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Michael Saylor’s Strategy to join Wall Street elite with $14 billion windfall

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Michael Saylor’s Strategy is likely to register an unrealized gain of about $14 billion in the second quarter, putting the once floundering enterprise software maker turned leveraged Bitcoin proxy among the select ranks of corporate titans such as Amazon.com Inc. and JPMorgan Chase & Co.

Unlike the ten or so U.S. multinationals whose operating profits are expected to exceed $10 billion last quarter by generating billions of dollars in sales, the former MicroStrategy Inc. can attribute the eye-popping results to a rebound in the price of Bitcoin and a fairly recent accounting change when it comes to valuing its massive holdings of the cryptocurrency. Strategy is forecast to post only about $112.8 million in second-quarter revenue from the software business, according to analysts surveyed by Bloomberg News. 

The likely record profit for the three months ended June 30 follows a barrage of criticism from naysayers such as Jim Chanos. The renowned short-seller has recommended an arbitrage trade to short the shares of Strategy and buy Bitcoin, betting the large premium the stock commands over the value of its token holdings will shrink. The call has sparked a war of words that has captivated Wall Street, with Chanos calling Saylor’s model to value the crypto-treasury firm “financial gibberish” while Saylor argued that Chanos just does not understand it. 

“Saylor definitely has a right to feel vindicated,” said Mark Palmer, an analyst at Benchmark Capital, who has maintained a “buy” rating on Strategy since February 2024. “He’s had people criticizing him for more than four years now and his company has outperformed all other stocks and even the S&P by a long mile.”

Strategy’s shares have soared over 3,300% since Saylor began buying Bitcoin in the middle of 2020 as a hedge against inflation. Bitcoin is up around 1,000% during the same period, while the S&P 500 has increased around 115%. The stock rose 40% in the second quarter as the S&P climbed 11%.   

In the first quarter, Strategy adopted an accounting change that requires valuing the firm’s now roughly $64 billion in Bitcoin at market prices. Strategy and fellow corporate buyers of Bitcoin are now recognizing the unrealized changes that often produce big swings in earnings. Strategy posted a record $4.2 billion loss the first quarter, which saw Bitcoin slump 12%. 

Prior to the accounting change, Strategy had been classifying its Bitcoin holdings similar to intangible assets like patents or trademarks. That designation forced Strategy to permanently mark down the value of its holdings when the price of Bitcoin dropped below the previous carrying value. Gains could only be recognized when tokens were sold. 

The company held 528,185 Bitcoin at the beginning of the quarter, worth over $43.5 billion when the tokens traded for about $82,444.71 each on March 31. The 30% appreciation in Bitcoin increased the market value of those holdings by over $13 billion alone, and the dozen weekly purchases since have tacked on over $600 million more to the unrealized gains, according to Bloomberg News calculations.

Strategy is expected to release second-quarter results in August. A company representative didn’t reply to a request for comment.

Even though the change in accounting was widely known, the first-quarter loss has triggered several class-action lawsuits alleging Strategy executives made untrue and misleading statements that resulted in harm to shareholders. Strategy said it intended to “vigorously defend against these claims” in a recent filing with the U.S. Securities and Exchange Commission. 



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Visa launches stablecoins advisory practice to keep up with crypto wave

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Another major financial institution is doubling down on stablecoins and on crypto. This time, it’s Visa. The company announced on Monday the launch of its Stablecoins Advisory Practice, a service which aims to aid fintechs, banks, and other businesses with their strategy and implementation of stablecoins. 

“Helping our clients grow is frankly the reason we exist in stablecoin,” said Carl Rutstein, global head of Visa Consulting and Analytics, in an interview with Fortune. “What Visa is doing in this space is just one more area where our clients have a need.” 

Stablecoins are a type of cryptocurrency designed to maintain a constant value by means of reserves that peg them to a fiat currency, typically the U.S. dollar. They have recently been embraced by a wide range of companies from the traditional financial sector following President Donald Trump’s signing of the Genius Act in July, legislation which creates rules for issuing the digital asset. In the months since, other payments powerhouses like Paypal and Mastercard have boosted their stablecoin capabilities. 

Rutstein said that Visa’s stablecoins advisory has dozens of clients, among whom are Navy Federal Credit Union, the credit union VyStar, and a financial institution called Pathward. He said the practice will help businesses with their strategy, tech and operations, and implementation of stablecoins. Its clients use cases for stablecoins include cross-border transactions, especially to countries with volatile currencies, and business-to-business transactions. After using Visa’s advisory, Rutstein said some businesses may push forward with stablecoins, while others may conclude there is not a customer need. The company said that it expects the practice will grow to hundreds of clients. 

