Did Michael Saylor Really Take a Day Off?
I woke up Monday expecting my Twitter (fine, X) feed to be flooded with the usual #MondayBuy memes. Instead—crickets. No laser-eyed GIFs, no Tesla cameo from Saylor, not even the ritualistic “I just bought another block of BTC” tweet. If you’re new to the circus, MicroStrategy—sorry, “Strategy” in the 8-K wording—has turned the first trading day of the week into a borderline religious ceremony. They scoop up a chunk of Bitcoin and the market either cheers or jeers, depending on its mood. But this Monday, nada. Zero. Zip.
Yet, by Tuesday afternoon the same company filed a Q2-2025 report showing a $14 billion unrealized gain and a fair-value stack of $64.36 billion. Talk about an upside surprise. So how do you make $14 billion without buying a single satoshi that week? Let’s unpack it, coffee in hand.
Here’s What Actually Happened
First, some raw numbers, because—call me a data nerd—I think the market’s memory is short:
- Total Bitcoin held: 281,430 BTC (still the same as the last disclosed purchase on June 23, 2025)
- Carrying value on the books: $12.88 billion (they still use impairment accounting, which is bananas, but that’s for another rant)
- Fair value as of June 30: $64.36 billion
- Quarter-over-quarter unrealized gain: $14.02 billion
- Average purchase price: $45,781 per BTC
- Spot price at quarter close: $228,625 (Coin Metrics closing index)
I’ve noticed a lot of folks on Crypto-TikTok conflating fair-value gains with cash flow. Nope. These are paper gains recognized under the newer fair-value option FASB just let public companies use for crypto. It’s a sea change: MicroStrategy can now mark up (and down) Bitcoin each quarter. Q2 was the first full quarter where the rule kicked in, and boy did it flatter the P&L.
Why the Missing Monday Didn’t Matter—At Least Not Yet
Here’s my working theory: Saylor doesn’t want to chase a vertical candle. Bitcoin’s been grinding higher ever since the Ether ETF approval headlines in April. Volume on Coinbase Pro tripled week-over-week, and on-chain trackers like Glassnode show miner reserves at a six-year low. Scarcity is real. So maybe, just maybe, Strategy executives saw more upside in letting their existing stash do the heavy lifting. You don’t buy more when your cost basis is already sub-$46K and market is frothing above $225K—unless, of course, you’re Maximalist Max.
But that raises a juicy question: Is #MondayBuy dead? In my experience, crypto never kills a meme. It just hibernates until sentiment flips. Remember when everyone declared NFTs finished in 2023? (Cue Pudgy Penguins now sold at Walmart.) I suspect we’ll see a #MondayBuy the next time BTC prints a double-digit dip. For now, the company is sitting on an eye-watering 398% unrealized return, so why rush?
The Market’s Knee-Jerk Reaction Was… Confusing
Here’s the part that honestly left me scratching my head: MSTR shares opened down 3.4% the morning after the filing, even though they basically announced they’re swimming in crypto profits. The options desk on Deribit immediately priced in +10 vol for next-month calls, suggesting traders expected a pop that never came. It reminded me of that old Wall Street aphorism:
“If you promise to shoot the moon every quarter, eventually the market only cares when you hit Mars.”
One possible explanation—borrowed from @DylanLeClair’s thread—is that arbitrage funds use MSTR as a quasi-spot ETF. When Bitcoin rallies faster than the stock, they short BTC and long MSTR, betting convergence. Q2’s big markup might have prompted those desks to unwind, temporarily pressuring the share price. If you follow the flow on Token Terminal, you’ll see open interest on CME Bitcoin futures fell by $380 million that same day. Coincidence?
Zooming Out: The “Treasury-as-a-Service” Experiment Is Working
I’ve long joked MicroStrategy is now a levered Bitcoin trust with a software side hustle. But give credit where it’s due: they’re beating most hedge funds by simply holding. Let’s compare:
- ARK’s flagship fund: +41% YTD
- Galaxy Vision Fund: +112% YTD
- Strategy’s BTC stash: +177% YTD (mark-to-market)
Even the top-performing traditional equities lag behind. Nvidia’s monstrous run clocks in at +156% YTD. Strategy outperformed by parking assets in cold storage and tweeting once a week. Talk about asymmetric risk. Yes, there’s leverage from their 2028 convertible notes, but interest expense looks manageable—$46 million this quarter versus a $14 billion accounting win. If rates drop in H2 (FedWatch Tool places a 72% probability for a cut by September), that carry cost shrinks further.
