Michael Saylor, founder and executive chairman of Strategy, said in a recent interview with The Diary Of A CEO that AI helped the company design a new Bitcoin-backed financing instrument after traditional capital-raising channels had reached their limits. He said that process eventually led to $15 billion in credit assets sold through STRK and other tools.
The interview moved well beyond financing. Saylor also laid out his views on fiat currency debasement, housing, gold, equity indexes, career choices in the AI era, long-term company building, and the rationale behind Strategy’s recent sale of a small amount of Bitcoin.
How Saylor says AI helped create a new funding path
Asked whether reports were true that he had used AI to raise $15 billion last year, Saylor said they were. In his telling, AI helped Strategy address a problem he described as one no one in history had faced before. His message to young people was direct: do not try to outwork robots on volume; use AI to do something that had not been done before.
Saylor said the process started in early 2025. At the time, Strategy held tens of billions of dollars worth of Bitcoin and wanted to raise more capital to buy more BTC. The company had already pushed through the usual channels. He said it had reached the limit of what it could raise in the equity market, had become the world’s largest issuer of convertible bonds, and had also run into constraints there. Without a new kind of security or credit instrument, growth would stall.
That pushed him toward AI. Saylor said he began working on the concept of a Bitcoin-backed preferred stock. He described preferred stock as a hybrid instrument with wide flexibility in its terms: it can be structured with put features to resemble debt, or conversion features to resemble equity.
When lawyers and bankers on Wall Street were asked about the idea, he said the response was almost always the same: no one had done it before, other people do not do it, and therefore Strategy should not do it either. Saylor said the company had to move outside those boundaries if it wanted to keep expanding.
The aim, he said, was to build a short-duration credit instrument that could trade around its $100 par value rather than swing with interest rates and market conditions, something closer to a money-market style product that still offered yield. In his view, the only way to hold that price stability was to adjust the dividend rate every month.
Saylor said no one in history had created a preferred stock with a variable dividend rate. It was not illegal, he said; it simply had not been conceived or needed before. Strategy then asked ChatGPT whether the structure could work. According to Saylor, the answer was yes, and the AI produced a detailed framework for terms and design.
That work went to market as STRK. Saylor said Strategy completed a $250 million IPO, which he called the biggest IPO of the year, then followed with another $8 billion in additional issuance. Together with other instruments, he said, the company sold $15 billion of credit assets.
Why he thinks AI tools are now basic equipment
The host brought up another point from the discussion: only 2% of households currently have a ChatGPT or AI subscription. Did that leave room for broad business arbitrage by ordinary people?
Saylor’s answer was that anyone serious about creating value needs to become fluent with one or more AI tools. He put them in the same category as computers, reading and writing: foundational instruments rather than optional extras. From there, he said, the real work is pairing AI with domain-specific knowledge to rebuild existing products and services or create new ones.
His case against fiat as a long-term store of wealth
When the conversation turned to his broader mission, Saylor said he is trying to explain digital empowerment and Bitcoin to the world. He called Bitcoin a digital currency and, over the long run, the best capital asset. What makes it different, in his view, is that an individual can actually own it, and no force stronger than the owner can take it away.
He contrasted that with fiat cash and the banking system. In his framing, fiat is permissioned money. He said that if someone tries to carry a stack of U.S. dollars through airport security and authorities discover it, the cash can be seized. If the same money is deposited in a bank for safekeeping, the bank as counterparty determines whether it can be kept or withdrawn. A large cash withdrawal in a short period can trigger a report to the Treasury and further scrutiny.
Cross-border transfers are also part of his argument. Saylor said sending money from one country to another may require approvals through the sender’s bank, the recipient’s bank, the two countries’ central banks, and intermediary correspondent banks, adding up to seven different institutions.
From 1926 Miami Beach land to a 7% annual erosion in purchasing power
Saylor said inflation and currency debasement remain invisible to most people. He used Miami Beach to make the point. Around 100 years ago, in 1926, one acre of waterfront land there sold for $10,000, he said. He added that he owns a house in the area and still has the old deed: two acres cost $20,000, and the whole house cost $100,000.
