Analysis

Michael Saylor: Madman or Visionary? MicroStrategy Boss Liquidates $216M Company Stock To Buy Bitcoin… Again

Jim Haastrup

Key Insights

  • Michael Saylor, CEO of MicroStrategy, is selling $216 million of company stock to buy more Bitcoin.
  • MicroStrategy, under Saylor's leadership, has become one of the largest institutional Bitcoin holders
  • The company currently owns over 189,000 Bitcoins at a total cost of $3.16 billion.
  • Saylor's Bitcoin bets have paid off handsomely. MicroStrategy's stock price has skyrocketed 411% in 2023, dwarfing Bitcoin's own 170% gain

MicroStrategy's executive chairman, Michael Saylor, has just made another move that has people talking.

In recent news, the MicroStrategy boss just announced his intention to sell a portion of his company shares and use the funds to buy more Bitcoin.

This is after spending billions buying Bitcoin even during the thick of the last bear market.

At this point, it becomes important to ask: Is Saylor taking things too far at this point, or is he one of the biggest Bitcoin visionaries out there?

Saylor To Buy $216 Million BTC With Company Stock

Saylor began exercising his stock options awards on 2 January this year, as per a filing he made with the SEC this week. 

The stock options were awarded to him in April 2014 and are set to expire on April 30, 2024.

According to reports, Saylor has already cashed in $3.44 million on the sale of his first batch of 5,000 shares on January 2, at an average price of $688.32 per share.

Saylor first declared on November 2, 2023, during MicroStrategy's third-quarter results call, that he intended to sell his shares.

Saylor also says that over the following four months, he intends to sell 5,000 shares a day, which will amount to $216 million at the present market price.

Saylor declared that he would pay his "personal obligations" with the money, and use the rest to buy more Bitcoin for his own account.

Saylor is free to sell up to 400,000 shares of his vested options between 2 January 2024, and 26 April 2024, according to a prior filing made with the SEC on 1 November last year.

At the time of writing, Saylor still has about 385,000 shares available for sale, which, at the current market price, might bring in an additional $265 million.

A Bullish Bet On Bitcoin

Considering how optimistic he is about cryptocurrencies, Saylor's choice to sell his shares and purchase further Bitcoin is not surprising.

Saylor has been one of the business world's most outspoken supporters of Bitcoin from the start, and he has guided MicroStrategy into becoming one of the biggest institutional Bitcoin holdings.

MicroStrategy has reportedly spent around $3.16 billion, or $16,726 per Bitcoin, since August 2020 to acquire a total of 189,150 Bitcoins.

The company's Bitcoin holdings are estimated to be worth $8.5 billion as of January 2, 2024, a 169% increase.

Microstrategy's holdings

Saylor has made it clear time and time again that he plans to hold Bitcoin for the long run, and that he believes it is a better store of wealth and hedge against inflation. In addition, he has urged other companies and investors to take his lead and use Bitcoin as a reserve asset.

MicroStrategy also announced on 27 December last year, that it had used the money from a convertible senior note issuance that it had closed on 11 December, to buy an extra 14,620 Bitcoin for $615 million.

A Stellar Performance For Microstrategy

Saylor's investment in Bitcoin has increased both his personal net worth and the valuation of MicroStrategy, increasing the company stock price by almost 411% (which dwarfs Bitcoin's 170% gain over 2023).

The market valuation of MicroStrategy as of January 2, 2024, is around $11.4 billion, an increase from $2.6 billion the previous year.

Microstrategy's valuation

Prominent investors have also taken notice of MicroStrategy's stock performance. One such investor is Cathie Wood, the founder and CEO of ARK Invest.

Wood has been purchasing MicroStrategy shares for her ARK Next Generation Internet ETF (ARKW), which as of January 2, 2024, held around $300 million worth of MicroStrategy shares.

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