Michael Saylor’s Strategy to raise $2B in convertible debt to expand Bitcoin holdings

Michael Saylor’s Strategy is going all in—again. The company announced on Tuesday that it is raising $2 billion in 0% convertible senior notes to buy more Bitcoin, betting even bigger on the long-term value of its holdings.

The debt offering, open only to qualified institutional buyers, includes an option to raise an extra $300 million if demand is high. The notes mature in 2030, won’t pay interest, and won’t increase in value over time, according to Strategy’s announcement. Investors can convert them into cash or shares of Strategy’s stock, depending on what the company decides.

The notes are redeemable starting in 2027, but only if Strategy’s stock price surpasses 130% of the conversion price for a set period. If that happens, Strategy can buy back the notes at face value plus any special interest owed, per the announcement.

If Strategy faces a fundamental change, such as a major acquisition or restructuring, investors can demand repayment on March 1, 2028. The conversion rate and final terms will be determined at pricing, based on Strategy’s stock performance on the day the deal is finalized.

Bitcoin acquisition and debt strategy

Strategy has been using debt to buy Bitcoin for years, and this latest one actually follows a pattern: raise cash, buy Bitcoin, and wait for the price to rise. The company plans to use the $2 billion for general corporate expenses, but its real focus is accumulating more Bitcoin.

In 2024, Strategy bought 258,320 BTC for $22.07 billion, paying an average of $85,447 per Bitcoin, including fees. The company didn’t sell a single Bitcoin, despite price fluctuations.

As of December 31, 2024, Strategy held 447,470 BTC, valued at $23.9 billion. But its outstanding debt hit $7.27 billion, with $35.1 million in annual interest costs.

The company posted a net loss for 2024, mostly due to $1.79 billion in Bitcoin impairment losses. If Bitcoin’s market price crashes, Strategy’s ability to meet financial obligations could be at risk. The company warned in a 10-K SEC filing that it “may not be able to regain profitability” if Bitcoin’s fair value continues to drop.

Strategy has been dealing with old accounting rules that force companies to write down Bitcoin losses, but never adjust gains unless sold. That changes in January 2025 with new FASB fair-value accounting rules. Gains and losses will now be recorded in net income each quarter, creating massive fluctuations in reported profits.

The new rules will immediately apply a $12.75 billion adjustment to Strategy’s retained earnings. But there’s a catch: tax liabilities could surge. The company warned that unrealized Bitcoin gains might trigger the 15% Corporate Alternative Minimum Tax (CAMT) under the Inflation Reduction Act of 2022.

“If we become subject to the CAMT, it could result in a material tax obligation that we would need to satisfy in cash,” Strategy said. The tax applies to companies with over $1 billion in annual adjusted financial income, and unless the law is amended, Strategy could owe huge taxes by 2026.

The company also faces tax risks across multiple jurisdictions, with uncertainty around deferred tax assets and liabilities, as selling Bitcoin at higher prices than its cost basis will likely trigger some serious capital gains taxes.

Strategy’s debt offering is private—only qualified institutional buyers under Rule 144A can participate. The notes won’t be registered with the SEC and can’t be publicly sold without an exemption. Investors interested in the deal must attend a live webinar on February 19, 2025, where the company will go over terms, risks, and expectations.

“Access to the Video Webinar and completion of the investor survey does not mean you will receive an allocation in this proposed convertible notes offering,” Strategy clarified today.

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