Michael Saylor's Bold Bitcoin-Backed Funding Model: High Stakes in a Volatile Market

August 15, 2025
Michael Saylor's Bold Bitcoin-Backed Funding Model: High Stakes in a Volatile Market
  • The 'Stretch' securities carry high coupons of 8-10%, representing expensive long-term debt, and are non-cumulative, meaning missed dividends need not be repaid, which introduces risk if Bitcoin prices decline.

  • These preferreds are unique because they do not mature, pay guaranteed dividends, or give investor control, serving as a flexible way to finance Bitcoin purchases without diluting existing shareholders.

  • Since January 2024, Strategy has raised over $40 billion through various equity and fixed-income instruments, including approximately $6 billion this year from four preferred offerings, with notable retail investor participation.

  • The success of this model hinges on Bitcoin's value remaining stable; a decline in Bitcoin prices could threaten Strategy's ability to meet dividend obligations and maintain its capital structure.

  • Paying perpetual dividends using Bitcoin poses risks, especially if Bitcoin's value drops, potentially forcing Strategy to sell Bitcoin to meet obligations, although selling Bitcoin is off-limits in their strategy.

  • Supporters see the 'Stretch' preferreds as a clever way to buy Bitcoin without selling crypto, but critics warn that payouts could become costly if Bitcoin's price declines.

  • Critics like Jim Chanos have called the 'Stretch' notes 'crazy,' highlighting their high risk and Strategy's maxed-out leverage, which involves betting against the stock while holding long Bitcoin positions.

  • Saylor aims to shift away from traditional funding methods, planning to retire billions in convertible notes and issue more preferred stocks over four years to support his Bitcoin-centric strategy.

  • Saylor's aggressive approach underscores his unwavering conviction in Bitcoin, despite the high risks associated with this unconventional financing method.

  • Michael Saylor, chairman of Strategy (formerly MicroStrategy), is pioneering a risky new financing approach by issuing Bitcoin-backed perpetual preferred stock called 'Stretch' to fund Bitcoin acquisitions.

  • This innovative 'BTC Credit Model' aims to raise up to $100 billion, or even $200 billion if demand is strong, by creating income securities supported by Bitcoin, despite its volatility and lack of cash flow.

  • Strategy is developing a flexible funding structure with 'Stretch' preferreds that pay variable dividends, do not mature, and do not grant voting rights, blending features of debt and equity.

Summary based on 2 sources


Get a daily email with more Crypto stories

More Stories