Billionaire Michael Saylor enters the Bloomberg Wealth Index

In the world of tech and finance, Michael Saylor's name has been making waves. The co-founder and executive chairman of MicroStrategy, Saylor has found himself back among the world's wealthiest, decades after losing his initial fortune.

Born in 1965 in Lincoln, Nebraska, Saylor studied at the Massachusetts Institute of Technology, graduating with honours in 1987. His journey in the tech industry began shortly after, and by the turn of the millennium, he had amassed a significant fortune.

However, the dot-com bubble burst in 2000, and Saylor's wealth took a hit. In a move that was part jest, part political statement, he announced a presidential candidacy. But the setback was temporary.

Fast forward to 2020, and Saylor found himself at the helm of MicroStrategy once again. The company, after weathering a stock crash, had refocused on enterprise software and maintained a stable position in the tech sector for two decades. The turning point came in August 2020, when Saylor redirected MicroStrategy's treasury towards Bitcoin, starting with a $250 million purchase.

Today, MicroStrategy is the largest publicly traded holder of Bitcoin, with over 580,000 Bitcoin tokens, valued at around $60 billion. This decision has significantly boosted Saylor's wealth, which, as of September 5, 2025, is estimated to be $7.37 billion.

Saylor's position remains uniquely exposed to Bitcoin's volatility, unlike his peers whose wealth is spread across diverse sectors. However, he has fully embraced his role as Bitcoin's most active defender, regularly speaking at industry conferences, engaging with regulators, and frequently publishing analyses on Twitter.

MicroStrategy's Bitcoin purchases now represent over 2% of the fixed supply of Bitcoin. Saylor's personal fortune is primarily derived from his stake in MicroStrategy, holding nearly 20 million shares in the company, divided between categories A and B. Although Bloomberg excludes Saylor's personally owned Bitcoin (17,732 tokens) from its wealth estimate, he has also realized substantial gains by selling some of his MicroStrategy shares.

In May 2024, Saylor sold over $410 million worth of MicroStrategy shares. Despite this, he embodies not just a wealthy CEO, but also a symbol of Bitcoin's advancement in traditional finance. Saylor's blend of technical expertise and public presence has made him a notable figure in both financial circles and the crypto universe.

As of now, Saylor holds his largest stock shares primarily in MicroStrategy, which is the company best known for his bitcoin holdings. There is no public information indicating he holds major stock shares in other companies aside from his aggressive bitcoin investments and involvement with MicroStrategy's bitcoin purchases. No evidence suggests significant stakes in companies outside MicroStrategy related directly to Saylor.

Saylor's journey—from an Internet billionaire, through regulatory battles, to becoming Bitcoin's corporate face—demonstrates a consistent ability to reinvent himself. His story serves as a testament to the power of resilience and adaptability in the ever-changing landscape of technology and finance.