Michael Saylor, the Bitcoin Maximalist Who Pitched Microsoft on the Future of Digital Money

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MicroStrategy founder Michael Saylor tried to convince Microsoft shareholders to put some of the company's cash into bitcoin during a shareholder vote in December 2024.

Saylor's plea failed by a wide margin, with less than 1% of Microsoft shareholders voting in favor of the proposal. However, Saylor's appearance at the meeting provided him with yet another opportunity to spread his gospel of bitcoin and tout the benefits of converting as much cash as possible into that single digital asset. It's a story that Wall Street has been gobbling up.

MicroStrategy shares are up 477% this year as of Friday's close, second only to AppLovin among all U.S. tech companies valued at $5 billion or more, according to FactSet data. That follows a 346% gain in 2023.

While the rally was in full force well before November of this year, Donald Trump's election victory, funded heavily by the crypto industry, propelled the stock even more. The shares have climbed 60% since the Nov. 5 election, and finally exceeded their dot-com era high from 2000 on Nov. 11.

Saylor has long talked about bitcoin in an evangelical fashion and co-authored a book about it in 2022 titled "What is Money?" But his critics have gotten louder than ever of late, describing Saylor as a cult-like leader and his strategy as a "ponzi loop" that involves issuing debt and equity to buy bitcoin, watching MicroStrategy's stock price go up, and then doing more of the same.

"Wash, rinse, repeat — what could possibly go wrong?" wrote Peter Schiff, chief economist and global strategist at Euro Pacific Asset Management, in a Nov. 12 post on X to his 1 million followers.

Saylor, who has 3.8 million followers, addressed the growing chorus of skeptics last week in an interview with CNBC's "Money Movers."

"Just like developers in Manhattan, every time Manhattan real estate goes up in value, they issue more debt to develop more real estate, that's why your buildings are so tall in New York City," Saylor said, in a clip that's been posted to X by his legion of fans. "It's been going for 350 years. I would call it an economy."

Saylor is a frequent guest on CNBC, making appearances on various programs throughout the year. He also agreed to two interviews with CNBC.com, one in September and another soon after the election.

The first of those chats came back at the Lotte, just a few elevator stops from the penthouse where he stayed the night before his stock hit the Nasdaq. Saylor was delivering a conference keynote at the hotel and taking meetings on the side.

He wore a designer suit and an orange Hermes tie, matching bitcoin's designated color. The election was less than two months away, and crypto companies were pumping money into the Trump campaign after the Republican nominee and ex-president, who previously called bitcoin a "scam against the dollar," started guaranteeing a much more crypto-friendly administration.

Two months earlier, in July, Trump delivered a keynote at the biggest bitcoin conference of the year in Nashville, where he promised to fire SEC Chair Gary Gensler, an industry critic, and said the U.S. would become the "crypto capital of the planet" if he won.

"I think the election year has inspired the crypto community to find its voice, and I think it has catalyzed a lot of enthusiasm that was latent," Saylor said in the September interview. "When Trump came out tentatively positive, that was a big boost to the industry. When he came out fully positive, that was another boost."

Until this year, MicroStrategy was one of the few ways many institutions could buy bitcoin. Because MicroStrategy was an equity, investment firms didn't need any special provisions to own it. The environment changed in January, when the SEC approved spot bitcoin exchange-traded funds, allowing investors to buy ETFs that track the value of bitcoin.

Since Trump's victory, it's all been up and to the right. Bitcoin is up about 41% and BlackRock's ETF has climbed 39%. Gensler is preparing to leave the SEC, and Trump has picked deregulation advocate and former SEC Commissioner Paul Atkins to replace him.

Venture capitalist David Sacks, an outspoken conservative who hosted a fundraiser for Trump in San Francisco, will be the "White House A.I. & Crypto Czar," Trump announced earlier this month in a post on his Truth Social platform.

"With the red sweep, bitcoin is surging up with tailwinds, and the rest of the digital assets will also begin to surge," Saylor told CNBC in a phone interview, soon after the election. He said bitcoin remains the "safe trade" in the crypto space,