Jason Colaco

Worked at MicroStrategy from 1999-2024. Currently a retired investor focused on Bitcoin, MSTR & BTC Treasury Companies.

[Jason Colaco @jcolaco]

@phongle That’s awesome to hear @phongle!!! We always had the best tech.

[Jason Colaco @jcolaco]

@Heeler999 @ActuallyClimber that straddle setup can definitely create a huge tax headache under IRC §1092.

[Jason Colaco @jcolaco]

@phongle @BloombergTV @kgreifeld STRC above $100 and mNav moving upwards nicely. Nice work dude, hope all is well!

[Jason Colaco @jcolaco]

@SInow 4

[Jason Colaco @jcolaco]

@HermesLux I would expect an announcement like that at MSTR World, not on an earnings call.

[Jason Colaco @jcolaco]

Bear case on the pref shift: replacing low-coupon, maturity-bounded converts with high-carry perpetual prefs isn’t deleveraging—it’s swapping refi risk for permanent yield drag and a dilution ratchet on common.

Stability helps at the margin, but continuous pref issuance raises fixed charges, widens spreads in stress, and risks underperforming BTC in flat or down regimes. Works in strong uptrends; path-dependent and fragile if capital markets tighten. Dylan, would love to hear your thoughts here.

[Jason Colaco @jcolaco]

Fast-forward to Jan ’29:
pref dividends covered, zero forced BTC sell risk. Even at only 20% CAGR, MSTR’s 673K+ BTC is >2x+ from entry. Issuing common at ≥1.0x mNAV to deploy $1B+ into BTC is economically accretive and the best action for shareholders. Anything else leaves value on the table. In hindsight, everyone will wish @saylor had bought even more at these prices.

[Jason Colaco @jcolaco]

When we (MSTR) chose Northern Virginia as HQ, it was for talent and proximity to the federal government.

In hindsight, that decision looks prescient. As MSTR evolves into a BTC Treasury company, having HQ + 800+ employees inside the DC orbit could become a real strategic edge. Strategy is a very well known company within the beltway.

[Jason Colaco @jcolaco]

@saylor

[Jason Colaco @jcolaco]

@PunterJeff — with the MSCI decision on Jan 15 looming, short interest still ~11% of float, and $2.19B in USD reserves…

Do you think MSTR has considered opportunistically deploying some of that cash for common share buybacks if mNAV flips negative post-announcement? Could put a hard floor under the stock and trigger a serious short squeeze. Beauty is they’d sell no BTC.

Or is the strategy strictly offensive—maximize BTC accumulation, no defensive capital actions? Curious how you’re thinking about it.

[Jason Colaco @jcolaco]

@kantan3340 @saylor @Strategy Yup, preferreds could lose the ROC designation, not worth the risk

[Jason Colaco @jcolaco]

This isn’t a binary call. MSCI can easily punt or carve out a middle ground. Even in a worst-case scenario, forced selling would be dripped out over months — $1.5–$2.5B is a rounding error relative to MSTR’s liquidity and market cap.

More importantly, an outright exclusion would also hit Trump-linked entities, which makes that path politically and practically unlikely. The market is already pricing in the downside. The asymmetry now clearly favors upside if MSCI blinks or delays.

[Jason Colaco @jcolaco]

If your time horizon is short, the preferreds make more sense. If you can handle the volatility, MSTR should outperform BTC over time — even though there will always be stretches where it doesn’t. That volatility is the risk premium. Endure it, and you get rewarded. Good luck in 2026!

[Jason Colaco @jcolaco]

If you’re bearish on MSTR but bullish on BTC, the math just doesn’t work. BTC per share is way up, mNAV is near the floor, and the balance sheet is stronger than ever. Dividend payment risk is a non-issue with their huge USD and BTC reserves. Sentiment dislocation has caused the recent price movement— the fact that guys like Jim Chanos are no longer short should tell you something. Good luck over the next few months…

[Jason Colaco @jcolaco]

@Instttrrffd @SmithsonBrennan There are two numbers that matter, when you buy and when you sell. If the volatility of the common is too much, the prefereds are probably a better vehicle for you.

[Jason Colaco @jcolaco]

@1stPrinciples4L @HermesLux Common stock prices track mNAV and BTC price action. mNAV acts as a key sentiment gauge, while BTC thrives on market liquidity—boosting confidence and valuations alike.

[Jason Colaco @jcolaco]

@scraymondjr @HermesLux The large cash reserve raise last week would seem to indicate some type of large pref raise is coming. With BTC prices where they are, MSTR wouldn’t have put it in USD unless there was a strategic purpose. As @saylor said, “green dots beget orange.”