Written by: Billy Bambrough
Compiled by: AididiaoJP
The best storyteller in the Bitcoin space has once again left everyone speechless.
Michael Saylor, Executive Chairman of Strategy (formerly MicroStrategy), whose net worth fluctuates wildly with Bitcoin's price. According to Forbes' latest estimate, his current net worth is approximately $4 billion. In 2020, he transformed this originally enterprise software company into a Bitcoin hoarding machine, and his wealth curve has since almost perfectly followed the coin's price.
Over the past six years, Strategy has accumulated nearly 850,000 Bitcoins, with a current market value slightly over $50 billion. The company's Bitcoin reserve once approached $55 billion. These coins were largely not purchased with profits from core business operations but were acquired through continuous issuance of debt, equity, and preferred stock.
Now, Saylor attributes the most crucial fundraising round of the past year—approximately $15 billion—directly to artificial intelligence.
On August 6th, he said to host Steven Bartlett on the popular podcast *The Diary Of A CEO*: "I used AI to make $15 billion last year."
The crypto world instantly exploded.
Saylor immediately clarified: This $15 billion is not personal profit he pocketed, nor is it company book profit. It is the actual capital raised from the market through a series of Bitcoin-backed preferred stock products. This money was almost entirely used to buy more Bitcoin.
He broke down the numbers: One preferred stock product alone raised about $10.5 billion ($2.5 billion in the initial IPO, with subsequent shelf offerings selling another $8 billion), while several related products contributed a combined total of about $4 billion, adding up to roughly $15 billion.
This is the part that truly stunned both Wall Street and the crypto community—these preferred stock products were essentially "conversed" into existence by Saylor and his team, piece by piece, using ChatGPT.
The Traditional Financing Path Reached Its End
By early 2025, Strategy had become one of the world's largest issuers of convertible bonds. The convertible bond route was largely exhausted, and continuing to issue common stock would severely dilute shareholders. The company already held Bitcoin worth about $30 billion, but to continue large-scale accumulation, it needed to find a completely new financing instrument.
Saylor didn't call for another investment bank brainstorming session. He simply opened ChatGPT.
He later recalled: "We went and asked AI: Can you design a security that sits between common stock and traditional debt? AI said, of course you can, you do this, that, and the other thing..."
ChatGPT helped him outline a structure never truly implemented before—a Variable Rate Dividend Preferred Stock. The core design: the dividend rate could be flexibly adjusted monthly (later changed to bi-weekly), with the goal of keeping the preferred stock's market price consistently stable around its $100 par value. This way, it would neither fluctuate wildly like common stock nor have the repayment pressure of traditional bonds, while still continuously funneling capital to the company for buying coins.
Bankers and lawyers initially objected collectively: "No one has ever done this in history."
Saylor's response was hardcore: "Is it illegal? No. Why hasn't anyone done it? Because no one previously had a reason to do it."
AI not only provided the structural design but also helped the team devise responses to regulatory and legal challenges. Ultimately, these products launched successively in the first half of 2025.
The core products were:
- STRK (Perpetual Strike Preferred Stock): 8% fixed dividend, payable in cash or common stock, convertible to common stock, offering some upside potential.
- STRC (Perpetual Stretch Preferred Stock): Variable dividend (currently set at an annualized 12%), paid bi-weekly, designed specifically to keep the price as close to the $100 par value as possible, targeting stable income.
- STRF (Perpetual Strife Preferred Stock): Non-convertible, more fixed-income-like, higher priority, targeting conservative investors.
STRC was the most controversial and also the largest fundraising product. It fell from near par value to around $75 by late June but has rebounded strongly in recent weeks, approaching the $100 target price again. Saylor's team has even publicly stated that "getting STRC back to the $99-$100 range" is one of their most important current operational goals.
Common Stock Halved While Company Hoards Cash
While preferred stock fundraising surged ahead, Strategy's common stock crashed alongside Bitcoin's price. Over the past year, the common stock's market value evaporated by about 80%. The company also began actually selling Bitcoin—the latest public disclosure showed a sale of 1,638 coins in one week, netting about $104.7 million, used partly to pay preferred stock dividends and partly to repurchase its own preferred stock.
Saylor's explanation for this is blunt: on one hand, it's "vaccinating the market," getting people accustomed to the idea that Strategy will also sell coins; on the other hand, it's to genuinely cover debt and dividend payments.
Currently, besides Bitcoin worth approximately $55 billion, the company has amassed around $4 billion in cash reserves. According to management, this sum is sufficient to cover approximately two years of dividend and interest payments, eliminating the need for frequent fundraising.
Some Call it "Terrifying," Others Praise it as "Genius"
After the news broke, tech investor and All In podcast host Jason Calacanis fired off on X: "Is this a terrifying confession from Saylor or a brilliant use of AI?"
But others stand on the opposite side. Bill Barhydt, CEO of the Bitcoin and crypto wealth platform Abra, immediately replied: "History will show this to be an absolutely brilliant piece of financial engineering at the tail end of the US debt cycle. If you can borrow dollars and put them into a fixed-supply asset with fast adoption, you should. Saylor can't legally invest this money into securities (as he's not a company under the Investment Company Act of 1940), so that leaves Bitcoin and gold. He will certainly make mistakes, but the strategy itself is smart."
Saylor himself elevated the matter to a methodological level: "Don't learn the things AI already knows how to do. What you really need to learn is how to get AI to do something no one has ever done before. To achieve earth-shattering success, you have to find that magical opportunity."
This isn't the first time he's publicly thanked ChatGPT. In May 2025, at the company's developer conference, he mentioned using ChatGPT's deep 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 vault in 2020 to reinventing financing instruments with AI in 2025, Saylor has once again proven: in the crypto world, the most valuable thing is never Bitcoin itself, but the people daring enough to use new tools to amplify it.
$15 billion wasn't money directly spat out by AI. It was a traditional entrepreneur using a new tool to pry open a crack in traditional financial rules, then funneling money ceaselessly into Bitcoin.
As for where this money will ultimately take Strategy and Bitcoin, no one dares to conclude yet. But at least in the summer of 2026, Saylor has once again firmly fixed everyone's attention on "what AI can help people do that has never been done before."
