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Michael Saylor’s Strategy faces toughest test yet as MSTR slumps

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Billionaire Michael Saylor has been in tight spots before but nothing like this. The share price of Saylor’s firm, Strategy, which owns over 3% of the world’s Bitcoin, is down dramatically. Worse, the company faces twin headwinds in the form of a bearish crypto market and an impending rule change that will likely trigger a mass selloff of its stock. On Monday, the company announced a $1.2 billion reserve fund to meet impending interest and dividend obligations, but that did little to prop up its shares. All of this fueled fresh attacks from Saylor’s critics who say Strategy’s unusual business model, which revolves around selling stock to buy Bitcoin, is unsustainable or even a Ponzi scheme.

Saylor has ridden out storms in the past. That includes an accounting scandal in 2000 that almost sank one of his previous companies and saw him lose $6 billion of his personal fortune in a day. Saylor’s defenders, meanwhile, dismiss critics as knee-jerk Bitcoin detractors who don’t understand the currency or the corporate finance techniques underlying Strategy’s operations.

Saylor may escape from this bind, as he has in the past, but this time the stakes are higher. In recent years, Strategy’s purchases have helped fuel crypto’s record rise, and turned Saylor into Bitcoin’s leading evangelist. This means any move by Strategy to dump part of its holdings—something its CEO hinted last week could happen—would not only depress prices, but could spark a crisis of confidence and a broader selloff. Meanwhile, a further plunge in Strategy’s share price could not only threaten its future viability, but spur the collapse of dozens of other firms that have copied its business model. The coming months are likely to demonstrate once and for all whether Saylor is a pioneer in crypto finance, as his backers claim, or just another high-stakes gambler whose luck has run out.

A looming $8 billion selloff

The crypto industry likes to hail October as “Uptober,” but this year failed to deliver the customary double-digit price boost. Instead, the month brought one of the biggest wipeouts in the industry’s history, and for Strategy, the month brought an extra helping of bad news when, on Oct. 10, financial giant MSCI proposed a new rule that would exclude it from a series of popular indexes.

This delisting process, which looks set to go into effect in February, would oblige fund managers around the world to shed their holdings of Strategy, and other firms whose assets consist of 50% or more of crypto. In November, JPMorgan warned the rule change could see funds dump $2.3 billion worth of Strategy shares, and that the selloff could climb to over $8 billion if other index compilers followed MSCI’s example.

The market’s growing awareness about MSCI’s plans has already triggered a selloff. Shares of MSTR (the MSTR ticker sign reflects Strategy’s previous name, Microstrategy) are down around 50% since Oct. 1. This has led a key metric known as mNAV, which reflects the value of a crypto company’s shares as a ratio of its Bitcoin holdings, to drop below one on several recent occasions. For a company whose mNAV a year ago reached around 2.45, the current figure underscores how the longtime premium that Strategy shares held over Bitcoin has evaporated.

In response to such a spate of bad news, most CEOs would have issued a series of muted statements asking for patience. But Saylor is not an ordinary CEO and has instead responded by cranking up the number of memes he posts on social media. The memes extol Bitcoin and depict Saylor in AI-generated action hero poses—leading his many acolytes to retweet the memes or post their own version of them.

These meme tactics have served Saylor well in the past, turning Strategy into a momentum play during bull markets. More recently, though, the gimmick has failed to stanch the stock’s downturn, and last month, Saylor posted a rare social media misfire. Seeking to rebut a rumor the company was selling its Bitcoin, Saylor shared an image of himself riding a life preserver in storm-tossed seas as a flaming ocean liner sank behind him. Critics, including Saylor fans, pointed out the meme implied Strategy’s captain was saving himself at a time of trouble rather than going down with his ship.

Regardless of Saylor’s intent, the minor controversy raises questions about whether Strategy will resort to selling its Bitcoin holdings—a move the company has portrayed as unthinkable but, in recent weeks, appears set to accept.

