@WhatsApp How do deal with scammers who will no doubt reserve famous usernames (with registered trademarks) and try to scam people the second you launch through impersonation scams?
This is very measured, and it's great to see. Michael took an even more thoughtful and disciplined approach than I had suggested.
This is a win for Bitcoin, a win for the common shareholders, and a win for the preferred holders. If Bitcoin can remain around $60,000 while Strategy sells up to $1.25 billion of BTC, it would be a huge validation of the Strategy model as a Bitcoin treasury company. It would also strengthen the investment case for the other Digital Asset Treasury (DAT) companies.
Congratulations to Michael and the entire team. Well done.
So here's a story about the Düsseldorf University Hospital where heart patients are sweltering in 38°/100.4° temperatures right now because this 15-year-old building lacks central A/C.
I taught at the law faculty of this university for 15 years. When the law faculty built a new expansion in 2005, I asked whether it would be air-conditioned. They said: "No, because then every building on campus would ask for it". I thought to myself, "Well, that's Europe for you. Crabs in a bucket."
Then the university announced plans for this new building, the one you see in the picture, which would be the main university hospital. That was in 2013 or thereabouts. Shortly thereafter, they published the plans and sketches online. No A/C infrastructure visible.
At some sort of faculty function, I asked the dean or assistant dean of the medical faculty whether they were going to install central air-conditioning on this building. "It's no problem if lawyers are brain-fuddled because of the heat -- in fact it might be a bonus! -- but surgeons? Patients?"
The dean answered: "Well, we asked, but the construction board and city officials said no, because if this new building gets air-conditioning, then all the older buildings on the university campus will demand it."
"Even though this is a fucking hospital?" I asked with typical American coarseness.
"Yes, even though it's a hospital," responded the dean, staring with chagrin into his beer.
And so now dozens of people recovering from open-heart surgery are bathing in their own sweat. Across the country, thousands of people are dying in un-air-conditioned hospitals right now.
As in all former heatwaves, there will be institutional pressure at all levels to attribute their deaths to underlying ailments, not the fact that they sweltered for over a week in brutal temperatures.
Imagine telling someone in 1999…
The year is 2026.
The President is Donald Trump in his second non consecutive term.
The richest man in the world is PayPal cofounder Elon Musk… but not because of fintech or Paypal. Because of rockets, electric cars, AI, satellites, brain chips and something called “Boring Company”.
Apple is worth trillions but its main business isn’t computers… its selling glass rectangles everyone stares at for 9 hours a day.
People don’t watch TV. They watch teenagers explain geopolitics, finance, and relationship advice in ~60 second videos.
The biggest taxi company owns no taxis.
The biggest hotel company owns no hotels.
The most powerful media companies are social networks where everyone argues with strangers for free.
Kids are making millions filming themselves playing video games.
AI Robots write emails, code, legal memos, songs, essays, and breakup texts.
The internet is mostly bots arguing with humans who are trying to prove they aren’t bots.
You can summon a car, groceries, a doctor, a date, a private jet, or a dog walker from your phone.
People pay real money for invisible currencies, digital monkeys, AI girlfriends and pictures that disappear after 24 hours.
The richest companies in the world don’t sell oil, steel, or cars. They sell attention, compute, data, and addiction.
And somehow, after all of that everyone is still using Excel.
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Mastermind playbook for MicroStrategy:
I think Saylor pushed the financial engineering too far. Maybe it ultimately works, maybe it doesn't. But I think it's fair to say the original MicroStrategy playbook is effectively over.
Ironically, I think he's now setting up what could become one of the best distressed trades of the next cycle.
If this plays out the way I think it will, the preferred stack could eventually trade at 30%+ yields as unpaid dividends accrue and claims begin to compound. That's when things get interesting.
Here's how I think the sequence unfolds:
• mNAV goes solidly negative.
• Saylor stops issuing common stock.
• Saylor suspends preferred dividends.
• He waits, hoping Bitcoin bails him out.
• June 2028 becomes judgment day - not because the converts mature (they don't until 2029), but because the put rights become exercisable, potentially forcing a refinancing or triggering a default.
