Imagine a boss who enters the room, turns the table, and asks who really knows what they are doing. This is the crypto market. One day, headlines emerge announcing the end of everything. The next, billions change hands while no one is looking.
Bitcoin itself has been called a fad, bubble, scam, and internet toy. Yet, large investors continue to buy, old wallets keep moving, and activity on the networks shows no signs of abandonment. While part of the public panics, another part quietly adjusts their position.
The question is that none of this happens by chance. Those who survived the most violent cycles learned quickly that emotion is costly and information is worth gold. It is not about guessing the next peak but understanding why some people get it right more often.
Fortunately, some of these great minds left traces — repeated decisions, avoided mistakes, and clear patterns. Let's see what was necessary to come from nothing and build success in this market.
Michael Saylor and MicroStrategy's big bet on Bitcoin
Michael Saylor, co-founder of MicroStrategy (a business intelligence software company), became one of Bitcoin's biggest evangelists among executives. In August 2020, he initiated a major change in the company's treasury: instead of holding cash, he began buying Bitcoin. That month, MicroStrategy announced the purchase of 21,454 BTC for about $250 million, using part of its resources, in a “hedge against inflation” strategy. Saylor explained that he believed in Bitcoin as “a reliable store of value and an attractive investment asset, with long-term appreciation potential greater than holding cash.” He also cited macro factors – such as massive financial stimulus during the pandemic, possible devaluation of fiat currencies, and global uncertainties – that motivated this decision, comparing Bitcoin to “digital gold”: “harder, stronger, faster, and smarter than any money that preceded it.”
From this initial decision, MicroStrategy maintained an intense pace of purchases. Between August and September 2020, 38,250 BTC (~$425 million) were added to the treasury. In December 2020, the company raised $650 million in convertible debentures specifically to buy more bitcoins. In June 2021, it used about $489 million in cash to acquire another 13,005 BTC (at $37,617 each). These constant movements made it clear that Saylor saw Bitcoin as the flagship of the company's financial strategy, even above its own software business. In a press release, he summed up: MicroStrategy now had 105,085 bitcoins, costing $2.741 billion. In other words, in a few years he transformed traditional cash into a massive reserve in BTC.
How Saylor convinced investors and the market
A key point in Saylor's strategy was to convince shareholders and analysts that this plan made sense. He did not make this decision alone: he needed to educate traditional investors about Bitcoin. According to reports, it took about six months for the board and large funds to understand the movement. Saylor promoted webinars, exclusive Q&A sessions, and even a special section of educational materials about Bitcoin on the company's website. In a conference call, for example, 10 of the 25 questions from analysts were about cryptocurrencies. Saylor's message to the market was clear: “we will use our excess cash to buy Bitcoin as a hedge against the depreciation of the dollar.” He argued that while government bonds and cash yielded almost zero, Bitcoin offered the chance of much greater gains in the long term. Phong Le, then CFO of MicroStrategy, summed it up well: buying $250 million in Bitcoin “gives us the opportunity to achieve better returns and preserve capital value over time, compared to holding cash.” In short, Saylor promised shareholders a long-term strategy focused on asset growth – if all went well, Bitcoin profits would elevate the company; if it went wrong, the maximum risk was a decline in book value, without affecting the core software business.
Strategies to accumulate more $BTC
To accumulate such large amounts of Bitcoin, Saylor adopted creative fundraising methods. Instead of using only operational profits, MicroStrategy issued debt and sold shares specifically to buy BTC. For example, in December 2020 it raised $650 million in convertible debentures and applied almost all of it to more bitcoins. In 2024, it followed the same path: in June 2024 it issued $800 million in new convertible notes (maturity 2032) and used those funds to buy over 12,000 BTC in the second quarter. Saylor called this practice “smart leverage”: MicroStrategy exchanges part of its equity (new shares) or debt for more bitcoins because it believes it is more profitable than distributing dividends. In October 2024, he announced a $42 billion plan ($21 billion in equity and $21 billion in debt) specifically to intensify Bitcoin purchases in the coming years. In summary, the strategy was clear: whenever the capital markets allow, the company raises new money (selling shares or bonds) and converts it into Bitcoin, as a way to grow its crypto reserve over time.
The long-term vision
Michael explains that he sees Bitcoin as “digital gold” and a store of value for the 21st century. He highlights the finite supply of 21 million coins: unlike money printed by central banks, Bitcoin has a scheduled issuance that will be capped soon. Therefore, according to him, its scarcity and security (robust network) will sustain the price in the long run. In interviews and statements, Saylor emphasizes characteristics of Bitcoin such as global acceptance, independence from governments, and technical transparency. He even predicted that with increasing adoption, the price of Bitcoin could reach $1 million per coin in the future. In summary, the philosophy is: big purchases today pay off in the future. For Saylor, short-term volatility doesn't matter – as long as the trend is upward in the long run. Analysts like Jameson Lopp even comment that this strategy was “a fundamental shift in corporate cash management,” treating Bitcoin not as a short-term bet, but as a fixed component of the company's balance sheet.
