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Strategy
Executive Chairman · MSTR
Michael Saylor founded business analytics software firm Strategy (formerly MicroStrategy) and ran it as CEO until 2022, when he moved into the chairman's role.
One of the best-known executives of the Internet bubble, Saylor was a multibillionaire in the late 1990s thanks to his stake in Strategy.
He fell from the billionaire ranks after questionable accounting led to a restatement of financial results and the dotcom bust crashed the stock.
He's a billionaire again thanks to timely bitcoin investments. In 2020, he disclosed he personally bought 17,732 bitcoins for $175 million.
He has steered Strategy's corporate coffers into bitcoin, spending billions to accumulate more than 800,000 bitcoins.
A former rocket scientist, Saylor studied aeronautics and astronautics at MIT on an Air Force scholarship before founding Strategy in 1989.
Est. net worth
$4.44B
As of Sep 14, 2026
Forbes rank
#1,074
Billionaires 2026
