convertible preferred stock

Michael Saylor runs the company that owns 847,000 Bitcoin, roughly 4% of everything that will ever exist, and he sat down with Steven Bartlett on The Diary of a CEO for a conversation that is far broader than the thumbnail suggests. Yes, he defends Bitcoin. He also explains why he recently sold some of it after years of telling people to sell a kidney first, walks through how he used ChatGPT to invent a security that had never existed and raised $15 billion with it, argues that buying a house is a worse store of value than most people think, disagrees with Elon Musk about whether money survives the age of abundance, and closes by recommending eleven volumes of history and a stack of Nassim Taleb.

TLDW

Saylor’s core claim is that currency is not a store of value and never has been: the US dollar has lost roughly 7% of its purchasing power per year for a century measured against scarce desirable property, the average fiat currency collapses in about 29 years, and anyone parking savings in a money market is losing five or six points of real wealth annually. His answer is to own capital assets that robots, factories and AI cannot produce infinitely, which he ranks by six-year returns as gold at 12%, the S&P 500 at 15%, the NASDAQ at 18% and Bitcoin at 33%. He explains why Florida property tax makes residential real estate a leaky vessel, why commercial real estate works only if you can pass costs to tenants, and why Bitcoin is the one option available to someone in Turkey, Argentina or a war zone. The AI half of the conversation is arguably more surprising: he used ChatGPT to design STRK, the first variable-dividend-rate convertible preferred stock in history, brought it to market as a $2.5 billion IPO, sold another $8 billion off the shelf, and describes the whole exercise as making $15 billion with a tool that costs $20 a month. From there he covers the S-curve theory of what to study, why you should never try to outwork the robots, the slop tsunami hitting content creators and what is left of a moat, why dilutive expansion kills more good businesses than competition does, and his ten rules originally written for a billionaire’s newborn twins. The back half is the substantive part: a detailed account of the reflexive doom loop that short sellers built around Strategy, why selling Bitcoin at around $59,000 was the only way to break it, the 3.2% appreciation rate at which the company can fund its dividends forever, and his forecast of roughly 30% annual Bitcoin appreciation for twenty years. He ends on applied statistics and Will Durant.

Thoughts

The strongest thing in the first half is not the Bitcoin advocacy, it is the reframing of what a savings account actually is. Saylor’s Miami Beach anecdote, an acre of waterfront that cost $10,000 a century ago and now costs $10 million or more, is doing real analytical work: he is measuring the dollar against scarce desirable property rather than against a basket of consumer goods that technology keeps making cheaper. Under that lens, the official inflation number is close to meaningless and the honest rate of monetary decay is around 7% a year. That is the frame worth stealing whether or not you buy a single satoshi. Where it gets slippery is the return table he uses to close the argument. Gold at 12%, S&P at 15%, NASDAQ at 18% and Bitcoin at 33% are all six-year figures, and a six-year window ending in the present is exactly the window that flatters the most volatile asset. He is careful enough to say the S&P has done about 10% over a hundred years, but he does not extend the same discipline to Bitcoin, which does not have a hundred-year record to extend.

Around the 33-minute mark the conversation turns into the most interesting thing in it, and it has nothing to do with what Bitcoin is worth. Saylor describes being boxed in: Strategy had maxed out equity issuance, had become the largest issuer of convertible bonds in the world, and had no scalable way left to raise money. Rather than accept the ceiling, he sat down with ChatGPT and designed a preferred stock with a dividend rate the company can reset every month, something nobody had ever built, not because it was illegal but because nobody had needed it. The lawyers and bankers gave him the answer institutions always give, which is that it has not been done. That is the actual lesson, and it is a better one than the AI-productivity advice everyone else is selling: the constraint that stopped him was not knowledge, it was the professional class whose incentive is to never be the first. It is worth being precise about the headline, though. He did not earn $15 billion. He sold $15 billion of credit, which is to say he borrowed it, and the loop only closes if Bitcoin cooperates over the life of those obligations. Calling that “making” $15 billion is a marketing decision, not an accounting one.

