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When Microsoft first invested $1 billion in OpenAI in 2019, the deal received no more attention than your average corporate venture round. The startup market was blazing hot, and artificial intelligence was one of many areas attracting mega-valuations, alongside electric vehicles, advanced logistics and aerospace.

Three years later, the market looks very different.

Startup funding has cratered following the collapse of public market multiples for high-growth, money-losing tech companies. The exception is artificial intelligence, specifically generative AI, which refers to technologies focused on producing automated text, visual and audio responses.

No private company is hotter than OpenAI. In November, the San Francisco-based startup introduced ChatGPT, a chatbot that went viral thanks to its ability to craft human-like replies to users’ queries about nearly any topic.

Microsoft’s once under-the-radar investment is now a major topic of discussion, both in venture circles and among public shareholders, who are trying to figure out what it means to the potential value of their stock. Microsoft’s cumulative investment in OpenAI has reportedly swelled to $13 billion and the startup’s valuation has hit roughly $29 billion.

That’s because Microsoft isn’t just opening up its fat wallet for OpenAI. It’s also the arms dealer, as the exclusive provider of computing power for OpenAI’s research, products and programming interfaces for developers. Startups and multinational companies, including Microsoft, are rushing to integrate their products with OpenAI, which means massive workloads running on Microsoft’s cloud servers.

Microsoft is integrating the technology into its Bing search engine, sales and marketing software, GitHub coding tools, Microsoft 365 productivity bundle and Azure cloud. Michael Turrin, an analyst at Wells Fargo, says it could all add up to over $30 billion in new annual revenue for Microsoft, with roughly half coming from Azure.

What does that mean for Microsoft’s investment and broader arrangement?

“It’s so good that I have investors asking me how they pulled it off, or why OpenAI would even do this,” Turrin said in an interview.

However, the financial implications are anything but straightforward.

OpenAI was founded in 2015 as a nonprofit. The structure changed in 2019, when two top executives published a blog post announcing the formation of a “capped-profit” entity called OpenAI LP. The current setup restricts the startup’s first investors from making more than 100 times their money, with lower returns for later investors, such as Microsoft.

After Microsoft’s investment is paid back, it will receive a percentage of OpenAI LP’s profits up to the agreed-upon cap, with the rest flowing to the nonprofit body, an OpenAI spokesperson said. A Microsoft spokesperson declined to comment.

Greg Brockman, an OpenAI co-founder and one of the blog post’s authors, wrote in a 2019 Reddit comment that, for investors, the system “feels commensurate with what they could make investing in a pretty successful startup (but less than what they’d get investing in the most successful startups of all time!).”

It’s an unfamiliar model in Silicon Valley, where maximizing returns has long been the priority of the venture community. Nor does it make much sense to Elon Musk, who was one of OpenAI’s founders and early backers. Several times this year, Musk has tweeted his concerns about OpenAI’s unconventional structure and its implications for AI, particularly given Microsoft’s level of ownership.

OpenAI was created as an open source (which is why I named it ‘Open’ AI), non-profit company to serve as a counterweight to Google, but now it has become a closed source, maximum-profit company effectively controlled by Microsoft,” Musk tweeted in February. “Not what I intended at all.”

Brockman said on Reddit that if OpenAI succeeds, it could “create orders of magnitude more value than any company has to date.” As a major OpenAI investor, Microsoft would benefit.

Aside from its investment, leaning on OpenAI has the potential to help Microsoft dramatically reverse its fortunes in AI, where it’s stumbled publicly and didn’t build a meaningful business on its own. Microsoft pulled the Clippy assistant from Word, Cortana from the Windows taskbar and its Tay chatbot from Twitter.

Unlike areas such as advertising or security, Microsoft hasn’t disclosed the scale of its AI business, though CEO Satya Nadella said in October that revenue from its Azure Machine Learning service had doubled for four consecutive quarters.

If nothing else, the work with OpenAI has given Nadella bragging rights. Here’s what he said at Microsoft’s annual shareholder meeting in December, a month after ChatGPT was launched:

“When I think about Azure, one of the things that we have done, in fact, in the context of even ChatGPT, which today is one of the more popular AI applications out there, guess what? It’s all trained on the Azure supercomputer.”

