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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

On the eve of MicroStrategy‘s stock 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 most exquisite hotel room he’d ever seen, paid for by lead underwriter Merrill Lynch.

The next morning, Saylor went to the floor of the Nasdaq to watch his company’s stock open. He recalled seeing a note scrolling across the ticker, warning traders: “Please do not confuse MSTR with MSFT.” The latter belonged to Microsoft, the software giant that had gone public 13 years earlier.

MicroStrategy shares popped 76% in their debut, joining the parade of tech companies benefiting from the dot-com boom.

“It was a good day,” Saylor told CNBC.

More than 26 years later, MicroStrategy and Microsoft were again linked together, but for an entirely different reason. In December 2024, Saylor stood before Microsoft’s shareholders to try and convince them that the company, now valued at over $3 trillion, should put some of its $78.4 billion in cash, equivalents and short-term investment into bitcoin.

“Microsoft can’t afford to miss the next technology wave, and bitcoin is that wave,” Saylor said in a video presentation that he released on X last week. The post has more than 3.6 million views.

Saylor has gone all in on that strategy. MicroStrategy has purchased 439,000 bitcoin since mid-2020, a stockpile that’s now worth about $42 billion and is the basis for the company’s market cap explosion to $82 billion from roughly $1.1 billion when the plan was put in place.

MicroStrategy’s software unit, which specializes in business intelligence, generates just over $100 million in revenue a quarter. After zooming up in 1998 and 1999, the stock crumbled in the dot-com bust, losing almost all its value. In the decades that followed, it slowly bounced back before rocketing up due to bitcoin.

Four years into its bitcoin buying spree, MicroStrategy is the world’s fourth-largest holder, behind only creator Satoshi Nakamoto, BlackRock’s iShares Bitcoin Trust and crypto exchange Binance.

At Microsoft, the shareholder vote supported by Saylor failed by a wide margin — less than 1% of its investors voted for it.

But the spectacle provided Saylor, now 59, with yet another opportunity to preach the 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 to only 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.”

Watch CNBC's full interview with MicroStrategy's Michael Saylor

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.

‘Inspired the crypto community’

Two months earlier, in July, Trump delivered a keynote at the biggest bitcoin conference of the year in Nashville, Tennessee, 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, but as a “digital assets framework” is put into place for the broader crypto market, “there’ll be a surge in the entire digital assets industry,” he said.

“Taxes are coming down. All the rhetoric about unrealized capital gains taxes and wealth taxes is off the table,” Saylor said. “All of the hostility from the regulators to banks touching bitcoin” also goes away, he added.

Republican presidential nominee and former U.S. President Donald Trump gestures at the Bitcoin 2024 event in Nashville, Tennessee, U.S., July 27, 2024.

Kevin Wurm | Reuters

MicroStrategy has gotten even more aggressive with its bitcoin purchases. Saylor said in a post on Dec. 16, that over a six-day stretch starting Dec. 9, his company had acquired 15,350 bitcoin for $1.5 billion.

So far this year, MicroStrategy has acquired 249,850 bitcoin, with almost two-thirds of those purchases occurring since Nov. 11.

“We were going to do it regardless,” Saylor said, referring to the election results. “But what was a headwind has become a tailwind.”

A week before the election, MicroStrategy announced in its quarterly earnings release a plan to raise $42 billion over three years. That included a stock sale of up to $21 billion through financial firms including TD Securities and Barclays, opening up that much more liquidity for bitcoin purchases.

Saylor told CNBC it was “probably the single most important earnings call in the history of the company.”

No amount of ownership is too much for Saylor, who predicted in September that bitcoin could hit $13 million by 2045, which would equal 29% growth annually.

“We’ll just keep buying the top forever,” he said in the same TV interview where he compared bitcoin to New York real estate. “Every day is a good day to buy bitcoin. We look at it as cyber-Manhattan.”

Saylor talks glowingly about bitcoin as the foundation of a new digital economy that will only get bigger. But even since his bitcoin strategy got underway in 2020, there have been pockets of severe pain for investors — the stock lost 74% of its value in 2022 before soaring the past two years.

Still, he’s advising companies to mimic his strategy. Microsoft didn’t listen, but Saylor said there are plenty of “zombie companies,” with core businesses that aren’t going anywhere that could make better use of their cash.