Visa is by no means new to crypto. In 2023, the company piloted stablecoin settlement using USDC, and it now has over 130 stablecoin-linked card issuing programs in more than 40 countries. Visa also has about $3.5 billion in annualized stablecoin settlement volume. 

“Stablecoins may represent an opportunity to enhance speed and lower cost in payments,” said Matt Freeman, senior vice president of Navy Federal Credit Union, in the statement. “So with the support of Visa, we are evaluating how this technology could fit into our broader strategy to deliver meaningful value to our 15 million members worldwide.”

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.



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Not all CEOs favor Trump’s executive order to block state AI laws

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Good morning. What do companies in health care, insurance, utilities, construction, professional services, financial services, education, transportation, waste management, and alcohol/cannabis distribution, among others, have in common? They’re regulated at the state level. In certain areas (food safety, environmental standards and data privacy), a mix of state and federal mandates apply. Washington sets the baseline, and individual states layer on laws that aim to reflect the priorities of local voters. In the absence of a federal missive, like Roe v. Wade in legalizing abortion, state regulations apply.

So one might assume that CEOs would welcome Donald Trump’s executive order on AI last week that blocks state laws setting AI standards in favor of “a minimally burdensome national standard.” Silicon Valley types like OpenAI CEO Sam Altman, venture capitalist Marc Andreessen and, of course, AI czar David Sacks, praise the move as necessary for America to compete against the bête noire of China. But seven leaders I spoke with had more mixed views. (I spoke to them without attribution to encourage honest feedback.)

Nobody wants a growing patchwork of state laws that cause confusion, rising compliance costs, or what one person called “a race to be the Delaware of AI.” But neither do they want a vacuum when it comes to mitigating the risks or a situation where laws are set by the White House instead of Congress. Among the concerns:

The Executive Order is probably not legal. Everyone agreed that Trump can’t dismiss state rights with the stroke of a pen. As law firm Fisher Phillips notes, “all current and pending state and local AI laws will remain enforceable unless and until a court blocks them through an injunction, or Congress passes a federal law that preempts them.” The consensus: Congress should act—and fear-mongering doesn’t help. “I’m in a state with a lot of regulation and a lot of innovation,” said one California-based CEO. “What matters is resources, talent and technology.”

Businesses want clarity and protection. Tennessee’s ELVIS Act protects individuals from the unauthorized use of AI to mimic their voice and likeness; Texas prohibits its use for unlawful discrimination or sexually explicit content. Colorado requires companies to inform consumers when AI is used for high-stakes decisions from hiring to lending. Smaller businesses want the behemoths of tech kept in check. “Rules can level the playing field,” said one source, “and it’s more expensive to set standards in court.”

The U.S. needs to maintain its competitive edge. The EU Artificial Intelligence Act gives people the right to opt out of having their data used to train models, which stifles innovation. China has an AI Plus framework and President Xi Jinping has proposed creating a World Artificial Intelligence Cooperation Organization (WAICO) to promote a global governance system. The U.S. needs to, as one person put it, have a seat at the table with laws that protect copyright, patents, market access and consumer protections while driving regulation. “I’d rather have less regulation than more regulation,” an enterprise tech leader told me on Friday, “but I’d rather have some regulation than no regulation.”

Contact CEO Daily via Diane Brady at diane.brady@fortune.com

Top news

Weekend mass shootings

Australia Prime Minister Anthony Albanese has vowed action to tighten gun laws after a father and son, using legally licensed firearms, killed 15 people at a Hanukkah celebration at Bondi Beach. Meanwhile, Brown University has called off final exams and sent students home early after a gunman killed two and injured nine in an on-campus shooting. 

David Zaslav’s potential payday

Warner Bros. Discovery CEO David Zaslav is poised to collect as much as $1 billion from the sale of WBD if the bidding war between Netflix and Paramount continues to drive up the company’s stock price. His enormous payout will contrast starkly with the job cuts that are expected regardless of which deal goes through and the cost-cutting he’s already imposed at WBD. 

Volkswagen’s Germany closure

Volkswagen will cease production at a Dresden, Germany, plant on Tuesday, the first time it’s shuttered a production facility in Germany in 88 years. Europe’s largest automaker is contending with weak demand in China and Europe and the sting of U.S. tariffs. 

Private equity squeezes fire departments

Companies backed by private equity firms are quietly buying up the public safety systems needed to fight fires and increasing costs for budget-constrained U.S. fire departments, 85% of which are crewed by volunteers. 

