The Financial Moves of MicroStrategy Founder Michael Saylor

The Financial Moves of MicroStrategy Founder Michael Saylor

Michael Saylor, the founder of MicroStrategy, has been actively selling off shares of his brainchild over the past several months. As part of a stock-sale agreement entered into last year, Saylor has the authorization to unload up to 400,000 shares until April of this year. So far, he has successfully cashed in 370,000 shares, totaling about $372.7 million in value, which accounts for over 90% of the agreed-upon shares outlined in the agreement. This stock-sale agreement, known as a 10b5-1 plan, allowed Saylor to sell up to 5,000 shares daily from January 2 to April 25, with the shares tied to a vested stock option set to expire in 2024. The sale of these shares has significantly reduced his Class A holdings, with only 30,000 shares remaining after the latest disclosed sale.

Despite a 37% decline from its March peak, the stock of MicroStrategy has experienced significant growth, rising 91% this year following a remarkable 346% surge in 2023. As the largest shareholder in MicroStrategy, Saylor’s Class B holdings are estimated at $2.3 billion. In addition to his Class B holdings, Saylor holds 400,000 Class A shares acquired through an option granted in 2014, which he is currently selling off. This discreetly disclosed sales plan was outlined in the company’s third-quarter earnings filing in November. While Saylor has been making substantial stock sales, a majority of his wealth is tied up in his Class B holdings of MicroStrategy, along with the 17,732 BTC he acquired in 2020, now valued at approximately $1.1 billion.

MicroStrategy has been actively accumulating Bitcoin since 2020, with holdings now exceeding 214,000 BTC. These assets, which make up roughly 1% of the total existing BTC supply, are valued at approximately $13.6 billion, constituting the majority of MicroStrategy’s $21.3 billion market capitalization. The surge in Bitcoin this year has further increased MicroStrategy’s returns, with the launch of spot BTC exchange-traded funds (ETFs) in January driving interest in the market. Additionally, the Bitcoin halving, which occurs every four years and halves rewards for Bitcoin miners, has attracted more participants to the market. In a market where consumers have the option to purchase Bitcoin directly on various exchanges or invest in new ETFs, Saylor sees MicroStrategy’s advantage as a leveraged BTC play without the associated management fees.

Last month, MicroStrategy announced that it had raised $782 million through a convertible debt sale at an interest rate of 0.625%. The company specifically stated its intention to acquire more BTC with the proceeds from this sale. This move highlights MicroStrategy’s continued commitment to investing in Bitcoin and leveraging its position to drive returns for shareholders. Michael Saylor’s strategic financial decisions and focus on Bitcoin investments have played a significant role in shaping the company’s financial trajectory and market performance.

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