The MicroStrategy Playbook (Summarized)
Saylor’s strategy since August 2020:
- Issue corporate debt (convertible bonds, loans)
- Dilute shareholders (sell MSTR stock)
- Buy Bitcoin at any price
- HODL forever (never sell, no matter what)
- Leverage more debt to buy more Bitcoin
- Repeat
Current stats (as of Feb 2025):
- Bitcoin holdings: 714,644 BTC
- Total cost: $54.4 billion
- Average buy price: $76,056 per Bitcoin
- Current BTC price: ~$70,000
- Paper loss: ~$4.3 billion
And yet, Saylor keeps buying.
———|———-|———-|——–| | Bitcoin spot | $11,000 | $70,000 | +536% | | MSTR stock | $135 | $1,400 | +937% |
MSTR peaked at $1,900 in March 2024, now down 26%.
“See? MSTR outperformed Bitcoin!”
Not so fast.
MSTR has massively diluted shareholders:
- 2020: 10.7 million shares outstanding
- 2025: 18.5 million shares outstanding
- Dilution: 73%
On a per-share basis, adjusted for dilution:
- MSTR return: +541%
- Bitcoin return: +536%
Barely better than just buying Bitcoin, but with:
- Corporate risk (debt, regulations, Saylor’s health)
- Dilution risk (he can keep issuing shares)
- No self-custody (you don’t own the Bitcoin)
- Tax inefficiency (MSTR is taxed as income, BTC is capital gains)
You’re taking on MORE risk for the same returns.
Flaw #4: He’s Wrong About Bitcoin’s Role in a Portfolio
Saylor’s pitch: > “Bitcoin is the ultimate store of value. It will replace gold, bonds, and real estate.”
This is delusional.
Bitcoin is:
- Volatile: 50-80% drawdowns every cycle
- Correlated: Trades with Nasdaq (0.73 correlation)
- Speculative: Most people own it hoping for gains, not as “digital gold”
Gold:
- Stable: Rarely drops more than 20%
- Uncorrelated: Inverse to stocks during crises
- Proven: 5,000 years of wealth preservation
Reality:
- Bitcoin might be “digital gold” someday
- But right now, it’s “digital growth tech stock”
- Treating it like a stable reserve asset (a la Saylor) is insane
Flaw #5: The “Never Sell” Mantra Is Financially Irresponsible
Saylor says: > “We will never sell Bitcoin. Not at $100K, not at $1 million, not ever.”
This is cult behavior, not investing.
Scenario 1: Bitcoin goes to $150K (3x from $50K cost basis)
- Rational investor: Take 30-50% profits, de-risk
- Saylor: Buy more with leverage
Scenario 2: Bitcoin crashes to $30K
- Rational investor: Reassess thesis, consider tax-loss harvesting
- Saylor: Buy more with leverage
He’s removing ALL optionality.
In finance, optionality = value. The ability to pivot, sell, reallocate = prudent risk management.
Saylor is playing Russian roulette with MSTR shareholders’ money.
The Bull Case: When Saylor Looks Like a Genius
Okay, let’s be fair. Here’s when Saylor’s bet pays off:
Scenario: Bitcoin goes to $200K+ by 2027
- MSTR’s 714K BTC → worth $142 billion
- Debt is easily refinanced or converted to equity
- Stock price 5-10x from here
- Saylor becomes richest man on Earth
- Everyone who doubted him looks stupid
Is this possible? Yes. Is it likely? Debatable. Is it prudent corporate strategy? Absolutely not.
Even if Bitcoin hits $200K, Saylor’s strategy was reckless. He got lucky, not smart.
How to Invest in Bitcoin (Without Being Saylor)
If you believe in Bitcoin’s long-term thesis, here’s the RIGHT way:
1. Allocate 5-15% of Portfolio
- Not 100%
- Not leveraged
- Just a reasonable position
2. Self-Custody Your Bitcoin
- Don’t buy MSTR stock (you’re paying for Saylor’s hubris)
- Buy Bitcoin directly, store in cold wallet
3. Have an Exit Plan
- If Bitcoin hits your target (e.g., $150K), take 30-50% profits
- Rebalance into other assets
- Don’t marry your positions
4. Diversify
- Bitcoin + stocks + bonds + gold + real estate
- Don’t put all eggs in one basket
5. Admit You Could Be Wrong
- Bitcoin might not go to $1M
- Have humility
- Adjust when new information emerges
This is how adults invest. Saylor’s approach is for gamblers.
FAQ
Q: But Saylor made billions. Isn’t he smarter than you? A: He made billions by getting lucky on timing (2020-2021 bull run). If he started this in 2021, MSTR would be bankrupt by now. Luck ≠ skill.
Q: What if Bitcoin goes to $500K? A: Then Saylor looks like a genius. But a broken clock is right twice a day. Just because a reckless bet pays off doesn’t make it smart.
Q: Should I short MSTR? A: Only if you’re confident Bitcoin stays below $60K for 6+ months. Otherwise, too risky. Better to just avoid it entirely.
Q: Is Saylor a fraud? A: No. He genuinely believes in Bitcoin. But true believers often make the worst investors because they lack objectivity.
Featured image: Michael Saylor at Bitcoin conference with MSTR stock chart overlay Data sources: MicroStrategy SEC filings, TradingView, Yahoo Finance
Related Reading
- Bitcoin Mining Death Spiral: What Happens If BTC Stays Below $60K?
- Why Bitcoin’s 4-Year Cycle Theory Is Dead (And What Comes Next)