The creator-economy stretch in the middle is where Bartlett pushes back hardest and where Saylor is weakest, then unexpectedly strong. Bartlett lays out the supply shock plainly: a kid can point five agents at five platforms and post five hundred videos overnight while attention stays roughly fixed, and the top five podcasters in his own category are down at least half. Saylor’s first answer is essentially “use AI to make and distribute it better,” which is the answer everyone gives and solves nothing, since everybody has the same tool. His second answer is much better and it arrives through Led Zeppelin. His observation is that when a new platform appears, a handful of people push it to about 95% of what it can do within roughly ten years, and then it is done: Beethoven with the piano, Page with amplification, Zuckerberg with the web, Mr Beast with YouTube. The implication for anyone building now is uncomfortable and useful. The opportunity is not to do the current thing better, it is to find the twelve to twenty-four month window where a new capability has just become commercially viable and to be the first one standing in it. He then applies this to his own company without flinching: Strategy is not clever, it was simply first to combine digital capital, digital credit and a treasury structure, and being first by twelve months compounded into being twenty times larger than the nearest competitor.

The section that earns the episode is the sale explanation, and it is a genuinely good piece of financial reasoning that almost nobody covering the story has laid out this clearly. The market had built a self-referential trap: because Strategy owns 4% of all Bitcoin, traders concluded it could never sell without crashing the price, which meant the $55 billion on its balance sheet was effectively unsellable, which meant it was worth nothing, which meant the dividends were unfundable, which meant the credit was worthless, which meant the equity was worthless. Every link in that chain depends on the first assumption, and the only way to break an assumption about what you cannot do is to do it. He sold at around $59,000, Bitcoin traded up, and the chain broke. His backflip analogy is exactly right, and the disclosure that follows is the number that should have been the headline: the break-even is 3.2%, meaning if Bitcoin appreciates by that much annually, Strategy can fund every dividend from Bitcoin sales indefinitely without ever touching the equity. That single figure tells you more about whether the structure survives than any price target does, and it is buried at minute 89 of a 99-minute interview.

Then he closes with the answer that quietly undermines his own forecast, and to his credit he does not seem to notice or does not mind. Asked what he believes that 99% of people do not, he says: go back and learn applied statistics, specifically Fooled by Randomness, Skin in the Game and The Black Swan, because the one thing AI cannot give you is a continuous real-time stream of common sense about whether a signal is meaningful or just noise. This is the man who forty minutes earlier extrapolated 30% annual returns for twenty years from a six-year sample. The second recommendation is better still: he read all eleven volumes and fourteen thousand pages of The Story of Civilization, and what he took from it was that almost nothing is new, including currency debasement, which people date to Nixon in 1971 when in fact every currency in recorded history has been debased. That is an argument against his own novelty premise and in favour of his monetary one at the same time, and it is the most intellectually honest thing he says all episode. “Education is wasted on the youth” is a throwaway line, but the substance underneath it, that you cannot appreciate history until you have lived enough of it to recognise yourself in it, is the part of the conversation most worth acting on.

