Michael Saylor lost a lot in the Dot-Com Bubble and Bitcoin Crash. Now he aims to recover again

Michael Saylor is off a Billion dollar on his bet on Bitcoin (BTC) and just resigned as CEO at MicroStrategy (MSTR), the software company he founded in the 1980s.

Being trapped is a familiar thing to 57-year-old Saylor. After the dotcom bubble burst in March 2000, Jim Kramer, CNBC host, pointing to To breakdown MicroStrategy as an aid. The stock decreased 62% in a day after MicroStrategy announced accounting errors, wiping out $6 billion from Saylor’s fortune and heralding a landmark end to the soaring flying days of the early internet. Later that year, the US Securities and Exchange Commission brought, then settledaccounting charges against MicroStrategy, Saylor, and other company executives.

Then Saylor and Microstrategy spent two decades mostly under the radar of Wall Street. Not that he was suffering. MicroStrategy has continued to deliver, developing software for businesses. Saylor lived in a mansion in Miami Beach, Florida, which resembles a Spanish colonial mansion. a last visit By a CoinDesk reporter, she revealed a colorful cherub on the hallway ceiling, gold plates and crimson red wallpaper in the dining room, a stage outside the office library filled with guitars, drums and whatever else the band might need, and a picture of a Sailor modeled like an old English sailor — with laser eyes. A yacht was floating aft, where the crew lived full time so Saylor could travel whenever he wanted.

What brought Saylor back to center stage was bitcoin. Fear of inflation Led it in 2020 To start investing MicroStrategy funds in native cryptocurrency. The company’s cash flow is starting to head into bitcoin. he is Wall Street bankers’ pockets are lined up By selling debt to raise funds to buy bitcoin. In the process, he has boldly turned his dormant software company into a bitcoin vault. Overall, MicroStrategy has spent around $4 billion on digital assets. MicroStrategy stock has become a proxy for holding bitcoin. The stock price is moving up and down at a steady pace with the movement of bitcoin.

He has become something of a bitcoin preacher who highly praises the religion. His great prediction included the prediction that Bitcoin would eventually be Worth $100 Trillionroughly what All stocks in the world Collectively they deserve it now.

“After studying everything scientifically on Earth, I have concluded that Bitcoin is the best inflation hedge,” he told CoinDesk during an interview in November at the Miami Beach mansion. “We buy bitcoin as fast as we can with whatever money we find around.” His Advice As Bitcoin Was Close To Its Record High? “If you have bitcoin, don’t sell it. If you don’t have bitcoin, buy it. If your bitcoin is moving, wait.”

Fast forward to today. MicroStrategy’s stock has lost about two-thirds of its value since it peaked last year, weighed down by the current bitcoin bear market. This week, Saylor Ladder The CEO title of Fong Lo, who was the head of MicroStrategy, turned CEO, pledging to put all his focus on bitcoin investing. Le now runs the legacy software business.

Saylor was not immediately available for an interview for this story.

So who is Michael Saylor?

Saylor was born in Lincoln, Neb, to a military family, and grew up around bases. This included Wright-Patterson Air Force Base near Dayton, Ohio. He joined MIT on an Air Force scholarship and became Second Lieutenant in the Air Force.

He launched MicroStrategy in his early 20s after convincing his employer, DuPont (DD), to give him $100,000 and free office space and computer equipment, Charlie told Rose during an interview February 2000. Saylor’s antics was visible at the time, providing a glimpse of what was to come with bitcoin.

“I think you’ll see over the next decade that people are going to use traffic-routing software on every major highway,” Tell Rose 22 years ago. We will use it to decide which hospital to go to or which medication to take. We will use it to offset all the interest rate differentials in the finance market and get a better deal from our bank and possibly a better trade in the stock market.”

But he immediately noticed potentially serious downsides to the technology as well, about a month before his stock plunged. “If the program breaks, civilization stops in exactly the same way that if you shut down air traffic control at a major airport, traffic will stop dramatically,” Saylor told Rose, “and that’s the exciting thing about technology.”

Darren Feinstein, co-founder of the Bitcoin Mining Council, knows Saylor because the CEO of MicroStrategy helped form the advocacy group in May 2021.

“He’s a genius businessman,” Feinstein said in an interview after Saylor’s job change. “You say something and he already knows what you’re going to say,” Feinstein said, when asked how Saylor was doing during the meetings. “It works on a completely different level.”

After stepping down as CEO of MicroStrategy, some observers initially predicted that the bitcoin buying was over. They soon learn that this is not the case. Saylor intends to go deeper now that he is CEO.

“In my next job, I intend to focus more on Bitcoin,” Saylor chirp Early Wednesday.

Read more: Michael Saylor is Bitcoin’s Cyber ​​Hornet

Owen Ashraf contributed to reporting this story.