This week on the GeekWire Podcast: Newly unsealed court documents reveal the behind-the-scenes history of Microsoft and OpenAI, including a surprise: Amazon Web Services was OpenAI’s original partner. We tell the story behind the story, explaining how it all came to light.
Microsoft CEO Satya Nadella and former UK Prime Minister Rishi Sunak at the World Economic Forum in Davos. (Screenshot via LinkedIn)
Bicycles for the mind. … Information at your fingertips. … Managers of infinite minds?
Microsoft CEO Satya Nadella riffed on some famous lines from tech leaders past this week in an appearance at the World Economic Forum in Davos, Switzerland, and offered up his own trippy candidate to join the canon of computing metaphors.
Nadella traced the lineage in a conversation with former UK Prime Minister Rishi Sunak.
“Computers are like a bicycle for the mind” was the famous line from Apple’s Steve Jobs.
“Information at your fingertips” was Bill Gates’ classic Microsoft refrain back in the day.
And now? “All of us are going to be managers of infinite minds,” Nadella said. “And so if we have that as the theory, then the question is, what can we do with it?”
He was referring to AI agents — the autonomous software that can take on tasks, work through problems, and keep going while you sleep. Microsoft and others have been talking for the better part of a year now about people starting to oversee large fleets of them.
Nadella said it’s already reshaping how teams are structured. At Microsoft-owned LinkedIn, the company has merged design, program management, product management, and front-end engineering into a single new role: full-stack builders. Overall, he called it the biggest structural change to software teams he’s seen in a career that started at Microsoft in the 1990s.
“The jobs of the future are here,” Nadella said, putting his own spin on a famous line often attributed to sci-fi writer William Gibson. “They’re just not evenly distributed.”
Nadella’s comments came during a live stream for LinkedIn Premium members, hosted from Davos by LinkedIn VP and Editor in Chief Daniel Roth, after Sunak mentioned his two teenage daughters, and the world they’ll enter. Young people may not manage lots of people at age 20 or 21, he said, “but they will be managing a team of agents.”
Sunak was referencing an essay by Goldman Sachs CIO Marco Argenti in Time.
The agentic shift, Argenti wrote, requires “moving from being a sole performer to an orchestra conductor” — your team now includes AI agents that “must be guided and supervised with the same approach you would apply to a new, junior colleague.”
Nadella agreed, saying “we do need a new theory of the mind” to navigate what’s coming, before he offered up his new metaphor about managing infinite minds.
In other remarks at Davos, Nadella made headlines with his warning that AI’s massive energy demands risk eroding its “social permission” unless it delivers tangible benefits in health, education, and productivity. Energy costs, he added, will decide the AI race’s winners, with GDP growth tied to cheap power for processing AI tokens.
Whether “infinite minds” catches on like “bicycles” and “fingertips” remains to be seen. But it’s definitely more psychedelic. And if this shift is stranger than what came before, maybe we do need a mind-expanding metaphor to make sense of it all.
Sam Altman greets Microsoft CEO Satya Nadella at OpenAI DevDay in San Francisco in 2023. (GeekWire File Photo / Todd Bishop)
The launch of the AI lab that would redefine Microsoft caught the tech giant by surprise.
“Did we get called to participate?” Satya Nadella wrote to his team on Dec. 12, 2015, hours after OpenAI announced its founding. “AWS seems to have sneaked in there.”
Nadella had been Microsoft CEO for less than two years. Azure, the company’s cloud platform, was five years old and chasing Amazon Web Services for market share. And now AWS had been listed as a donor in the “Introducing OpenAI” post. Microsoft wasn’t in the mix.
In the internal message, which hasn’t been previously reported, Nadella wondered how the new AI nonprofit could remain truly “open” if it was tied only to Amazon’s cloud.
Within months, Microsoft was courting OpenAI. Within four years, it would invest $1 billion, adding more than $12 billion in subsequent rounds. Within a decade, the relationship would culminate in a $250 billion spending commitment for Microsoft’s cloud and a 27% equity stake in one of the most valuable startups in history.
New court filings offer an inside look at one of the most consequential relationships in tech. Previously undisclosed emails, messages, slide decks, reports, and deposition transcripts reveal how Microsoft pursued, rebuffed and backed OpenAI at various moments over the past decade, ultimately shaping the course of the lab that launched the generative AI era.
More broadly, they show how Nadella and Microsoft’s senior leadership team rally in a crisis, maneuver against rivals such as Google and Amazon, and talk about deals in private.