Advanced distressed discussion:
Assuming these instruments are treated as securities, there's an interesting bankruptcy wrinkle. If they become unsecured claims, post-petition interest generally stops accruing, and claim amounts are determined under the Bankruptcy Code. That creates a strong incentive for convert holders to organize quickly and push for a pre-packaged or pre-arranged restructuring.
One bonus: this isn't technically a single-asset real estate case, so there may be enough runway for management to extend the process another 90-120 days after a filing. That could push a restructuring into late 2028.
Bottom line:
Next 1-6 months: I think the common, preferreds, and especially the converts remain expensive. The common is probably the cleanest short simply because of its liquidity and the number of dilution paths - additional equity issuance, preferred dividend overhang, or satisfying convert obligations with stock or cash.
Next 6-18 months: If the common and preferreds ultimately get wiped or heavily impaired, the distressed debt could become one of the most attractive convex risk/reward opportunities heading into the next Bitcoin cycle.
But what do I know? I only do this for a living.
Saylor should probably just rip the band-aid off.
Sell 100–200k BTC, raise $5–10 billion of cash, and sit on it.
Then stop playing defense. Tell everyone demanding immediate action to wait. Buy back the converts opportunistically at distressed prices, or let holders exercise their put rights when they come due. At the same time, launch tenders for any preferreds that trade well below par.
Once the market believes the liquidity runway is secure, the negotiating leverage shifts dramatically. In distressed investing, cash isn't just liquidity - it's optionality.
I like Nic and generally agree with a lot of his work, but I think he's using the wrong framework here. This isn't a CCC bond. It's a distressed special situations security.
I've spent the better part of two decades in distressed credit and roughly the last 12 years buying distressed crypto. I've competed with or worked alongside many of the largest distressed investors. When I ask myself who the marginal buyer of STRC is today, it isn't a traditional high-yield fund.
It's an opportunistic credit fund. Those funds don't wake up looking for 15% returns. They generally need 30%+ IRRs before they commit capital to something this uncertain.
Today you can buy:
• Government refund claims targeting 10-15% IRRs.
• Distressed crypto claims with recoveries denominated in dollars and often substantial collateral protection for 20-25%+ IRRs.
STRC is riskier than both. You're subordinated. There are essentially no meaningful lender protections. The dividend is non-cumulative. The collateral is one volatile asset. There is negative convexity.
And unlike a traditional distressed loan, you don't control the collateral or have meaningful enforcement rights. This isn't lending against Bitcoin.
It's taking directional Bitcoin exposure through a structurally weak preferred security.
There's an important distinction people miss.
Common shareholders have a fiduciary relationship with management. Creditors don't. Management's job is to obtain the cheapest possible financing for shareholders - not to create an attractive security for creditors.
To Strategy's credit, they did exactly that. They issued extraordinarily issuer-friendly paper because the market let them. Good for them!
But once that paper leaves the hands of income-oriented crypto investors, who is the next buyer? That's the question. I think it's an opportunistic distressed investor. And that buyer isn't showing up for a 15-20% required return. They're looking for something closer to a 30%+ IRR.
At an 11.5% coupon, that implies a price of roughly $38.33 (11.5 ÷ 30%), versus about $76.67 for a 15% yield and $57.50 for a 20% yield. Maybe 30% isn't exactly the right number. Maybe it's 35%. Maybe it's 40%. But I think anchoring this off CCC spreads misses who the actual marginal buyer is.
JUST IN: Michael Saylor's 'Strategy' currently has a $14,000,000,000 unrealized loss on its Bitcoin investment.
Tom Lee's 'Bitmine' currently has a $10,500,000,000 unrealized loss on its $ETH investment.
Today's video: https://t.co/RJgtHJA6lc
- Bitcoin bounced. Again.
- But MiCA and Saylor looming. One day at a time!
- Update on HYPE NEAR ONDO ZEC SpaceX and others
Should you quit your job and become an investor?
- Your “safe” job isn’t safe anymore.
- AI is rewriting the rules of work - and those who adapt early will own Era Digitalis.
9 years ago, I left one of the best jobs in the world and discovered what’s on the other side. ⚡️
@yunta_tsai In other words:
To build good AI models you need:
- what good looks like
- the structure in the input data
- clean data bcz Shannon
Did I understand you?