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About This Episode
The Hurdle Rate crew is back to cover the latest. Another Big Buy for Strategy. Semler Scientific adds Natalie Brunell to their Board. Jamie Dimon reminds us that Bitcoin is akin to smoking cigarettes.
In This Episode
- Another Big Buy for MSTR
- Semler Scientific adding Natalie Brunell to their Board
- Jamie Dimon’s recent quote
- US Debt gets Downgraded
- Class action lawsuit vs Strategy
Episode Summary
Key Themes: STRK scaling; leverage timing; board alignment; bank hostility; S&P 500 setup.
Strategy Keeps Expanding Its Capital Stack
The episode opened with Strategy’s latest Bitcoin buy and the growing role of STRK in its capital raising suite. Jeff noted that Strategy had reached roughly 576,000 Bitcoin and that STRK made up its biggest weekly share yet of ATM issuance. Ben said that while STRK is still small relative to total issuance, the key point is direction: Strategy is clearly working to make preferreds a larger part of the funding engine.
STRK Matters More Than ATM Complaints
Ben argued that many investors are looking at the structure too narrowly. Instead of focusing only on common stock issuance used to support future dividends, he said the right way is to evaluate the full transaction: the premium captured on STRK, the Bitcoin bought with that capital and the long-term dilution profile. In his view, preferreds can be far more accretive than critics assume.
Strategy Is Likely Waiting for Better Debt Windows
Ben said Strategy now has enough scale to be more selective, using the ATM and preferreds in calmer periods while saving larger convertible raises for moments when Bitcoin is moving higher and volatility improves terms. Jeff agreed that the debt market is there; the company is likely just waiting for the right opportunity.
Higher Bitcoin Means More Debt Capacity
Jeff noted that as Bitcoin rises, Strategy’s credit profile improves quickly because the collateral behind its securities expands faster than the liabilities. Ben added that the company still sits below its stated leverage band, leaving plenty of room to lever up more if Bitcoin runs. Their shared view was that Strategy has substantial unused capacity.
Board Alignment
The group discussed Semler adding Natalie Brunell to its board. Matt said Bitcoin treasury companies increasingly need directors who understand Bitcoin treasury strategy, not just traditional governance. Ben agreed, arguing that if treasury operations drive a large share of shareholder value, boards need people aligned with that reality.
Jamie Dimon’s Bitcoin Criticism Reflects Bank Incentives
The episode pushed back on Jamie Dimon’s latest anti-Bitcoin comments. Ben argued that banks are naturally hostile because Bitcoin threatens deposit gathering, lending spreads and the friction banks profit from. Matt added that large banks are not neutral observers here; they are defending a business model that Bitcoin directly challenges.
S&P 500 & Short Pressure, Lawsuits Come With Scale
Jeff said that Strategy’s size and earnings make S&P 500 inclusion harder to ignore, even if the committee delays. He also noted that more short attacks, negative narratives and lawsuits are likely as Bitcoin treasury companies grow larger. The class action against Strategy was framed mostly as predictable noise around a high-profile, well-capitalized company.
Main Takeaway: Strategy is shifting from pure speed to tactical execution—scaling preferreds, waiting for better debt windows and strengthening its capital structure as Bitcoin rises, even as banks and critics push back harder.