When the Biggest BTC Buyer Becomes a Seller, Who is Catching the Falling Knife After Strategy Sold 3,588 Bitcoins?

Compiled & Edited: Shenchao TechFlow

Hosts/Guests: Austin Campbell, Zero Knowledge Group; Ram Ahluwalia, Lumida Wealth CEO; Chris Perkins, Franklin Crypto

Podcast Source: Bits + Bips (Unchained Network)

Original Title: Strategy Sells Bitcoin Again to Cover Dividends

Broadcast Date: July 7, 2026

Key Takeaways

This episode of Bits + Bips roundtable is set against the backdrop of Michael Saylor's Strategy selling Bitcoin for the second time in a month—3,588 BTC, cashing out approximately $216 million to pay preferred stock dividends. The three regular guests (also co-hosts) Austin Campbell, Ram Ahluwalia, and Chris Perkins dissect this structural turning point from their respective professional perspectives: When the largest BTC buyer becomes a regular seller, the mNAV premium disappears, preferred shares fall below par value, and the cycle of "printing stock to buy Bitcoin" is broken—what cards does Strategy have left?

Austin opens with a remark from a hedge fund friend—"Saylor holds 5% of Bitcoin. Maybe the thing will take off after he blows up"—highlighting the brutal logic of the crypto market: When someone becomes the protagonist, their collapse might actually be the catalyst. Ram analyzes the dilemma from a macro trader's perspective: selling BTC destroys the narrative, issuing new shares dilutes MSTR. He also mentions hearing Saylor speak twice in London, where Saylor is vehemently defending preferred stock dividends to rebuild confidence. Chris, with his investment banking background, points out that the foundation of financial engineering has been shaken since the mNAV disappeared.

But the discussion goes far beyond Strategy. The three delve into the capital structure issues of tokens vs. equity—why no successful cases of "token + equity" coexistence exist, Pokémon card analogies, and the judgment that 99% of tokens will eventually go to zero. The stablecoin war is another major topic: Tether abandoning the European MiCA market, the "utility problem" of stablecoins (can you buy a cup of coffee with a stablecoin?), the governance black hole of the 140-member OUSD alliance, and Robinhood entering the government money market. The latter half extends to the strategic significance of bank stablecoins—Scott Bessent's "Eurodollar market repatriation" theory, JPMorgan potentially becoming the first trillion-dollar market cap bank, the obsolescence of non-US banks' dollar deposit business—and a valuation breakdown of the Securitize IPO. Finally, they touch on the AI/semiconductor capital absorption effect and the crypto market's return to fundamentals.

Highlights of Key Insights

On Strategy Selling BTC and the "Three-Body Problem"

• "A friend who does global macro told me it's hard to see the next wave of institutional adoption from pensions, sovereign wealth funds, and central banks because Saylor is sitting on 5% of Bitcoin. His exact words were: 'Maybe the best thing is for that guy to blow up, and then this thing will actually rally.'"
• "Whenever someone becomes the protagonist in the crypto market, their downfall is imminent. Strategy has been the protagonist for a while."
• "The crypto narrative is now stuck on this MicroStrategy. Strategy isn't crypto, crypto isn't Strategy, but we're all stuck here. Just like when Bloomberg talked every day about PIGS (Portugal, Italy, Greece, Spain), the market eventually moves on."
• "His behavior today makes it clear—he's protecting the dividend, hoping this will bring back confidence."

On the Disappearance of mNAV and the Breakdown of Financial Engineering

• "They have two paths: issue common stock to dilute MSTR, or sell Bitcoin to suffer narrative damage."
• "When the mNAV premium disappeared, the cycle of 'printing stock to buy Bitcoin' was broken. You can't arbitrarily issue more because the market no longer gives you a premium."
• "BTC actually rose during the sell-off week—Josh Mandel and Pete Rizzo both noticed. It performed like a buyback. But the bear side will say: the premium is dead, BTC hasn't really rallied yet, and it's now a seller."