For this story, GeekWire dug through more than 200 documents, many of them made public Friday in Elon Musk’s ongoing suit accusing OpenAI and its CEO Sam Altman of abandoning the nonprofit mission. Microsoft is also a defendant. Musk, who was an OpenAI co-founder, is seeking up to $134 billion in damages. A jury trial is scheduled for this spring.
OpenAI has disputed Musk’s account of the company’s origins. In a blog post last week, the company said Musk agreed in 2017 that a for-profit structure was necessary, and that negotiations ended only when OpenAI refused to give him full control.
The recently disclosed records show that Microsoft’s own leadership anticipated the possibility of such a dispute. In March 2018, after learning of OpenAI’s plans to launch a commercial arm, Microsoft CTO Kevin Scott sent Nadella and others an email offering his thoughts.
“I wonder if the big OpenAI donors are aware of these plans?” Scott wrote. “Ideologically, I can’t imagine that they funded an open effort to concentrate ML [machine learning] talent so that they could then go build a closed, for profit thing on its back.”
The latest round of documents, filed as exhibits in Musk’s lawsuit, represents a partial record selected to support his claims in the case. Microsoft declined to comment.
Elon helps Microsoft win OpenAI from Amazon
Microsoft’s relationship with OpenAI has been one of its key strategic advantages in the cloud. But the behind-the-scenes emails make it clear that Amazon was actually there first.
According to an internal Microsoft slide deck from August 2016, included in recent filings, OpenAI was running its research on AWS as part of a deal that gave it $50 million in computing for $10 million in committed funds. The contract was up for renewal in September 2016.
Microsoft wanted in. Nadella reached out to Altman, looking for a way to work together.
In late August, the filings show, Altman emailed Musk about a new deal with Microsoft: “I have negotiated a $50 million compute donation from them over the next 3 years!” he wrote. “Do you have any reason not to like them, or care about us switching over from Amazon?”
Musk, co-chair of OpenAI at the time, gave his blessing to the Microsoft deal in his unique way, starting with a swipe at Amazon founder Jeff Bezos: “I think Jeff is a bit of a tool and Satya is not, so I slightly prefer Microsoft, but I hate their marketing dept,” Musk wrote.
He asked Altman what happened to Amazon.
Altman responded, “Amazon started really dicking us around on the T+C [terms and conditions], especially on marketing commits. … And their offering wasn’t that good technically anyway.”
Microsoft and OpenAI announced their partnership in November 2016 with a blog post highlighting their plans to “democratize artificial intelligence,” and noting that OpenAI would use Azure as its primary cloud platform going forward.
Harry Shum, then the head of Microsoft’s AI initiatives, with Sam Altman of OpenAi in 2026. (Photo by Brian Smale for Microsoft)
Internally, Microsoft saw multiple benefits. The August 2016 slide deck, titled “OpenAI on Azure Big Compute,” described it as a prime opportunity to flip a high-profile customer to Azure.
The presentation also emphasized bigger goals: “thought leadership” in AI, a “halo effect” for Azure’s GPU launch, and the chance to recruit a “net-new audience” of developers and startups. It noted that OpenAI was a nonprofit “unconstrained by a need to generate financial return” — an organization whose research could burnish Microsoft’s reputation in AI.
But as the ambition grew, so did the bill.
‘Most impressive thing yet in the history of AI’
In June 2017, Musk spoke with Nadella directly to pitch a major expansion. OpenAI wanted to train AI systems to beat the best human players at competitive esports, Valve’s Dota 2. The computing requirements were massive: 10,000 servers equipped with the latest Nvidia GPUs.
“This would obviously be a major opportunity for Microsoft to promote Azure relative to other cloud systems,” Musk wrote in an email to OpenAI colleagues after the call.
Nadella said he’d talk about it internally with his Microsoft cloud team, according to the email. “Sounds like there is a good chance they will do it,” Musk wrote.
Two months later, Altman followed up with a formal pitch. “I think it will be the most impressive thing yet in the history of AI,” he wrote to Nadella that August.
Microsoft’s cloud executives ran the numbers and balked. In an August 2017 email thread, Microsoft executive Jason Zander told Nadella the deal would cost so much it “frankly makes it a non-starter.” The numbers are redacted from the public version of the email.
“I do believe the pop from someone like Sam and Elon will help build momentum for Azure,” Zander wrote. “The scale is also a good forcing function for the fleet and we can drive scale into the supply chain. But I won’t take a complete bath to do it.”
