The Pomp Podcast - Did Michael Saylor Give Up on Bitcoin? | Anthony Pompliano

Episode Date: June 3, 2026

Anthony Pompliano breaks down why Michael Saylor and Strategy selling 32 bitcoin is not a sign of lost faith — it's a calculated signal to credit rating agencies and the traditional finance world. In this episode, we cover why Strategy sold a fraction of its bitcoin holdings, how the sale was designed to prove bitcoin's liquidity to skeptical rating agencies, why Pomp's own company ProCap Financial did the same, and why this is actually a bullish milestone for bitcoin's march toward mass adoption.=======================Uphold is the easiest way to buy and sell crypto unlike any other platform allowing you to trade in just one step between any supported asset. Check them out at https://www.uphold.com/pomp/ This video includes a paid sponsorship with Uphold. I’m compensated by Uphold for promoting its products and services and may receive commissions from referrals. Terms apply. Not available in all jurisdictions. Digital assets are risky and may result in the total loss of your capital.=======================Arch Public is an agentic trading platform that automates the buying and selling of your preferred crypto strategies. Sign up today at https://www.archpublic.com and start your automated trading strategy for free. No catch. No hidden fees. Just smarter trading.=======================0:00 - Why did Strategy sell 32 bitcoin?1:38 - Jeff Walton on bitcoin's zero credit value in banking3:07 - What the sale is actually signaling to rating agencies4:21 - Michael Saylor explains it himself8:24 - Pomp's take: why this is bullish, not bearish9:23 - Why ProCap also sold bitcoin last week10:19 - Bitcoin approaching a tipping point & what comes next

Michael Saylor has sold 32 Bitcoin and the world is asking, has Michael Saylor lost faith in Bitcoin? Will Bitcoin die? What is going to happen to strategy? All of those questions are important, but before we get to the answers, we must first understand what exactly has happened here. Now, strategy owns over 843,000 Bitcoin in total, and they sold 32 of them. That is 0.000037% of all Bitcoin they hold. Just look at this chart right here to see how ridiculous it is, of how small amount of Bitcoin they've actually sold.

But that's not going to stop all the haters from coming out of the woodwork and saying that Michael Saylor has lost all faith. He no longer believes in Bitcoin. It is over. For example, take Peter Schiff. He says that last week, MicroStrategy sold 32 Bitcoin for about $2.5 million

at an average price of $77,135. Since Bitcoin's biggest buyer has now become a seller, where will the new demand come from to sustain the pyramid? Bitcoin's already below 72K, which is about 7% below where Saylor sold. Now, of course, there's a lot of people here that Michael Saylor has sold. I saw people talking online saying

they may sell their Bitcoin if Saylor's selling his. But before you do that, it's important to understand why did Michael Saylor sell Bitcoin? The answer can be found in a very nuanced aspect of traditional finance. See, all these companies that are holding Bitcoin on their balance sheet, most of the different vendors, regulators,

or different service providers, they gave zero value to that Bitcoin. The belief was that if you're never going to sell the Bitcoin, then what is it really worth? How could you say that Bitcoin has any value if you simply are going to hold it forever and you're unwilling to sell it?

Don't take my word for it though. Jeff Walton had a great explanation for this. Take a listen. David, all of this has happened so far with the global banking standards providing zero credit for Bitcoin as capital on a balance sheet. Right.

Zero. The S&P 500 gave Strategy a B-minus issuer credit rating and they valued the $60 billion of Bitcoin on their balance sheet at zero. Which actually seems like an opportunity because if you as an investor don't value that at zero, you value that at something else. Greater than one.

All of a sudden there is an edge there that somebody can take advantage of. Alpha is created. Yeah, that's probably the last legacy hurdle that if that changes the scale of capital that's going to come into bitcoin is absolutely astronomical because right now if if a bank were to hold bitcoin on their balance sheet they would be punitive on their capital requirements for the comp for the for the bank so it doesn't make sense to hold insurance companies same thing they can't hold it like they get zero ability to

leverage against it so like why would you hold it i'll just i will hold mstr instead so this is what What makes companies like yours, True North and Strategy actually disruptive is because you are doing the thing that no one else can or would otherwise do just because the bureaucracy, it hasn't supported it yet. We are transforming the asset. We are the transformers to purify the asset into different forms. Now, I tend to think that this is a very good way to think about this, is if nobody is going to give you value for Bitcoin on your balance sheet, you have to show them that it does have value. And there were a couple of people across the market who explicitly called this out. Take Mark Moss as one example. He says that strategy is not Bitcoin.