On Tokens vs. Equity

• "We already have Delaware corporate law and centuries of capital structure. You can slice cash flow into different layers of debt, and what's left is called equity. There's no third thing called a 'token' that can be inserted into this stack."
• "If you have common equity, a token likely needs to function like preferred stock or debt to have independent meaning. If it's just another form of equity, you might as well tokenize your equity directly."
• "Pokémon cards are a good analogy—the company issuing the cards and the cards themselves are two different things. You can tokenize a product without necessarily tokenizing equity."
• "Looking at the next decade, 90% of the current top 500 tokens will disappear. I think it'll be 99%."
• "Druckenmiller said during the dot-com bubble: 'I've already learned that lesson; I don't need to learn it again.'"

On the Stablecoin Wars

• "Stablecoins are the new net interest income. Everyone wants to grab that interest. Tether made so much money doing the most basic product—how can I do the same?"
• "The biggest challenge for all stablecoins right now is utility. You can transfer, but what can you actually do with a stablecoin? Can you buy a cup of coffee with it?"
• "Tether's stance is clear: This is soccer, not football. They won't play by European rules. BNP Paribas can't afford not to do business in France, but Tether can simply abandon a market."
• "OUSD is a 'plan with a plan.' 140 members with completely different economic goals, and the details aren't filled in yet. The hardest part—governance—was skipped; they pushed the technology out first."

On Bank Stablecoins and Market Dynamics

• "Stablecoins are essentially the repatriation of the Eurodollar market. If JPMorgan or Bank of America issues a stablecoin, they can earn NIM from a Thai merchant or a Chinese supplier."
• "JPMorgan could become the first trillion-dollar market cap bank. They're already above $900 billion, spending $13-16 billion annually on technology."
• "The biggest losers might be non-US banks offering dollar deposit accounts. If I can buy a stablecoin directly, why go through a local bank with terrible exchange rates and fees?"
• "Securitize's current trading is more like a call option—you're betting on a 10% chance it's worth $18 billion and a 90% chance it's worthless."
• "Last quarter, every S&P 500 sector underperformed the broader market except semiconductors. Capital is being siphoned off by AI."

"Maybe After He Blows Up, This Thing Will Actually Rally"

Austin Campbell: Before we officially start, I want to share a conversation. I was chatting with a friend who does global macro, one of the best traders I know. I asked him what he thought about Bitcoin. He said it's hard to see the next wave of institutional adoption—pensions, sovereign wealth funds, central banks—happening while Saylor holds 5% of Bitcoin and has such a massive presence as an individual. His exact words were: "Maybe the best thing is for that guy to blow up, and then this thing will actually rally, and then everyone else will pile in." Whenever someone becomes the protagonist in the crypto market, their downfall is imminent. Strategy has been the protagonist for a while. It also makes me think, in a sense, they've become an obstacle to Bitcoin's rise—and that in itself creates their own problems.

National Security, Export Controls, and the Crypto Industry

Austin Campbell: Before diving into the main topic, I want to raise a bigger issue. The government is now trying to control crypto from a new angle—not by preventing the release of code, but by controlling who can use it. They want to use export control laws to restrict access to things already published under the First Amendment. This is essentially picking winners and losers without applicable laws or due process.

National security is of course important, but we can't just say "national security" and close our eyes without asking why. We can't tell people to "use stablecoins, use crypto rails to build your financial life" and then, in an instant, cut it all off due to national security or export controls. The crypto industry isn't angry enough about this. This is our fight.

Strategy Sells Again: 3,588 BTC, $216 Million

Austin Campbell: Let's get to the main topic. Strategy sold 3,588 Bitcoin, cashing out approximately $216 million. This is the largest sell-off so far, following a previous small sale of 32 BTC to pay preferred stock dividends. The question is clear: After the MSTR premium disappeared, will selling Bitcoin to cover dividends become routine? Is Strategy still an accumulator, or has it become a regular seller?

Let's start with the facts. They broke a multi-year streak of not selling, first selling 32 BTC, then 3,588 a month later. As of July 5, Strategy holds 843,775 Bitcoin, with $2.55 billion in dollar reserves and a cost basis of $75,700 per BTC—far above the current trading price of just over $60,000. MSTR first dipped below 1 on June 27, hitting 99 cents, before recovering somewhat. STRC hit a low of 74.57, and I saw it back around 90 before the show. The dividend rate was raised by 50 basis points to 12%. The new authorization framework allows the sale of up to $1.25 billion in Bitcoin, along with an STRC preferred repurchase program.