“The traditional advice would be, you do a transformational acquisition, you find that you need a merger partner. You’re dead in the water. Go find somebody to merge with,” Saylor said at the Lotte in September. “Bitcoin is the universal merger partner, right? The real appeal of digital capital is you can fix any company.”

WATCH: CNBC’s full interview with MicroStrategy CEO Michael Saylor

Watch CNBC's full interview with MicroStrategy's Michael Saylor

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DoorDash CEO Tony Xu is taking on the role of industry consolidator in food delivery

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DoorDash CEO Tony Xu is taking on the role of industry consolidator in food delivery

Tony Xu, co-founder and CEO of DoorDash Inc., smiles during the Wall Street Journal Tech Live conference in Laguna Beach, California, on Oct. 22, 2019.

Martina Albertazzi | Bloomberg | Getty Images

During the depths of the Covid pandemic, with restaurants around the country facing an existential crisis, DoorDash CEO Tony Xu had an unconventional proposal. He wanted to cut commissions.

Chief Business Officer Keith Yandell worried that such a move would result in a massive hit to profits ahead of the company’s planned IPO. But Xu made a persuasive case.

“If restaurants don’t thrive, we cannot,” Yandell told CNBC in a recent interview, recalling Xu’s perspective at the time. “We need to take a leadership position.”

The company ended up sacrificing over $100 million in fees, Xu later said.

Since starting DoorDash on the campus of Stanford University in 2013, the now 40-year-old CEO has navigated the notoriously cutthroat and low-margin business of food delivery, building a company that Wall Street today values at close to $90 billion. The stock has emerged as a tech darling this year, jumping 23%, while the Nasdaq is still down for the year largely on tariff concerns.

More than four years after its IPO, net profits remain slim. But that’s not getting in the way of Xu’s mission to become an industry consolidator, using a combination of cash and new debt to fuel an acquisition spree at a time when big tech deals remain scarce. Earlier this month, DoorDash scooped up British food delivery startup Deliveroo for about $3.9 billion and restaurant technology company SevenRooms for $1.2 billion.

“What we’ve delivered for a customer yesterday probably isn’t good enough for what we will deliver for them today,” Xu told CNBC’s “Squawk Box” after the deals were announced.

This week DoorDash announced the pricing of $2.5 billion in convertible debt, and said the proceeds could be used in part for acquisitions.

Doordash food delivery service in New York City on Feb. 13, 2025. 

Danielle DeVries | CNBC

The San Francisco-based company has a history with scooping up competitors to grow market share. In 2019, it bought food delivery competitor Caviar for $410 million from Square, now known as Block. About two years later, DoorDash said it was paying $8.1 billion for international delivery platform Wolt. The deal was its last big transaction until this month.

When DoorDash entered the food delivery market, it had to face off against the likes of GrubHub and Seamless, which later joined forces. That combined entity was bought late last year by restaurant owner Wonder Group. In 2014, Uber launched Uber Eats, which is now DoorDash’s biggest competitor in the U.S.

“It’s a very competitive market, and I think merchants do have choice,” Xu said in the CNBC interview. “What we’re focused on is always trying to innovate and bring new products to match increasing standards and expectations from customers.”

DoorDash didn’t make Xu available for an interview for this story, but provided a statement about the company’s acquisition strategy.

“We’re very picky, very patient, and conscious that, for most companies, deals don’t work out in hindsight,” the company said. “When we see an opportunity that brings value to customers, expands our potential to empower local economies around the world, and has a path to strong long-term returns on capital, we tend to push our chips in.”

Taking on the suburbs

DoorDash differentiated itself early on by cornering suburban markets that had fewer delivery options, while other players attacked city centers. When Covid shut down restaurant dining in early 2020, DoorDash capitalized on the booming demand for deliveries. Revenue more than tripled that year, and grew 69% in 2021.

Colleagues and early investors credit a customer-first focus for much of Xu’s success. Gokul Rajaram, who joined DoorDash through its Caviar acquisition, described Xu as “the best operational leader in the U.S.” after Amazon founder Jeff Bezos.

Restaurants haven’t universally viewed DoorDash as an ally. Commissions can reach as high as 30%, which is a hefty cut to fork over. Many restaurants have reluctantly paid the high fees because of DoorDash’s dominant market share, which reached an estimated 67%. In 2021, the company introduced three tiers of pricing, with a basic option at 15% for more price-sensitive businesses.

