michaelsaylor

Michael Saylor: I used AI to make $15 billion last year.
Steven Bartlett: You did?
Michael Saylor: I did. Because the AI gave us a solution to the problem that no one had ever encountered before in the history of the world. And so my advice is: don’t try to outwork the robots. What you want to do is ask the AI to do something that’s never been done before. And if you want to create these incredible success things, you want to locate the magic opportunity. I know this because I’m a technology entrepreneur, and we’re the biggest buyer of Bitcoin in the world. So what is my mission? I’m preaching the gospel of digital empowerment and Bitcoin as digital money. And it’s going to be the best long-term capital asset. And you can actually own something and someone more powerful than you can’t take it away from you.
Steven: What do you mean they can’t take Bitcoin from you?
Michael: So this is a stack of currency. You walk through an airport on this, they ask you if you have cash. They just take it. So cash in a physical form is a problem. So what do you do? You put it in the bank. So the bank then decides whether you get to keep it and whether you get it back. But I could move a million dollars of Bitcoin from here to anywhere, to London, to anywhere in cyberspace in a few seconds. So the last thing in the world you want to save is money.
Steven: So what about this? Why not just put all of my money into gold?
Michael: Well, gold is up 12% a year, but Bitcoin is up 33.
Steven: What about the S&P 500?
Michael: You’re going to get double the performance from BTC that you would get from like the S&P index.
Steven: So should I buy a house?
Michael: I will tell you why you shouldn’t buy a house.
[Brief discussion of selling some Bitcoin recently after advising people to “sell a kidney if you must but keep the Bitcoin,” plus preview of wealth-building strategies and 10 rules for young adults. Host plug for subscribing.]
Background & Core Message on Bitcoin
Steven: Michael, because of your success as a technology entrepreneur, you are a multi-billionaire from my math and you’re heavily focused on digital currencies at the moment, specifically Bitcoin. What else do we need to know about you in terms of what you’ve built and accomplished outside of that?
Michael: I always wanted to make a technical contribution. So the early business was business intelligence—how do you extract intelligence from large raw data sources—and that was what MicroStrategy did. We created a global business intelligence company. And I think in 2020, when the COVID lockdowns took place and the world turned upside down, that was when I discovered my greatest idea, and it wasn’t even my idea, right? It was Satoshi’s idea. But I discovered Bitcoin in 2020 and the company today is $60 billion, but we peaked about $125 billion. So we got somewhere between 100 and 200 times bigger since we discovered Bitcoin.
Steven: And when you speak to the general public now… what is the essence of the message that you’re aiming to communicate to them?
Michael: Bitcoin is digital empowerment, digital capital. We’re living through the digital transformation of assets, and this is just as profound a transformation as digital intelligence. The real profound breakthrough of Bitcoin is this idea that you can take economic energy, convert it to digital form, and tightly bind it to the person, the family, the company, or the country. … If what you’re interested in is empowerment and fairness and equity for the small company, the small family, the small person, the small country, the weak—how do you do it? Well, you basically encrypt the money, put it in cyberspace, protect it with a private key. So like now you can actually own something and someone more powerful than you can’t take it away from you.
On Money Debasement, Houses, Stocks, Gold
Michael (on why cash/savings lose value): One acre of land in Miami Beach on the water cost about $10,000 a hundred years ago… Today that same acre is $10–20 million. … The dollar lost about 7% of its economic value every year for 100 years running. … The best currency… lost 7% of its value every year… That’s the best it’s ever going to get. … The average fiat currency collapses in about 29 years.
On houses: There’s a 2% property tax on houses in Florida, which means… every 36 years you actually pay the cost of the house in tax to the government. Not a very good store of value… You’re taking on a massive tax load and a maintenance load. Commercial real estate can be better because rents can offset costs while the underlying asset appreciates ~7%/year. But residential ownership with high mortgage rates, taxes, and insurance can crush you. Bitcoin is compelling because the average person shouldn’t have to become a real-estate or tax expert.
On S&P 500: It’s returned ~15% over the past 6 years (longer-term closer to 10%). Better than pure cash, but Bitcoin has done roughly double that recently.
On gold: Up ~12% a year recently (vs. S&P ~15%, Nasdaq ~18%, Bitcoin ~33%). Gold, S&P, and Bitcoin are all capital assets (scarce things robots/AI/factories cannot produce infinite amounts of). Avoid non-capital assets (soybeans, oil, cotton, etc.). Choice of capital asset depends on location and situation—Bitcoin is especially useful in war zones or places with capital controls because it is portable and hard to seize.
AI, Robots, Age of Abundance
Michael: Technology fails until it succeeds. … In 2023 the AI started working. We’ve affected the digital transformation of intelligence. Cars are going to drive themselves. Anything that takes massive human labor… the AIs will think for us. Put the AI into the robot… We’ll get to the point of perfect products. …
On Elon Musk’s “age of abundance” comments (money becomes less relevant): He’s half right. Consumer/utilitarian goods will become abundant. But there will always be scarce desirable goods (Hamptons house, private jet, yacht, high-end experiences, status goods). Money and wealth will still matter because humans are aspirational and status-oriented. Hierarchy of wants persists even after basic needs are met.
On job displacement: There will be dislocation and political unrest, but also new jobs (podcaster didn’t exist 20 years ago; Instagram creators, etc.). Free-market societies that allow new businesses to form will handle the transition better by creating opportunities for displaced people.
[Sponsor segments for Cometeer coffee and Pipedrive CRM.]
How AI Helped Generate ~$15 Billion
Michael: I used AI to make $15 billion last year. … Let’s go back to me in 2025. We have a company that has… $30 billion of Bitcoin. We want to raise capital to buy more Bitcoin. We maxed out the equity markets. We became the largest issuer of convertible bonds in the world and we maxed out the convertible bond market. …
We needed to invent a new type of security / credit instrument. … We used AI to design a convertible preferred stock called STRK. When we did it, no one had ever created a preferred stock that was backed by Bitcoin before. … Lawyers and bankers said “no one’s ever done it before… we don’t think you should do that.” We said everything else is maxed out—we have to do something never done before using digital capital + digital intelligence + digital treasury.
We created instruments with features like variable dividend rates (to keep the price stable around par, short-duration credit-like). No one had created a variable-dividend preferred stock before. We asked the AI (ChatGPT / OpenAI): Can we do it? “Of course you can… just do this, this, and this.” We iterated past the objections.
Result: Brought the IPO to market (~$2.5 billion, biggest of the year at the time), then shelf registration and more sales totaling roughly $10.5B of one instrument + $4B of others → ~$15 billion of credit raised, equating to significant value creation for the company.
Key advice: Don’t try to outwork the robots. Ask the AI to do something that’s never been done before. Locate the “magic opportunity.” You have to govern the state space / constraints of your situation. The people who get ahead will be those who know what questions to ask AI.
Later Sections (summarized from available portions + chapter markers)
• Real moat in an AI-driven world: Long-term thinking, hard/scarce things, asking novel questions of AI rather than competing on tasks AI can already do.
• Standing out with AI-generated content: Focus on unique insight, taste, and originality that AI amplifies rather than replaces.
• Bitcoin accumulation strategy, who shouldn’t invest in Bitcoin, one contrarian belief, and 10 rules/advice for young adults entering adulthood (building strong foundations, long-term capital allocation, etc.).
• Discussion of the recent partial Bitcoin sale: Done to break a market narrative that Strategy could never sell any Bitcoin (or Bitcoin/stock would go to zero), demonstrating liquidity and ability to meet obligations without systemic risk. Company still holds ~847,000 BTC (largest corporate holder after Satoshi’s inactive holdings).
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