Michael Saylor, who just resigned as CEO of MicroStrategy (MSTR), the software business he created in the 1980s, is lost almost $1 billion on his bitcoin (BTC) wager.
The 57-year-old Saylor is accustomed to finding himself in a precarious situation. Jim Cramer, the anchor of CNBC, cited the demise of MicroStrategy as a trigger for the dot-com boom in March 2000.
After MicroStrategy disclosed accounting errors, the stock fell 62% in a single day, wiping out $6 billion from Saylor's riches and signalling the end of the period of the early Internet's frenzied growth.
The U.S. Securities and Exchange Commission filed accounting allegations against MicroStrategy, Saylor, and other business leaders later that year, which were later settled.
Some observers first believed the bitcoin purchase had ended once he left his position as CEO of MicroStrategy. They soon discovered that is not the case. As executive chairman, Saylor wants to dig even further.