DoorDash needs the high fees in order to stay in the black. The company’s contribution profit as a percentage of total marketplace volume hovers below 5%.

DoorDash CFO: We are focused on scaling the business to drive profitability

Colleagues who have known Xu for decades say the food delivery entrepreneur hasn’t changed much since the early days of the company.

Yandell said Xu once took advice from his young daughter, who complained about a routing issue while accompanying him on food delivery orders. All employees, including Xu, are required to complete orders and handle support calls every year as part of the company’s WeDash program.

In a part of the country known for the pomp of its wealthy founders, Xu has a very different reputation.

Early workers recall memories of Xu pulling up in a dilapidated green 2001 Honda Accord to team events, or participating in company knockout basketball games referred to as “knockys,” next to the animal hospital in Palo Alto, which DoorDash briefly called its headquarters. Xu also personally approved every offer for the company’s first 4,000 employees.

Xu spends many mornings answering customer service complaints. He often drops his kids off at school and, after tucking them in at night, hops on calls with international regions, colleagues say. Xu is an avid Gold State Warriors basketball fan but has a soft spot for the Chicago Bulls, having spent many years in Illinois. Once or twice a week, Xu squeezes in a morning run, and will often do so while traveling to explore different neighborhoods and stores.

Xu was born in China and moved with his family to Champaign, Illinois, in 1989. Growing up, he played basketball and mowed lawns to save up for a Nintendo. He told Stanford’s View From the Top podcast in 2021 that the experience, and watching his parents hustle, taught him how to “earn your way into better things.”

His “characteristics became the company’s values,” said Alfred Lin, an early DoorDash investor and partner at venture firm Sequoia.

Xu often attributes his entrepreneurial spirit to his parents. His mother worked as a doctor in China, and juggled three jobs in the U.S. for over a decade, saving up enough to eventually open a medical clinic. His father worked as a waiter while pursuing a Ph.D. Xu said on the podcast that watching his mom gave him a deep understanding of what it takes to run a small business, which came in handy in DoorDash’s early years as he was trying to convert restaurants into customers.

‘Ten times harder’

Employees say Xu has a reputation for detecting hidden talents among his colleagues. Jessica Lachs, the company’s chief analytics officer, was working as a general manager assisting with DoorDash’s Los Angeles launch when Xu guided her toward her passion for data.

“He believes in leaning into the things you’re really good at, rather than trying to be mediocre at a lot of things,” she said.

After Toby Espinosa, DoorDash’s ads vice president, lost a deal with a major fast food company during his early years at the startup, Xu told him to work “10 times harder” and become an expert in his field. A few years later, the company secured the partnership, Espinosa said.

Grit and struggle defined the early years of DoorDash. The founding team of four managed deliveries around Stanford and Palo Alto though a Google Voice number directed to their cellphones.

DoorDash emerged out of a Stanford business school course known as Startup Garage, taught by Professor Stefanos Zenios. The class requires students to present a business idea, test it, and then pitch it to investors.

Zenios said Xu stood out with his data-driven approach and natural leadership qualities. The team tested two different ideas, including a platform that helped small businesses better track the effectiveness of their marketing, he recalls. Zenios called the idea to target suburban areas a “brilliant insight.”

Xu and his team entered Y Combinator in the summer of 2013. The three-month startup accelerator program is known for spawning companies like Airbnb, Stripe and Reddit. Every session culminates with a demo day in front of some of Silicon Valley’s biggest investors.

The DoorDash idea excited Paul Buchheit, creator of Gmail and a partner at Y Combinator. But like many other potential investors, Buchheit was skeptical about the economic model.

“You had a talented team of founders working on what I thought was an idea that had potential,” he said. “That’s basically the formula for a good startup.”

On pitch day, the company failed to lure any venture firms, but Buchheit later participated as a seed investor.

Shortly after demo day, DoorDash encountered Saar Gur of Charles River Ventures. Gur had been looking for a food delivery platform to back and was conducting due diligence on another company when a friend led him to DoorDash.

By the end of their first meeting, they were “finishing each other’s sentences,” Gur said.