Today, he said, the same acre on Miami Beach is worth $10 million or even $20 million. On that basis, he argued that the dollar price had risen 1,000-fold over a century. His conclusion was that the U.S. dollar, which he described as the strongest and best fiat currency in the world, has still been losing purchasing power at roughly 7% a year.
At that rate, he said, wealth is cut roughly in half every decade, and that is the best-case version of fiat. In developing countries, he said, annual debasement can run as high as 14%, with full collapse over roughly 30 years. He named Brazil, Argentina and Mexico as examples of severe inflation. His broader claim was blunt: holding wealth in cash or bank deposits can amount to losing accumulated savings over a 10- to 30-year horizon.
Housing, gold, the S&P 500 and Bitcoin
The host then asked about the traditional path many people are taught to follow: get a degree, work a stable job, save money and buy a house. Saylor said home ownership is only a plausible wealth strategy in a small number of areas with very low property taxes and sound management. In most places, he said, homeowners face mortgage rates as high as 7% plus heavy taxes and insurance costs.
He used Florida as an example, citing a 2% property tax rate. That means, he said, that over 36 years a homeowner effectively repays the full cost of the house to the government in taxes alone. Maintenance expenses add more pressure. For that reason, he does not see residential housing as a strong store of value.
Commercial real estate, in his view, is somewhat better because taxes, insurance and maintenance can be passed through in rents. Even if the rent itself does not produce much profit, the underlying land may still appreciate at 7% annually. Still, he said, that is too complicated for most people. He questioned why ordinary households should be forced to become experts in real estate, tax management or stock picking.
On gold and U.S. equity benchmarks, Saylor offered a set of return comparisons. Over the past six years, he said, gold has returned about 12% annually, the S&P 500 about 15%, the Nasdaq about 18%, and Bitcoin 33%.
He did not dismiss gold or the S&P 500 outright. The S&P 500, he said, accessed through ETFs such as SPY, has delivered about 10% annualized over the past 100 years, enough to offset 7% annual debasement in the dollar and still leave 2% to 3% of extra gain. The issue, in his view, is access. These are privilege assets of the Western world. Someone living in Turkey, Argentina, Brazil or Africa may not be able to buy the S&P 500, QQQ or high-quality U.S. real estate with ease.
That is where Bitcoin stands apart for him. He called it the world’s only universal capital asset. He also argued against putting family wealth into non-capital assets such as soybeans, crude oil or cotton because robots and AI can produce those in unlimited quantities. Capital should be directed, he said, toward scarce assets that AI, robots and factories cannot infinitely replicate: an ounce of gold, equity in the world’s best 500 companies, and Bitcoin’s fixed supply of 21 million coins.
His response to the idea that abundance makes money irrelevant
The host brought up Elon Musk’s view of a future age of abundance, where AI and robots satisfy all material needs, work becomes optional, and money loses importance as a database for allocating labor.
Saylor said Musk was only half right. He agreed that consumer goods, consumables and functional goods such as clean water, electricity, basic healthcare, free entertainment and food will become extremely cheap and abundant as technology advances.
What will not become cheap or abundant, he said, are scarce assets people compete to own. Technology may help everyone afford water, chocolate and ice cream, but it cannot give everyone a Hampton mansion, a private jet or a superyacht. Human beings, in his telling, remain status-driven and will continue to seek exclusivity and rank.
He used a restaurant analogy. Water may be free, but a customer with more money buys a $5 Coke, then vodka or premium tequila, and eventually a $38 specialty cocktail. If the state gave everyone a basic home, someone would still want one twice as large. If everyone went skiing, people would still compete for the best mountain with the fewest crowds. So in his view, money does not disappear because the desire for scarce, exclusive resources does not disappear.
The S-curve argument and what young people should study
Asked what an 18-year-old should study, Saylor centered his answer on the S-curve in the history of science. A technology can remain stagnant for centuries or longer, he said, as flight did before 1903. Once it crosses a threshold, growth turns explosive. Within a little more than 60 years, humanity moved from planes flying 20 miles per hour to manned rockets landing on the moon.
