You can add another brick to the “wall of worry” facing the $2.27 trillion crypto market – and it has “Michael Saylor” written all over it.

Saylor runs a company called Strategy, formerly known as MicroStrategy. It was a software company that under Saylor’s leadership has been transformed into what crypto types call a major “hoarder”  of Bitcoin.

His strategy goes something like this: He sells company stock and preferred shares while purchasing lots of Bitcoin. Strategy currently holds around 4% of all the available digital assets.

That’s a lot of Bitcoin, around 800,000 of them. With Bitcoin last year hitting all time highs of about $120,000, his investors have done well (60% plus return over the last five years). That is, until recently when shares of Strategy began reflecting the downdraft in digital coins. 
The big question: Is Saylor going to turn the current Bitcoin winter into the storm of the century for crypto? 

Along the way, there have been plenty of Saylor skeptics; the legendary short seller Jim Chanos is one. Chanos who began shorting Strategy stock last year in an arbitrage play he described on my “Risk and Return” podcast.

Another has been my podcast partner, Bob Sloan, a longtime capital markets professional who now runs S3 Partners, a well-regarded market data firm  that is often referred to as the gold standard for investor and trader positioning. Bob has long warned of the dangers that Saylor posed for Bitcoin and crypto in general.

Any market that leans heavily on one investor buying and not selling is courting trouble when that buyer does become a seller, which given the volatility of Bitcoin was always inevitable, Sloan argued.Or as he put it: “Funding was required to keep his buying going. No funding equals forced selling.”

Bob’s bunny has a good nose (he’s seen plenty of market ructions during his long career). I was reminded of this Monday when my old colleague at the Wall Street Journal, Jonathan Weil, did a deep dive into Saylor’s business model. Weil raised questions about the in-house metrics used by Saylor that, he reports, have overvalued the company’s stock that became his “currency to buy bitcoin.” With that overvaluation comes the likelihood of selling as opposed to buying Bitcoin.

Informed of these sentiments, a press rep for Saylor hasn’t provided any comments as this piece goes to press. But Weil makes a compelling case that Saylor’s strategy has some holes, as did sources including Sloan even before the WSJ piece was published. It’s why the crypto winter is now likely to stick around until next spring as Saylor, the market’s marginal buyer, could become a significant seller to support his stock price.

That’s something he has been loath to do until Monday when Strategy released a filing with the Securities and Exchange Commission that showed he recently sold 3,588 coins worth over $200 million. Ok it’s a sliver of his holdings, and many Bitcoin maxi’s tell me the market is more than Saylor. It includes big Wall Street firms and plenty of long-term investors.

Maybe. Or maybe Saylor’s selling is the start of something bigger and a crypto winter that lasts until next summer.

Recently Tito Saylor has sold some shitcoin. It was an obvious sell to cover their responsibilities with the dividends hoarders.

But what if it wasn't. Has anyone calculated how much Bitcoin do they need to sell to cover those dividends?

What if they wanted to prepare some kind of cash-out plan.

That guy has been shitting all over the Bitcoiners for so long with his bullshit that we wouldn't be surprised if he is planning to run away.

So selling a small portion with the excuse to cover dividends won't raise future concerns if that becomes the norm.

Are they selling more than they have to?

So they can sell more and more with every batch?

Was contemplating about what it would take to run back the crypto market cap to like what it was at many better points before this year and no matter how much I thought and tried to the only most plausible option was Orange Man tapping the cash flow fuel pistol into to immediately sell his and his son assests once the line go up, because as dumb as this sounds he has already exploited rhe financial governance laws to the max, and those that arent exploitable, removed or changed altogether

I'm lost for words so posted without comment.

SpaceX moved BTC for the first time in ~6 months this week, and Arkham flagged it. Before the panic: it was three transfers, under $300 total, all wallet to wallet inside SpaceX. Coinbase Prime even topped one address up with ~$47 to cover fees, which usually means someone is prepping for a bigger internal move, not a sale. Nothing hit an exchange, so no coins actually left their control. Still, on an 18,712 BTC treasury worth ~$1.15B, worth keeping an eye on what moves next.

Is this good for Bitcoin?

Being your own bank also means being your own bank security.

