I’ve been a trader and investor for 44 years. I left Wall Street long ago—-once I understood that their obsolete advice is designed to profit them, not you.
Today, my firm manages around $5 billion in ETFs, and I don’t answer to anybody. I tell the truth because trying to fool investors doesn’t help them, or me.
In Daily H.E.A.T. , I show you how to Hedge against disaster, find your Edge, exploit Asymmetric opportunities, and ride major Themes before Wall Street catches on.
I’m hosting a webinar entitled “Why Covered Call ETFs Suck and What to Do Instead” (More Info Below) November 14 2-3pm. Sign Up Here
Table of Contents
H.E.A.T.
I just came back from the Cantor Crypto Conference and am more confident than ever that crypto will transform our financial system. In honor of that I wanted to take a deeper dive on MicroStrategy’s preferred’s. Longer term readers know I’m not a fan of bonds, except preferred shares and p&c companies (which as basically unconstrained bond funds)….
MicroStrategy’s Capital Stack: Convertibles, Crypto, and the Preferred Puzzle
MicroStrategy ($MSTR) has built one of the most ambitious capital stacks in the public market. Since 2020, it's been issuing convertible debt and preferred stock to buy Bitcoin — and it now holds nearly half a million BTC. The benefit? Enormous optionality if Bitcoin rips. The risk? A growing stack of claims ahead of common shareholders.
Alongside billions in low/zero-coupon convertibles, MicroStrategy has launched four classes of preferred shares — $STRK, $STRF, $STRD, and $STRC — each designed to raise cash without issuing common stock or increasing debt service. These preferreds come with high fixed dividends, remote conversion rights, and varying structures. For yield-focused investors willing to underwrite some crypto-credit risk, they offer asymmetric opportunity. But not all are created equal.
Each one is a little different — and that difference matters.
Key Structures and Coupons
Ticker | Name | Coupon | Convertible | Cumulative | Seniority | Notes |
|---|---|---|---|---|---|---|
$STRK | Strike | 8.00% | ✅ (0.1 MSTR/share, $1,000 conversion) | ✅ Yes | Junior to STRF | Income + upside optionality |
$STRF | Strife | 10.00% | ❌ No | ✅ Yes | Senior to STRK | Pure income, no equity kicker |
$STRD | Stride | 10.00% | ❌ No | ❌ No | Junior to STRK & STRF | Highest yield, most risk |
$STRC | Stretch | Starts 9%, variable | Partial (structured to adjust price near $100) | ✅ Yes | Likely junior to STRF | Designed to stay stable near par |
What Makes Them Interesting
All four classes offer high income tied to a Bitcoin proxy, but with varying degrees of upside, volatility, and risk:
$STRK is a hybrid: an 8% yield with a long-dated call option on MSTR baked in. The conversion only makes sense if the stock trades above $1,000 again, but if Bitcoin flies, that option matters. You’re getting paid to wait for a blowoff top.
$STRF is pure yield — 10% annual income, cumulative, and structurally senior to $STRK. It doesn’t convert, but that’s what makes it stable. It’s the preferred of choice if you’re neutral or bearish on MSTR but want to collect income before common shareholders ever get paid.
$STRD is the riskiest: 10% yield, but non-cumulative and junior to both $STRF and $STRK. You’ll get paid — until you don’t. It trades at a discount for a reason. If MSTR ever skips a dividend, STRD investors don’t get it back.
$STRC is the newest and most flexible. It starts at a 9% yield, but is variable, adjusting to keep the price near $100. It’s less directional than STRK and less yield-focused than STRF — a middle path for more tactical investors.
Key Takeaways for Investors
If you want Bitcoin exposure with upside, $STRK gives you a long-term call option on MSTR + an 8% yield.
If you want income without volatility, $STRF gives you a 10% fixed coupon and sits above $STRK in the capital stack.
If you want maximum yield and don’t mind risk, $STRD pays 10%, but it’s non-cumulative and bottom of the stack.
If you want a more stable preferred, $STRC adjusts its coupon to stay near $100 — good for investors prioritizing price stability over yield chasing.
All are perpetual — no maturity date — and rely on MicroStrategy’s ability to fund dividends through BTC sales, ATM equity, or cash flow.
MicroStrategy is one of the few public companies offering retail-accessible, high-yield income that’s tied to Bitcoin performance — but without full crypto volatility. You’re not buying common stock; you’re buying structured exposure to Saylor’s macro thesis: Bitcoin wins big, and shareholders who funded it share in the upside.