Okay, But What Could Go Wrong?
I’m bullish, but not blind. Three risk flags blink bright red on my dashboard:
- Regulatory whiplash: The SEC still hasn’t formally blessed MicroStrategy’s approach. Gensler could wake up tomorrow and decide that “investment company” rules apply, forcing painful restructuring.
- Leverage decay: Convertible notes are fine when BTC moon-lambos. They’re brutal if we retrace 60%. We’ve seen drawdowns like that five times since 2013.
- Liquidity mirage: A $64 billion fair value looks chunky, but the company can’t unload more than a sliver without tanking the market. Their stack equals 1.43% of total supply. OTC desks would choke.
Still, none of these risks are new, and the market has largely priced them in—or at least shrugged them off. If anything, the fair-value accounting shift reduces downside shocks because impairment losses used to slaughter EPS every bear market.
Why This Matters for Your Portfolio
If you’re an everyday investor (yes, even you with 0.08 BTC in a Ledger), MicroStrategy’s Q2 print is more than corporate trivia:
- Saylor’s “Bitcoin standard” thesis just got new ammo. The man can now point to audited GAAP numbers—no spreadsheet gymnastics—confirming near-5x returns.
- Volatility insurance is expensive. Implied vol on Bitcoin options spiked after the filing, signaling the market expects bigger swings. Plan your entry and exit accordingly.
- Correlation alert. When MSTR stumbles, it drags crypto-adjacent equities (COIN, MARA, RIOT) with it. Keep an eye on those if you’re diversified into miners or exchanges.
In my view, the most overlooked angle is the psychological one: a publicly listed company now holds more Bitcoin than the governments of Germany, the U.K., and Canada combined. That normalizes BTC on balance sheets in a way no ETF can match. The next CFO pitching a 1% treasury allocation won’t look reckless; they’ll look late.
If You’re Wondering Whether to Copy-Paste the Playbook…
I’ve talked to half a dozen SaaS founders in the past month, and every conversation eventually drifts to “Should we put part of our treasury into Bitcoin?” My honest answer? Know your risk tolerance and financing structure first. Strategy can stomach a 50% drawdown because they generate steady enterprise analytics revenue. A Series A startup with a 24-month runway, not so much.
Think of MicroStrategy’s balance sheet as a Call Option on Digital Scarcity™. They pay a fixed premium—interest on notes—in exchange for unlimited upside. You, dear reader, can replicate that only if you’re comfortable with the same volatility and have either cash flow or patient investors.
Where the Chart Nerds See Things Going Next
Technicals matter, even if Saylor claims to ignore them. On the weekly, BTC just closed above the 3.618 Fibonacci extension from the 2020-2021 cycle. Historical precedents suggest a 12-15% pullback is likely before the next leg. If that dip arrives in late July, don’t be stunned if the #MondayBuy bat-signal reappears. TradingView watchlists are already peppered with alerts at $198K—a round psychological level that coincides with 50-day EMA support.
I’m penciling in mid-August for potential fireworks. Why? The Jackson Hole Symposium often catalyzes macro moves, and crypto has danced to Powell’s tune since 2022. If the Fed finally whispers “rate cuts,” risk assets—including BTC—could rip. Strategy might preload ammo by issuing another convertible tranche (their shelf registration still has $1.7 billion unused). That would set the stage for a fresh buying spree.
Wrapping Up: The Numbers Whisper Louder Than the Tweets
I confess, part of me misses the dopamine rush of that Monday announcement. Yet this week’s silence proved something more profound: MicroStrategy doesn’t need to buy to win. Let the on-chain data do the talking. A $14 billion boost with zero new coins is a mic-drop moment.
For the rest of us, the takeaway is clear. If conviction plus time equals outsized gains, then patience might be the most underrated tool in crypto. The next time your group chat fumes over missing a pump, remember: Strategy just showed that sometimes, doing nothing is the ultimate power move.
