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July 1, 2025

Saylor’s Strategy Resumes Using Common Shares to Buy Bitcoin

June 30, 2025 at 01:58 PM
3 min read
Saylor’s Strategy Resumes Using Common Shares to Buy Bitcoin

It seems Michael Saylor and MicroStrategy are, once again, embracing their unique playbook: leveraging the company’s common shares to fuel its insatiable appetite for Bitcoin. This latest move is particularly noteworthy as it comes on the heels of pointed criticism from veteran short-seller Jim Chanos, who has publicly questioned the very foundation of Saylor's audacious strategy.

For months, the market had watched as MicroStrategy, under Saylor's visionary yet often polarizing leadership, accumulated a vast treasury of Bitcoin. While much of that acquisition was initially financed through various debt offerings – a strategy that itself drew considerable attention – the firm has historically tapped into its equity base as well. Chanos, a renowned figure in the financial world known for his sharp analytical insights into companies he believes are fundamentally flawed, recently put MicroStrategy squarely in his crosshairs. He effectively characterized the company as a highly leveraged play on Bitcoin, arguing that its primary business of software analytics had become secondary to its digital asset holdings.

The core of Chanos's critique wasn’t just about the volatility of Bitcoin itself, but the method of financing its acquisition. Issuing new common shares to buy a volatile asset like Bitcoin, in his view, creates a potentially precarious financial structure. It dilutes existing shareholders while exposing them to the wild swings of the crypto market, all bundled within a publicly traded software company.


Yet, Saylor, a self-proclaimed Bitcoin maximalist, clearly remains unfazed. His conviction in Bitcoin as the ultimate store of value and the future of digital finance appears unshakable. For him, MicroStrategy isn't just a software firm; it's transforming into a de facto corporate treasury vehicle, designed to hold and accrue as much Bitcoin as possible. From his perspective, using common shares to acquire more of what he believes is the world’s most significant digital asset isn’t a risk, but a strategic imperative to maximize long-term shareholder value – albeit through an unconventional lens.

The mechanism itself is fairly standard for public companies looking to raise capital: an "at-the-market," or ATM, offering. This allows MicroStrategy to sell newly issued shares directly into the open market, typically through an investment bank acting as an agent, without the need for a large, one-off public offering. While this provides flexibility and allows the company to raise capital incrementally based on market conditions, it does inherently lead to shareholder dilution. Each new share issued represents a smaller piece of the overall company for existing investors.


What’s truly fascinating here is the sheer resilience of Saylor’s vision in the face of such high-profile skepticism. It underscores the deep philosophical divide in the financial world between traditional value investing and the burgeoning, often disruptive, digital asset economy. For critics, MicroStrategy represents a dangerous experiment in financial engineering; for proponents, it's a bold, forward-thinking strategy that offers a unique pure-play exposure to Bitcoin within a traditional equity framework.

As MicroStrategy resumes this particular aspect of its Bitcoin acquisition strategy, all eyes will be on how the market reacts and, perhaps more importantly, how Bitcoin itself performs. Saylor has consistently shown a willingness to march to the beat of his own drum, and this latest move simply reinforces that conviction. It’s a compelling narrative, to be sure, and one that continues to push the boundaries of corporate treasury management in the digital age.

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