AI Engineers Saylor's Bitcoin Billions
Strategy founder transformed chatbot experiments into unprecedented financial products that already raised $180 million last week
Wall Street's most aggressive Bitcoin accumulator just revealed his secret weapon: AI is researching his investments and designing the securities funding them.
During Strategy's annual conference yesterday, Saylor said that the company's novel preferred stock offerings — the financial instruments powering its massive Bitcoin accumulation — were designed with the help of AI.
"Those two preferred stocks, Strife and Strike, are the first AI-designed securities that I know of, certainly in our industry. We did a convertible preferred stock; it had never been done before. We listed it on Nasdaq; it had never been done before," Saylor explained during a conversation with CEO Phong Le.
Strategy's Perpetual Strike Preferred Stock (STRK) and Perpetual Strife Preferred Stock (STRF) were launched early this year specifically to fund Bitcoin purchases. STRK offers a hefty 13% dividend payable in cash or MSTR stock and is convertible into common stock, while STRF offers 10% yield with a focus on stability for fixed-income investors.
The results speak volumes.
Saylor described leveraging artificial intelligence not for simple automation, but for sophisticated financial modeling and navigating complex legal territory.
"I would put this chat in deep research mode and I would grind it, and it would grind through 50 sources and work for 15 minutes and come back, it doesn't necessarily give me the answer that I can immediately act on, but it gives me somewhere between 80% and 95% of what I need," Saylor said.
This approach to financial innovation has delivered notable results. Strategy's stock has outperformed every company in the S&P 500 — even surpassing Nvidia during the same period, despite the AI chip maker's meteoric rise.
Strategy isn't just using AI to buy Bitcoin — it's now creating products with it. CEO Phong Le unveiled "Mosaic," which he described as "the first-ever within Strategy GenAI-created product," designed to revolutionise corporate data analytics.
Le framed Mosaic through a distinctly crypto-centric lens, positioning it as doing for data what Bitcoin does for capital — freeing it from middlemen and returning control to creators.
"What you own should be yours. It's your data. Don't give (AI companies) the rights to then go train an AI with your data. And if you want them to do so, sell your data — in fact that's a great way to make money," said Le.
This data sovereignty approach aligns with crypto's ethos of decentralisation and challenges the monopolistic data practices of tech giants.
Strategy has continued to attract bullish ratings from Wall Street analysts, despite recording a $5.9 billion loss on its Bitcoin holdings in Q1 2025. Both Benchmark and Bernstein reiterated their "buy" recommendations this week, highlighting the company's aggressive accumulation strategy.
The momentum remains in full force, with an additional 1,895 Bitcoin purchased between April 28 and May 4 for approximately $180 million, funded through sales of both common and preferred stock.
While most companies are using AI to optimise existing business models, Strategy is deploying it to reinvent financial structures entirely.
"The explosion of productivity with digital property and digital intelligence and digital labor will create an explosion in demand for digital capital," Saylor argued, sketching a vision where AI naturally complements Bitcoin.
"Consensus thinking won't result in success in a world of 400 million competitive companies," he said.
If AI can design better securities than traditional financial engineers, what other aspects of our financial system might be reimagined through artificial intelligence?
The bold experiment continues, with Strategy raising capital, buying Bitcoin, and now deploying AI across its operations.