Strategy’s Bitcoin plan draws scrutiny amid capital changes

Strategy, the company formerly known as MicroStrategy, faces renewed attention after its June capital plan and the disclosure of a recent Bitcoin sale. The firm reports 843,775 Bitcoin on its balance sheet and disclosed a sale of 3,588 BTC days after announcing the new capital framework on June 29, 2026.

In March 2000 MicroStrategy announced restatements for fiscal 1998 and 1999 and later said it would restate 1997 results. The stock fell sharply, dropping from about $260 to $86 in one session and later to $33 after the additional restatement. The company and top executives settled civil charges with the U.S. Securities and Exchange Commission; the executives paid a joint $10 million fine without admitting liability.

Michael Saylor, the company’s CEO at the time and now executive chairman, rebuilt the business over the following two decades. On August 11, 2020, the company bought its first $250 million of Bitcoin and designated Bitcoin as its primary treasury reserve asset. The firm continued to add Bitcoin through repeated purchases from 2020 onward.

On June 29, 2026, Strategy unveiled a capital framework that permits sales of Bitcoin to fund dividends on perpetual preferred stock, build cash reserves and repurchase securities. Days after that announcement the company disclosed a sale of 3,588 BTC, its largest disposal since the firm began treating Bitcoin as its primary treasury reserve asset in 2020.

Public filings show Strategy has raised capital through convertible notes and perpetual preferred shares used to buy additional Bitcoin. As of late May 2026 the company reported roughly $6.7 billion in convertible notes outstanding and about $15.5 billion in perpetual preferred stock outstanding.

Observers differ on the implications of the company’s structure. Drew Forman, senior vice president and head of strategy at Talos, described the capital changes as a pragmatic evolution of the company’s treasury approach and said attention should be paid to how positions are financed, managed and monetized. David Trainer, chief executive of New Constructs, argued that the company’s equity functions as a leveraged wrapper around a volatile asset with limited earnings support from the software business. Aswath Damodaran, a finance professor at NYU Stern, used strong language to question the decision to concentrate so much of a public company’s valuation on a speculative asset.

Company filings show the software business now represents a much smaller portion of the balance sheet relative to Bitcoin holdings. Observers have noted that prolonged market stress, a significant fall in Bitcoin prices or tighter capital markets could require larger Bitcoin sales, more costly financing or slower growth, according to public commentary and analyst statements.