Saylor’s Strategy: How AI Helped Supercharge a $52B Bitcoin Bet

By Rachel Lourdesamy May 07, 2025 In AI, Bitcoin, Microstrategy
Source: Michael Saylor, Executive Chairman of Strategy at Strategy World 2025. via YouTube.
  • Michael Saylor reveals that AI powers Strategy’s decision-making, analysing data rapidly to support high-level financial and legal strategies.
  • Strategy now holds more than US$52 billion worth of Bitcoin, which is 2.6% of the total supply.
  • Strategy’s new novel preferred stocks STRK and STRF were created with the help of AI and designed to fund future Bitcoin acquisitions.

Strategy – formerly known as MicroStrategy – is leveraging artificial intelligence to take its Bitcoin investment strategy further.

At the recent Strategy World event in Florida, Strategy Executive Chairman Michael Saylor revealed that he has integrated the use of AI into the company’s financial operations, enabling the creation of new financial products and driving its Bitcoin-focused strategy.

The company now holds more than half a million coins, which is about 2.6% of Bitcoin’s total supply. These holdings are worth more than US$52 billion (AU$80 billion) today – a 200-fold increase from its original investment five years ago.

Related: Saylor Buys Again: Strategy Loads Up on Bitcoin Worth $285.8 Million

Advertisement

According to Saylor, AI has been critical in this transformation. He explained how he often tasks AI with analysing large tranches of data in a matter of minutes – something that would take his teams of experts days or weeks to complete. This enables him to make high-level decisions quickly and efficiently.

The world requires that you be smarter, faster, stronger.

Michael Saylor, Executive Chairman, Strategy

Saylor said, “It doesn’t necessarily give me the answer that I can immediately act on, but it gives me somewhere between 80%-95% of what I need and then I take that to the finance department, I take it to the legal department.”

Launching AI-driven financial instruments

Earlier this year the company launched Strategy’s Perpetual Strike Preferred Stock (STRK) and Perpetual Strife Preferred Stock (STRF), preferred stock offerings developed with the help of AI. These offerings are designed to support the company’s plan to raise capital for further Bitcoin acquisition. The company recently purchased an additional 1,895 Bitcoin with capital partly raised from the sale of STRK. 

Both stocks offer attractive yields and feature unique features such as perpetual dividends and call options.

“Those two preferred stocks, Strife and Strike, are the first AI-designed securities that I know of, certainly in our industry,” Saylor said and credited AI with helping to navigate the financial and legal red tape surrounding their creation. 

We did a convertible preferred stock; it had never been done before. We listed it on Nasdaq; it had never been done before.

Michael Saylor, Executive Chairman, Strategy

With AI now embedded in both its strategic planning and product innovation, Strategy is building a blueprint for the future of corporate finance. 

Advertisement

Related: Michael Saylor Signals More Bitcoin Buys as Strategy’s Holdings Soar

Rachel Lourdesamy
Author

Rachel Lourdesamy

Rachel is a freelance writer based in Sydney with experience within financial services, marketing, and corporate communications in the APAC region. An avid reader and a graduate of the University of Sydney, she covers topics including business, finance and human interest.

You may also like