They're a public company navigating public equity markets. The Bitcoin sale was a maneuver to signal rating agencies and credit analysts demonstrating the tools they can and would deploy to protect preferred holders if needed. In that sense, the sale is not a change of heart. You can see this in the sample size. It's a signal the company is willing to monetize part of its Bitcoin reserve when its capital structure demands it. I agree with Mark, and I think that it is very obvious to see what they're doing here.

But he's not the only one. James Thorne also tweeted out, and he said that MicroStrategy did not sell Bitcoin because it lost face in the asset. It's sold to demonstrate that it can turn its hoard into hard cash to meet dividend obligations when required. In my opinion, for rating agencies and credit analysts, realized liquid resources carry more weight than unrealized gains in a volatile asset when they assess coverage and resilience. In that sense, the sale functions less as a change of heart and more as a signal that the company is willing to monetize part of its Bitcoin reserve when its capital structure demands it.

Now, you don't have to believe Mark or James or me, though. Michael Saylor himself talked about this just a few weeks ago. Take a listen to why Saylor said that he may one day sell some Bitcoin. Here it is. But there's been a bit of confusion in the market about where the dividends come from. You know, how do we pay the dividend? And for most of the history of the instrument, we sold common equity, MSTR equity, to pay the dividend. MSTR equity is a derivative of Bitcoin. It normally trades at a premium to Bitcoin. And

so we were selling a Bitcoin derivative. But some people worried that we wouldn't be able to sell the equity in the future. And then there are short narratives that we have to sell the equity. And then there are other narratives that the company won't sell its Bitcoin. And that kind metastasized to, well, if they're not going to sell their Bitcoin, it must not have any value and they can never sell it. And if they can't sell it, then we can't count the Bitcoin as an asset on the balance sheet. So if you had $65 billion worth of something and people wanted to value it at zero, it's not very good, right? We don't want the credit rating agencies to think the company has $0 of assets. We want the credit rating agencies to think we have $65 billion of

assets. And, you know, there are also trolls on the Internet that continually complain that this is a Ponzi scheme because we sell equity in order to fund a preferred dividend. Well, what we want to do is we want to reinforce the business model is we sell credit to make a capital investment in an asset, Bitcoin, digital capital. The capital investment accretes over time faster than the dividend. We then monetize the capital gain and we pay the dividend. We think that the best way to punctuate this, to make it very clear, is to make the point that the company doesn't have to sell common stock ever. We can simply sell highly appreciated Bitcoin in order to pay a dividend. And if we do that, you're capturing a capital gain to pay a credit dividend. The analogy is like

a real estate development company raises capital by issuing a credit instrument, buys land at $10,000 an acre, develops it, it's worth $100,000 an acre, and then they monetize that capital appreciation. You could sell the land at $100,000 an acre. You could rent the land after you fully developed it. You could refinance the land. But nobody questions a real estate development company that makes a capital investment with a credit income. What we're doing is the same thing with Bitcoin. And we want to make sure that the market understands that. So there you have it.

If you never sell your Bitcoin, then the critics will say it has no value. But Saylor has 843,000 or more Bitcoin. He sold 32 of them. It is literally such a small percent. It is just like a speck of dust in the universe. Everyone relax, calm down. I don't think Michael Saylor

has lost faith in Bitcoin whatsoever. ever. Today's episode is brought to you by Uphold. Are you someone who's tired of juggling multiple apps just to trade, earn, stake, or spend your crypto? Then listen up, because Uphold does all of that in one single unified platform. You can access 300 plus crypto and fiat currencies with an interface that works for you, whether you're a beginner or an expert. Uphold also features any to any swaps, where you can swap crypto to fiat, fiat to metals, and tokens to tokens directly in the app. If you prefer self-custody, Uphold's Vault gives you multi-stick security, key recovery, direct trading access, and peace of mind without giving up convenience.