Key Takeaways

Saylor’s company holds 847,000 Bitcoin, roughly 4% of the total supply, and he says the only entity that has never sold more Bitcoin than he has is Satoshi.
Strategy is worth about $60 billion at the time of taping and peaked near $125 billion, growing somewhere between 100 and 200 times since adopting Bitcoin in 2020.
Cash in physical form can be seized at an airport, and cash in a bank is a claim on a counterparty that decides whether you get it back and files paperwork with the Treasury if you ask for too much.
Moving money internationally can require the permission of your bank, the recipient’s bank, two central banks and a correspondent bank, which is why Saylor calls fiat “permissioned money.”
An acre of Miami Beach waterfront cost $10,000 about a hundred years ago and is now worth $10 million to $20 million, implying the dollar lost roughly 7% of its economic value every year for a century.
The US dollar is the best-performing major currency of the last hundred years, and it still has a purchasing-power half life of about 35 years. Most other currencies lose 14% a year and collapse in around 30.
Saylor argues against buying a house as a wealth strategy: Florida’s 2% property tax means you pay the full value of the home in tax every 36 years, on top of maintenance and insurance.
A house is still better than cash. Commercial real estate is better than a house because tax, insurance and maintenance can be passed through to tenants while the asset appreciates.
The conventional safe path of a money market account paying 3% nets about 1.5% after tax against 7% currency decay, which is a loss of five or six points of real wealth every year for life.
Six-year annualised returns he cites: gold 12%, S&P 500 15%, NASDAQ 18%, Bitcoin 33%. He credits John Bogle for making the index the default liquid capital asset.
His test for a capital asset is whether a factory, a robot or an AI can produce infinite quantities of it. Soybeans, crude oil and cotton fail. An ounce of gold, a share of the S&P 500 and one of 21 million Bitcoin pass.
Gold, the S&P and diversified US real estate are Western options. Someone in Turkey, Argentina, Venezuela or most of Africa cannot access them, which is the argument for Bitcoin as the universally available capital asset.
On Elon Musk’s age of abundance thesis, Saylor says he is half right: consumer goods become abundant, but scarce desirable goods never do, and money therefore does not lose relevance.
His illustration is the hierarchy of affluence. Water is the proletarian drink, then soda, then vodka, then a $38 specialty tequila. Give everyone a house and someone wants one twice as big.
Henry VIII had no clean water, heating, cooling, x-rays or dental crowns. Technology delivered all of it to the middle class, and yet nobody stopped wanting the Hamptons house or the private jet.
Saylor used ChatGPT to design STRK, a convertible preferred stock backed by Bitcoin with a dividend rate the company can reset monthly. No variable-dividend-rate preferred stock had ever existed.
It came to market as a $2.5 billion IPO, the largest of the year to date, then another $8 billion off a shelf registration, totalling $10.5 billion of that instrument plus $4 billion of others, which is where the $15 billion figure comes from.
The lawyers and bankers said it had never been done and therefore should not be attempted. Saylor’s counter was that every conventional path had already been exhausted.
Bartlett cites a statistic that only 2% of households currently pay for an AI subscription, framing it as an open arbitrage for anyone willing to use the tools seriously.
Saylor’s advice on AI is not to learn what the AI can already do but to learn how to ask it to do something that has never been done before.
The S-curve is his model for what to study. Flight went from impossible to Moon rockets in 66 years, then stalled: aircraft efficiency improved only about 15% between 1975 and 2025.
The mistake students make is enrolling at the top of an S-curve, in a field that has already hit diminishing returns and may not move materially for a century.
He judges the smartphone to be near the end of its curve, noting the iPhone went from a utility score of 5 to 70 quickly, then 70 to 90, and has been at 91 or 92 for years. Smart glasses are the next attempt.
Bartlett describes trying Meta’s unreleased device, a plain thin cotton wrist strap with no screen that pairs with glasses and lets you click on interface elements in your peripheral vision.
Saylor says study technologies that let you build things your parents would call magic, and quotes Elon Musk’s rule that the biggest engineering mistake is optimising a part that should not exist.
Bartlett raises the supply shock in content: agents can post hundreds of videos overnight while attention is roughly fixed, and the top five podcasters in his niche are all down at least 50% over 12 to 24 months.
Saylor’s answer is that the moat is the most talented content, and cites an hour-long 3D animated walkthrough of a 16th century warship that held his attention despite zero prior interest in the subject.
His platform theory: within roughly ten years of any new technology, a few geniuses do 95% of everything possible with it and become permanent. Beethoven with the piano, Led Zeppelin with amplification, Mr Beast with YouTube.
The goal is to locate the magic opportunity at the zero-to-one point where something has just become commercially viable. Arrive 36 months early and you hit a wall. The window is typically 12 to 24 months.
Bartlett’s team spent 24 months failing at AI dubbing before the underlying translation technology improved enough that Spanish view duration now exceeds English. Saylor’s response is that guests become the moat.
On timelines: succeeding in under four years means you got lucky, four to ten years is normal, and if you have not succeeded in ten you are probably not cut out for that business.
The most common cause of failure in his view is dilutive expansion, the great single restaurant that becomes a terrible chain of 37. People always underestimate the maintenance obligation.
Healthy growth looks like a chambered nautilus or a Fibonacci sequence, where each new business is built on the foundation of the last. Standard Oil, Ford, Boeing and Microsoft all grew this way, as did Amazon Prime after a decade of losses.
His ten rules, originally written for a billionaire’s newborn twins to open on their 21st birthday: focus your energy, guard your time, train your mind, train your body, think for yourself, curate your friends, curate your environment, keep your promises, stay cheerful and constructive, upgrade the world.
Strategy carries about $6.5 billion of convertible debt and $15 billion of preferred stock against roughly $58 billion of assets, having raised about $65 billion in total to buy Bitcoin.
Saylor says Bitcoin could fall to $5,000 a coin and the company would still be over-collateralised against its debt.
The reason he sold Bitcoin was to break a market narrative that Strategy could never sell, a belief that led short sellers to price $55 billion of Bitcoin at zero and conclude the credit and equity were worthless.
He sold at around $59,000 and Bitcoin traded up, disproving the thesis. The break-even is 3.2%: if Bitcoin appreciates that much annually, the company can fund dividends from Bitcoin forever without selling equity.
Selling more is not the primary strategy. If the common stock trades at a premium to the underlying Bitcoin they fund with equity, and only if it trades at a discount do they sell Bitcoin to protect the stock.
His forecast is roughly 30% annual Bitcoin appreciation for the next 20 years, slowing to about 20%, which he frames as outperforming the S&P index by a factor of 1.5 to 2.
Who should not buy Bitcoin: anyone who needs the money back within 12 weeks. The right holder has capital they will not need for four years and ideally ten.
For a young person with limited money, he would not spend $500,000 on a university education but would absolutely spend $20 to $200 a month on the best available AI subscription before investing anything.
His closing recommendation is applied statistics via Taleb’s books, because AI cannot supply a continuous real-time stream of common sense about what is signal and what is noise.
He also read all eleven volumes and 14,000 pages of Will and Ariel Durant’s history of civilisation as an adult, concluding that most supposedly new ideas were discovered and rediscovered many times before.
His example: people date currency debasement to Nixon leaving the gold standard in 1971, but every currency in recorded history has been debased.

