Bitcoin evangelist Michael Saylor has made $370 million from MicroStrategy stock sales this year
Michael Saylor, chairman and chief executive officer at MicroStrategy, during an interview at the Bitcoin 2023 conference in Miami Beach, Florida, US, on Thursday, May 18, 2023.
Eva Marie Uzcategui | Bloomberg | Getty Images
MicroStrategy founder and bitcoin evangelist Michael Saylor entered into a stock-sale plan with his company last summer that allowed him to unload up to 400,000 shares in the first four months of 2024.
It was a timely agreement for the 59-year-old crypto billionaire.
With the plan more than 90% of the way to completion, Saylor has netted about $370 million from this year’s stock sales, thanks to the stratospheric rise in value of MicroStrategy, which is effectively a bitcoin holding company.
Saylor, who started MicroStrategy in 1989 as a software and tech consulting business and still serves as chairman, has emerged as a bitcoin hero in recent years, telling CNBC last month the cryptocurrency is going to “eat gold.” His company has used its balance sheet and tapped the capital markets to acquire more than 214,000 bitcoins since announcing its strategy to enter the crypto market in mid-2020.
Those assets, equal to about 1% of the total number of bitcoins minted to date, are now worth about $13.6 billion, accounting for the bulk of MicroStrategy’s $21.3 billion market cap. The stock has been a Wall Street darling of late, climbing 91% this year — despite a 37% pullback from its March high — after soaring 346% in 2023, one of the best performers across the U.S. stock market.
Saylor is the largest MicroStrategy shareholder, with Class B holdings worth about $2.3 billion. At the end of 2023, Saylor owned another 400,000 Class A shares due to an option he received in 2014. Those are the shares he’s selling with speed.
Buried near the end of its third-quarter earnings filing on Nov. 1, MicroStrategy announced that the company and Saylor had entered into an agreement, called a 10b5-1 plan, in September, allowing the founder to sell as many as 5,000 shares every trading day from Jan. 2 to April 25 of this year, up to a total of 400,000 shares. The shares were tied to a “vested stock option, which expires if unexercised on April 30, 2024.”
As of this week, Saylor has sold 370,000 shares totaling $372.7 million, according to filings. His Class A holdings are down to 30,000 shares as of the latest sale disclosed on Thursday.
MicroStrategy didn’t respond to requests for comment.
Mark Palmer, an analyst at Benchmark, called the stock sales “entirely programmatic” because of the trading plan executed last year and not at all a reflection of Saylor’s confidence in MicroStrategy or his view of the stock price.
There’s a differing view in the retail investor world, however. Numerous posts on Reddit suggest that Saylor is perhaps selling for other reasons, with some members of the r/MSTR subreddit speculating that he’s using the cash to buy bitcoin directly. Some say they’re selling along with Saylor. The stock is down 29% in April, while bitcoin has dropped 11%.
‘Easy enough to find the truth’
Palmer, who has a “buy” rating on the stock, countered that such a point of view “would be a misread” by investors and traders.
“What we’re seeing here is very straightforward and all of it’s been disclosed already,” Palmer said. “It’s easy for those who either may not understand the details or those who understand the details but might have a short on the stock to twist things around a bit. As is typically the case, it’s easy enough to find the truth.”
Even with the stock sales, the majority of Saylor’s wealth remains wrapped up in his Class B holdings of MicroStrategy, along with the 17,732 bitcoins he purchased in 2020 that are currently worth about $1.1 billion.
Much of the rally in bitcoin and related investments has to do with the emergence of bitcoin exchange-traded funds, which received regulatory approval earlier this year, and the upcoming halving this week. The technical event happens every four years, cutting rewards for bitcoin miners in half and reducing the pace at which new bitcoins enter the market.
In a market where consumers can buy bitcoin directly on various exchanges or choose a host of new ETFs, Saylor has said the ongoing advantage of MicroStrategy is that it’s a leveraged bitcoin play without the management fee. The company can raise money to go deeper in crypto, and last month said it reeled in $782 million “to acquire additional bitcoin.” The cash came from a convertible debt sale at 0.625% interest.
“Is there any company in the world that you wouldn’t like to invest in that could borrow $1 billion at less than 1% interest to invest in your best idea?” Saylor said on CNBC’s “Squawk Box” in March. He added that the company’s leverage leads to volatility, which “attracts capital, and we can then leverage more.”
Benchmark’s Palmer said there are plenty of reasons to remain bullish on MicroStrategy, especially with the halving just around the corner. Following past halving events, the price of bitcoin has jumped.
“If I were in a situation where I had shares in MicroStrategy, this is time where I’d very much want to be holding on to them,” Palmer said.
Tesla CEO Elon Musk attends the Saudi-U.S. Investment Forum, in Riyadh, Saudi Arabia, May 13, 2025.
Hamad I Mohammed | Reuters
Tesla’s shares have finally turned positive for the year.
After a dismal first quarter, which was the worst for the stock in any period since 2022, and a brutal start to April, following President Donald Trump’s announcement of sweeping new tariffs, Wall Street has again rallied around the electric vehicle maker.
