Michael Saylor Has Rebranded Strategy from a Low-Profile Software Firm to a Global Leader in the Corporate Acquisition of Bitcoin

The Financial Times' new movie, “Michael Saylor's $40BN Bitcoin Bet”, tells the story of how one man's belief in cryptocurrency transformed the whole enterprise.

The Financial Times has released a new film highlighting the story of how one man's belief in cryptocurrency transformed an entire enterprise.

In August 2020, Michael Saylor, the chairman and CEO of Strategy, began his Bitcoin journey with an initial investment of $250 million from the company's treasury reserves.

"I personally like to think of it as an investment in the future of the world, but it's certainly a large and material deployment of capital," said Saylor in the movie.

That first step quickly evolved into a broader strategy of long-term accumulation. Over the next few years, Strategy went on to spend billions of dollars buying Bitcoin, making a big bet on the future of the digital asset.

The company's valuation soared to over $100 billion in 2025 following Bitcoin's surge past $100,000.

How Strategy Buys Bitcoin at a Discount

What makes Strategy's model distinctive is the fact that it can mop up capital several times greater than the actual value of its Bitcoin holdings. The company's stock is constantly traded at premiums, sometimes reaching twice the net asset value of its crypto reserves.

This gap enables Strategy to issue new shares or bonds, raising billions of dollars to buy more bitcoin at a discount price.

In the period of November 2024-January 2025, Strategy managed to collect $12 billion in Equity and debt issuance and acquired more than 200,000 Bitcoins.

Such a cyclical process of capital raising and accumulation of Bitcoins has been dubbed by certain investors as the "infinite money glitch". It is a model that relies on market optimism, and for the time being, it's working.

Strategy's Wild Ride with Crypto Faith

The stock of Strategy has risen by almost 400% during the last year, outperforming industry behemoths such as Apple and Nvidia. Its transformation has resulted in a loyal investor base that views the company more like a proxy for Bitcoin than a tech company.

Saylor is aggressively pushing for Bitcoin on the internet and believes that its price will be at $1 million in a decade and $13 million after 2045.

In early 2025, Bitcoin hit a low of $75,000 amid a wave of economic uncertainty, which resulted in Strategy reporting an unrealized loss of $6 billion. The company also introduced financial products such as preferred stocks, some of which have to be paid in fixed monetary dividends, straining its liquidity.

As the movie implies, Strategy's success depends entirely on the future rise of Bitcoin. If that increase stalls, the audacious financial experiment conducted by the company would come crumbling down.