Selling stock to buy Bitcoin

In late November, Strategy acquired 130 Bitcoin, bringing its total hoard to an even 650,000, which is worth around $58.5 billion at early December prices. For context, that amounts to around 3.1% of Bitcoin’s total supply of 21 million (95% of which has been mined), and makes Strategy the biggest holder of the currency save for its creator, Satoshi Nakamoto, whose 1.1 million coins are believed to be gone forever.

According to Saylor, the company has paid an average price of $74,436 per Bitcoin, spending a total of around $48.4 billion, including fees and expenses. In order to pull this off, Strategy has needed a source of capital, and given that Bitcoin does not produce any yield, the company’s go-to technique has been to sell common shares to fund its purchases.

A big upside to this approach is that, unlike debt, common shares do not create any financial obligations for the company. That’s not the case, though, with preferred shares—and Strategy has issued plenty of these as well, which obliges it to pay regular dividends to shareholders. These obligations include payments of roughly $200 million that are due by Dec. 31, the bulk of which are owed in the form of dividends (Strategy, like most companies, also carries some debt).

In order to project a sense of financial stability, Strategy took the unusual step in early December of creating a so-called dollar reserve of $1.4 billion that Saylor says will be enough to cover the next 21 months of dividend obligations.

Saylor announced the reserve fund at a Dec. 1 investor presentation where he added, with his usual bravado: “It’s our intention to keep stacking Bitcoin.” In the near future, though, that goal is likely to be aspirational and Strategy may instead find itself selling Bitcoin instead.

“We can sell Bitcoin and we would sell Bitcoin if we needed to fund our dividend payments below 1x mNAV,” Strategy CEO Phong Le said on a podcast last Friday. It was a remarkable statement from a company that is premised on the value of Bitcoin always increasing. More remarkable was when Saylor, who frequently exhorts the popular hold-on-to-your-Bitcoin phrase “HODL,” repeated on Monday that Strategy could sell some Bitcoin.

On Tuesday, Strategy CFO Andrew Kang qualified the statement by saying the company planned to sell Bitcoin as a last resort and only if mNAV stays below one for a “very extended period.”

Whatever the specifics, Strategy’s acknowledgment it could sell Bitcoin combined with the new dollar reserve fund has sparked a new wave of vitriol from Strategy critics. Those include Peter Schiff, an advocate for the gold industry and longtime crypto critic, who claims the company is coming undone, and that Saylor is the “biggest con man” on Wall Street.

If Schiff’s view—hardly a consensus one—is correct and Strategy has to liquidate, then the broader crypto market could be hit hard since the selloff would almost certainly trigger a downward price spiral for Bitcoin. Even if Strategy has to sell only a portion of its holdings, it could trigger a contagion in which hundreds of other so-called digital asset treasuries (DATs) do the same.

But even as skeptics label Strategy and the DAT model as a house of cards built on financial chicanery, others view them as early leaders in an emerging category of crypto banks.

‘All the bad news is out there’

Whatever one thinks of Saylor, there is no denying he is a natural showman. In his Dec. 1 presentation announcing the new U.S. dollar reserve, he displayed a futuristic-looking spaceship in garish green and orange with a Bitcoin powered reactor at its core. “Think of [the dollar reserve] as a $USD battery. We’re basically using a nuclear reactor to spin a generator to charge a battery,” explained Saylor.

Courtesy of Strategy

For Saylor’s detractors, all of this smacks of the worst type of hucksterism. Others see a visionary who is using compelling metaphors and imagery to help the public understand a complex new financial mechanism.

The latter include Sebastian Bea, a former longtime BlackRock executive and Olympic rower, who is now president of a digital asset treasury called ReserveOne. According to Bea, Saylor is pursuing a sophisticated long-term strategy, and has surrounded himself with a team of corporate finance experts, including board member Peter Briger, who has had a distinguished career at Goldman Sachs and Fortress Investment Group.

In this context, Saylor’s plans to purchase a growing supply of Bitcoin by tapping into capital markets for equity, commodities, and derivatives makes sense. As he and Strategy’s CFO explained this week, that plan includes bringing in revenue by lending Bitcoin and selling covered call options.