Detailed Summary

The Last Thing You Want to Save Is Money

Saylor opens by describing his own arc: MicroStrategy was a business intelligence company built around extracting insight from large raw data sources, and it was the 2020 lockdowns that pushed him toward Bitcoin. The company is worth about $60 billion at the time of the interview and peaked around $125 billion, which he characterises as growing 100 to 200 times since the pivot. His framing for the general public is “digital empowerment,” the idea that economic energy can be converted into digital form and bound tightly to a person, a family, a company or a country in a way that someone more powerful cannot sever.

With physical cash on the table in front of him, he makes the confiscation argument concretely. Walk through an airport with a stack of currency and it can be taken. Put it in a bank and the bank becomes a counterparty that decides whether you get it back, asks why you want it, and files a form with the Treasury if the amount is large. Move it across borders and you may need the permission of up to seven institutions. His contrast is a bearer instrument: a physical coin with an encrypted chip worth a million dollars that slides across a table, or a private key written on a piece of paper, or a text message. Two people in Africa can trade Bitcoin for a truck without the permission of seven banks and sixteen governments.

The Miami Beach Math and Why He Says Not to Buy a House

Asked what ordinary people misunderstand about the money sitting in their accounts, Saylor reaches for a deed. His own waterfront property in Miami Beach sold for about $100,000 roughly a hundred years ago, with the two acres of land accounting for about $20,000 of that. Today an acre on the same water is worth $10 million to $20 million. That thousandfold move in the same nominal dollars implies the currency shed about 7% of its economic value every year for a century. Measured that way, the best currency in the world halves in purchasing power roughly every 35 years. Most currencies lose 14% a year and collapse in about 30, which he illustrates with Brazil, Argentina, Mexico and Venezuela.

The natural follow-up is whether to buy a house, and here Saylor is more contrarian than his reputation suggests. A house is a better store of value than cash, but Florida’s 2% property tax means the owner pays the entire value of the home to the government in tax every 36 years, before maintenance and insurance. A 7% mortgage stacked on top of high tax and insurance can flip the investment from wealth-building to wealth-destroying. Commercial real estate is structurally better because the carrying costs can be passed to tenants, leaving the underlying asset to appreciate around 7% a year, but he notes that this requires genuine business skill. His real objection to all of it is that the average person should not have to become a tax expert, a landlord, a restaurateur or a stock picker just to avoid losing money slowly.

The Capital Asset Test: Buy What the Robots Cannot Print

Bartlett walks him through the alternatives one at a time. On index funds, Saylor credits John Bogle’s real contribution as the recognition that currency is not a store of value and real estate is illiquid and high maintenance, leaving an ETF as the practical liquid capital asset. He puts the S&P at about 15% over six years and around 10% over a century, meaning a two or three point premium over currency decay in exchange for volatility, which he calls a perfectly reasonable conventional choice. Gold he describes as not an awful idea at 12%. His six-year table runs gold 12, S&P 15, NASDAQ 18, Bitcoin 33.

The organising principle underneath is a single test. Do not invest in anything a factory, a robot or an AI can generate in infinite quantities. Soybeans, crude oil and cotton fail that test. An ounce of gold, a share in the 500 most desirable companies in the world, and one of 21 million Bitcoin pass it. Which one you should hold depends on where you live and what your mindset is, and here he makes his strongest situational case: gold, the S&P, QQQ and diversified American real estate are Western-world options that a citizen of Turkey, Argentina or most African countries simply cannot access. If you live in a war zone and may need to cross a checkpoint, the answer is the asset you can carry in your head.

