Michael Saylor lost big in the Dot-Com bubble and Bitcoin crash. Now he aims to bounce again

Michael Saylor lost about a billion dollars on his bitcoin (BTC) bet and has just stepped down as CEO of MicroStrategy (MSTR), the software company he founded in the 1980s.

Being in a predicament is familiar territory for 57-year-old Saylor. After the dot-com bubble burst in March 2000, CNBC host Jim Cramer pointed to the collapse of MicroStrategy as a catalyst. The stock plummeted 62% in a single day after MicroStrategy announced accounting errors, wiping out $ 6 billion from Saylor’s wealth and marking a major end to the high-flying days of the early Internet. In the same year, the US Securities and Exchange Commission filed, and subsequently resolved, accounting charges against MicroStrategy, Saylor, and other company executives.

Saylor and MicroStrategy therefore spent two decades mostly under the Wall Street radar. Not that he was suffering. MicroStrategy continued to focus on enterprise software development. Saylor lived in a mansion in Miami Beach, Florida that looks like a Spanish colonial mansion. A recent visit by a CoinDesk reporter revealed painted cherubs on the atrium ceiling, gold paneling and crimson red wallpaper in the dining room, a stage beyond the office library filled with guitars, drums, and anything else a band may need, and a portrait of Saylor styled as an old English sailor – with laser eyes. A yacht floated in the back, where a crew lived full time so that Saylor could travel whenever he wanted.

What brought Saylor back to center stage was bitcoin. His fear of inflation prompted him in 2020 to start investing MicroStrategy’s cash in the original cryptocurrency. The company’s cash flows began to be routed to bitcoin. He lined the pockets of Wall Street bankers by selling debt to raise money to buy bitcoin. In the process, he boldly turned his sleepy software company into a bitcoin repository. In all, MicroStrategy spent approximately $ 4 billion on digital assets. MicroStrategy shares have become a proxy for holding bitcoins. The share price moves up and down in tandem with the movements of bitcoin.

He has become something like a bitcoin preacher spitting out religiously fervent praise. His grandiose predictions included that bitcoin will ultimately be worth $ 100 trillion, roughly what all shares in the world are collectively worth now.

“After scientifically researching everything on Earth, I have concluded that bitcoin is the best hedge against inflation,” he told CoinDesk during a November interview at the Miami Beach mansion. “We buy bitcoins as fast as possible with all the money we find around.” Was his advice as bitcoin close to his record? “If you have bitcoin, don’t sell it. If you don’t have bitcoin, buy it. And if your bitcoin is moving, wait.

Fast forward to today. MicroStrategy’s stock has lost about two-thirds of its value since last year’s peak, dragged down by the current bear market for bitcoin. This week, Saylor handed the title of CEO to Phong Le, who had been president of MicroStrategy, and stepped up to the role of executive president, pledging to focus all his attention on investing in bitcoin. Le now manages the legacy software business.

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

So who is Michael Saylor?

Born in Lincoln, Neb., Into a military family, Saylor grew up around the bases. This included the Wright-Patterson Air Force Base near Dayton, Ohio. He attended the Massachusetts Institute of Technology on an Air Force scholarship and became an Air Force lieutenant.

He launched MicroStrategy in his early 1920s after convincing his employer, DuPont (DD), to give him $ 100,000 and free office space and computer equipment, Saylor told Charlie Rose in a February 2000 interview. Saylor’s quirk was visible then, offering a glimpse of what would happen with bitcoin.

“I think in the next decade you will see that people will use software to route traffic on all major highways,” he told Rose 22 years ago. “We will use it to determine which hospital we go to or what drug we take. We will use it to arbitrate all interest rate spreads in the financial market and get a better deal from our bank and probably better trade in the stock market. ”

But he also immediately noticed the serious potential drawbacks of the technology, about a month before his stock plummeted. “If the software crashes, civilization crashes in the same way that if you disrupt air traffic control at a large airport, traffic will come to a halt,” Saylor told Rose. adding, “And that’s what’s exciting about technology.”

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

“He’s a brilliant entrepreneur,” 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 is doing during meetings. “He works on a completely different level.”

After he stepped down as CEO of MicroStrategy, some observers initially speculated that the bitcoin purchase was over. They quickly learned that this is not the case. Saylor intends to go even deeper now that he is executive president.

“In my next job, I intend to focus more on bitcoin,” Saylor tweeted Wednesday early.

READ MORE: Michael Saylor is Bitcoin’s Cyber ​​Hornet

Aoyon Ashraf helped bring this story back.

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