out to me about what you think about all of this uh whether i've missed anything in in kind of my thoughts and so on but in the meantime i hope you have a great weekend i hope you've survived the heat wave um if you're in europe and and so on uh and as always look after yourselves goodbye Thank you.