Chris, with your investment banking background; Ram, having done a lot of investing. Saylor has shifted to selling Bitcoin from the balance sheet instead of continuing to issue MSTR stock. What does this tell you?

The Dilemma: Sell Bitcoin or Dilute Stock

Ram Ahluwalia: Two paths. Issue common stock—dilute MSTR, the stock price falls. Or sell Bitcoin—damage the narrative. Last week we mentioned the possibility of a short squeeze rebound in MSTR, and we saw it in the news. More constructively, STRC and STRF have started moving towards par value in recent days. They need to push them back to par. If they succeed, they can catch their breath; if not, it's a problem. I still see this as a trading asset, susceptible to a violent short squeeze rebound, and we might be in the middle of one now. I also want to compare the dates of their Bitcoin sales to the announcement dates—if BTC held steady or even rose during the sell-off, that's quite encouraging.

I was in London last week. First, I attended a Goldman Sachs event—packed, heavily oversold, the amount of institutional building was undeniable. Then I went to a Robinhood event; the DeFi stuff they're doing is pretty impressive. Before that, I heard Saylor speak twice. He focused intensely on defending and protecting the preferred stock dividend, trying to convince the audience of his commitment to Bitcoin. He's navigating this three-body problem.

Austin Campbell: This also cuts to the divergence between bulls and bears. The bulls will say: mNAV is back to 1.09, STRC is recovering, and BTC actually rose during the sell-off week—Josh Mandel and Pete Rizzo both noticed, it performed like a buyback. The bears will say: the premium is dead, BTC hasn't really rallied, and it's now a seller. Roland and Peter Schiff have both pointed this out. My question is: Even if preferred shares have recovered significantly, Saylor might sit tight for a while, but if BTC doesn't rise, won't we be back to square one in a year?

Ram Ahluwalia: My guess is that last week, fast-money traders came in to buy the dip when volume collapsed. That's hot money, not long-term holders. They'll likely sell into strength to take profits.

Chris Perkins: From an investment banking perspective, when the mNAV premium disappeared, the cycle of "printing stock to buy Bitcoin" was broken. You can't issue more arbitrarily because the market no longer gives you a premium. So you have to look to the asset side. Selling Bitcoin is viable from an accounting standpoint—cost basis $75,700, market price around $60,000, a book loss but cash inflow. The problem is that this action itself tells the market: You no longer unconditionally believe in your own thesis.

The "Three-Body Problem": The Strategy-Bitcoin-Crypto Narrative Lock

Chris Perkins: Unfortunately, we're stuck. The crypto narrative is now bottlenecked by MicroStrategy. Strategy isn't crypto, crypto isn't Strategy, but we're all stuck here, and it feels like we need to digest this before moving forward. It reminds me of opening Bloomberg and seeing only PIGS—Portugal, Italy, Greece, Spain—every single day. The market eventually moved on.

I'm ready to turn the page. What's somewhat encouraging is that BTC showed considerable resilience today. There are also some positive tailwinds—like Trump expressing support for crypto on the day his account went live. I look forward to us moving past this three-body problem and returning to fundamentals and details of other projects. Crypto equals Bitcoin, Bitcoin equals crypto, so Strategy equals crypto—I hope to break this equation.

There's also an emerging related debate: Does value flow to tokens or to equity? You see it in both private and public markets. Some people dismissively say, "All value is in equity; everything else is nonsense." I think it's more complex than that.

Tokens vs. Equity: No Third Form of Capital

Austin Campbell: I think both can work, but the hard part is having both simultaneously—unless you very carefully define their respective rights. We already have Delaware corporate law and centuries of capital structure. You can slice cash flow into different layers of debt, pay employees and creditors, and what's left is called equity. There's no third thing called a "token" that can be inserted into this stack. You can make a token act like equity or debt, but making it a new concept alongside debt and equity—that's tough.

If you have common equity, a token likely needs to function like preferred stock or debt to have independent meaning. If it's just another form of equity, you might as well tokenize your equity directly. You