Grayscale’s Zach Pandl advises Strategy to sell $3B in Bitcoin to cover cash obligations

The company that bet its entire identity on never selling Bitcoin might need to sell a lot of Bitcoin.

Zach Pandl, Head of Research at Grayscale, has recommended that Strategy, the company formerly known as MicroStrategy, should offload at least $3B worth of Bitcoin to meet its cash obligations over the next two years. The suggestion excludes one convertible note, meaning the actual financial burden could be even steeper.

The math behind the recommendation

Pandl’s case is rooted in straightforward arithmetic. Strategy’s capital structure, particularly its preferred stock STRC, has created a dividend burden that the company cannot easily ignore. STRC has recently hit new lows, suggesting investors are already pricing in trouble.

According to Pandl, raising the STRC dividend by just 50 basis points would pile roughly $100M in additional obligations onto the company over two years.

A Grayscale research note from June 4 highlighted that Strategy has limited ability to accumulate more Bitcoin at current share prices. In English: the flywheel that powered the company’s entire strategy, issuing equity at a premium to buy more Bitcoin, may be grinding to a halt.

The company reportedly sold 32 Bitcoin around June 1, a modest amount by Strategy’s standards but symbolically significant. When a company built on the premise of perpetual accumulation starts selling, even small amounts get noticed.

Strategy has also racked up an estimated $14B in unrealized losses tied to the volatility of its Bitcoin-heavy treasury.

Why this matters beyond one company

Strategy isn’t just any Bitcoin holder. It’s the largest corporate holder of Bitcoin in the world, and its treasury strategy became the template that dozens of imitators tried to copy.

The pitch was elegant in its simplicity. Issue stock or convertible debt at favorable terms, use the proceeds to buy Bitcoin, watch Bitcoin appreciate, and repeat. When Bitcoin goes up, the stock goes up, which makes it easier to raise more capital, which lets you buy more Bitcoin. It’s a virtuous cycle. Until it isn’t.

Dividend obligations don’t disappear when Bitcoin’s price dips. Preferred stockholders still expect their checks.

If Strategy were to actually execute a $3B sale, the market impact could be substantial. That kind of supply hitting the market would create meaningful downward pressure on Bitcoin prices, at least in the short term.

What this means for investors

The dividend burden on STRC preferred shares is a structural problem, not a temporary one.

Investors should watch STRC’s price action closely. Preferred stock hitting new lows while the parent company sits on $14B in unrealized losses is not a combination that inspires confidence.

The question now is whether Strategy’s leadership accepts Pandl’s advice or doubles down on the accumulation thesis. The math doesn’t care about conviction, and $3B in obligations has a way of making even true believers reconsider.