MicroStrategy strategy director Jarrod Patten has quietly unloaded nearly $9 million worth of company stock over the past three months, according to recent SEC filings — a sign of mounting pressure on the firm’s preferred securities and fresh scrutiny over how the company will fund dividend payments.
Details from the filing show Patten exercised options to acquire 1,500 Class A shares at a strike price of $18.236 and flipped them immediately on the open market for roughly $134 per share, netting about $200,000. That trade is part of a broader pattern: Patten has sold 55,750 MSTR shares in the last three months, generating close to $9 million. He still holds 28,406 Class A shares, stakes in several Series A perpetual preferred offerings and 44,250 unexercised director options.
Investor focus has shifted to MicroStrategy’s ability to cover preferred dividend obligations. Market maker QCP estimates the company’s current liquidity can sustain those dividend payments for about seven and a half months. If funding becomes tighter, QCP warns the company may face tough choices — raising fresh capital (and diluting shareholders), or selling more Bitcoin.
Those concerns followed a flurry of recent balance-sheet moves. MicroStrategy repurchased nearly $1.5 billion of convertible notes due in 2029 while raising roughly $200 million via share sales; a portion of those proceeds was later used to buy about $100 million in Bitcoin. At the same time, the company’s STRC preferred stock — the “Stretch” series — sank to a record low of $89, roughly 11% below its intended $100 par value, adding scrutiny to the capital structure.
In another notable development, MicroStrategy disclosed selling 32 BTC (around $2.5 million) to fund STRC dividend payments — its first known Bitcoin sale after years of an accumulation-first approach. Insider selling has been broader: filings show CEO Phong Le, CFO Andrew Kang and former EVP Wei-Ming Shao collectively sold millions in MSTR shares in March, and both Kang and Patten trimmed holdings as the stock slid.
The market has reflected those pressures. MSTR closed 5.09% lower at $116.56 on Wednesday and fell another 2.1% to $114.04 on Thursday, leaving the stock down about 31% over the past month. Bitcoin traded near $63,850 at press time, off nearly 2% in the prior 24 hours.
Despite the pullback, major Wall Street analysts remain bullish on MicroStrategy. Bernstein reiterates a buy with a 12-month target of $450; TD Cowen targets $350; Citigroup $260; and BTIG $250. For now, investors will be watching insider activity, STRC’s performance, and whether the firm leans on its Bitcoin holdings or external capital to shore up preferred dividends.
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