Google’s SpaceX gain

Google parent Alphabet is poised to record another gain as the value of SpaceX nears $800 billion. Elon Musk’s rocket company completed a tender offer that priced shares at $421. Alphabet joined Fidelity Investments in a $1 billion funding round in 2015 in exchange for what was then a 10% stake in SpaceX. 

Christmas kitsch boom

Connecticut is cashing in on its role in sappy Christmas movies. Locations in the state are the settings for at least 22 Christmas movies by Hallmark, Lifetime and others, and it’s now promoting tours of the quaint towns and cities where the predictable—but hugely popular—movies are filmed.

The markets

S&P 500 futures are up 0.44% this morning. The last session closed down 1.07%. STOXX Europe 600 was up 0.75% in early trading. The U.K.’s FTSE 100 was up 0.88% in early trading. Japan’s Nikkei 225 was down 1.31%. China’s CSI 300 was down 0.63%. The South Korea KOSPI was down 1.84%. India’s NIFTY 50 was down 0.07%. Bitcoin went to $90K.

Around the watercooler

The Asian Infrastructure Investment Bank’s first president defends China’s role as ‘responsible stakeholder’ in a less multilateral world by Nicholas Gordon

Kevin Hassett says he’d be happy to talk to Trump everyday as Fed chair, but the president’s opinion would have ‘no weight’ on the FOMC by Jason Ma

Atlantic CEO Nick Thompson on how he learned to ‘just keep moving forward’ after his famous firing at 22 by Nick Lichtenberg

Everything the Trump administration is doing in Venezuela involves oil and regime change—even if the White House won’t admit it by Jordan Blum

CEO Daily is compiled and edited by Claire Zillman and Lee Clifford.



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Rob Reiner, comedy legend who directed ‘When Harry Met Sally’ and ‘Spinal Tap,’ dead at 78

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Rob Reiner, the son of a comedy giant who went on to become one, himself, as one of the preeminent filmmakers of his generation with movies such as “The Princess Bride,” “When Harry Met Sally …” and “This Is Spinal Tap,” has died. He was 78.

Reiner and his wife, Michele Singer, were found dead Sunday at their home in the Brentwood neighborhood of Los Angeles. A law enforcement official briefed on the investigation confirmed that Reiner and Singer were the victims. The official could not publicly discuss details of the investigation and spoke to The Associated Press on condition of anonymity.

Authorities were investigating an “apparent homicide,” said Capt. Mike Bland with the Los Angeles Police Department. The Los Angeles Fire Department said it responded to a medical aid request shortly after 3:30 p.m.

Reiner grew up thinking his father, Carl Reiner, didn’t understand him or find him funny. But the younger Reiner would in many ways follow in his father’s footsteps, working both in front and behind the camera, in comedies that stretched from broad sketch work to accomplished dramedies.

“My father thought, ‘Oh, my God, this poor kid is worried about being in the shadow of a famous father,’” Reiner said, recalling the temptation to change his name to “60 Minutes” in October. “And he says, ‘What do you want to change your name to?’ And I said, ‘Carl.’ I just wanted to be like him.”

After starting out as a writer for “The Smothers Brothers Comedy Hour,” Reiner’s breakthrough came when he was, at age 23, cast in Norman Lear’s “All in the Family” as Archie Bunker’s liberal son-in-law, Michael “Meathead” Stivic. But by the 1980s, Reiner began as a feature film director, churning out some of the most beloved films of that, or any, era. His first film, the largely improvised 1984 cult classic “This Is Spinal Tap,” remains the urtext mockumentary.

After the 1985 John Cusack summer comedy, “The Sure Thing,” Reiner made “Stand By Me” (1986), “The Princess Bride” (1987) and “When Harry Met Sally …” (1989), a four-year stretch that resulted in a trio of American classics, all of them among the most often quoted movies of the 20th century.

A legacy on and off screen

For the next four decades, Reiner, a warm and gregarious presence on screen and an outspoken liberal advocate off it, remained a constant fixture in Hollywood. The production company he co-founded, Castle Rock Entertainment, launched an enviable string of hits, including “Seinfeld” and “The Shawshank Redemption.” By the turn of the century, its success rate had fallen considerably, but Reiner revived it earlier this decade. This fall, Reiner and Castle Rock released the long-in-coming sequel “Spinal Tap II: The End Continues.”

All the while, Reiner was one of the film industry’s most passionate Democrat activists, regularly hosting fundraisers and campaigning for liberal issues. He was co-founder of the American Foundation for Equal Rights, which challenged in court California’s ban on same-sex marriage, Proposition 8. He also chaired the campaign for Prop 10, a California initiative to fund early childhood development services with a tax on tobacco products. Reiner was also a critic of President Donald Trump.

