A bitcoin whale’s last word at the helm

Michael Saylor would most like to be remembered for his contribution to society as an educator, the CEO tells Axios in his last days as head of the software company he co-founded in the 1980s.

The big picture: But what stands out from Saylor’s 33-year tenure at the helm of MicroStrategy is the $4 billion bet on bitcoin that began with one big purchase in August 2020 — the largest acquisition of bitcoin by a publicly traded company at the time.

• “No one could afford to buy $250 million in bitcoin with cash,” he acknowledges.

Why it matters: The strategy opened the back door for traditional firms to gain exposure to bitcoin as MicroStrategy began issuing corporate debt and taking out loans to buy more bitcoin. It now has 129,699 of them.

• The more bitcoins MicroStrategy bought, the more the stock began to move in step with the world’s largest digital asset. (Great for shareholders when bitcoin prices just went up; not so hot right now.)

Catch up quickly: Saylor announced this week that he was dropping CEO from his title, overshadowing the company’s billion-dollar net loss for the second quarter, largely due to its bitcoin holdings.

Context: Alongside MicroStrategy’s bitcoin transformation, Saylor has also transformed, from a relatively obscure head of a software company the average person never interacts with, to bitcoin evangelist.

• Saylor changed his Twitter profile picture to show laser eyes shortly after MicroStrategy’s bitcoin effort, and his feed now reads like the stream-of-conscious ramblings of a bitcoin maximalist. He now has 2.6 million followers.
• The Bitcoin purchase also led to greater scrutiny.

What they say: MicroStrategy reported losses in seven of the eight quarters since the company began buying bitcoin, a recent Wall Street Journal article noted.

The other side: “[The article] suggests that I made a big bet and lost, and now I’m forced to step down as CEO,” Saylor said.

• “There’s really no truth to that. I’m still the chairman and overseeing the investment committee for the bitcoin strategy, and I’m the controlling shareholder of the company,” he said. – I am still employed.
• Saylor also counters MicroStrategy’s stock performance at the time, saying shares jumped from about $120 a share to highs above $1,000.
• Yes, but: Since bitcoin’s swoon, shares have fallen to about $313.

Saylor is defensive when people are critical of the bitcoin strategy but seem to enjoy when people bash him for what he used to think about bitcoin.

• “I famously tweeted something like ‘bitcoin will be regulated out of existence.’ People still make fun of me for that,” he said, laughing.
• The actual tweet from December 2013 was: “#Bitcoin’s days are numbered. It seems only a matter of time before it suffers the same fate as online gambling.”
• “I lived to disagree with myself. Everyone rejects bitcoin when they first hear about it,” he said. “I’ve gone from cynic, skeptic, trader, technocrat and finally to a maxi.”

What will be next: Beyond MicroStrategy: “If I look at my importance in the world right now. It’s clear that my importance is to be a spokesperson and an advocate for digital property rights.”

• Saylor showcases a podcast he did with Lex Fridman that got over 3.8 million views.
• “When you calculate what it means to address 3.8 million people, it’s like having 10,000 people in your room listening to you every hour for who knows how many hours,” he said. “There’s more communication in that one podcast than every meeting I’ve ever had in my entire life, to date.”

The bottom line: “In my new role as CEO, I can advocate for bitcoin and be an emissary to the bitcoin community and engage more in discourse. Change my life for the better,” he said.