Of course, this gigantic bet did not go without criticism. Gold bugs like Peter Schiff called Saylor a “charlatan” for abandoning gold, and skeptical analysts pointed to liquidity and pricing risks. But Saylor remains unfazed: he repeats that volatility is “Satoshi's gift to the faithful” – that is, those who stay benefit from the best buying prices. For example, he said in an interview that the company could withstand an 80–90% drop in the price of Bitcoin and still remain standing, precisely because it is focused on the long term. In early 2026, when Bitcoin fell to around $70–75 thousand, Saylor continued buying – in just a few days, over 22,000 BTC were acquired. His argument tends to be: “The only real risk would be to admit defeat and stop buying.” In other words, market turbulence did not make him back down. On the contrary, he reinforced: each bear market (down cycle) was an opportunity to accumulate, while most sold. In summary, he deals with criticism by insisting on the long-term vision and using every drop to buy cheaper, always aiming for results decades ahead.
The current position in Bitcoin
Today, MicroStrategy's position (now rebranded as Strategy, Inc.) is impressive. By the end of 2024, it held about 447,470 BTC costing $27.97 billion. In November 2025, this number had risen to approximately 649,870 BTC. And in January 2026, it was reported that Strategy had accumulated around 709,715 bitcoins in total. This amount represents about 3.2% of all bitcoins that will ever exist. Furthermore, Saylor revealed that these 709,000 BTC cost, on average, $53,924 each. At current market value, this is tens of billions of dollars in Bitcoins. The company continues to say that it will maintain BTC as its main reserve asset, adjusting the treasury accordingly (since, starting in 2025, it began to account for Bitcoin at market value instead of cost). In short, Saylor fulfilled his bet: today MicroStrategy/Strategy is the largest corporate Bitcoin treasury in the world.
Arthur Hayes's journey in the crypto world
Arthur Hayes was born in Detroit in 1985 and grew up in Buffalo (New York). He was a brilliant student: he attended a private school and graduated in Economics and Finance from the Wharton School (University of Pennsylvania) in 2008. Shortly after, he moved to Hong Kong to work in investment banking. He started at Deutsche Bank (2008–2011) as an equity derivatives trader and then went to Citigroup, where he was head of the ETF market-making unit. This experience in complex derivatives markets gave him the foundations he would later use in crypto.
At the end of 2013, at 28 years old, Hayes was laid off from Citigroup. It was then that he decided to “create something” new, blending his talent for financial instruments with a new passion: Bitcoin. In a future account, he stated that free of constraints, he wanted to apply his knowledge of derivatives to the world of cryptocurrencies. After leaving traditional finance, he saw Bitcoin as a unique opportunity. He began using Bitcoin arbitrage strategies between Asian exchanges – for example, selling on one and buying on another – transporting cash between Hong Kong and China in a backpack. This was the first step of his immersion into the crypto ecosystem.
In 2014, he teamed up with British colleague Ben Delo and engineer Sam Reed to found BitMEX. The idea was to create a cryptocurrency exchange aimed at professional traders, focused not on selling coins themselves but on derivative contracts – that is, leveraged bets on the price of Bitcoin. Hayes and the founders even invented a new type of contract: the perpetual swap, which has no expiration date and allows trading 24/7. Thus, an investor could bet on Bitcoin with up to 100x leverage, which amplified gains (and risks) in an unprecedented way.
Foundation of BitMEX and meteoric rise
The bet paid off. In a short time, BitMEX became a giant: in its first year, it earned over $1 billion. In 2018-2019, BitMEX became the most traded crypto derivatives exchange in the world. Arthur claimed: “We are the largest trading platform in the world, considering who trades crypto products.” The platform reached extraordinary daily volume peaks – trading $16 billion in a single day, and about $1 trillion in a year. During this period, British newspapers even called him one of the “youngest self-made billionaires” in crypto.
His fame came from both technology and style. Hayes cultivated an image of a bold and provocative executive (similar to a TV character), living in Hong Kong, skiing in Japan, and openly discussing markets. He donated millions to charities – for example, $2.24 million to a university fund in 2019 – but also made strong statements about regulations. He was known for praising BitMEX's maximum leverage (“Trading without leverage is like driving a Lamborghini in first gear,” he once joked on his blog) and for showing extreme confidence in the business he helped create. All this made him a very influential figure in crypto until mid-2020.