In February, Microsoft held a press event at its headquarters in Redmond, Washington, to announce new AI-powered updates to its Bing search engine and Edge browser. Altman was one of the featured speakers.

It’s been a bumpy ride since then, as the Bing chatbot has held some highly publicized and creepy conversations with users, and it also served up some incorrect answers at the launch. Somewhat fortunately for Microsoft, Google’s rollout of its rival Bard AI service was underwhelming, leading employees to describe it as “rushed” and “botched.”

Despite the early hiccups, the enthusiasm for new technologies based on large language models, or LLMs, is palpable across the tech industry.

At the core of OpenAI’s bot is an LLM called GPT-4 that’s learned to compose natural-sounding text after being trained on extensive online information sources. Microsoft has an exclusive license on GPT-4 and all other OpenAI models, the OpenAI spokesperson said.

There are plenty other LLMs available.

Last month, Google said it had given some developers early access to an LLM called PaLM.

Startups AI21 Labs, Aleph Alpha and Cohere offer their own LLMs, as does Google-backed Anthropic, which has picked Google as its “preferred” cloud provider. Like Altman and Musk, Anthropic cofounder Dario Amodei, who was previously vice president of research at OpenAI, has expressed concerns about the unbridled power of AI.

In 2021, Anthropic registered in Delaware as a public-benefit corporation, signifying an intention to have a positive impact on society even as it pursues profits.

“We were and are focused on developing innovative structures to provide incentives for safe development and deployment of AI systems and will have more to share on this in the future,” an Anthropic spokesperson told CNBC in an email.

Across the industry, one thing is clear: it’s early days.

Quinn Slack, CEO of code-search startup Sourcegraph, said he hasn’t seen proof that the OpenAI partnership has given Microsoft a notable advantage, even though he called OpenAI the top LLM provider.

“I don’t think people should look at Microsoft and say they’ve totally locked up OpenAI and OpenAI is doing their bidding,” Slack said. “I truly believe people there are motivated to build amazing technology and make it as widely used as possible. They view Microsoft as a great customer but not someone that’s controlling. That’s good, and I hope it stays that way.”

OpenAI has plenty of skeptics. Late last month the nonprofit Center for Artificial Intelligence and Digital Policy called on the Federal Trade Commission to stop OpenAI from releasing new commercial releases of GPT-4, describing the technology as “biased, deceptive, and a risk to privacy and public safety.”

When considering potential exits for OpenAI, Microsoft — which does not hold an OpenAI board seat — would be the natural acquirer given its close entanglement. But that sort of deal would likely attract regulatory scrutiny, because of concerns about AI and about Microsoft stifling competition. By remaining an investor and not becoming OpenAI’s owner, Microsoft could avoid Hart-Scott-Rodino reviews from U.S. competition regulators.

“I’ve gone through it. It’s painful,” said David Zilberman, a partner at Norwest Venture Partners.

Based on its existing valuation, the more probable path for OpenAI is an eventual IPO, said Scott Raney, a managing director at Redpoint Ventures.

According to PitchBook data, OpenAI is on pace to generate $200 million in revenue this year, up 150% from 2022, and then $1 billion in 2024, which would imply 400% growth.

“When you raise at a $30 billion valuation, it’s kind of like, there’s no turning back at that point,” Raney said. You’re saying, “Our plan is to be a big independent standalone company.”

OpenAI’s spokesperson said there are no plans to go public or get acquired.

WATCH: Why ChatGPT is a game changer for AI

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Tesla Optimus robotics vice president Milan Kovac is leaving the company

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Tesla Optimus robotics vice president Milan Kovac is leaving the company

Tesla displays Optimus next to two of its vehicles at the World Robot Conference in Beijing on Aug. 22, 2024.

CNBC | Evelyn

Tesla’s vice president of Optimus robotics, Milan Kovac, said on Friday that he’s leaving the company.

In a post on X, Kovac thanked Tesla CEO Elon Musk and reminisced about his tenure, which began in 2016.

“I want to thank @elonmusk from the bottom of my heart for his trust and teachings over the decade we’ve worked together,” Kovac wrote. “Elon, you’ve taught me to discern signal from noise, hardcore resilience, and many fundamental principles of engineering. I am forever grateful. Tesla will win, I guarantee you that.”