The stock rose 3.6% on Monday to $410.26, topping its closing price of 2024 by over $6. It’s up 85% since bottoming for the year at $221.86 on April 4. A new filing revealed that CEO Elon Musk purchased about $1 billion worth of shares in the company through his family foundation.
It’s the second straight year Tesla has bounced back after a down first quarter. Last year, the shares fell 29% in the first three months before ending up 63% for 2024.
In recent weeks, analysts have praised the EV maker’s proposed pay plan for Musk, which could amount to a $1 trillion windfall for the world’s richest person over the next decade. The company has also gotten a boost from its new MegaBlocks battery energy storage systems that Tesla ships preassembled to businesses looking to lower their power costs or make greater use of electricity from renewable resources.
Even with the rebound, Tesla is the second-worst performer this year among tech’s megacaps, ahead of only Apple, which is down about 5% in 2025. Tesla is still in the midst of a multi-quarter sales slump due to an aging lineup of EVs and increased competition from lower-cost competitors in China, namely BYD.
Tesla has seen a consumer backlash, in part because of Musk’s political activities, including spending nearly $300 million to propel President Trump back to the White House and his work with the Trump administration to slash the federal workforce.
Tesla leadership has been working to shift investors’ attention to other topics such as robotaxis and humanoid robots.
However, the company has yet to deliver vehicles that are safe to use without a human onboard and ready to take control if needed. And while Musk is touting Tesla’s Optimus robots, which he says will be able to do everything from factory work to babysitting, a product is still a long way from hitting the market.
WATCH: Musk’s share purchase
Google CEO Sundar Pichai gestures to the crowd during Google’s annual I/O developers conference in Mountain View, California on May 20, 2025.
Camille Cohen | Afp | Getty Images
Alphabet has joined the $3 trillion club.
Shares of the search giant jumped more than 4% on Monday, pushing the company into territory occupied only by Nvidia, Microsoft and Apple.
The stock got a big lift in early September from an antitrust ruling by a judge, whose penalties came in lighter than shareholders feared. The U.S. Department of Justice wanted Google to be forced to divest its Chrome browser, and last year a district court ruled that the company held an illegal monopoly in search and related advertising.
But Judge Amit Mehta decided against the most severe consequences proposed by the DOJ, which sent shares soaring to a record. After the big rally, President Donald Trump congratulated the company and called it “a very good day.”
Alphabet shares are now up more than 30% this year, compared to the 15% gain for the Nasdaq.
The $3 trillion milestone comes roughly 20 years after Google’s IPO and a little more than 10 years after the creation of Alphabet as a holding company, with Google its prime subsidiary.
CEO Sundar Pichai was named CEO of Alphabet in 2019, replacing co-founder Larry Page. Pichai’s latest challenge has been the surge of new competition due to the rise of artificial intelligence, which the company has had to manage through while also fending off an aggressive set of regulators in the U.S. and Europe.
The rise of Perplexity and OpenAI ended up helping Google land the recent favorable antitrust ruling. The company’s hopes of becoming a major AI player largely ride with Gemini, Google’s flagship suite of AI models.
Technology
Bessent: TikTok deal ‘framework’ reached with China, Trump and Xi will finalize it Friday
Samuel Boivin | Nurphoto | Getty Images
The U.S. and China have reached a ‘framework’ deal for social media platform TikTok, Treasury Secretary Scott Bessent said Monday.
“It’s between two private parties, but the commercial terms have been agreed upon,” he said from U.S.-China talks in Madrid.
Both President Donald Trump and Chinese President Xi Jinping will meet Friday to discuss the terms. Trump also said in a Truth Social post Monday that a deal was reached “on a ‘certain’ company that young people in our Country very much wanted to save.”
Bessent indicated that the framework could pivot the platform to U.S.-controlled ownership.
TikTok did not immediately respond to a request for comment.
The comments came during the latest round of trade discussions between the U.S. and China. Relations have soured between the two countries in recent months from Trump’s tariffs and other trade restrictions.
At the same time, TikTok parent company ByteDance faces a Sept. 17 deadline to divest the platform’s U.S. business or face being shut down in the country.
U.S. Trade Representative Jamieson Greer said Monday that the deadline may need to be pushed back to get the deal signed, but there won’t be ongoing extensions.
Congress passed a law last year prohibiting app store operators like Apple and Google from distributing TikTok in the U.S. due to its “foreign adversary-controlled application” status.
But Trump postponed the shutdown in January, signing an executive order in January that gave ByteDance 75 more days to make a deal. Further extensions came by way of executive orders in April and in June.
Commerce Secretary Howard Lutnick said in July that TikTok would shutter for Americans if China doesn’t give the U.S. more autonomy over the popular short-form video app.
As for who controls the platform, Trump told Fox News in June that he had a group of “very wealthy people” ready to buy the app and could reveal their identities in two weeks. The reveal never came.
He has previously said he’d be open to Oracle Chairman Larry Ellison or Tesla CEO Elon Musk buying TikTok in the U.S. Artificial intelligence startup Perplexity has submitted a bid for an acquisition, as has businessman Frank McCourt’s Project Liberty internet advocacy group, CNBC reported in January.
Trump told CNBC in an interview last year that he believed the platform was a national security threat, although the White House started a TikTok account in August.
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