Michael Saylor, president and CEO of MicroStrategy, during an interview at the Bitcoin 2023 conference in Miami Beach, Florida, U.S., on Thursday, May 18, 2023.
Eva Marie Uzcategui | Bloomberg | Getty Images
On the eve Micro-strategystock market debut in June 1998, founder Michael Saylor stayed in a penthouse suite at the Lotte New York Palace in midtown Manhattan. Saylor, who was 33 at the time, says it was the greatest hotel room he had ever seen, paid for by major insurer Merrill Lynch.
The next morning, Saylor went to the Nasdaq trading floor to watch his company's stock price. He recalled a note floating around the exchange warning traders: “Please do not confuse MSTR with MSFT.” The latter belonged to Microsofta software giant that had gone public 13 years earlier.
MicroStrategy shares surged 76% in their debut, joining a parade of technology companies benefiting from the dot-com boom.
“It was a good day,” Saylor told CNBC.
More than 26 years later, MicroStrategy and Microsoft were reunited, but for a completely different reason. In December 2024, Saylor appeared before Microsoft shareholders in an attempt to convince them that the company, now valued at more than $3 trillion, should commit some of its $78.4 billion in cash, equivalents and short-term investments to bitcoins.
“Microsoft cannot afford to miss the next technology wave, and bitcoin is that wave,” Saylor said in a video presentation, stating that released in October last week. The post has over 3.6 million views.
Saylor went all out with this strategy. Since mid-2020, MicroStrategy has purchased 439,000 bitcoins, and the stock is now worth about $42 billion and underpins the company's market capitalization to explode to $82 billion from about $1.1 billion when the plan was implemented.
MicroStrategy's business intelligence software division generates just over $100 million in revenue per quarter. After rising in 1998 and 1999, the company's stock crashed in the dot-com crash, losing almost all of its value. In the following decades, the situation slowly returned to normal rocket up because of bitcoin.
Four years after the bitcoin buying frenzy, MicroStrategy is a global solution fourth largest holderbehind the sole creator Satoshi Nakamoto, BlackRock's iShares Bitcoin Trust and the Binance cryptocurrency exchange.
At Microsoft, a shareholder vote supported by Saylor was largely unsuccessful, with less than 1% of investors voting for him.
But the spectacle provided Saylor, now 59, with another opportunity to preach the gospel of bitcoin and tout the benefits of turning as much cash as possible into this single digital asset. It's a story Wall Street is soaking up.
MicroStrategy shares are up 477% this year since Friday's close, second Just AppLovin among all U.S. tech companies worth at least $5 billion, according to FactSet data. This represents an increase of 346% in 2023.
Although the rally gained full force well before November of that year, Donald Trump electoral victory, financed heavily by the crypto industry, fueled the stock even further. The company's stock has surged 60% since the November 5 election and ultimately surpassed the 2000 dot-com era high on November 11.
Saylor has long spoken evangelically about bitcoin and co-authored a 2022 book on the subject titled “What is Money?” But his critics have recently become louder than ever, describing Saylor as a cult-like leader and his strategy as “ponzi loop” this involves issuing debt and equity to buy bitcoin, watching MicroStrategy's share price rise, and then doing more of the same.
“Wash, Rinse, Repeat – What Could Go Wrong?” – wrote Peter Schiff, chief economist and global strategist at Euro Pacific Asset Management, in a November 12 report write to X for his 1 million followers.
Saylor, who has 3.8 million followers, addressed the growing chorus of skeptics last week in an interview on CNBC's “Money Movers.”
“Just like developers in Manhattan, every time Manhattan property values go up, they issue more debt to build more properties, which is why the buildings in New York are so tall,” Saylor said in a clip posted on X by her legion of fans. “It's been going on for 350 years. I would call it the economy.”

Saylor is a frequent guest on CNBC and appears on various programs throughout the year. He also agreed to two interviews with CNBC.com, one in September and another shortly after the election.
The first of these chats took place at Lotte, just a few elevator stops from the apartment where he had spent the night before his stock hit the Nasdaq. Saylor gave a speech at a conference at the hotel and attended meetings on the side.