For all of this to work, though, the value of Bitcoin will have to keep appreciating. This notion strikes crypto skeptics as absurd, but crypto advocates point out correctly that Bitcoin has grown faster than nearly any other asset over the past decade, and is poised for longer-term gains as large entities ranging from sovereign wealth funds to university endowments add it to their portfolios. In the latest bullish signal, Vanguard—which has refused to add crypto to its portfolio for years—elected to add Bitcoin and other crypto ETFs this week.

If Bitcoin does keep appreciating, Strategy will be able to keep obtaining credit against the surplus value in the same way a company can do with real estate in a desirable market. There will of course be downturns but, according to Bea, Strategy “has planned for this” and has a healthy overall asset to debt ratio.

Bea adds that the recent wave of digital asset treasury companies are akin to a new type of bank, and that their model is evolving rapidly. He points out that some, including ReserveOne, are based around cryptocurrencies like Ethereum that do provide yield unlike Bitcoin, which provides additional breathing room on the corporate finance front. Bea acknowledged that the impending move by MSCI to exclude DATs from indexes could be a significant headwind, and said that companies based around crypto holdings need time to evolve.

Cosmo Jiang, a partner at the crypto-focused venture capital firm Pantera, likewise believes that digital asset treasuries—including a Solana-focused company he is backing—will become a permanent feature of the financial landscape.

“We’re seeing the genesis of a whole new category of business,” Jiang told Fortune, adding that DATs are poised to earn significant revenue from the fast-growing world of decentralized finance.

In separate remarks to Bloomberg, Jiang made the case that the sector is currently at a low point, but that the current malaise around Strategy and similar firms is temporary. “We’re at the point where all the bad news is out there, and the bears are the loudest voices in the room.”

Jiang noted, however, that many in the recent wave of crypto-hoarding companies are unlikely to survive, and that the business model required not just a stash of tokens, but deep experience in capital markets and corporate finance.

“There will be two or three large winners” for each major cryptocurrency, he predicted. If this is the case, the coming months will likely determine whether one of those is Strategy.





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Treasury Secretary Bessent insists Trump’s tariff agenda is ‘permanent,’ saying the White House can recreate it even with a Supreme Court loss

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The Supreme Court is in the process of deciding the fate of President Trump’s tariffs, but even if the administration loses, it might not matter, said Treasury Secretary Scott Bessent.

At issue is the Trump administration’s use of the International Emergency Economic Powers Act (IEEPA) to justify some of its tariffs, including its baseline 10% duty on almost all nations. IEEPA, passed by Congress in 1977, gives the President “broad authority” on economic issues like tariffs after declaring a “national emergency,” for which the White House has pointed to elevated fentanyl imports from abroad.

Although not guaranteed, it’s possible the Supreme Court will decide the fentanyl crisis can’t be used as an emergency to justify broad tariffs on U.S. trading partners, which would make many of the administration’s tariffs invalid. In that case, the White House will just pivot to another justification to make tariffs permanent, said Bessent during the New York Times DealBook Summit this week. 

“We can recreate the exact tariff structure with 301’s, with 232’s, with the, I think they’re called 122’s,” he said, referring to several sections of various trade acts that could serve as alternatives to the administration’s current justification for its tariffs.

When interviewer and DealBook editor Andrew Ross Sorkin questioned whether these measures could exist permanently, Bessent replied “permanently.” He later clarified that tariffs under Section 122 of the Trade Act of 1974 would not be permanent.

In sum, the Constitution gives Congress purview over tariffs, but over the years it has given the executive branch more leeway to levy them through the trade acts mentioned by Bessent. 

Each of the sections Trump’s team may consider comes with its own set of pros and cons. Section 122 would be the quickest method to restore tariffs in the case of a Supreme Court loss because it doesn’t require an investigation on a trading partners’ practices. Using this justification would let the government levy tariffs up to 15%, with certain limits, but only for 150 days before congressional action is required.

