Strategy holds 843,775 BTC as dot-com ghost haunts Saylor's bet

Michael Saylor has done something he spent five years insisting he never would: sell Bitcoin.

Strategy, the corporate Bitcoin treasury giant formerly known as MicroStrategy, sold $218 million worth of BTC in 2026 — less than 0.5% of its 843,775-coin hoard — and authorized the sale of up to $1.25 billion under a new Digital Credit Capital Framework announced June 29. The company now holds $3 billion in U.S. dollar reserves alongside its $54 billion Bitcoin stack, according to SEC filings and executive chairman Michael Saylor's public updates.

"The broader takeaway is that Bitcoin is increasingly being treated as an institutional asset class," Forman, an analyst who tracks the company, told Cointelegraph. He said Strategy's willingness to sell Bitcoin is less a departure from Saylor's long-held accumulation strategy than a practical reality of managing a multi-billion-dollar corporate balance sheet.

The shift comes 26 years after MicroStrategy's accounting scandal wiped out more than 87% of its market value in weeks. On March 20, 2000, the company announced it needed to restate financial results for fiscal years 1998 and 1999 due to accounting errors. Its stock collapsed from $260 to $33 per share by April 13. Saylor and two executives paid a $10 million fine to settle SEC charges, without admitting liability.

The capital structure has changed, but the concentration risk remains

Today's Strategy looks fundamentally different from the software company that imploded during the dot-com era. The software business is now a rounding error next to the balance sheet. Strategy runs $6.7 billion in convertible notes and $15.5 billion in perpetual preferred stock, used specifically to buy more Bitcoin. Annualized dividend and interest obligations total roughly $1.8 billion.

David Trainer, chief executive of investment research firm New Constructs, argues the underlying problem has merely shifted form. "Different mechanism, same underlying problem: the equity is a leveraged wrapper around a volatile asset, with no fundamental earnings power supporting the valuation," he said. "Once you're structurally reliant on issuance and issuance becomes value-destructive, the company has to either sell Bitcoin, take on more expensive financing or simply stop growing."

Aswath Damodaran, professor of finance at NYU Stern School of Business, was blunter. "Saylor is insane (not an insult, just a diagnosis) and is either a fool or a knave," he told Cointelegraph. "It hurts my brain cells just thinking about MSTR and I don't have enough to waste on it."

The premium problem

Strategy's stock trades 80% below its November 2024 record high, reflecting investor concern that the premium above net asset value — the key mechanism enabling the company to issue equity at favorable terms — may be disappearing. If that premium vanishes, the company loses its primary tool for raising cheap capital to buy more Bitcoin.

The company raised $466.7 million through MSTR share sales between July 6 and July 12, boosting its dollar reserve by $450 million to $3 billion, while keeping its Bitcoin holdings unchanged. CEO Phong Le described the approach as an evolution "from one-way capital issuance to active capital management."

Skeptics argue the model only works if Bitcoin keeps appreciating and investors continue providing new capital. Some have warned that, under prolonged market stress, those dynamics could contribute to a so-called death spiral in Strategy's financial model. Bitcoin traded far from its all-time high above $126,000 reached in October 2025, with the company's average purchase price of $75,476 per coin sitting well above current market levels.

Whether Saylor has rewritten his legacy will not be decided by the next bull run, but by how well Strategy performs if the markets continue to turn against it.

This article is for informational purposes only and does not constitute investment advice.