Where He Splits From Elon Musk on the Age of Abundance

Bartlett reads out Musk’s position at length: that if AI and robotics can satisfy all human needs, money loses relevance as a database for labour allocation, that universal high income replaces universal basic income, that work becomes optional like a sport, and that the true constraints of the future are energy and mass rather than finance. Saylor’s verdict is that Musk is half right. Utilitarian and consumer goods will become abundant and progressively cheaper. Scarce desirable goods will not.

His evidence is historical. Henry VIII had no clean water, heating, cooling, x-rays or dental crowns, and technology has since delivered all of it to the middle class along with infinite Coca-Cola and Hershey bars. Yet nobody gets a Hamptons house, a private jet or a yacht by default. What happens with every wave of affluence is that humanity invents a new luxury tier and a new trophy asset. He calls water the proletarian drink and traces the ladder upward through soda, vodka and $38 specialty tequila, asking why anyone pays $300 for dinner when three dollars a day can feed a person. Give people universal healthcare and they want private healthcare. Give everyone a house and someone wants one twice the size. Bartlett suggests this is because humans are status-oriented animals, and Saylor offers a gentler reading: it is also just that this mountain peak has better snow than that one this week.

On employment he is less sanguine. New job categories will appear, as podcasting and content creation did within the last twenty years, but he doubts they will appear fast enough to absorb displacement, and he expects political unrest. His prescription is more economic freedom rather than less, on the grounds that a permissive market generates tens of thousands of business categories nobody conceptualised, and those are what absorb the people the technology displaces. He points to the absurd end state of the alternative, citing a report that some lawyers oppose autonomous vehicles because they earn money litigating car accidents.

How He Used ChatGPT to Invent a Security and Raise $15 Billion

This is the segment the video’s opening line is built on, and the story holds up better than the framing. By the start of 2025 Strategy had roughly $30 billion of Bitcoin, had maxed out the equity markets, and had become the largest issuer of convertible bonds in the world with no further room to grow. Saylor went to ChatGPT and started designing a hybrid instrument, neither common equity nor a bond, that would be backed by Bitcoin. The result was STRK, a convertible preferred stock. Nobody had created a Bitcoin-backed preferred before, which made it a combination of financial engineering, digital asset engineering and securities law all at once.

The harder problem was making a short-duration credit instrument trade stably around par, so that buyers could purchase at 100, sell at 100, collect the yield, and ignore interest rate sensitivity. The only way to pin the price is to float the dividend, so they built an instrument whose dividend rate can be changed every month. Saylor is explicit that this had never been done in the history of the world, that it was not illegal, and that nobody had done it simply because nobody had needed to. The professional advisers responded with the standard institutional answer, which is that it has not been done and therefore should not be. He overruled them because the alternative was a growth ceiling. The instrument came to market as a $2.5 billion IPO, the largest year to date, then raised another $8 billion through a shelf registration, and combined with $4 billion of other instruments produced roughly $15 billion of credit sold.

Bartlett draws the general lesson for viewers: if a tool this cheap can produce a novel multi-billion dollar security, there is an arbitrage available to anyone willing to learn it, particularly given that only 2% of households currently pay for an AI subscription. Saylor’s version of the advice is to become adept with more than one model, treat it as basic literacy alongside reading and arithmetic, and pair it with genuine domain expertise. The prompt he suggests is not “what should I ask” in the abstract but a properly constrained state space: a baker in Lagos and a firefighter in Los Angeles face entirely different input conditions. His aspiration is to build something magical, like software that does the work of a million accountants for ten dollars a month.

Do Not Outwork the Robots: The S-Curve Theory of What to Study

Asked what he would tell an 18 year old choosing a degree, Saylor answers with the S-curve. Humanity tried to fly for a thousand years with no progress, then flew in 1903, and within 66 years went from 20 miles an hour to Moon rockets. Then the 737 and 747 arrived in the mid-1970s and the curve flattened so completely that aircraft are only about 15% more efficient half a century later. Semiconductors, by contrast, have not hit their limit yet, which is why the last fifty years of breakthroughs concentrated in computer science. The mistake is to enrol at the top of a curve, in a field where no material progress may occur for a hundred years because the limiting factor, in aviation’s case propulsion, has not moved.