The other two sections, as Bessent pointed out, have no time limit or limit on the tariff rate that can be levied, although they have other caveats. To justify tariffs under Section 301 of the Trade Act of 1974, the administration would need to conduct an investigation into practices by its trading partners it sees as “unjustifiable” or “unreasonable.” Trump did this successfully during his first administration to justify tariffs on China in 2017.

Alternatively, the administration could turn to Section 232 of the Trade of the Trade Expansion Act of 1962 and try to justify tariffs as an issue of national security. The White House is already using this justification to underpin its tariffs on steel, aluminum, and autos and those are not being scrutinized by the Supreme Court. 

Finally, experts have previously told Fortune, Trump could also ask Congress to pass a bill giving the president explicit authority to levy tariffs. Although it would require some caveats in terms of scope, and possibly duration of the tariffs, it would likely receive bipartisan support, international trade law expert and University of Kansas Law School professor Raj Bhala told Fortune

Despite the options in the administration’s back pocket, Bessent said he was optimistic about the White House’s chances at the Supreme Court. 

He also said a loss in court would be “a loss for the American people,” and pointed to the fact that China agreed to tighten control over exports of precursor chemicals used to make fentanyl earlier this year—a decision which he attributes to pressure created by the administration’s tariffs.

“I have been very consistent on this, that tariffs are a shrinking ice cube. The ultimate goal is to rebalance trade and to bring back domestic production,” Bessent said.



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Before running the world’s most valuable company, Jensen Huang was a 9-year-old janitor in Kentucky

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The CEO of the world’s most valuable company didn’t learn about America through elite universities or tech incubators. His education started in a rural Kentucky boarding school where the students smoked, carried knives, and the youngest student on campus, at 9 years old, was assigned to clean the toilets.

That student was Jensen Huang.

In a recent podcast appearance with Joe Rogan, the Nvidia CEO traced that improbable starting point back to his parents, who had sent him and his brother to the United States in the mid-1970s with almost nothing. The family had been living in Bangkok during one of Thailand’s periodic coups, and his parents decided it was no longer safe to keep the children there. They contacted an uncle they had never visited in Tacoma, Wash., and asked him to find a school in America that would accept two foreign boys with almost no savings.

He found one: Oneida Baptist Institute in Clay County, Ken., one of the poorest counties in the country then and now. The dorms had no closet doors, no locks, and a population of kids who smoked constantly–Huang said he also tried smoking for a week, at 9 —and settled disputes with knives. Huang’s roommate was a 17-year-old wrapped in tape from a recent fight; the “toughest kid in school,” he said. Every student had a job. His brother, was sent to the tobacco fields the school ran to fund the school—“kind of like a penitentiary”—while Huang became the janitor, cleaning the bathrooms for a hundred teenaged boys (“I just wished they would be a bit more careful” in the bathroom, he joked.)

That indefatigable cheerfulness, even when describing scenes that sound brutal to almost anyone else, ran through the entire interview. 

Huang said most of his memories from that period were good, and remembers the time he told his parents his amazement after eating at a restaurant: “Mom and dad, we went to the most amazing restaurant today. This whole place is lit up. It’s like the future. And the food comes in a box and the food is incredible. The hamburger is incredible.”

“It was McDonald’s,” Huang laughed. 

Indeed, these memories were relayed to his parents late; the boys were navigating all of this alone. International phone calls were too expensive, so his parents bought them a cheap tape deck. Once a month, they recorded an audio letter describing their lives in coal country and mailed it back to Bangkok. Their parents taped over the same cassette and mailed it back.

Two years later, Huang’s parents finally made it to America, with just suitcases and only a bit of money. His mother worked as a maid. His father, a trained engineer, looked for work by circling openings in the newspaper classifieds and calling whoever picked up. He eventually found a job at a consulting engineering firm designing factories and refineries.

“They left everything behind,” Huang said. “They started over in their late thirties.”

He still carries one memory from those early years that he said “breaks my heart.” Not long after his parents arrived in the U.S., the family was living in a rented, furnished apartment when he and his brother accidentally broke a flimsy particle-board coffee table. 