Tesla is developing Optimus with the aim of someday selling it as a bipedal, intelligent robot capable of everything from factory work to babysitting.

In a first-quarter shareholder deck, Tesla said it was on target for “builds of Optimus on our Fremont pilot production line in 2025, with wider deployment of bots doing useful work across our factories.”

During Tesla’s 2024 annual shareholder meeting, Musk characterized himself as “pathologically optimistic,” then claimed the humanoid robots would lift the company’s market cap to $25 trillion at an unspecified future date.

In recent weeks, Musk told CNBC’s David Faber that Tesla is now training its Optimus systems to do “primitive tasks,” like picking up objects, open a door or throw a ball.

Competitors in the space include Boston Dynamics, Agility Robotics, Apptronik, 1X and Figure.

Kovac had previously served as the company’s director of Autopilot software engineering. He rose to lead the company’s Optimus unit as vice president in 2022.

Musk personally thanked Kovac for his “outstanding contributions” to the business.

Tesla didn’t respond to a request for comment.

WATCH: Tesla panel talks impact of Musk’s feud with Trump

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Tesla already had big problems. Then Musk went to battle with Trump

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Tesla already had big problems. Then Musk went to battle with Trump

President Donald Trump holds a news conference with Elon Musk to mark the end of the Tesla CEO’s tenure as a special government employee overseeing the U.S. DOGE Service on Friday May 30, 2025 in the Oval Office of the White House in Washington.

Tom Brenner | The Washington Post | Getty Images

Tesla has been facing massive challenges trying to get back on track after a disastrous first quarter. Those headwinds strengthened considerably this week.

CEO Elon Musk officially concluded his term with the Trump administration at the end of May, hitting the 130-day mark, the maximum time allowed for a “special government employee.” On his way out the door, Musk expressed sharp criticism of the Trump’s signature spending bill that’s being debated in Congress due to its expected impact on the national debt.

What started off as a policy disagreement quickly escalated into an all-out online brawl, with Musk and President Donald Trump hurling insults at one other from their respective social media platforms. After Musk called the “one, big beautiful bill” an “abomination” and rallied his followers on X to “kill the bill,” Trump said Musk had gone “CRAZY” and threatened to end government contracts and cut off subsidies for Musk’s companies. Musk responded, “Go ahead, make my day.”

The rift sent Tesla shares plummeting 14% on Thursday, wiping out roughly $152 billion in value, the most for any day in the company’s 15 year-history on the public market. While Musk is still the richest person in the world on paper, his net worth plunged by $34 billion, according to Bloomberg’s Billionaires Index.

More importantly, the spat brought about the collapse to a relationship that blended business, politics and power in a manner virtually unprecedented in U.S. history. The ramifications to Tesla, which fell out of the trillion-dollar club on Thursday, could be severe, and not just because Trump is reportedly considering selling or giving away the red Model S he purchased in March after turning the White House lawn into a Tesla showroom.

A senior White House official told NBC News on Friday that the president was “not interested” in having a call with Musk to resolve their feud.

Trump-Musk feud: Here's what's at stake for the Tesla CEO

Ire from the Trump administration could influence everything from future regulation, investigations and government support for Tesla, to decisions on tariff exemptions the company has been seeking in order to purchase Chinese-made manufacturing equipment.

Tesla shares were badly underperforming the broader market before the Musk-Trump breakup. Revenue slid 9% in the first quarter from a year earlier, with auto revenue plummeting 20%, due to the combination of increased competition from lower-cost EV makers in China and a consumer backlash to Trump’s political activities and rhetoric.

It’s certainly not what Tesla shareholders were expecting, when they sent the stock up about 30% in the days following Trump’s election victory in November. After spending close to $300 million to return Trump to the White House, Musk was poised to have a major role in the administration and be in position to push through regulatory changes in ways that benefited his companies.

Instead, his company has suffered, and Musk’s behavior is largely to blame.

One of his most divisive actions in leading the Trump administration’s Department of Government Efficiency (DOGE) was the dismantling of USAID, which previously delivered billions of dollars of food and medicine to more than 100 countries.

Beyond the U.S., Musk has endorsed Germany’s far-right extremist party AfD, and gave a gesture that many viewed as a Nazi salute at an inauguration rally.

