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🐳 Daily Edition: Has Saylor's Time Finally Come?

🐳 Daily Edition: Has Saylor's Time Finally Come?

As Bitcoin falls under Strategy's cost basis, the STRC dividend payments weigh heavily on the balance sheet - where does Michael Saylor go from here?

Will McKinnon & Beluga
June 24, 2026

In partnership with

The crypto market has had a rough week so far as Bitcoin struggles to defend the $60k mark, with all of the post-Trump-election gains we enjoyed now evaporated. Aside from the macro headwinds that are affecting risk assets as a whole, it seems the market’s growing concern over Michael Saylor’s Strategy is weighing fairly heavily on everyone’s favorite orange coin.

For those who haven’t followed the story, Saylor introduced a new equity offering of preferred stock under the ticker STRC with a variable dividend structure (paid in cash, not BTC), based on a $100 par value. This was done in order to secure more fuel for their BTC buying frenzy, and while it looked good while things were going up, it’s had the opposite effect through the sell off: STRC ended today at a fresh low of about $80, down 20% since the end of May.

Strategy’s mNAV Flywheel Simplified, Source: Beluga, data per Strategy company filings

The main equity, MSTR, also now trades at a discount to its Bitcoin NAV - this means their usual strategy of issuing stock at a premium to NAV to buy more BTC isn’t possible anymore, while they’re simultaneously feeling the weight of these cash dividend payments to STRC holders. This led to their “inoculating the market” with a 32 BTC sale which while trivial in size (32 BTC is about 0.004% of their holdings), resulted in a highly reflexive reaction in price. In other words, the market didn’t react to the coins sold, but rather why the coins were sold.

So how does this story end? Well, there are basically three outcomes: 1) The Doom Loop, in which BTC stays under their cost basis, mNAV remains depressed, and they’re forced to accelerate BTC sales which will further crush the price. 2) Cockroach Mode, in which Strategy stops buying BTC, lives off of its current ~$2.25B in cash, and simply survives as there is no maturity wall for STRC forcing liquidation of their holdings. And finally, 3) Reflexive Recovery, where macro turns, BTC reclaims the mid-$70’s, and we all forget this ever happened until the next time Bitcoin starts selling off.

We all know past performance is not necessarily indicative of future results, but I do have to say this is far from the first time the mainstream has been convinced Michael Saylor is going under. To me, the situation is not as dire as it may appear at first glance, and Saylor is no stranger to massive drawdowns.

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