Michael Saylor Outlines Strategy’s Bear Market Playbook at Bitcoin Vegas

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By James Van Straten|Edited by Parikshit Mishra

May 30, 2025, 8:49 a.m.

Strategy Executive Chairman Michael Saylor at the Digital Asset Summit in New York City on March 20, 2025. (Nikhilesh De)
  • If mNAV falls below 1, Strategy would sell preferred instruments (STRK, STRF) and repurchase common shares to restore value and confidence.
  • Operational flexibility through leverage, recapitalization tools, and ATMs across multiple markets is central to the company’s resilience.

Disclaimer: The analyst who wrote this piece owns shares of Strategy (MSTR)

At the Bitcoin conference in Las Vegas, Strategy (MSTR) Executive Chairman Michael Saylor was asked how the company would respond if its multiple to net asset value (mNAV) fell below 1, as it did during the previous bear market.

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In response, Saylor drew an analogy to the Grayscale Bitcoin Trust (GBTC), stating, “GBTC is a closed-end trust… a corporate entity that has no operational flexibility to manage its capital structure.”

He emphasized that unlike GBTC, Strategy is an operating business with the ability to take on debt and manage its capital dynamically. Saylor argued that “for any company to fall down to below 1 mNAV, the shareholders have lost faith in the management structure of the business.”

If Strategy’s stock “went to $1 tomorrow,” he said, the company would respond by selling its preferred stock or fixed income instruments STRK and STRF and use the proceeds to repurchase common stock, thereby recapitalizing the company.

Highlighting the importance of flexibility, Saylor stated, “To create value, you need to create option value to generate as much optionality as possible. The more options, the greater the value.”

He concluded by asserting, “The thing that makes our company a monster is having multiple at-the-market offerings (ATMs) in multiple capital markets,” underscoring Strategy’s multi-channel access to liquidity and financial resilience.

James Van Straten is a Senior Analyst at CoinDesk, specializing in Bitcoin and its interplay with the macroeconomic environment. Previously, James worked as a Research Analyst at Saidler & Co., a Swiss hedge fund, where he developed expertise in on-chain analytics. His work focuses on monitoring flows to analyze Bitcoin’s role within the broader financial system.

In addition to his professional endeavors, James serves as an advisor to Coinsilium, a UK publicly traded company, where he provides guidance on their Bitcoin treasury strategy. He also holds investments in Bitcoin and Strategy (MSTR).

James Van Straten

 

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