In response, in recent months, there were numerous cases of vandalism or arson of Tesla facilities or vehicles in the U.S., as well as waves of peaceful protests at Tesla stores and service centers in North America and Europe.

Advertisements in protest of Musk have appeared in New York’s Times Square, and at bus shelters in London, urging people to boycott Tesla, some labeling the company’s EVs as “swasticars.” The Vancouver International Auto Show even removed Tesla from its exhibitors’ list fearing the company’s presence would cause safety problems.

On top all that are President Trump’s sweeping tariffs, which have led to concerns that costs will increase for parts and materials crucial for EV production. In its first-quarter earnings report in April, Tesla refrained from promising growth this year and said it will “revisit our 2025 guidance in our Q2 update.”

Board is mum

Pension funds that invest in Tesla have said the “crisis” at the company requires a leader to work a minimum of 40 hours per week to focus on solving its problems.

Public officials are echoing that sentiment, and calling on Tesla’s board to take action.

New York City Comptroller Brad Lander said on Thursday in s statement to CNBC that the “schoolyard fight” between Trump and Musk highlights how “Tesla’s weak accountability measures and poor governance threaten not only the company’s financial stability and shareholder value, but also the future of homegrown EV production.”

Brooke Lierman, comptroller of Maryland, told CNBC in an email that the company’s board “is not doing its job to ensure that there is a CEO at Tesla who is putting the company’s interests first.”

Since Musk’s name is synonymous with Tesla, the board needs to ensure that Tesla can stand on its own regardless of who’s leading the company, she added.

“Musk’s behavior continues to threaten the future of Tesla,” Lierman said. “As long as Tesla is identified with Elon Musk and he continues to be a polarizing figure, he will continue to damage the brand which is a huge part of Tesla’s value.”

Musk didn’t respond to a request for comment. CNBC also reached out for comment to board chair Robyn Denholm and directors and executives who work in government relations and in the office of the CEO. None of them responded as of the time of publication.

Elon Musk interviews on CNBC from the Tesla Headquarters in Texas.

CNBC

Tesla investors focused on business fundamentals are justified in their skepticism.

The company has failed to roll out innovative and affordable new model EVs, while Chinese competitors like BYD have flooded the market, particularly in Europe.

Analysts at Goldman Sachs on Thursday lowered their price target on Tesla mostly due to the outlook for 2025. Deliveries this quarter are tracking lower for the U.S., the analysts noted, while European sales saw a 50% year-over-year decline in April and another double-digit drop in May. China sales from those two months were down about 20% from a year earlier.

Quality is also a problem. Tesla has announced eight voluntary recalls of the Cybertruck in 15 months due to a range of issues including software bugs and sticking accelerator pedals.

Robotaxi ready?

Musk is urging investors to largely ignore the core business and look to the future, which he says is all about autonomous vehicles and humanoid robots.

But even there, Tesla is behind. In AVs the company has ceded ground to Alphabet’s Waymo, which is operating commercial robotaxi services in several U.S. markets. After a decade of missed deadlines, Musk has promised a small launch of a Tesla driverless ride-hailing service in Austin this month.

The Austin robotaxi service will operate in a geofenced area, Musk said in a recent interview with CNBC’s David Faber, and will begin with a small fleet of just 10 to 20 Model Y vehicles with Full Self-Driving (FSD) Unsupervised technology installed. If all goes well, Musk has said, Tesla will try to rapidly expand its driverless offerings to other markets like San Francisco and Los Angeles.

Watch part 1 of CNBC's interview with Tesla CEO Elon Musk

What consumers won’t be seeing anytime soon are the Cybercab and Robovan vehicles that Tesla touted at its “We, Robot” event last year to drum up customer and investor enthusiasm.

On Friday, Milan Kovac, Tesla’s vice president of Optimus robotics, announced he was leaving after joining the company in 2016. Musk thanked him for his “outstanding contribution” in a post on X.

Still, there are plenty Tesla bulls and Musk fanboys who are believers in the CEO’s vision. The stock’s 4% rebound on Friday is a sign that some saw an opportunity to buy the dip.

“I think the real story here is the investor base of Tesla literally doesn’t care about anything,” Josh Brown, CEO of Ritholtz Wealth Management and CNBC PRO contributor, told CNBC’s “Halftime Report” Friday. “This is still a nothing matters stock.”

