The one who spoke the loudest this year was undoubtedly Michael Saylor, the founder of MicroStrategy. In an interview, he repeatedly mentioned: always entering the market at the highest point, continuously buying is a way of exiting, and there is no reason to sell winners to buy losers. We will analyze Saylor's unique investment strategy in this article.
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ToggleBitcoin market value reaches $1.9 trillion, becoming the 7th largest asset in the world
According to 8marketcap data, gold is the largest asset in the world, with a market value of $17.9 trillion. Apple is second with a market value of $3.7 trillion, and NVIDIA is third with $3.4 trillion. Bitcoin ranks 7th with a market value of $1.9 trillion.

Saylor mentioned in the interview that Bitcoin is different from the seven giants, as it is not a company but an asset, similar to gold, with the function of storing value.
Saylor's net worth exceeds $8.5 billion
Michael Saylor is the largest investor in MicroStrategy, owning nearly 20 million MicroStrategy shares. In 2020, he personally owned 17,732 BTC.
- MicroStrategy stock: Saylor owns 381,900 Class A shares and 19,616,680 Class B shares, a total of 19,998,580 shares. Calculated at 1/7 of the closing price of $341.43, the value is about $6.8 billion.
- Bitcoin: Estimated at a BTC price of $96,000, 17,732 BTC is worth about $1.7 billion.
Furthermore, Saylor stated last year when executing the sale of MicroStrategy shares that he would invest the proceeds in his own financial planning, including buying BTC. Therefore, his net worth is estimated to be much higher than the $8.5 billion.
No salary, only stock options
Saylor reported the sale of 315,000 MicroStrategy (MSTR) shares last year, with the sale taking place daily from January 2, 2024 to April 25, selling 5,000 shares per day. Saylor explained that these were company options he received in 2014, and he had chosen to take only a $1 salary. These options would expire if not exercised, and he would invest the cash proceeds, including in BTC. Even after selling these shares, he still owns the majority of MicroStrategy's stock.
Many public company executives choose not to take a salary, preferring to receive company stock options. This is not only because they believe in the long-term development of the company, but also for tax considerations, as options typically have a longer exercise period, allowing them to choose to sell at higher stock prices (recognizing capital gains income when selling the stock), rather than a fixed salary that must be reported annually without flexibility.
Saylor's HODLer spirit
In the crypto world, the "HODLer spirit" refers to the attitude of holding cryptocurrencies for the long term and refusing to sell. This spirit emphasizes confidence and patience in cryptocurrencies, where holders will not easily sell their assets regardless of market fluctuations. They are also called "diamond hands", meaning the holders are as firm and unwavering as diamonds until they reach their set goals.
Saylor's famous quote, "Always entering at the highest point, continuous buying is a way of exiting", is the best embodiment of the HODLer spirit.
His HODLer spirit is not only shown in Bitcoin. Saylor mentioned in a 2012 speech that he was bullish on Apple's stock, and called those who sold that stock idiots! At the time, Apple's stock price was only $20. Calculated based on the split-adjusted cost and today's stock price, he has made over 300 times his money.
No reason to sell winners to buy losers
In business operations, management will choose to "eliminate the weak and keep the strong", eliminating unprofitable departments. But many investors often use a "mean reversion strategy" to handle their assets, selling well-performing assets (winners) and buying poorly performing assets (losers), hoping the assets will always revert to their expected prices.
Saylor stated: There is no reason to sell winners to buy losers! This points out this investment bias, as good assets will have a persistent upward trend, and as long as the fundamentals have not changed, there is no reason to sell profitable assets. This is also different from many investors' habit of "averaging down".
It can only be said that Saylor not only has a successful company, but also has a unique and persistent side in his investments!
Risk Warning
Cryptocurrency investment is highly risky, and its price may fluctuate dramatically. You may lose your entire principal. Please carefully evaluate the risks.