But every S-curve matures. Saylor pointed to the mid-1970s, when the Boeing 737 and 747 had already been designed and aviation was nearing the limits imposed by physics and propulsion. Fifty years later, he said, planes are only about 15% more efficient than they were in 1975.
He called it a major mistake to begin learning a field only after its S-curve is already flattening and marginal gains are shrinking. Once a technology enters stagnation, he said, there may be no meaningful breakthrough for another 100 years. He put smartphones in that category, arguing that since the iPhone 6 or 7 there has been no real qualitative shift in form, thickness or battery technology. His recommendation was to study digital intelligence and digital assets.
When the host asked about conventional professions such as doctors, lawyers and accountants, Saylor’s answer was unusually sharp: do not become a surgeon, do not become a lawyer, do not become an accountant, and do not become a driver. In his view, those jobs are fundamentally exposed to AI substitution.
People should not focus on skills AI can already perform, he said. They should learn how to ask AI edge-case questions that no one in civilization has answered before. For creators and workers more broadly, the only durable moat is to pursue things that are extremely hard and scarce. His example was using AI to translate and distribute content accurately across 100 languages.
He added that every period of technological expansion produces a group of people who push a new tool to its limit in the first decade after it becomes viable. He cited Beethoven in relation to the piano and Mark Zuckerberg in relation to the internet. The task, as he sees it, is to identify the exact moment a technology becomes commercially viable and then go all in on that zero-to-one opening.
Long-term company building and the Amazon example
The host also asked whether long-term thinking still offers an edge at a time when younger workers often feel pressure to get rich quickly or change careers repeatedly. Saylor said it does.
He pointed to Elon Musk again, saying Musk’s businesses stack on one another. Solve rocket launch economics and low-cost access to orbit, and that creates an advantage for launching Starlink satellites. Starlink then serves global internet demand, while battery systems and supercharging infrastructure support Tesla.
He then used the nautilus, which grows along a Fibonacci spiral, as a model for durable expansion under pressure. The healthiest growth strategy, he said, is to extend naturally from a stable existing base. When a second business has nothing to do with the first and is linked only by ownership, the structure is unstable, like building a tower in sand.
Saylor said the world’s great enterprises, naming Standard Oil, Ford, Boeing and Microsoft, were all built on top of existing customers, distribution networks or financial assets.
For a modern case, he turned to Amazon Prime. Amazon, he said, absorbed years of criticism about losing money while spending a full decade building a free and fast logistics distribution system. Once that moat was in place, a simple price increase notice of $10 more per month created $12 billion in annual net cash flow and unlocked $250 billion of market value.
His 10 principles for young people
Later in the interview, Saylor explained the backstory behind a list he has shared as guidance for younger people. He said it originated at a cocktail event on a billionaire’s yacht on the French Riviera. Another billionaire, who had just welcomed twins, asked friends for advice he could give the children on their 21st birthday. Saylor sat down and condensed his thoughts into 10 principles.
- Focus the mind: do not chase every good idea when you are young, because that dilutes and destroys your core advantage.
- Value time: time is the most precious non-renewable asset.
- Train the mind: study fundamentals, read widely, and build a deep and varied base of knowledge and culture.
- Train the body: a weak body will not hold up in harsh competition.
- Think independently: people, media and machines all try to shape what you believe, so clear judgment matters.
- Choose friends carefully: you become like the people around you, so stay close to talented, positive and inspiring people and avoid the opposite.
- Choose your environment carefully: build a bright, happy place to live and work rather than letting yourself sink into dark and oppressive surroundings.
- Keep your word: one breach of trust can be lasting, and resources flow toward people whose reliability is absolute.
- Stay optimistic and constructive: however bad things get, optimism matters because people want to work with constructive people.
- Change the world: wake up with a mission to reshape it. Saylor cited Satoshi Nakamoto and Bitcoin as an example of giving 8 billion people genuine economic sovereignty and a perfect digital asset.