He applies the same lens to the smartphone and concludes it is finished as a growth platform. The iPhone rose from a utility score of about 5 to 70 in a hurry, then 70 to 90 over a few iterations, and has been pinned at 91 or 92 ever since. Nobody should start a company to build another iPhone. The live question is smart glasses that weigh nothing, see what you see, hear what you hear, know where you are, and connect to a model you can simply talk to. Bartlett describes trying Meta’s forthcoming device, a thin cotton wrist strap with no screen that pairs with glasses and lets him click through interfaces in his peripheral vision. Saylor’s extrapolation runs through contact lenses to a Neuralink-style implant, and he half-seriously recommends studying fantasy literature, because the talisman that makes you omniscient with no interaction cost is the correct product spec. He caps it with Musk’s engineering principle: the number one mistake is optimising a part that should not exist.

Pressed on specific careers, he declines surgeon, lawyer, accountant and driver in turn. His actual answer is that you should study digital intelligence or digital assets, and more fundamentally that you should learn to ask the marginal question civilisation has not yet answered. Value creation means bringing something into the world that was not there before, and the way to fail is to keep working harder at the same thing while automation eats it.

The Slop Tsunami and What Is Left of a Creator Moat

Bartlett stress tests the advice against his own industry. Frontier models can generate video, images and text at scale, so a teenager anywhere can run five agents overnight and post five hundred videos, while demand for attention is roughly fixed and the Financial Times reports young people’s screen time actually declining. He notes that the top five podcasters in his category are each down at least 50% over the last 12 to 24 months, and admits the business feels insecure.

Saylor’s first answer is to enhance the content and the distribution with AI. His better answer is that the moat is talent, and his example is a riveting hour-long 3D animated reconstruction of a 16th century warship built from the keel up, a subject he had no prior interest in and could not look away from. He then generalises through music history. A new platform appears, a handful of geniuses push it to roughly 95% of its potential inside a decade, and they are remembered permanently: Beethoven and Chopin with the piano, Led Zeppelin once electric guitars and amplification converged around 1971, Swedish House Mafia and Avicii with sampling, Justin Bieber and Mr Beast with YouTube. Facebook happened precisely when the web could support it. The play is not to compete inside a mature platform but to locate the magic opportunity at the exact moment something becomes commercially viable, a window he estimates at 12 to 24 months. Arrive 36 months early and you hit a wall.

He applies this to his own company without ego: Strategy was the first to combine digital capital, digital credit and a digital treasury model, and none of it could have been built ten years ago or on anything other than Bitcoin. They did not plan it. They committed to something they found, got punched in the face a hundred times, recalibrated and kept going. The result is a company twenty times larger than the next comparable one, and he says a billion dollars of marketing could not have bought the same outcome.

Bartlett offers his own theory in return: pursue what is hard and scarce, because hard and scarce are the same thing. Getting Michelle Obama or Saylor into the room is his moat. Saylor agrees and adds that guests become the distribution channel, then points at Bartlett’s three-year translation project as the better example. Twenty-four months of failure with data scientists in the corner of the office, then the underlying translation technology improved and Spanish view duration overtook English. The unglamorous parts were the killers: Spanish runs longer than English so a three-hour video becomes three hours ten, and every thumbnail and title needs translating across twenty languages. Bartlett notes his failure and experimentation team tried 60 things in a year, five worked, two were game-changing.

Dilutive Expansion and Growth Like a Chambered Nautilus

On persistence, Saylor’s numbers are blunt: success in under four years is luck, four to ten years is normal, and if you have not made it by ten you are probably not cut out for that business. But the failure mode he cares about is not giving up too early, it is succeeding and then diluting. People get good at one thing in their thirties, decide they are good at everything, and split their attention ten ways. His image is the great restaurant that becomes a chain of 37 mediocre ones, and his observation is that nobody ever built a failed chain without first having a genuinely good single location. People always underestimate the maintenance obligation. The disciplined move is to make the one thing twice as good rather than make ten things 10% better, and to kill a moderate success rather than nurse it.

