Bitcoin believer Michael Saylor's assets surged by nearly $900 million this year

Bitcoin faithful believer Michael Saylor has benefited from the recent surge in Bitcoin and MicroStrategy stock prices, with estimated gains of nearly $900 million in assets this year. Saylor once said he would "buy in at the top forever," and continues to buy Bitcoin as MicroStrategy's exit strategy, embodying the HODLer spirit.

Saylor's Assets Increase by Nearly $900 Million This Year

CNBC data shows that Michael Saylor is the largest investor in MicroStrategy, owning approximately 12% of the company. In 2020, he personally owned 17,732 Bitcoins.

• MicroStrategy stock: Up 39% year-to-date, with 12% of the outstanding 17 million shares, unrealized gains amount to $550 million.
• Bitcoin: Up 46% year-to-date, with 17,732 Bitcoins, unrealized gains amount to $340 million.

Embracing the HODLer Spirit

According to a report from early January, MicroStrategy founder Michael Saylor filed with the SEC to sell 315,000 shares of MicroStrategy stock under the code MTSR, starting from January 2, 2024, to April 25, selling 5,000 shares per day. Saylor explained that these were options he received in 2014, and as he chose to only take a $1 salary initially, these options would expire if not exercised. He will use the cash from the sale for his financial planning, including buying Bitcoin. Even after selling these shares, he still retains a majority of the company's equity.

Saylor's recent stock sales could bring in over $200 million in cash for him personally, and he stated that he will use it for his financial planning, including buying Bitcoin. It seems that this loyal Bitcoin believer continues to uphold the HODLer spirit, keeping financial operations simple, holding for the long term, and reaping significant wealth.

When asked in a recent interview if he considers taking profits, he mentioned his philosophy of "always entering at the high point" and continuing to buy Bitcoin, which is MicroStrategy's exit strategy.

Saylor's Financial Mastery

Aside from his unwavering stance on Bitcoin, Saylor is also a master of financial operations, both in personal tax planning and company financial operations.

Tax Savings through Change of Residence

In August 2022, Michael Saylor was sued by the Attorney General of the District of Columbia, where he had lived for over 10 years without paying any income tax. Because U.S. citizens, in addition to federal taxes, must report income taxes to the state where they reside and earn income, and with varying tax rates across states, according to the latest data from the Tax Foundation, the tax rate in Washington D.C. is as high as 10.75%, while Florida has no income tax. Saylor changed his residence to avoid high income tax rates.

The MicroStrategy tax evasion case is about to go to court. Did Michael Saylor's sale of Bitcoin really help the company save on taxes?

MicroStrategy's Tax Savings through Bitcoin Sales

MicroStrategy, aiming to become a "Bitcoin development company" by continuously buying Bitcoin, sold 704 Bitcoins at the end of 2022 for approximately $11.8 million in cash, at an average price of $16,776. Two days later, they bought 810 Bitcoins for approximately $13.6 million, at an average price of $16,845, leaving many puzzled by selling low and buying high. In their filings, MicroStrategy described their attempt to deduct losses from selling Bitcoins from previous capital gains. If federal tax law allows for such gains and losses to be deducted, MicroStrategy could receive tax discounts.

Discounted Repayment through Borrowing from Banks

MicroStrategy once borrowed over $200 million from Silvergate Bank using Bitcoin as collateral. However, during a bank crisis last year, Silvergate decided to cease operations and liquidate the bank. MicroStrategy managed to repay all its debts to Silvergate with only $161 million! It can be said that MicroStrategy and CEO Michael Saylor are truly masters of financial maneuvers! While others lose their investment, they profit even when others go out of business!

MicroStrategy's brilliant move of repaying Silvergate's loan at a discount and once again increasing their Bitcoin holdings.