That ran in the family, too. Reiner’s father opposed the Communist hunt of McCarthyism in the 1950s and his mother, Estelle Reiner, a singer and actor, protested the Vietnam War.

“If you’re a nepo baby, doors will open,” Reiner told the Guardian in 2024. “But you have to deliver. If you don’t deliver, the door will close just as fast as it opened.”

‘All in the Family’ to ‘Stand By Me’

Robert Reiner was born in the Bronx on March 6, 1947. As a young man, he quickly set out to follow his father into entertainment. He studied at the University of California, Los Angeles film school and, in the 1960s, began appearing in small parts in various television shows.

But when Lear saw Reiner as a key cast member in “All in the Family,” it came as a surprise to the elder Reiner.

“Norman says to my dad, ‘You know, this kid is really funny.’ And I think my dad said, ‘What? That kid? That kid? He’s sullen. He sits quiet. He doesn’t, you know, he’s not funny.’ He didn’t think I was anyway,” Reiner told “60 Minutes.”

On “All in the Family,” Reiner served as a pivotal foil to Carroll O’Connor’s bigoted, conservative Archie Bunker. Reiner was five times nominated for an Emmy for his performance on the show, winning in 1974 and 1978. In Lear, Reiner also found a mentor. He called him “a second father.”

“It wasn’t just that he hired me for ‘All in the Family,’” Reiner told “American Masters” in 2005. “It was that I saw, in how he conducted his life, that there was room to be an activist as well. That you could use your celebrity, your good fortune, to help make some change.”

Lear also helped launch Reiner as a filmmaker. He put $7.5 million of his own money to help finance “Stand By Me,” Reiner’s adaptation of the Stephen King novella “The Body.” The movie, about four boys who go looking for the dead body of a missing boy, became a coming-of-age classic, made breakthroughs of its young cast (particularly River Phoenix) and even earned the praise of King.

With his stock rising, Reiner devoted himself to adapting William Goldman’s 1973’s “The Princess Bride,” a book Reiner had loved since his father gave him a copy as a gift. Everyone from François Truffaut to Robert Redford had considered adapting Goldman’s book, but it ultimately fell to Reiner (from Goldman’s own script) to capture the unique comic tone of “The Princess Bride.” But only once he had Goldman’s blessing.

“At the door he greeted me and he said, ‘This is my baby. I want this on my tombstone. This is my favorite thing I’ve ever written in my life. What are you going to do with it?’” Reiner recalled in a Television Academy interview. “And we sat down with him and started going through what I thought should be done with the film.”

Though only a modest success in theaters, the movie — starring Cary Elwes, Mandy Patinkin, Wallace Shawn, André the Giant and Robin Wright — would grow in stature over the years, leading to countless impressions of Inigo Montoya’s vow of revenge and the risky nature of land wars in Asia.

‘When Harry Met Sally …”

Reiner was married to Penny Marshall, the actor and filmmaker, for 10 years beginning in 1971. Like Reiner, Marshall experienced sitcom fame, with “Laverne & Shirley,” but found a more lasting legacy behind the camera.

After their divorce, Reiner, at a lunch with Nora Ephron, suggested a comedy about dating. In writing what became “When Harry Met Sally …” Ephron and Reiner charted a relationship between a man and a woman (played in the film by Billy Crystal and Meg Ryan) over the course of 12 years.

Along the way, the movie’s ending changed, as did some of the film’s indelible moments. The famous line, “I’ll have what she’s having,” said after witnessing Ryan’s fake orgasm at Katz’s Delicatessen, was a suggestion by Crystal — delivered by none other than Reiner’s mother, Estelle.

The movie’s happy ending also had some real-life basis. Reiner met Singer, a photographer, on the set of “When Harry Met Sally …” In 1989, they were wed. They had three children together: Nick, Jake and Romy.

Reiner’s subsequent films included another King adaptation, “Misery” (1990) and a pair of Aaron Sorkin-penned dramas: the military courtroom tale “A Few Good Men” (1992) and 1995’s “The American President.”

By the late ’90s, Reiner’s films (1996’s “Ghosts of Mississippi,” 2007’s “The Bucket List”) no longer had the same success rate. But he remained a frequent actor, often memorably enlivening films like “Sleepless in Seattle” (1993) and “The Wolf of Wall Street” (2013). In 2023, he directed the documentary “Albert Brooks: Defending My Life.”

In an interview earlier this year with Seth Rogen, Reiner suggested everything in his career boiled down to one thing.

“All I’ve ever done is say, ‘Is this something that is an extension of me?’ For ‘Stand by Me,’ I didn’t know if it was going to be successful or not. All I thought was, ‘I like this because I know what it feels like.’”



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