“I just still remember the look on my mom’s face,” he said. “They didn’t have any money, and she didn’t know how she was going to pay it back.”

For Huang, moments like that define the stakes his parents accepted when they came to the U.S. “with almost no money”.

“My parents are incredible,” he said. “It’s hard not to love this country. It’s hard not to be romantic about this country.”

Jensen Huang’s humble beginnings inspired Nvidia principles

That way of seeing America—as a place where people will give you a chance if you’re willing to take one—is how Huang explains Nvidia’s early, unlikely bets. 

Huang came up with the idea for Nvidia while sitting in a booth at a Denny’s, where he had worked first as a dishwasher and then a busboy. He wanted to build a chip that could power 3D graphics on a personal computer, and it was at that Denny’s booth that he met two friends to sketch out what would become the company.

Long before the company became synonymous with the AI boom, Huang kept steering it toward ideas that few people understood and even fewer believed in. CUDA was one of them. When Nvidia introduced it in 2006, the cost of the chip roughly doubled, revenue did not move, and the company’s valuation fell from about $12 billion to between $2 and $3 billion.

“When I launched CUDA, the audience was complete silence,” he said. “Nobody wanted it. Nobody asked for it. Nobody understood it.”

CUDA is the software layer that turns the graphics chips into general purpose compute engines, making them capable of large neural networks. Now, of course, nearly every major AI model today runs on hardware that depends on CUDA. 

The same thing happened when he introduced Nvidia’s first AI supercomputer, the DGX1. The launch drew “complete silence,” he said, and there were no purchase orders. The only person who reached out was none other than Tesla CEO Elon Musk, who told him he had “a nonprofit AI lab” that needed a system like this.

Huang assumed that meant the deal was impossible.

“All the blood drained out of my face,” he told Rogan. “A nonprofit is not buying a $300,000 computer.”

But Musk, the world’s richest man, insisted. So Huang boxed up one of the first units, loaded it into his car, and drove it to San Francisco himself.

In 2016, he walked into a small upstairs room filled with researchers— Berkeley robotics pioneer Pieter Abbeel, OpenAI cofounder Ilya Sutskever, and others—working in a cramped little office. That room turned out to be OpenAI, long before it became the most discussed AI organization in the world. Huang left the DGX1 with them and drove home.

Looking back, even as the CEO of a $4.5 trillion company who now draws crowds and autograph-seekers wherever he goes, he doesn’t describe any of this as foresight or heroism. To him, it’s simply the continuation of the risks his parents took when they sent two boys across the world with almost nothing.

“We really believed it, and so if you believe in that future, and you don’t do anything about it you’re going to regret it for your life,” Huang said.



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Nintendo’s 98% staff retention rate means the average employee has been there 15 years

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Good morning. When experienced employees leave–whether they get laid off, or jump ship for a better opportunity–they take their years, if not decades, of experience with them. Over time, the company loses that institutional knowledge.

Nintendo, the Japanese video game giant, is an example. Its Japanese employees spend an average of 15 years at the company, which boasts a yearly retention rate of 98%. That’s not just better than the layoff-prone video game industry, it’s better than most of Japan. The average Japanese worker spends 11 years at their company; in the U.S., that number is closer to four.

“The people who first made Nintendo’s hits are still working at the company,” Keza MacDonald, the author of Super Nintendo, a forthcoming book about the developer, told me recently. “For the last 50 years, these people have been passing down knowledge and training up a new generation of Nintendo creatives.” 

Both Nintendo’s business and creative leaders have long tenures at the company. Current president Shuntaro Furakawa joined the company in 1994 as an accountant. Shigeru Miyamoto, the brains behind franchises like “Super Mario” and “The Legend of Zelda,” joined as a staff artist in 1977. 

There is a risk that companies that rely too much on institutional knowledge get stuck in their ways. Yet Nintendo, according to MacDonald, has combined institutional knowledge with fresh ideas to continuously replenish its pipeline of fun games: “It’s not like the oldest guy gets to decide what’s a good idea and what isn’t. Everyone puts ideas in.”