Uphold is also 100% reserved, meaning no fractional practices and proof of reserves are updated every 30 seconds so you can verify your assets anytime. For US users, you can even earn yield on dollars with a USD interest account. No fees, no minimums, and funds are insured up to $2.5 million through the Atomic Cash Suite program. If you want one app for your entire digital asset life, check out Uphold today. Go to Uphold.com to learn more. Uphold.com. Go check them out today. In fact, I think the exact opposite is true, is that through this sale, all of a sudden, every credit analyst and all of these different vendors, all of these different market commentators, they now have to put value on Bitcoin. They have to look at the balance sheet

to these companies and say, you know, maybe Bitcoin has actual value. Maybe it could be sold and turned into dollars when and if it's needed. That is how Bitcoin continues its trek of mass adoption. See, in traditional finance, you can't simply just be a religious zealot. You have to understand what is the environment that you're operating in. And it takes someone like Michael Saylor, who's been a public company CEO for 25 years or longer, to say, you know what, I'm going to do the thing that's going to answer the critics. I'm going to do the thing that is actually going to prove that Bitcoin is this valuable asset that I've been telling everyone. And selling 32 Bitcoin may have actually been a $2.5 million investment in getting that done. Now, this is

all happening on the backdrop of Bitcoin becoming much, much more valuable and also getting to more adoption. And it's not just Saylor and Strategy that are selling Bitcoin. Our publicly traded company, ProCap Financial, which trades under the ticker BRR on NASDAQ, we also sold Bitcoin last week. We sold just over 50 Bitcoin, but not because I gave up faith in Bitcoin, not because I don't believe in the future prospect of Bitcoin, but actually for the exact opposite reason. See, our stock was trading at almost a 50% discount to the actual Bitcoin that was on the balance sheet. And so by selling Bitcoin at 1x NAV and buying back shares at 0.5 NAV, that means that all existing shareholders actually got more Bitcoin exposure. See,

this is the thing is as Bitcoin enters the traditional market, what you are going to find is that people who run these companies, these funds, or hold this asset, they have to be smart capital allocators. And so in a way, not only was I able to sell Bitcoin and actually increase everyone's Bitcoin exposure, Strategy was able to actually sell Bitcoin and show the world that the Bitcoin

on their balance sheet has value. Everyone is trying to optimize for how do we make sure that Bitcoin is successful? How do we make sure whether it's shareholders, individuals, institutions, or eventually governments have exposure to the asset? Don't think that most people you see making these different decisions,

they're not giving up on the asset. It's the exact opposite. They're doing the things that are necessary to actually help the asset be successful. And I know that there's a lot of noise out there. I know there's a lot of people who don't understand or don't agree, and that's okay. It's the beauty of Bitcoin.

It's decentralized. Everyone has a voice. Everyone can go ahead and pontificate on the pros and cons, on the positives and the negatives, on trying to understand where is the risk and where's the potential reward. You can look at Joe Burnett when he says that Bitcoin is approaching a tipping point

and almost nobody sees it coming. The BlackRock Bitcoin ETF was one of the most successful ETF launches in history. We now have publicly traded companies issuing low volatility US dollar instruments to buy Bitcoin. We have the president of the United States saying America will be the Bitcoin capital of the world while the US dollar debt crisis only continues to worsen. At the same time, many Bitcoiners sentiment is absolutely terrible. They think the ETFs are a negative. They think issuing low volatility US dollar instruments to acquire Bitcoin is a negative.

I believe that view is deeply mistaken. The hive mind of market participants operating in open, free public markets is learning. It can print abundant, low-volatility US dollar instruments to acquire an absolutely scarce asset. Be prepared to possibly watch Bitcoin melt faces over the coming 12 to 24 months. Now, the reason why this is interesting

is because the idea of a speculative attack on Bitcoin has always been there. We have seen people like Pierre Rochard and many others talk about this for years. The idea is to get dollars, which are losing value, and use those depreciating dollars to buy Bitcoin, which is an appreciating asset. People have been doing this for a long time.

How do you think so many people own homes in America? They take the depreciating dollars and they buy an asset in a home that appreciates in value. And the ARB is where wealth is generated. We now are seeing this happen all over finance when it comes to Bitcoin. And I believe that what Saylor and Strategy just did, it's just going to be another data point on a timeline.

of Bitcoin marching from an asset that was created and almost no one knew about all the way until the world recognizes that you need a scarce, digital, non-sovereign, decentralized asset in the world that we're headed towards. And I believe that Bitcoin will be the king and remain the king for a very long time to come.