Bartlett raises long-termism, comparing a tower built in ten seconds to one built over ten years, and noting that Musk built a battery and a charging network rather than buying either. Saylor’s model for healthy growth is the chambered nautilus, a creature that keeps building on its own existing structure, or a Fibonacci sequence where each business is the foundation for the next. SpaceX earned the cheapest cost to orbit and then filled orbit with Starlink. Coca-Cola already delivers a pallet to 87,000 restaurants, so the natural extension is one more drink on the pallet. Standard Oil, Ford, Boeing and Microsoft all grew by leveraging existing customers, distribution or assets. When your second business is unrelated to your first except that you own both, you are not building on a foundation. His test is simple: if nobody in the world is better situated to do this thing than you, you are probably fine. If 97 companies have more assets in that space, you are betting none of them react. Amazon Prime is his case study, losing money on shipping for a decade to build a moat that later converted into roughly $12 billion a year in cash flow from a single price increase.

Ten Rules Written for a Billionaire’s Newborn Twins

The list has an origin story. At a cocktail party on the French Riviera, another guest mentioned he had just had twins and was collecting written advice from friends into a book his children would be given on their 21st birthday. Saylor sat down and wrote ten items. Focus your energy, because you cannot chase every good idea. Guard your time, because just because you can do a thing does not mean you should. Train your mind, meaning get a real education and build a cultured base. Train your body, because if you are weak you will not make it. Think for yourself, because everybody in the world wants to program you, and the fact that famous, rich and beautiful people all agree does not make them right. Curate your friends, because you become who you surround yourself with and cynical people will either want you to fail or fail to inspire you. Curate your environment, because nothing obliges you to live and work somewhere ugly. Keep your promises, because people remember when you did not, and the ones who trust you are the ones who invest in you and lift you. Stay cheerful and constructive, because people want to work with someone who is. And upgrade the world, because having a mission is what makes getting up worthwhile.

His own mission he describes as preaching the gospel of digital empowerment, and he credits Satoshi with giving economic property rights to eight billion people. Asked whether he would press a button guaranteeing immortality, he says he probably would, but that he wants to live as long as he can contribute and then move on gracefully. Asked why he does not devote himself to longevity research, his answer is characteristically narrow: there are eight billion people and many of them are far better qualified for that mission than he is.

Why He Sold Bitcoin After Telling People to Sell a Kidney First

Bartlett puts the question the audience actually wanted asked. Saylor has spent six years telling people to sell a kidney if they must but keep the Bitcoin, and then his own company sold some. Saylor’s first move is to reframe the scale: the only holder who has never sold more Bitcoin than he has is Satoshi, the company holds 847,000 coins, and it has a reasonable chance of never selling more than Satoshi if it keeps accumulating. On the balance sheet he gives specifics: about $6.5 billion of convertible debt and $15 billion of preferred stock against roughly $58 billion of assets, with about $65 billion raised in total, mostly to pump capital into the ecosystem. Bitcoin could fall to $5,000 a coin and the company would still be over-collateralised.

The actual reason for the sale is a reflexive trap. Two beliefs had taken hold in the market: that Bitcoin could not succeed unless Strategy kept buying, and that if Strategy ever sold it would crash both Bitcoin and the company. Short sellers took that second belief to its conclusion and priced the $55 billion of Bitcoin on the balance sheet at zero, because an asset you can never sell is not an asset. From there the chain writes itself: worthless assets means unpayable dividends, which means the credit goes to zero, which means the equity goes to zero, which means the company fails and takes Bitcoin with it. Saylor points out that Bitcoin trades $20 billion a day or more, so Strategy could meet every obligation while representing a hundredth of a percent of daily volume, but nobody believed the argument. His conclusion is the line the whole segment turns on: if you want people to believe you can do a thing, you have to do the thing. He compares it to being told to prove you can do a backflip, with jail as the penalty for failing.

So they sold, at around $59,000, and Bitcoin traded up. The narrative broke. The number he discloses next is the important one: the break-even is about 3.2%, meaning that if Bitcoin appreciates by that much, the company can fund its dividends forever purely by selling Bitcoin, without ever having to issue equity. That matters because the short thesis assumed Strategy would dilute the common stock into oblivion to service the preferred. Demonstrating that dividends can be funded from Bitcoin means the equity can trade at a premium, which in turn means the credit trades rationally, which benefits both classes of investor. He says selling is not the primary strategy: while the common trades at a premium to the underlying Bitcoin they will fund with stock, and only if it falls to a discount will they sell Bitcoin to defend the share price.

Who Should and Should Not Own Bitcoin

His price view is that Bitcoin appreciates roughly 30% a year for the next twenty years before slowing to about 20%, which he restates as outperforming the S&P index by a factor of 1.5 to 2. The suitability answer is narrower than his reputation implies. Bitcoin is for long-term capital investors with money they will not need for four years and ideally ten. A committed maxi who has spent a hundred hours studying it should buy a lot. Someone unsure should diversify across real estate, equities, other long-term assets and some Bitcoin. Anyone who needs the money back in twelve weeks should not own it at all.