These preferreds are not your grandfather’s muni bonds. They’re high-yield, long-duration instruments with Bitcoin risk embedded in the credit profile. They rank above common stock in a liquidation, but below MicroStrategy’s $8B+ of convertible debt.
They will outperform cash and bonds if BTC rises and MicroStrategy stays liquid.
They will underperform if BTC drops and the company is forced to suspend dividends or refinance on unfavorable terms.
Key Takeaways:
$STRK and $STRF: Better for income-focused investors. Safer dividend profile, but little upside unless MSTR > $1,000.
$STRD: Callable in 2029 — higher certainty of exit, but cap on upside.
$STRC: Highest yield variability, more speculative.
All are perpetual — no maturity = no guarantee you’ll ever be redeemed.
MSTR common still has higher upside, but more volatility and dilution risk.
In a world where fixed income barely pays and AI/Bitcoin continue to reshape markets, MicroStrategy’s preferred stack gives you a way to rent exposure to the crypto leverage machine — with cash flow, if you’re brave enough to hold the paper.
News vs. Noise: What’s Moving Markets Today
The “Great Rotation” Returns — Again
Value stocks are finally getting their moment — and everyone wants to believe this time is different. The Dow just topped 48,000 for the first time, outpacing the Nasdaq by the widest margin in months. Healthcare, industrials, and energy are perking up. Meanwhile, AI highfliers like $NVDA, $PLTR, $META, and $CRWV are sagging under the weight of sky-high expectations, power bottlenecks, and a funding machine that looks more like a debt pyramid than an organic growth story.
Interesting, ORCL retraced it’s entire September gap up….
Here’s the problem: we’ve seen this movie before. Rotations into value happen every time the Nasdaq blinks — and they rarely last. In 2024, small-caps rallied for a month before fading. In early 2023, energy led for six weeks. But each time, AI came roaring back because the capex flows never stopped. And they still haven’t. Even as sentiment cracks, hyperscalers are spending north of $400 billion this year on AI buildout, and $NVDA is projecting 56% YoY growth in its next print.
So is this rotation the real deal, or just another head fake? If you’re betting on value holding leadership, you’re implicitly betting that rates stay high, multiples compress, and AI capex stalls. That’s possible, but it hasn’t happened yet. And as long as the Fed stays on hold, rather than cutting aggressively, the market will keep playing both sides: defensives for year-end safety, and AI infrastructure for long-term upside.
Takeaways:
Value strength looks real — but rotational, not secular. It’s a positioning shift, not a macro pivot.
AI fragility is increasing. Valuations are stretched, funding is layered, and execution needs to be perfect — but the spending story is intact.
Watch the Fed. If December is a hold and not a cut, expect value to stay supported through year-end. If they do cut, the beta chase is back on.
Play both edges: own high-quality value ($ETN, $TPL, $PWR), and structure AI upside with defined-risk long premium trades. Skip the naked bets. The tide is shifting, and the water’s choppy.
The bull market’s still here — but the trade is getting narrower, pickier, and more asymmetric by the day.
A Stock I’m Watching
Today’s stock is Advanced Micro Devices (AMD)…..
AMD is going on offense. At its first analyst day in three years, the company projected a $1 trillion total addressable market in data center compute by 2030 and set bold targets: over 50% share in server chips, 40%+ in client, and 35%+ revenue growth annually. The stock ripped 9% on the update. The core of the AI bull case is its upcoming MI400 and MI500 GPU accelerators — and while the roadmap execution remains uncertain, AMD is positioning itself as the No. 2 contender to Nvidia in AI compute. With gross margin guidance now lifted to 55–58%, this is a “credible threat” story, not just a catch-up one. It’s early innings, but Helios (their rack-scale AI platform) could be AMD’s breakout moment — if they deliver.
How Else I Can Help You Beat Wall Street at Its Own Game
Inside H.E.A.T. is our monthly webinar series, sign up for this month’s webinar below….
Why Covered Call ETFs Suck-And What To Do Instead
Friday November 14, 2-3PM EST |
Covered call ETFs are everywhere — and everyone thinks they’ve found a “safe” way to collect yield in a sideways market. |
The truth? |
They cap your upside, mislead investors with “yield” that’s really your own money coming back, and often trail just owning the stock by a mile. |
Join me for a brutally honest breakdown of how these funds actually work — and what you should be doing instead. |
What You’ll Learn:
🔥 Why “high yield” covered call ETFs are often just returning your own capital |
The H.E.A.T. (Hedge, Edge, Asymmetry and Theme) Formula is designed to empower investors to spot opportunities, think independently, make smarter (often contrarian) moves, and build real wealth.
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