He wore a designer suit and an orange Hermes tie, matching the designated bitcoin color. With less than two months until the election, crypto companies have been pumping money into the Trump campaign after the Republican candidate and former president, who previously named bitcoin “fraud against the dollar”, began to guarantee a much more crypto-friendly administration.
“He inspired the cryptocurrency community”
Two months earlier, in July, Trump delivered a speech at the largest bitcoin conference of the year in Nashville, Tennessee, where he promised fire the SEC chairman Gary Genslerindustry critic, and said that if he wins, the United States will become the “crypto capital of the planet.”
“I think the election year inspired the crypto community to find their voice, and I think it generated a lot of latent enthusiasm,” Saylor said in a September interview. “When Trump was initially positive, it was a big boost for the industry. When he expressed himself completely positively, it was another boost.”
Until this year, MicroStrategy was one of the only ways many institutions could buy bitcoin. Because MicroStrategy was equity, investment firms did not need any special reserves to own it. The environment changed in January when SEC Approved Bitcoin exchange-traded spot funds that allow investors to buy ETFs that track the value of Bitcoin.
Since Trump's victory, everything has been on track. Bitcoin rose about 41% and the BlackRock ETF rose 39%. As Gensler prepares to leave the SEC, Trump has chosen a deregulation supporter and former SEC commissioner Paul Atkins replace him.
Venture capitalist David Sacks, an outspoken conservative who hosted a fundraiser for Trump in San Francisco, will be 'White House AI and Crypto Czar', Trump announced earlier this month in a post on his Truth Social platform.
“With the red tide, bitcoin is rising rapidly and the rest of the digital assets will start to rise as well,” Saylor said in a telephone interview with CNBC shortly after the election. He said bitcoin remains a “safe trade” in the crypto space, but with the introduction of a “digital asset framework” for the broader cryptocurrency market, “there will be explosive growth across the digital asset industry,” he said.
“Taxes are falling. “All the rhetoric about unrealized capital gains taxes and estate taxes is misplaced,” Saylor said. “All the regulatory hostility towards banks affecting bitcoin” also disappears, he added.
Republican presidential candidate and former U.S. President Donald Trump gestures during the Bitcoin 2024 event in Nashville, Tennessee, U.S., July 27, 2024.
Kevin Worm | Reuters
MicroStrategy has become even more aggressive with its Bitcoin purchases. Saylor said in post on December 16 that over a six-day period starting on December 9, his company acquired 15,350 bitcoins for $1.5 billion.
So far this year, MicroStrategy has purchased 249,850 bitcoins, with almost two-thirds of these purchases occurring since November 11.
“We were going to do it anyway,” Saylor said, referring to the election results. “But what was a headwind became a tailwind.”
A week before the election, she announced MicroStrategy in her quarterly magazine profit release plan to raise $42 billion over three years. This included selling up to $21 billion in shares through financial firms including TD Securities and Barclays, providing much greater liquidity for bitcoin purchases.
Saylor told CNBC it was “probably the most important earnings call in the company's history.”
No amount of ownership is too big for Saylor, who in September predicted that bitcoin could reach $13 million by 2045, which would represent 29% annual growth.
“We will just buy this top forever,” he said in the same television interview in which he compared bitcoin to New York real estate. “Any day is a good day to buy bitcoin. We look at it as cyber-Manhattan.”
Saylor speaks enthusiastically about Bitcoin as the foundation of a new digital economy that will only grow. However, even since his bitcoin strategy was launched in 2020, investors have suffered a number of major headaches, with the stock losing 74% of its value in 2022 before rising sharply over the past two years.
Still, he advises companies to emulate his strategy. Microsoft didn't listen, but Saylor said there were plenty of “zombie companies” whose core businesses were going nowhere where they could put their cash to better use.
“The traditional advice is: you make a transformational acquisition and find you need a merger partner. You are dead. Find someone you can connect with,” Saylor told Lotte in September. “Bitcoin is a universal merger partner, right? The real appeal of digital capital is that it can fix any business.”
TO WATCH: CNBC's full interview with MicroStrategy CEO Michael Saylor
