For years, Michael Saylor's Strategy (Nasdaq: MSTR) has reigned as the largest corporate Bitcoin (BTC) holder among publicly listed firms. But the company's prized Bitcoin funding machine is
For years, Michael Saylor's Strategy (Nasdaq: MSTR) has reigned as the largest corporate Bitcoin (BTC) holder among publicly listed firms.
But the company's prized Bitcoin funding machine is sputtering.
Now a veteran portfolio manager says Saylor is running out of good options.
Related: Milk Road co-founder reveals why Strategy's STRC isn't the 'ponzi' Schiff claims
STRC, nicknamed "Stretch," is Strategy's perpetual preferred stock, launched in July 2025 through a roughly $2.5 billion IPO.
It pays an 11.50% annual dividend, distributed semi-monthly in cash, with the rate adjusted monthly to keep the stock trading near its $100 par value.
The instrument is essentially a fundraising engine. When STRC trades above $100, Strategy issues new shares and funnels the proceeds into Bitcoin, without diluting common stock or breaching debt covenants.
But the loop only works above par. STRC is now at its lowest level since launch, trading near $88 at press time, down more than 11% over the past month.
Jeff Dorman, chief investment officer at digital-asset firm Arca and a portfolio manager with nearly two decades of experience, laid out a sober assessment on X on June 17.
"MSTR pickle continues," he wrote, arguing that the only short-term way to "save $BTC and $MSTR" is,
"Either sell an enormous amount of BTC and MSTR to help bring STRC back up near par, and at least buy yourself some time, or continue to watch every part of your cap structure melt because of the uncertainty you've created."
Dorman assigned rough odds to three outcomes. His base case, at 70%, is that Strategy keeps selling small amounts of MSTR monthly at "non-accretive levels," crushing the stock toward 0.70 mNAV while giving STRC holders "a glimmer of hope."
He puts a 25% chance on Saylor selling $3–$4 billion worth of Bitcoin to buy time.
Strategy's STRC drop over the past monthTrading View
But there is a 5% on the "nuclear option" of killing the dividends, which would close capital markets to him but halt a $1.7 billion annual cash drain.
Even now, Dorman highlighted, Strategy's multiple of net asset value (mNAV) stands around 1.15.
mNAV is a ratio used heavily in the Bitcoin-treasury world to judge whether a company's stock is trading above or below the value of the Bitcoin it holds.
As of press time, Strategy holds 846,842 BTC worth around $53.4 billion while its USD reserve holds $1.1 billion. The company has about $6.754 billion in debt, while the aggregate notional value of its preferred stock, including STRC, stood at $15.475 billion.
With the current numbers in mind, Dorman predicted that Strategy is "still going a lot lower (should trade at a discount to NAV now)."
MSTR stock closed 3.46% lower at $112.53 on Thursday.
Related: Michael Saylor finally addresses short-sellers as mNav drops