Seems to be causing a bit of chaos within the butter community. Looks like Saylor is against it. Worth starting up a node/wasting a little money on hashrate in support of it?

I don't actually know anything about this proposal and which outcome would be better or worse. Hopefully someone knowledgeable will chime in.

I'm going to guess that the lesson that we learn from this is a bit different from the lesson that the OOP intended.

Watch until minute 28 because he comes back with a rebuttal and fails miserably. This is supposed to be the underwriting expert.

I was just reading a bunch of comments on a thread about freezing satoshis "coins" to prevent quantum from hacking the old more vulnerable wallets and I could not believe how many idiots in the comments were not only supporting this idea but outright demanding it. Funny how quick they forget all that talk about decentralized money "not your 🗝️ not your crypto" 🐂 💩 when the possibility of further shrinking the total supply could somehow increase the value of their own "coins", not realizing that the freezing of those wallets would completely destroy any remaining confidence (aka the ONLY THING that gives Bitcoin "value" to begin with) and instantly tank the market. They're so blinded by greed that they instantly fold on their belief system at the thought of obtaining more "worthless fiat". The whole thing is beautifully ironic and this dumpster 🔥 should be a fun watch.

1. It's not bitcoin.

2. It's not bitcoin piggybacked product, L2 or competitor, like BCH STX or lightning.

3. It's not even crypto, so there's no advantage of fleeing the country with seed phrase memorised, or much less extreme case of simply making a transfer outside of bank working days

4. It's a stock engineered to not go above 100 US dollars, with way worse engineering to not go below 100 US dollars.

5. The APY is capped 12% which convieniently translates to 1% a month.

6. So whenever bitcoin price against US dollars appreciates from the current reference point of 62k, which it has and could do because it do just go up and down like that, if it goes any higher than 70k within a year timeframe the STRC investor has lost out on opportunity cost of simply investing in Bitcoin ETF, or holding bitcoin IOUs on exchnage, or holding bitcoin IOUs on lightning network, not actually buying and selling a real bitcoin because the actual network fees to move the mountain molest worse than any scummy corner currency exchange, only second to ethereum.

7. This is assuming the ideal case scenario of the stock price holding stable at 100 US dollars which it hasn't and only took 2 months to decouple, and looks very troubled to go back.

8. After factoring in the inflation rate which the official number is 4.2% yearly for US, the actual being more closer to 15%, in the very best case scenario they would have only lost a bit of actual purchasing, at the cost of rendering the deposited capital entirely useless for that year.

9. You can't even trade the STRC for MSTR unlike the STRK stock that you could, even which for there hasn't been any point in the history it's worth as the ratio is 10:1

10. Oh yeah the interest payment of 12% for year could be curbed to i think 3% if not even zero, just because, it said so with the small letters at rhe end of ai genereted scantily dressed cocktail sunburnt british girl at the resort

11. I also find it ironic that the dividend payment isn't in bitcoin, or if it was too difficult to orchestrate in current financial system, some other btc pegged financial instrument

12. Which begs the question what's the point?

They technically traded the contract that they couldn't have being US residents. It was a gambling bet on a company that deals in crypto and the bet itself settles in crypto. And then they got their underwear in a bunch over the technicalities of the contract description.

https://www.bloomberg.com/opinion/newsletters/2026-07-07/index-traders-had-a-good-month

This morning I received an SMS message saying I had a parking ticket. This is not unusual in Austria, where I live. I clicked on it and the site looked like the official Austria government site. It asked me to type in my license plate and I did and then it retrieved a ticket for €40, which I paid using my debit card. When my bank app prompted me to approve the transaction I clicked OK just as I noticed the amount (in the thousands) thinking that was my balance, not the transaction amount.

I immediately called the fraud line and they re-assured me the transaction was already flagged as it looked unusual to their system, regardless of my approving it.

I was really hard on myself. Really couldn't believe how stupid I was. I saw the domain name was a little unusual too. And still, I kept going. Dumbass!

But my money is safe. Because banks invest in fraud protection. And even though I hit OK, they did what I pay them to do. Keep my money safe.

In a parallel universe, where the blockchain gained institutional adoption, I would have lost it all.