Sequoia’s Lin initially passed on DoorDash after the Y Combinator pitch, but kept in touch with the team. Lin said he wanted to see data that showed the platform could penetrate beyond Stanford and Palo Alto, and retain customers. He ended up leading two institutional rounds, attaining a 20% stake for Sequoia at the time of the IPO.

“Tony always believed that his company would succeed, or they’ll find a way to succeed,” Lin said.

A food delivery messenger is seen in Manhattan. 

Luiz C. Ribeiro | New York Daily News | Tribune News Service | Getty Images

Shortly after its Y Combinator stint, DoorDash hit an early roadblock. Following a Stanford football game, a rush of orders bombarded its delivery system causing massive delays, Xu told Y Combinator’s CEO Garry Tan in an interview this year.

The founders refunded the orders and spent the night baking cookies, then driving them to customers early the next morning.

Oren’s Hummus co-owner Mistie Boulton said DoorDash still takes that approach. The team comes to meet with her every quarter and she serves as a beta tester for new products.

The restaurant, which started in Palo Alto and has since expanded to a half-dozen locations across the Bay Area, was one of DoorDash’s first clients, latching onto the opportunity to reach more customers beyond its small establishment that frequently had lines snaking out the door. 

“We just fell in love with the idea,” Boulton said. “The number one thing that encouraged and enticed me to want to work with them was Xu’s passion. He really is one of those people that you can count on.”

Wall Street is now counting on Xu’s ability to execute big deals, even with the company having this month surpassed $10 billion in delivery orders worldwide.

The acquisition of Deliveroo, based in London, marks a renewed effort by DoorDash to expand its presence overseas, following the purchase of Finland’s Wolt three years ago.

The cash deal for SevenRooms, a New York City-based data platform for restaurants and hotels to manage booking information, takes DoorDash into an entirely new category. Xu told CNBC that DoorDash is a “multi-product company now that’s operating on a global scale.”

Following the acquisition announcements, which coincided with a disappointing earnings report in March, analysts at Piper Sandler reiterated their hold recommendation on the stock.

One reason for concern, they said, was that “integrating multiple acquisitions at once may create some noise near-term.”

 WATCH: DoorDash CEO Tony Xu: Deliveroo & SevenRooms deals make us a multi-product company on a global scale

DoorDash CEO Tony Xu: Deliveroo & SevenRooms deals make us a multi-product company on a global scale

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Tesla shares set to wrap strong May as Elon Musk ends time with Trump’s DOGE

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Tesla shares set to wrap strong May as Elon Musk ends time with Trump's DOGE

Elon Musk is interviewed on CNBC from the Tesla headquarters in Texas.

CNBC

Shares of the Elon Musk-led automaker Tesla have rallied in May despite recent poor car sales numbers for the company in China and Europe, as the billionaire CEO promised to focus more on his businesses than politics.

Tesla shares are on track for an increase of more than 20% for the month.

The stock is still down about 12% for the year. Apple is down about 21% year-to-date, the worst of all the megacaps.

The bounceback in May comes as President Donald Trump marks the end of Musk’s time as a “special government employee” at the helm of the Department of Government Efficiency.

“This will be his last day, but not really, because he will, always, be with us, helping all the way,” Trump wrote on Truth Social. “Elon is terrific!”

Musk said on the most recent Tesla earnings call that his time spent running DOGE would drop significantly by the end of May, but that he plans to spend a “day or two per week” on government work until the end of Trump’s term.

Musk also planned to keep his office at the White House.

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Tesla year to date stock chart

The New York Times reported Friday that while Musk was campaigning for Trump last year, he had been taking drugs “well beyond occasional use” and was “facing an increasingly turbulent family life.”

The Times noted it was unclear if that habit carried over to his time in the White House, when he was also juggling Tesla and the other companies in his business empire — including SpaceX and X owner xAI, his artificial intelligence company.

Tesla’s European sales dropped by half, year-over-year for April.

Tesla sales in China, another massive market for battery electric vehicles, were down by about 25% year over year in the first eight weeks of the current quarter.

The carmaker has faced protests in reaction to Musk’s ties with Trump, and his endorsement of Germany’s far-right extremist party AfD.

Pension fund leaders recently called out Tesla’s board in a letter, demanding that they rein in Musk, and require him to work a minimum of 40 hours a week on Tesla to fix what they called the current “crisis.”

