Written by: Billy Bambrough

Translated by: AididiaoJP

The best storyteller in the Bitcoin community has once again left everyone confused.

Michael Saylor, Executive Chairman of Strategy (formerly MicroStrategy), has seen his wealth fluctuate dramatically with the price of Bitcoin. According to the latest estimates from Forbes, his net worth is currently around 4 billion dollars. In 2020, he completely transformed this company, originally focused on enterprise software, into a Bitcoin hoarding machine, and since then, his wealth trajectory has largely followed the price of the currency.

Over the past six years, Strategy has accumulated nearly 850,000 Bitcoins, currently valued at just over 50 billion dollars. The company’s Bitcoin reserves once approached 55 billion dollars. Most of these coins were not purchased through profits from core business, but rather acquired by continuously issuing debt, stocks, and preferred shares.

Now, Saylor attributes the most critical financing deal of the past year—about 15 billion dollars—directly to artificial intelligence.

On August 6, he told host Steven Bartlett on the popular podcast "The Diary Of A CEO": "I made 15 billion dollars with AI last year."

When this statement was made, the crypto community was instantly in an uproar.

Saylor quickly added clarification: the 15 billion dollars is not personal profit, nor is it an accounting profit for the company, but funds genuinely raised from the capital markets through a series of Bitcoin-backed preferred stock products. Almost all of this money is used to continue buying Bitcoin.

He broke down the figures specifically: one preferred stock product alone raised about 10.5 billion dollars (initial IPO of about 2.5 billion dollars, followed by shelf offerings raising about 8 billion dollars), while other related products contributed an additional 4 billion dollars, amounting to around 15 billion dollars in total.

This is what truly stunned both Wall Street and the crypto community—these preferred stock products were gradually "chatted" out by Saylor and his team using ChatGPT.

Traditional financing methods have reached their limit

By early 2025, Strategy had already become one of the largest convertible bond issuers in the world. The route of convertible bonds had nearly reached its limit, and continuing to issue ordinary stocks would severely dilute shareholders. At that time, the company already held about 30 billion dollars' worth of Bitcoin, but to continue increasing its position on a large scale, it had to find an entirely new financing tool.

Saylor did not hold a brainstorming meeting with investment banks; instead, he opened ChatGPT directly.

He later recalled: "We asked AI: Can you design a security that is between common stock and traditional debt? AI said, of course, you can do this, do that, and then do this..."

ChatGPT helped him outline a structure that had never been properly implemented before—variable dividend preferred stock. The core design is: the dividend rate can be flexibly adjusted monthly (later changed to bi-monthly), with the aim of keeping the market price of this preferred stock stable around the 100-dollar par value. In this way, it does not fluctuate as violently as common stock nor does it have repayment pressure like traditional bonds, while still continuously providing the company with funds to buy Bitcoin.

Bankers and lawyers initially opposed it together: "Historically, no one has done this."

Saylor's response was very hardline: "Isn't it illegal? Not illegal. Why hasn't anyone done it? Because in the past, no one had the reason to do it."

AI not only provided the structural design but also helped the team devise responses to regulatory and legal inquiries. Ultimately, these products began to roll out in the first half of 2025.

The core products included:

• STRK (Perpetual Strike Preferred Stock): 8% fixed dividend, payable in cash or common stock, convertible to common stock, with some upside potential.
• STRC (Perpetual Stretch Preferred Stock): Variable dividend (currently adjusted to an annualized 12%), bi-monthly payment, designed to keep the price as close to 100 dollars par value as possible, focusing on stable returns.
• STRF (Perpetual Strife Preferred Stock): Non-convertible, leaning towards fixed income, with a higher priority, targeting conservative investors.

STRC is the most controversial and also the largest in scale of financing. At one point, it dropped from around par value to about 75 dollars at the end of June, but in recent weeks, it has surged, approaching the 100 dollar target price again. Saylor's team has even publicly stated that getting STRC back to the 99-100 dollar range is one of their current most important business goals.

Common stock has been halved, but the company is hoarding cash

While preferred stock financing surged, Strategy's common stock collapsed alongside Bitcoin prices. Over the past year, the market value of common stock evaporated by about 80%. The company has also started selling actual Bitcoin—recently disclosed was the sale of 1,638 coins within a week, cashing out about 104.7 million dollars, with part used to pay preferred stock dividends and part to buy back its own preferred stock.

Saylor explained this very directly: on one hand, it was "vaccinating the market," getting everyone used to the idea that Strategy would also sell coins; on the other hand, it was genuinely covering debt and dividend expenses.

Currently, the company holds about 55 billion dollars in Bitcoin and has about 4 billion dollars in cash reserves. According to management, this money is sufficient to support around two years of dividend and interest expenses without needing to frequently raise funds.

Some call it "terrifying," others praise it as "genius"

After the news broke, tech investor and host of the All In podcast, Jason Calacanis, took to X to fire shots: "Is this Saylor's terrifying confession, or is it AI's brilliant application?"

But others stood completely on the opposite side. Bill Barhydt, CEO of the Bitcoin and crypto wealth platform Abra, immediately responded: "History will prove this to be a spectacular financial engineering at the end of the US debt cycle. If you can borrow dollars and then invest it in an asset with a fixed supply and fast velocity, you should do so. Saylor, by law, cannot invest this money into securities (because he is not a company under the Investment Company Act of 1940), so Bitcoin and gold are the only options left. He will certainly make some mistakes, but this strategy itself is smart."

Saylor himself has elevated this matter to a methodological level: "Don’t learn to do things that AI can already do. What you really need to learn is how to make AI do something that no one has ever done before. To achieve spectacular success, you must find that magical opportunity."

This is not the first time he has publicly thanked ChatGPT. In May 2025, at the company developer conference, he mentioned using ChatGPT's in-depth research mode to design the company's convertible preferred stock products.

AI + Bitcoin, Saylor is writing a new playbook

From transforming the company into a Bitcoin treasury in 2020 to reinventing financing tools with AI in 2025, Saylor has once again proven: in the crypto world, the most valuable thing is not Bitcoin itself, but those who dare to use new tools to amplify Bitcoin.

15 billion dollars is not money directly spat out by AI, but a traditional entrepreneur using new tools to pry open a crack in traditional financial rules, then continuously pouring money into Bitcoin.

As for where this money will ultimately take Strategy and Bitcoin, no one dares to make a conclusion yet. But at least in the summer of 2026, Saylor once again captured everyone's attention, firmly nailing it on "what AI can help people do that has never been done before."