Michael Saylor Turns Sixty: A Look at His Early Career, Dotcom Bubble Fortune Crash, and Bitcoin Strategy

Today, on February 4, Bitcoin evangelist and co-founder of MicroStrategy giant Michael Saylor has turned sixty. Four years ago, he radically changed

MicroStrategy co-founder and Bitcoin evangelist Michael Saylor has turned 60 on Saturday, February 4.

Four years ago, Saylor made drastic changes to his company’s business strategy, and stepped down from his role as CEO to become the executive chairman, focusing on the new Bitcoin strategy.

Saylor’s Early Career and Dotcom Bubble Fortune Crash

Born in 1965 in Lincoln, Nebraska, Saylor went on to co-found MicroStrategy in 1989, becoming the company’s chief executive officer after graduating from the Massachusetts Institute of Technology (MIT). At MIT, Saylor majored in aeronautics and astronautics, a fact he mentioned to Elon Musk while responding to one of his tweets, around the time MicroStrategy had begun pursuing its Bitcoin path.

I have just one ₿irthday Wish. pic.twitter.com/JPvCFSM1fC

Initially, MicroStrategy developed business analytics software and became highly successful during the dotcom bubble in the late 1990s. As a result, Saylor quickly became a multi-billionaire, largely due to his significant stake in MSTR.

However, questionable accounting led to a restatement of the company’s financial results as the bubble burst at the turn of the 2000s, and the price of MSTR stock crashed, leaving Saylor with almost no fortune. He later described this event as the darkest day of his life.

Saylor Becomes a Billionaire Again with Bitcoin

In August 2020, Saylor decided to allocate a portion of MicroStrategy’s cash reserves to begin purchasing Bitcoin and adding it to the company’s balance sheet. These purchases, while regular, were not yet very frequent. Nevertheless, the company continued to ramp up its BTC purchases under Saylor’s leadership.

Over the years, MicroStrategy has funded its Bitcoin purchases by selling debt to corporate investors in the form of senior convertible notes, which have an expiry date when they will be redeemed. Additionally, the company pays monthly yields from its Bitcoin units to MSTR holders.

As of the last purchase made earlier this month, and at the time of writing, MicroStrategy now holds 471,107 bitcoins, collectively valued at $46,982,964,048, following another drop that saw Bitcoin slip below the $100,000 level once more.

According to Forbes, Saylor personally owns 17,732 bitcoins, which are currently worth $1,766,553,159 at the present exchange rate. In 2025, Saylor’s personal net worth is estimated at $8.8 billion, largely attributed to his Bitcoin and MicroStrategy stock holdings, with the latter also trading at a premium, thanks to BTC.