Why Strategy sold a small amount of Bitcoin
One of the sharpest questions in the interview dealt with Saylor’s own recent actions. He had previously urged people to hold on to Bitcoin at all costs, but Strategy had recently sold part of its BTC holdings. Why?
Saylor said the first point to clarify is scale. In all of human history, he said, no person or entity other than the inactive Satoshi Nakamoto, who he said holds more than 1 million BTC, owns more Bitcoin than Strategy. He put the company’s holdings at 847,000 BTC.
He said the sale a few weeks earlier involved only a very small amount and was intended to break what he called a dangerous and near-delusional negative narrative in the market. According to that narrative, because Strategy held as much as 4% of global Bitcoin supply, it was so deeply tied to the system that it could never sell. Short sellers and skeptics, he said, argued that if Strategy sold even a single coin, both Bitcoin and Strategy stock would fall straight to zero.
From there, he said, they built the claim that Strategy’s $55 billion Bitcoin position was worthless, that the company would be unable to pay dividends on its preferred stock, and that debt, credit and equity would all enter a death spiral.
The host described that situation as a kind of credit blackmail. Saylor agreed and said the best response to someone insisting you cannot do a backflip is to do one right in front of them.
His market argument was that Bitcoin trades more than $20 billion a day, so selling a tiny fraction of a $55 billion position would not move the market in any meaningful way. Strategy therefore sold enough BTC to cover preferred dividends when Bitcoin was around $59,000 to $60,000. The result, he said, was that the price of Bitcoin rose rather than fell, and the narrative broke apart.
Saylor said that proved an important point to the market and to credit investors: Strategy’s break-even threshold is about 3.2% annual appreciation. If Bitcoin rises by more than 3.2% a year, the company can fund dividends permanently by selling very small amounts of BTC rather than issuing more common equity and diluting shareholders. He said that improved the trading profile of both Strategy’s equity and debt and protected shareholders and credit investors. Selling Bitcoin, he added, is not the company’s primary strategy; it was a way to commercialize the mechanics of the digital credit market.
His long-range Bitcoin outlook and advice for small investors
Asked where Bitcoin ultimately goes from here and what a 25-year-old with only a few hundred dollars to invest should do, Saylor gave a clear forecast. He said Bitcoin would appreciate about 30% a year for the next 20 years, then slow to 20% a year after that. In his view, that would amount to 1.5x to 2x the performance of the S&P 500.
For individuals with limited spare cash, he said the first recurring expense should be a $20 monthly subscription to the best AI service available, because that equips the mind. Beyond that, he said, excess long-term capital should be directed firmly into digital capital, meaning Bitcoin.
The two things he says mattered most after college
At the close of the interview, the host asked Saylor an anonymous question from a previous guest: what is one thing he deeply believes that he has rarely discussed publicly and that 99% of the world may not believe?
Saylor answered by naming two areas of study that shaped him most in adulthood.
The first was practical applied statistics, especially the works of Nassim Nicholas Taleb, including Fooled by Randomness, Skin in the Game and The Black Swan. Those books, he said, taught him how to distinguish meaningful data from misleading noise. In his view, that remains a category of judgment AI cannot replace.
The second was reading Will Durant’s The Story of Civilization in full. Saylor said the versions of history taught in school are often fragmented and compressed. Reading the full 14,000 pages as a mature adult, across art, culture, politics, war and technology, creates a very different level of respect for civilization.
One lesson from that reading, he said, is that many ideas modern people treat as profound or new had already appeared and been repeated hundreds of times in earlier eras, including in 15th-century Russia or older civilizations. On money, he said many people treat Nixon’s abandonment of the gold standard in 1971 as the start of debasement, but history points to a broader pattern: every country and every fiat currency eventually trends toward endless devaluation and self-destruction.
For Saylor, relearning history and mathematics as an adult strips away youthful arrogance. It reminds people that they are not the first to face these problems, and that earlier generations have already left behind ways through them.