Aug 5, 2022 - Economy & Business

A bitcoin whale's last word at the helm

Photo illustration of Michael Saylor.
Photo illustration: Aïda Amer/Axios. Photo: Courtesy of MicroStrategy

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 chief 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 its $4 billion bet on bitcoin that started with one large purchase in Aug. 2020 — the largest acquisition of bitcoin by a publicly-traded company at the time.

  • "No one had the cojones to buy $250 million of bitcoin with cash," he acknowledges.

Why it matters: The strategy cracked open the back door for traditional firms to gain exposure to bitcoin as MicroStrategy started issuing company debt and taking on loans to buy more bitcoin. It now has 129,699 of them.

  • The more bitcoins MicroStrategy bought, the more its stock started to move in tandem with the world's largest digital asset. (Great for shareholders when bitcoin prices were only going up; not so hot right now.)

Catch up fast: Saylor this week announced that he was dropping CEO from his title, eclipsing the company's billion-dollar net loss for the second quarter, in large part due to its bitcoin holdings.

Context: Alongside MicroStrategy's bitcoin transformation, Saylor, too, transformed, from relatively obscure chief of a software company the average person never interacts with, to bitcoin evangelist.

  • Saylor changed his Twitter profile picture to feature laser eyes shortly after MicroStrategy's bitcoin bet and his feed now reads like the stream-of-conscious ramblings of a bitcoin maximalist. He now has 2.6 million followers.
  • The bitcoin buying also brought greater scrutiny.

What they're saying: MicroStrategy reported losses in seven out of the eight quarters since the company started buying bitcoin, a recent Wall Street Journal article noted.

The other side: "[The article] suggests I made some big bet and lost and now I'm forced to step down from the CEO job," Saylor said.

  • "There's really no truth to it. I'm still chairman and oversee the investments committee for the bitcoin strategy, and I’m the controlling shareholder of the company," he said. "I'm still employed."
  • Saylor also counters with MicroStrategy's stock performance in that time, saying shares jumped from roughly $120 a share to a high of over $1,000.
  • Yes, but: Since bitcoin's swoon, shares have declined to roughly $313.

Saylor is defensive when folks are critical about the bitcoin strategy, but seems to enjoy when people dunk on him for what he used to think about bitcoin.

  • "I famously tweeted something like 'bitcoin will get regulated out of existence.' People still make fun of me for that," he said laughing.
  • The actual tweet from Dec. 2013 was: "#Bitcoin days are numbered. It seems like just 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 have gone from cynic, skeptic, trader, technocrat and finally to a maxi."

What's next: Beyond MicroStrategy: "If I look at my significance in the world right now. It's clear my significance is to be a spokesperson and advocate for digital property rights."

  • Saylor touts a podcast he did with Lex Fridman that got over 3.8 million views.
  • "When you calculate what that 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 exec chairman, I can advocate bitcoin and be an envoy to the bitcoin community and engage more in discourse. Change my life for the better," he said.

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