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Musk and Tesla have tried to re-focus on the company’s prospects in autonomous vehicle tech, humanoid robotics and artificial intelligence.

Bloomberg reported this week that Tesla plans to launch its long-delayed and much anticipated autonomous vehicle ride-hailing service in Austin, Texas, on June 12th.

Tesla has not confirmed that start date, but has been promising to launch a robotaxi ride-hailing service in Austin before the end of June.

Musk told CNBC’s David Faber in a recent interview that Tesla would start with a small fleet of Model Y Tesla vehicles equipped with the company’s newest, Unsupervised Full Self Driving hardware and software.

Musk has been promising investors a robotaxi vehicle for years, and the company has ceded ground to Waymo in the U.S. The Alphabet-owned robotaxi venture recently surpassed 10 million paid, driverless ridehailing trips.

Shares of Tesla have also benefitted from the company’s stronger position, relative to other U.S. automakers when it comes to weathering tariffs.

Tesla operates two massive vehicle assembly plants domestically, one in Fremont, California and another in Austin, Texas, and has more North American-made parts in its cars than most of its competitors.

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China calls out Trump for ‘abuse’ of semiconductor export controls

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China calls out Trump for 'abuse' of semiconductor export controls

Chinese President Xi Jinping and U.S. President Donald Trump.

Dan Kitwoodnicholas Kamm | Afp | Getty Images

China is calling out the U.S. for “discriminatory restrictions” in its use of export controls in the chip industry, after the Trump administration accused the world’s second-largest economy of violating a preliminary trade deal between the two countries.

“Recently, China has repeatedly raised concerns with the U.S. regarding its abuse of export control measures in the semiconductor sector and other related practices,” China U.S. embassy spokesperson Liu Pengyu told NBC News.

It’s the latest escalation in the simmering trade war between the U.S. and China, particularly as it pertains to artificial intelligence and the infrastructure needed to develop the most advanced technologies.

China’s response comes after President Donald Trump said early Friday in a social media post that China had violated a trade agreement. U.S. Trade Representative Jamieson Greer told CNBC in an interview that the “Chinese are slow rolling its compliance.”

On May 12, the U.S. and China agreed to a 90-day suspension on most tariffs imposed by either side. That agreement followed an economic and trade meeting between the two countries in Geneva, Switzerland.

“China once again urges the U.S. to immediately correct its erroneous actions, cease discriminatory restrictions against China and jointly uphold the consensus reached at the high-level talks in Geneva,” the embassy spokesperson said.

The statement didn’t specify any actions taken by the U.S. Earlier this month, China said the U.S. was “abusing” export controls after the U.S. banned American companies from importing or even using Huawei’s AI chips.

The U.S. has limited exports of some chips and chip technology to China as part of a national defense strategy dating back to the first Trump administration.

In 2019, President Trump cut off Huawei’s access to U.S. technology, which forced it to essentially exit the smartphone business for a few years before it could develop its own chips without use of U.S intellectual property or infrastructure. In 2022, the Biden administration first moved to cut off Chinese access to the fastest AI chips made by Nvidia and Advanced Micro Devices.

The restrictions have intensified of late, and earlier this week, chip software makers, including Synopsys and Cadence Design Systems, said they had received letters from the U.S. Commerce Department telling them to stop selling to China.

Nvidia, which makes the most advanced semiconductors for AI applications, has vocally opposed the U.S. export controls, saying that they would merely force China to develop its own chip ecosystem instead of building around U.S. standards.

Nvidia was told earlier this year that it could no longer sell its H20 chip to China, a restriction that the company said this week would cause it to miss out on about $8 billion in sales in the current quarter. The H20 chip was specifically designed by Nvidia to comply with 2022 restrictions, but the Trump administration said in April that the company needed an export license. Nvidia said it was left with $4.5 billion in inventory it couldn’t reuse.

“The U.S. has based its policy on the assumption that China cannot make AI chips,” Nvidia CEO Jensen Huang told investors on the company’s earnings call. “That assumption was always questionable, and now it’s clearly wrong.”

The Trump administration did rescind an expansive chip export control rule that was implemented by the Biden administration called the “AI diffusion rule,” which would have placed export caps on most countries. A new and simpler rule is expected in the coming months.

WATCH: AI trade remains work in progress

AI trade remains work in progress, says Goldman Sachs' Eric Sheridan

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