Michael Saylor just turned a dying software company into a $90 billion Bitcoin casino.
And Wall Street can’t look away.
MicroStrategy was supposed to be dead by 2020:
Revenue flat for a decade
Stock stuck at $120
Business intelligence software nobody cared about
$463M annual revenue (vs $90B market cap today)
Then Saylor did something insane.
He bet the entire company on Bitcoin.
Not just the cash reserves. Not just some profits. THE ENTIRE COMPANY.
Here’s the playbook that broke every MBA textbook:
Step 1: Take your $250M cash reserve → Buy Bitcoin
Step 2: Stock goes up → Issue more shares → Buy Bitcoin
Step 3: Issue convertible debt at 0% interest → Buy Bitcoin
Step 4: Repeat until you own 640,250 Bitcoin
The result? Stock went from $120 to over $400 post-split Market cap: ~$90 billion (Oct 2025)
But here’s where it gets WILD:
Saylor discovered the infinite money glitch.
MicroStrategy stock trades at a moving premium to its Bitcoin. Ranged from 20% to 100% premium in 2025 (e.g., ~90% in Feb 2025). Why? Investors prize the leverage and structure.
So hedge funds buy the convertible bonds. Not for the 0% interest. But to profit from the VOLATILITY.
It’s genius or insanity. Maybe both.
The numbers are staggering:
Owns 640,250 Bitcoin (3% of all Bitcoin that will ever exist)
Worth ~$72 BILLION (as of Oct 17, 2025)
Has issued multiple rounds of unsecured convertible notes (e.g., $3B in Nov 2024; $2B in Feb 2025)
$42 billion capital plan announced (aspirational target)
Currently no secured debt (no BTC-collateral margin calls)
Meanwhile, the actual software business?
Revenue down 6.6% in 2024 to $463M
That’s 0.5% of the company’s market cap
The business is now just a Bitcoin wrapper
This isn’t a company anymore. It’s a leveraged Bitcoin ETF wearing a trench coat.
And Saylor? He’s either:
The smartest CEO alive
The luckiest gambler in history
About to cause the most spectacular corporate collapse ever
There’s no in-between.
Want to know how committed Saylor is to this bet?
When Bitcoin critic Peter Schiff accused him of telling people to mortgage their homes for Bitcoin, Saylor tweeted:
“Sell a kidney if you must, but keep the Bitcoin.”
Schiff fired back: “First you told people to max out their credit cards and mortgage their homes to buy Bitcoin. Now you’re telling them to sell off their organs. Have you no shame?”
Saylor’s response?
“Sell Peter Schiff’s Kidneys, Keep the Bitcoin.”
This is who’s running a $90 billion public company. The man is literally telling critics to sell organs before Bitcoin.
If Bitcoin hits $1 million (as Saylor predicts), MicroStrategy becomes a trillion-dollar company.
If Bitcoin crashes to $10,000 and stays there? The math gets uncomfortable. But here’s the kicker: No forced liquidation. All current debt is unsecured. No margin calls. They can just... wait.
The craziest part?
OTHER COMPANIES ARE COPYING HIM.
Marathon Digital: Raised $950M in 0% convertibles (July 2025) Tesla: Still holding ~11,500 Bitcoin ($1.2B worth) 130+ public companies: Now holding Bitcoin treasuries
Wall Street’s reaction: 2020: “He’s lost his mind” 2021: “Maybe he’s onto something” Dec 2024: “Add him to the Nasdaq-100” Feb 2025: Company rebrands to ‘Strategy’ with Bitcoin logo
Even Citron Research (famous short sellers) said: “The valuation is completely disconnected from reality”
But the stock keeps going up.
Here’s what nobody’s talking about:
The software business is just theater now. They literally rebranded from “MicroStrategy” to “Strategy” Bitcoin symbol in their company logo. Saylor stepped down as CEO in 2022 to focus 100% on buying Bitcoin as Executive Chairman.
This is corporate finance’s “YOLO” moment.
Traditional metrics don’t apply:
P/E Ratio: Meaningless (mark-to-market swings)
Revenue Multiple: 190x (insane)
Book Value: It’s literally just Bitcoin
The bet is simple: Bitcoin goes up = Shareholders get rich Bitcoin goes down = Everyone gets nervous Bitcoin crashes below $10k = Things get spicy
No hedging. No diversification. No backup plan.
Just pure, concentrated, leveraged Bitcoin exposure.
I’ve analyzed thousands of companies. Never seen anything like this.
It’s either the trade of the century or the most public financial experiment in history.
The finale hasn’t been written yet.
But when it happens, business schools will study this for decades.
The question isn’t IF this ends spectacularly. It’s whether Saylor will be remembered as a visionary who saw the future...
Or the CEO who bet $90 billion on magic internet money and lost.
Place your bets.
The casino is open.
P.S. - Saylor personally owns 17,732 Bitcoin ($1.9 billion today) bought with his own money at $9,882 average. This madman is all in. No hedge. No exit. Just conviction.
What do you think - genius or insanity?
Note: Saylor’s “sell a kidney” comment was clearly hyperbolic rhetoric meant to emphasize his conviction about Bitcoin, not actual advice. The exchange highlights the intensity of the Bitcoin debate between prominent figures.
Receipts:
Rebrand to “Strategy” (Feb 5, 2025): press release
640,250 BTC holdings (Oct 13, 2025): press release
10-for-1 stock split (Jul 11, 2024): press release
$3B 0% convertibles (Nov 21, 2024): press release
$2B 0% convertibles (Feb 24, 2025): press release
$42B capital plan (Oct 30, 2024): press release
Premium analysis: CCN explainer
2024 revenue: Macrotrends chart
Marathon $950M 0.00% notes due 2032: MARA IR press release
Tesla BTC holdings: The Block treasuries tracker
“130+ companies” holding BTC: FT explainer
Nasdaq-100 reconstitution 2024: Nasdaq announcement
Saylor as Executive Chairman (Aug 2, 2022): company press, Investopedia recap
Saylor’s personal BTC (17,732 BTC): Bitcoin Magazine, Decrypt