Trading strategies: macro and liquidity cycles
He developed strategies that combine macroeconomic vision and timing of liquidity cycles. He often said that he studies “the pace at which governments print money” and how the market expects that pace to change. For him, this level of liquidity – the amount of money injected into the economy – is the key variable that drives scarce assets like Bitcoin and gold. In other words, when central banks create a lot of money (monetary expansion), Hayes sees it as a signal of potential bullishness in crypto.
• Bitcoin-focused portfolio: Hayes considers Bitcoin the safest asset against excessive monetary printing. He said he prefers to keep most of his wealth in Bitcoin, as he believes that, in the face of “chronic money printing,” Bitcoin will likely “outperform other assets.”
• “Shitcoins” for more Bitcoin: Although he is not a strict maximalist (ironically criticizing the term “useless coin” – shitcoin), he uses altcoins to gain more Bitcoin. As he commented: “We buy shitcoins and earn more Bitcoin”; in other words, he seeks quick gains in alternative coins and converts the profits to Bitcoin.
• Macroeconomic focus: He monitors events such as interest rate decisions and financial crises. For example, Hayes predicted that interest rate cuts and public bond issuances could alter global liquidity – and consequently create bullish opportunities in crypto. The important thing, according to him, is not the events themselves, but the political reaction to them: “when people start to think that money printing will slow down, the market reacts even before that happens.”
• Perpetual contracts and leverage: He also popularized perpetual contracts at BitMEX with extreme leverage. He progressively increased from 50x to 100x maximum leverage. This means that with 1 BTC collateral, the trader could open a position equivalent to 100 BTC. This extreme strategy attracted those looking for big gains from price movements, but also implied huge risks.
Each of Arthur's strategies was tied to his vision: times of high liquidity (amount of money in the market) favor Bitcoin, so he would go “long” on crypto during those periods. In times of liquidity contraction, he became more conservative. In summary, he surfed the liquidity cycles of global monetary policies, seeking to maximize gains with his leveraged bets. Hayes always studied macroeconomic patterns. He claims that when central banks expand the balance sheet – releasing more money – scarce assets like Bitcoin tend to rise. For him, understanding this liquidity cycle is crucial for positioning his portfolio.
Market vision and volatility
Arthur Hayes saw volatility as part of the game and not as an enemy. In his public analyses, he has stated that he believes in a future of constant “money printing” by governments to calm crises. In this scenario, safe-haven assets would gain value. He argues that Bitcoin is the safest way to preserve wealth in the long term, because its limited protocol (only 21 million coins) makes it immune to uncontrolled monetary inflation. In interviews, he even compared Bitcoin to an extreme sport: you can go slow and safe, but with more risk – “that's what makes this game exciting.” In summary, Hayes sees high volatility as an opportunity: in his words, “when everyone is scared and selling, it's time to buy” – because he believes that in the end, the long-term trend will be dictated by market liquidity.
Furthermore, he does not completely dismiss other assets. As manager of Maelstrom Fund (his investment fund created after leaving BitMEX), he allocates a portion to gold and government bonds (as a hedge) and maintains exposure to stablecoins, but always comparing returns against the Bitcoin benchmark. His consistent message is: if you can't outperform Bitcoin, why invest in anything else? Thus, he saw volatility and large movements as inherent to the crypto market – high risks in exchange for high potential gains in a growing liquidity economy.
Problems
Throughout his career, Arthur went through impressive highs, but also faced serious legal crises. Each of those moments was widely reported and controversial in both crypto and traditional media. Despite the controversies, Hayes maintained influence in the sector – today he walks as CIO of Maelstrom Fund, an investment fund he founded after the BitMEX case. His trajectory, from traditional markets to the center of the crypto regulatory storm, shows how a rebellious profile trader can achieve both success and attract great risks.
Honorable mentions | Big players
• Satoshi Nakamoto (Creator of Bitcoin)
He disappeared after launching the world's first decentralized money system. Never sold his BTC and let the code speak for itself. Changed the idea of money forever.
• Sam Bankman-Fried (SBF) Founder of FTX
He built one of the largest exchanges in the world in record time using arbitrage and aggressive marketing. He also became the biggest example of how mismanagement destroys empires.
• Paul Tudor Jones Traditional macro investor
One of the first billionaire managers to treat Bitcoin as protection against inflation. Helped legitimize BTC among large funds and Wall Street.
• Jack Dorsey (Founder of Twitter)
He publicly bet on Bitcoin as the future of money. Created initiatives focused on BTC and advocated decentralization as a political and technological principle.
Andreas Antonopoulos (Educator and author)
He did not get rich trading. He became famous for teaching Bitcoin to the world. He explained crypto simply when almost no one understood the subject.