FundStrat’s Tom Lee said the Tesla selloff was “overdone.”

Tesla’s market cap, which is dramatically inflated relative to every other U.S. car maker, is built on Musk’s vision of Tesla’s Optimus humanoid robots doing factory work and babysitting our children, while self-driving Cybercabs and Robovans make money carting around passengers.

Morgan Stanley’s Adam Jonas wrote in a note this week that, “Tesla still holds so many valuable cards that are largely apolitical,” pointing to what he sees as the company’s “AI leadership, autonomy/robotics, manufacturing, supply chain re-architecture, renewable power, [and] critical infrastructure.”

In terms of Tesla’s existing business, the most immediate impact from what’s happening in Washington D.C., is the rollback of EV credits in the current budget bill that Musk loudly opposes and that’s struggling to find sufficient support in the Senate. There’s also the matter of the tariffs and whether Tesla is able to get preferred treatment, a proposition that seems increasingly unlikely with the Musk-Trump fallout.

Matthew LaBrot, a former Tesla staff program manager, told CNBC that he’s not surprised that Musk blew up his relationship with the president. LaBrot was terminated earlier this year after sending an open letter in protest of Musk’s divisive political activity.

“I am devastated for the country and the climate, though Elon only has himself to blame,” LaBrot said in an interview. “Back a loose canon, expect stray canon fire.”

Tesla investors can’t know at the moment how much of Musk’s energy and time will now return to his lone public company, and the business responsible for the vast majority of his wealth. Even without politics, he still has SpaceX, AI startup xAI and brain tech startup Neuralink, among other businesses.

As of Thursday, Musk still had a West Wing office that hadn’t been cleaned out, two administration officials told NBC News. The space will likely be packed up in the coming days, one of the officials said.

And while his time in the Trump camp may be over, Musk has called on his followers to form a new party in the U.S.

“Is it time to create a new political party in America that actually represents the 80% in the middle?” he wrote on X on Thursday, in a post that’s now pinned at the top of his page. According to the post, 80% of 5.6 million respondents to the unofficial poll said “yes.”

Musk’s actions this week may have caused a permanent rift with the president. But one thing is clear — his company can’t get away from the White House.

WATCH: Impact of Musk’s feud with Trump

'Closing Bell Overtime' Tesla panel talks impact of Elon Musk's feud with Pres. Trump

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DocuSign stock tanks 18% after company cuts billings outlook

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DocuSign stock tanks 18% after company cuts billings outlook

The Docusign Inc. application for download in the Apple App Store on a smartphone arranged in Dobbs Ferry, New York, U.S., on Thursday, April 1, 2021.

Tiffany Hagler-Geard | Bloomberg | Getty Images

Shares of DocuSign tanked 18% in trading on Friday, a day after the e-signature provider reported stronger-than-expected earnings but slashed its full-year billings outlook.

Here’s how the company performed in the fiscal first quarter, compared with estimates from analysts polled by LSEG:

  • Earnings per share: 90 cents, adjusted, vs. 81 cents expected
  • Revenue: $764 million vs. $748 million expected

Billings, a closely-watched sales metric, came in at $739.6 million in the fiscal first quarter, which ended April 30. That was lower than the $746 million expected by analysts, according to StreetAccount. It also fell short of the company’s own forecast, which guided for billings between $741 million and $751 million.

For the current fiscal year, DocuSign said it expects billings of $3.28 billion to $3.34 billion, down from a range of $3.3 billion to $3.35 billion.

Read more CNBC tech news

In the first quarter of DocuSign’s 2026 fiscal year, revenue jumped 8% year over year to $764 million. Subscription revenue increased 8% from the same period a year ago to $746.2 million.

DocuSign reported net income of $72.1 million, or 34 cents per share, compared to net income of $33.8 million, or 16 cents per share, a year earlier.

For the fiscal second quarter, the company expects revenue to be between $777 million and $781 million, compared to consensus estimates of $775 million, according to LSEG. For the full fiscal year, DocuSign projected revenue of $3.15 billion to $3.16 billion. Analysts were expecting $3.14 billion, according to LSEG.

The company also announced an additional $1 billion stock buyback, taking its share repurchase plan to $1.4 billion.

DocuSign shares are down more than 16% year to date.

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