In Episode 12, True North Episode 12: The True North crew explores 2025 market outlook, MicroStrategy’s evolving Bitcoin strategy, catalysts like S&P 500 inclusion, options trading insights, and the evolving… Key discussion points include community growth, bitcoin holdings, catalysts, leaps options, options insights. Market context: MSTR closed at $331.70 with mNAV at ~1.92.
Market Snapshot
- Date: 1/8/25
- MSTR Open/Close: $335.25 / $331.70
- Volume: 18,212,600 shares
- mNAV: ~1.92
- Market Cap: ~$81.52B
- U.S. Market Cap Rank: 122
- BTC Held: 447,470
Chapters
- 00:00:00 — Market sentiment: Volatility and FUD affecting MicroStrategy’s stock.
- 00:04:22 — Community growth: Surging member count reflects increasing interest.
- 00:07:23 — Bitcoin holdings: MicroStrategy acquires 1,700 Bitcoin, strengthening assets.
- 00:15:29 — Catalysts: Market events and their potential impact on MicroStrategy stock.
- 00:18:20 — LEAPS options: Historic trades linked to Bitcoin’s four-year cycles.
- 00:21:13 — Options insights: Breaking down Josh Mandell’s insights.
- 00:26:53 — Exercise strategies: Tips for leveraging options contracts.
- 00:31:19 — Retail behavior: Common pitfalls of new investors in options trading.
- 00:33:39 — Long-term potential: MicroStrategy’s bullish thesis.
- 00:41:48 — Intrinsic value: Building a stronger floor for Bitcoin-per-share metrics.
- 00:51:14 — Martin Shkreli: Short positions and miscalculating MicroStrategy.
- 00:57:55 — Preferred stock: Flexible capital structures with strategic dividend options.
- 01:15:49 — Fair value: Transitioning in accounting and its market impact.
- 01:22:09 — S&P 500: Criteria for inclusion and potential effects.
- 01:43:59 — Price cycles: Investor sentiment and MicroStrategy’s market swings.
- 02:13:45 — California wildfires: Insurance challenges and rising premiums.
- 02:22:23 — Catastrophe bonds: New insurance market opportunities with blockchain.
- 02:24:59 — Future innovation: Pivoting the insurance industry toward technology.
Episode Summary
Key Themes: Balance-sheet leverage; January options expiration; preferred equity; convertible debt; digital credit; fair-value accounting; Bitcoin-per-share accretion; covered-call income.
Underleveraged Into 2025
Episode 12 opens with MicroStrategy entering 2025 from a position of unusual financial strength despite volatile trading and deteriorating retail sentiment. The company held approximately 447,000 Bitcoin worth $42.3 billion against $7.5 billion of liabilities, producing a liability-to-asset ratio near 17.9%, below its recent historical range. The panel estimates that MicroStrategy could issue roughly $3.5 billion of additional convertible debt and return toward a 25% leverage ratio. Bitcoin falling to approximately $16,917 would merely bring asset value in line with liabilities; it would not trigger liquidation because the debt is unsecured and lacks Bitcoin margin calls.
The January Expiration
The January 17 options expiration is presented as the most immediate market event. Long-dated calls first offered in 2022 had become deeply in the money, and many holders were considering exercising rather than selling. Although market makers were likely substantially hedged, concentrated share delivery and rapid movements around at-the-money strikes could still create a temporary gamma-driven overshoot. The practical lesson is less about predicting a squeeze than understanding broker procedures, cash requirements, taxes, and the risks of attaching leveraged positions to a single catalyst.
Tempered Catalyst Expectations
That caution extends to the broader 2025 calendar. Fair-value accounting, possible S&P 500 eligibility, political change, Bitcoin policy, and future capital raises are all constructive developments, but none guarantees an immediate repricing. The panel recalls Saylor saying that MicroStrategy keeps expectations low and operates a plan that does not depend on favorable index decisions or political assistance. Conversations with Saylor and treasury head Shirish Jajodia also reinforced the impression that the company is closely monitoring shareholders, counterparties, and market structure while preparing additional products.
Perpetual Preferred Design
The most important new product under discussion is perpetual convertible preferred stock. Ben expects MicroStrategy to structure it as equity rather than debt, placing it above common shares but below senior notes while preserving room for additional convertibles. Preferred investors would receive a dividend and lower volatility, with conversion features pushed far enough into the future to appeal to pensions, insurers, and endowments seeking income rather than short-term equity exposure. MicroStrategy could fund the dividends through operating cash flow or limited common-stock ATM issuance.
The Accretive Sequence
The sequencing could be highly accretive. Raising preferred equity to buy unencumbered Bitcoin would lower the leverage ratio again, allowing MicroStrategy to follow with a larger round of convertible debt. The panel speculates that preferreds and converts together could raise $8–$10 billion in the first quarter. New Bitcoin-backed convertible-bond ETFs would broaden demand beyond private hedge funds, creating another channel through which public capital can purchase corporate digital credit.
Earnings Versus BTC Yield
Fair-value accounting introduces a second valuation framework. Bitcoin appreciation would begin flowing through earnings, potentially producing positive trailing results and qualifying MicroStrategy for the S&P 500. The panel debates whether those gains deserve a conventional earnings multiple, with Dan arguing that BTC yield—the additional Bitcoin created per share through capital-market activity—is a cleaner earnings proxy. Regardless of the chosen metric, increasing Bitcoin per share raises MicroStrategy’s intrinsic-value floor through repeated mNAV expansions and contractions.
MSTY Tradeoffs
MSTY and self-managed covered calls offer income but involve tradeoffs. Investors face management fees, ordinary-income taxation, complex option mechanics, and capped upside during sudden MSTR rallies. They may suit income-focused or tax-advantaged accounts, but they do not replicate unrestricted common-stock exposure.
Main Takeaway: MicroStrategy began 2025 underleveraged and positioned to combine preferred equity, convertible debt, digital credit demand, and fair-value earnings into another expansion of Bitcoin per share.