Saylor Doubles Down: MicroStrategy Now Hunting $84B for Bitcoin—Despite $1.7B Paper Loss

Michael Saylor’s Bitcoin gambit just got bolder. MicroStrategy—now more hedge fund than software firm—has upped its capital raise target to a staggering $84 billion, doubling down while sitting on a record $1.7 billion unrealized loss. Wall Street analysts are either applauding the conviction or quietly updating their ‘how to lose friends and alienate shareholders’ playbooks.

The Leverage Playbook

Convertible debt, stock offerings, and now even whispers of collateralized Bitcoin loans—Saylor’s pulling every lever to keep accumulating. Meanwhile, BTC’s volatility has turned MicroStrategy’s balance sheet into a Rorschach test for crypto true believers.

Cynic’s Corner

Because nothing says ‘financial prudence’ like doubling your bet after the casino’s lights flicker. The CFOs of traditional corps are either sweating or taking notes—depending on how much Kool-Aid they’ve drunk.

Strategy Files to Sell Additional $21B in Shares After Exhausting Previous Offering

The Virginia-based company disclosed Thursday that it has filed to sell an additional $21 billion in common shares after depleting a previous program of the same size authorized in October.

It also doubled its debt issuance target from $21 billion to $42 billion, leaving $14.6 billion remaining under its current authorization.

The expanded programs are part of Strategy’s ongoing effort to finance Bitcoin acquisitions through equity and debt offerings.

Since launching its at-the-market equity program, the firm has sold roughly $20.9 billion in shares, with only $128 million left available for sale.

In an October statement, Strategy outlined its goal of raising $42 billion over three years through equity and fixed income instruments to increase its Bitcoin exposure beyond what traditional revenues could support.

Previously, Strategy classified its Bitcoin as intangible assets, a designation that required it to record permanent impairments when prices fell while only recognizing gains upon sale.

The new accounting approach brings more transparency but also amplifies short-term volatility in financial results.

JUST IN: Michael Saylor’s Strategy says it still has $57 billion left to raise to buy more #Bitcoin pic.twitter.com/3cgtX3vbWM

In Q1 2025, Strategy reported revenue of $111 million, a 3.6% year-over-year decline. However, subscription services revenue ROSE sharply to $37.1 million, up 61.6% from the same period last year.

Despite its roots in software, Strategy has repositioned itself as a Leveraged proxy for Bitcoin exposure under the leadership of Saylor, its outspoken founder and executive chairman.

The firm’s average purchase price for its Bitcoin holdings now stands at $68,459 per BTC as of April 28.

Public Companies Boost Bitcoin Holdings by 16% in Q1 2025

Publicly traded companies increased their Bitcoin holdings by 16.1% in the first quarter of 2025, signaling continued institutional interest in the leading cryptocurrency despite market volatility.

According to crypto asset manager Bitwise, total corporate Bitcoin holdings climbed to approximately 688,000 BTC by the end of Q1, with companies adding 95,431 BTC over the three-month period.

Bitwise reported the combined value of these holdings reached $56.7 billion, based on a Q1 closing price of $82,445 per Bitcoin—representing a 2.2% increase in value.

More recently, healthcare technology firm Semler Scientific expanded its Bitcoin holdings with a fresh $10 million purchase, signaling a continued strategic pivot toward digital assets.

The latest purchase brings the company’s total Bitcoin treasury to over 3,300 BTC, valued at approximately $300 million based on current market prices.