Bartlett pushes on the 25 year old with a few hundred dollars, asking whether they would be better served spending it on training their mind. Saylor’s answer splits the difference in a way that is more interesting than either option: he would not spend $500,000 on an expensive university education, but he would absolutely spend $20 to $200 a month on the best available AI subscription, framing the lower bound as roughly a Netflix subscription. Only after that does the investment question apply, and there his preference for digital capital is about portability. Real estate locks you to a city and carries maintenance and risk. Individual stocks carry the anxiety of picking correctly when most companies fail. Bitcoin travels with you.

The Two Things He Went Back and Studied

The show’s closing tradition is a question left by the previous guest, and this one asks what he believes that 99% of the world does not. His answer is that formal education is not the end of the process and two specific subjects are worth relearning as an adult. The first is practical applied statistics, which he associates with Taleb’s work on randomness, risk and the difference between meaningful signal and misleading noise. His justification is pointed: this is precisely what AI cannot do for you, because no model provides a continuous real-time stream of common sense about whether to cross the street while looking at your phone.

The second is history, read in full rather than in summary. He worked through all eleven volumes and roughly 14,000 pages of the Durants’ history of civilisation, choosing it because it covers art, culture, politics, technology and military affairs together rather than any one strand. What he took from it is deflationary in the best sense. Most of what people present as new and profound was discovered, forgotten and rediscovered a hundred times, with the story told differently each round. His example is monetary: people trace debasement to Nixon abandoning the gold standard in 1971, which is genuinely the point at which the dollar weakened faster, but every currency in history has been debased. He argues education is partly wasted on the young because they lack the life experience to recognise what they are reading, and that returning to it later cures the arrogance of believing you are the first person ever to face your problem. The empowering half of that realisation is that someone else already faced it and left a record of how they worked through it.

Notable Quotes

“So the last thing in the world you want to save is money.”
Michael Saylor, in the opening minutes, setting up the entire argument against cash as a store of value

“The US dollar lost 7% of its value every year going for 100 years. That’s the best it’s ever going to get. It’s not that good for everybody else.”
Saylor, around the 9 minute mark, after walking through the Miami Beach land math

“Don’t invest in things that a factory or a robot or an AI can generate infinite of.”
Saylor, at roughly 16 minutes, giving his one-line test for what counts as a capital asset

“I used AI to make $15 billion last year. And I used an AI to make $15 billion in a way that no one would ever conceive that you could make $15 billion.”
Saylor, at 33 minutes, introducing the STRK story that the video’s cold open is built on

“In the history of the world, no one ever created a variable dividend rate preferred stock. Is it illegal? No. Why has no one ever done it? No one ever had a reason to do it.”
Saylor, at 36 minutes, on the difference between impossible and merely unprecedented

“You don’t want to learn how to do things the AI can do. What you want to do is learn how to ask the AI to do something that’s never been done before.”
Saylor, at 46 minutes, answering what an 18 year old should study

“Don’t keep doing the same thing over and over, working harder and harder every year, fighting against the modern automation epidemic. Don’t try to outwork the robots.”
Saylor, at 59 minutes, to creators worried about being drowned in AI-generated supply

“The only person that’s never sold more Bitcoin than me is Satoshi.”
Saylor, at 85 minutes, opening his answer on why the company sold

“If you want people to believe that you can do a thing, you have to do the thing.”
Saylor, at 87 minutes, explaining why breaking the short sellers’ narrative required an actual sale

“The people that shouldn’t buy it are people that need the money back in 12 weeks.”
Saylor, at 92 minutes, on who Bitcoin is genuinely unsuitable for

“It helps you overcome the arrogance of thinking, oh, I’m the first guy in human history that ever encountered it. And what you’ll realize is no, you’re not.”
Saylor, in the final minutes, on why he read fourteen thousand pages of history as an adult

The full conversation runs about 99 minutes and covers considerably more ground than any summary can hold, including the segment on Meta’s unreleased wrist controller and the extended exchange on whether anyone can ever be as famous as Michael Jackson again. Watch the full interview here.

Tag: convertible preferred stock

Michael Saylor Explains Why He Sold Bitcoin, How He Used AI to Make $15 Billion, and Why Saving Cash Destroys Your Wealth