Nintendo has its share of flops, failed experiments, and puzzling business decisions–as does every firm. Yet the company maintains its share of the highly competitive video game industry against bigger, deeper-pocketed rivals like Sony and Microsoft

The few designers who’ve left Nintendo still have fond feelings about their time there. As Lee Schuneman, a former Nintendo game designer and now Efekta Education Group’s chief product officer, told our Brainstorm Design audience this week, “I got to work with some of the most talented game designers in the world, including people like [Shigeru Miyamoto] at Nintendo, and [learn] a whole range of lessons about how to make playful experiences.”

That goodwill may be the result of Nintendo avoiding the industry’s boom-bust churn and valuing the expertise its workforce accumulates.

Nintendo “is still, to this day, making games differently from everyone else,” MacDonald says. You can check out the rest of our mainstage sessions from Brainstorm Design here.—Nicholas Gordon

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

Top news

Netflix to acquire Warner Bros. Discovery studios 

The online streamer and the maker of the  Superman and Harry Potter franchises are expected to announce a sale of Warner’s studios and HBO Max business to Netflix, the WSJ reports. Paramount Skydance chief David Ellison lobbied the White House against the deal even though Netflix offered a richer valuation, according to the New York Post.

“China’s Nvidia” stages IPO

Moore Threads, a maker of GPUs based in Beijing went public today at a valuation of $1.1 billion and its stock rose by 400% on day one.

$10 billion a week on U.S. national debt

The calendar year may have a few weeks left to tick off, but as far as the government’s budget is concerned, we’re in fiscal 2026. The Treasury has already paid out a 12-figure sum to service the nation’s debt. Unlike the tax and calendar year, the government’s financial calendar runs to the end of September. According to Treasury data, in the nine weeks since, it has spent $104 billion in interest on its $38 trillion borrowing burden. That’s more than $11 billion a week, and already represents 15% of federal spending in the current fiscal year.

Poor labor data may have locked in Fed cut

Analysts may not have necessarily digested this week’s lackluster labor data with glee—but it sure didn’t dampen their spirits either. Wall Street is hoping for a Christmas miracle with a final interest rate cut from the Fed, bringing the base rate down to 3.5% to 3.75%, and recent jobs reports may just have sealed the deal.

U.S. lobbied against E.U. seizing Russian money

American officials urged Europe not to use frozen Russian assets as the basis of loans that would fund Ukraine’s defense against Moscow’s invasion of its Eastern flank. The funds could be used as an incentive to end the war, Washington argued.

January 6 pipe bomb suspect arrested

Brian Cole Jr., 30 of Woodbridge, Virginia, was the subject of a five-year-long investigation by federal officials

Wall Street forecasts S&P will hit 7,500

Analysts are publishing their notoriously unreliable annual stock market forecasts and this year nine investment banks are guessing that the market will rise about 10% in 2026.

The markets

S&P 500 futures were up 0.17%  this morning. The last session closed up 0.11%. STOXX Europe 600 was up 0.18% in early trading. The U.K.’s FTSE 100 was up 0.19% in early trading. Japan’s Nikkei 225 was down 1.05%. China’s CSI 300 was up 0.84%. The South Korea KOSPI was up 1.78%. India’s NIFTY 50 is up 0.55%. Bitcoin fell to $91.4K.

Around the watercooler

How a Texas gas producer plans to exploit the ‘mega trend’ of power plants for AI hyperscalers by Jordan Blum.

Battle for sports betting market heats up as Polymarket announces return to the U.S. by Carlos Garcia.

Nvidia CEO Jensen Huang admits he works 7 days a week, including holidays, in a constant ‘state of anxiety’ out of fear of going bankrupt by Jessica Coacci.

Kim Kardashian shaped Skims into a $5 billion brand—now she wants to help other entrepreneurs mold their skills for success by Emma Hinchliffe.

CEO Daily was compiled and edited by Jim Edwards and Lee Clifford.



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