The crew does a deep dive into MSTR, Bitcoin leverage, $STRK, and S&P 500 dynamics. Special guest LaDoger add his perspective on the behind-the-scenes from the True North event.
Market Snapshot
As of 5/14/25:
- Open: $420.40 | Close: $416.75
- Volume: 10,681,100 shares
- mNAV: ~2.13 | Market Cap: ~$113.94B
- BTC Holdings: 568,840
In This Episode
- 00:05:35 — True North Origins
- 00:11:37 — MSTR Financials
- 00:17:35 — New Markets
- 00:25:15 — $STRK’s purpose
- 00:32:14 — $STRK vs MSTR
- 00:37:12 — Conference Recap
- 00:45:46 — Grain of Salt reveal
- 00:59:02 — Investor Relations
- 01:03:50 — LaDoger’s HQ trip
- 01:07:07 — Why torque, not leverage
- 01:13:30 — S&P 500
- 01:33:03 — Media Critique
- 01:38:54 — Knowledge Gaps
- 01:50:25 — Optimism vs Reality
- 01:56:50 — Bitcoin treasury movement
- 02:18:40 — Final thought
Episode Summary
Key Themes: Capital gravity; S&P 500 qualification; preferred-stock torque; digital credit; institutional education lag; teeth scarcity; treasury-company proliferation; Strategy’s widening moat.
Conviction, Not Marketing
Episode 26 connects several major developments around Strategy: its increasingly powerful balance sheet, the slow institutional adoption of its preferred securities, potential S&P 500 inclusion, and the sudden proliferation of other Bitcoin treasury companies. Jeff begins by addressing accusations that True North is simply a paid marketing arm of Strategy. The group says its conviction comes from years of research and participation in the trade, while the success of True North World demonstrates how rapidly a sophisticated community has formed around Bitcoin equities and capital markets.
The Leverage Update
The weekly leverage update reinforces the panel’s core financial argument. Strategy held roughly 568,000 Bitcoin worth about $58.5 billion, compared with $8.2 billion of debt and $1.7 billion of preferred stock. That placed its leverage ratio near 14%, or roughly 8.6% after adjusting for convertible debt already trading like equity. Jeff describes the company as stronger than ever, with substantial capacity to issue more securities while remaining below its targeted leverage range. The balance sheet would only become undercollateralized at a Bitcoin price near $14,000, and even then the price would need to remain depressed through future maturities before creating a serious problem.
Preferred Stock Torque
The conversation then returns to Bitcoin torque and why preferred stock may be more valuable than traditional convertible bonds. Convert buyers typically short a large portion of the common stock immediately, creating near-term pressure on MSTR. STRK and STRF can raise capital without the same immediate common-equity dilution. Strategy is effectively issuing securities with dividends near 10% and investing the proceeds into an asset it expects to compound much faster. That spread between the fiat cost of capital and Bitcoin’s expected appreciation is the engine behind the company’s expanding digital credit platform.
The Education Lag
Jeff stresses that creating this market will take time. Drawing on his experience building a new reinsurance market for wildfire liability, he explains that institutional buyers must first understand an unfamiliar risk, observe its performance, and become comfortable with the structure. Retail investors may currently understand STRK and STRF better than many fixed-income managers. The products offer high income, transparent collateral, and—in STRK’s case—a perpetual conversion option into MSTR, yet much of the traditional market still has not progressed beyond understanding Bitcoin itself.
AI-Accelerated Structuring
The panel sees artificial intelligence as an important part of Strategy’s advantage. Saylor and the capital-markets team reportedly used AI to research precedents, test structures, and accelerate the creation of the preferred securities. Instead of spending months beginning with open-ended legal research, the team could approach lawyers with relevant filings, case law, and a proposed structure already assembled. The preferreds therefore represent not only financial innovation but a faster corporate development process that competitors may struggle to match.
Capital Gravity Converging
Potential S&P 500 qualification is described as the convergence point for this capital gravity. Jeff estimates that the index has roughly ten times the capital tracking it as the Nasdaq-100. Based on Strategy’s potential weighting, he suggests eventual passive demand could reach approximately $12.5 billion, before considering active managers attempting to front-run those flows. The more important moment may not be formal inclusion but the first earnings report that makes Strategy clearly eligible. Rising demand could lift the stock, allow Strategy to use its common ATM at higher prices, add more Bitcoin, improve the collateral supporting its preferreds, and attract still more capital.
Teeth Scarcity
The episode’s “teeth scarcity” joke comes from a Financial Times video that the panel believes badly misunderstood Strategy and Bitcoin. The interviewer’s comparison between Bitcoin’s scarcity and scarce human teeth becomes a symbol of the institutional knowledge gap. Rather than viewing the criticism as bearish, the panel sees it as evidence that traditional financial media remains far behind the market and that broader adoption has barely begun.
Winner-Take-Most Dynamics
The final discussion examines the explosion of new Bitcoin treasury companies. The group rejects the idea that the category is already a bubble, but expects clear winners and losers. Smaller companies may produce faster gains, yet they also carry greater liquidity, management, financing, and leverage risks. Many operating companies can benefit simply by sweeping excess cash into Bitcoin. Far fewer will be able to replicate Strategy’s bank-like model of issuing preferreds, convertibles, options, and other financial products at scale. Strategy’s collateral, liquidity, track record, and market access make that segment more likely to become winner-take-most.
Main Takeaway: Capital is beginning to converge around Bitcoin treasury equities and digital credit, but Strategy’s scale, liquidity, preferred stocks, and potential index inclusion give it a widening advantage that newer treasury companies will struggle to reproduce.