Ultimately, Microsoft passed. OpenAI contracted with Google for the Dota 2 project instead.
‘A bucket of undifferentiated GPUs’
Microsoft’s broader relationship with OpenAI was starting to fray, as well. By January 2018, according to internal emails, Microsoft executive Brett Tanzer had told Altman that he was having a hard time finding internal sponsors at Microsoft for an expanded OpenAI deal.
Altman started shopping for alternatives. Around that time, Tanzer noted in an email to Nadella and other senior executives that OpenAI’s people “have been up in the area recently across the lake” — a reference to Amazon’s Seattle headquarters.
The internal debate at Microsoft was blunt.
OpenAI CEO Sam Altman and Microsoft CTO Kevin Scott at Microsoft Build in 2024. (GeekWire File Photo / Todd Bishop)
Scott wrote that OpenAI was treating Microsoft “like a bucket of undifferentiated GPUs, which isn’t interesting for us at all.” Harry Shum, who led Microsoft’s AI research, said he’d visited OpenAI a year earlier and “was not able to see any immediate breakthrough in AGI.”
Eric Horvitz, Microsoft’s chief scientist, chimed in to say he had tried a different approach. After a Skype call with OpenAI co-founder Greg Brockman, he pitched the idea of a collaboration focused on “extending human intellect with AI — versus beating humans.”
The conversation was friendly, Horvitz wrote, but he didn’t sense much interest. He suspected OpenAI’s Dota work was “motivated by a need to show how AI can crush humans, as part of Elon Musk’s interest in demonstrating why we should all be concerned about the power of AI.”
Scott summed up the risk of walking away: OpenAI might “storm off to Amazon in a huff and shit-talk us and Azure on the way out.”
“They are building credibility in the AI community very fast,” the Microsoft CTO and Silicon Valley veteran wrote. “All things equal, I’d love to have them be a Microsoft and Azure net promoter. Not sure that alone is worth what they’re asking.”
But by the following year, Microsoft had found a reason to double down.
The first billion
In 2019, OpenAI restructured. The nonprofit would remain, but a new “capped profit” entity would sit beneath it — a hybrid that could raise capital from investors while limiting their returns.
Microsoft agreed to invest $1 billion, with an option for a second billion, in exchange for exclusive cloud computing rights and a commercial license to OpenAI’s technology.
The companies announced the deal in July 2019 with a joint press release. “The creation of AGI will be the most important technological development in human history, with the potential to shape the trajectory of humanity,” Altman said. Nadella echoed that sentiment, emphasizing the companies’ ambition to “democratize AI” while keeping safety at the center.
So what changed for Microsoft between 2018 and 2019?
In a June 2019 email to Nadella and Bill Gates, previously disclosed in the Google antitrust case, Scott cited the search giant’s AI progress as one reason for Microsoft to invest in OpenAI. He “got very, very worried,” he explained, when he “dug in to try to understand where all of the capability gaps were between Google and us for model training.”
Microsoft CEO Satya Nadella and OpenAI CEO Sam Altman at the Microsoft campus in Redmond, Wash. on July 15, 2019. (Photography by Scott Eklund/Red Box Pictures)
Nadella forwarded Scott’s email to Amy Hood, Microsoft’s CFO. “Very good email that explains why I want us to do this,” Nadella wrote, referring to the larger OpenAI investment, “and also why we will then ensure our infra folks execute.”
Gates wasn’t so sure. According to Nadella’s deposition testimony, the Microsoft co-founder was clear in “wanting us to just do our own” — arguing that the company should focus on building AI capabilities in-house rather than placing such a large bet on OpenAI.
Nadella explained that the decision to invest was eventually driven by him and Scott, who concluded that OpenAI’s specific research direction into transformers and large language models (the GPT class) was more promising than other approaches at the time.
Hood, meanwhile, offered some blunt commentary on OpenAI’s cap on profits — the centerpiece of its new structure, meant to limit investor returns and preserve the nonprofit’s mission. The caps were so high, she wrote, that they were almost meaningless.
“Given the cap is actually larger than 90% of public companies, I am not sure it is terribly constraining nor terribly altruistic but that is Sam’s call on his cap,” Hood wrote in a July 14, 2019, email to Nadella, Scott, and other executives.
If OpenAI succeeded, she noted, the real money for Microsoft would come from Azure revenue — far exceeding any capped return on the investment itself.
But the deal gave Microsoft more than cloud revenue.
According to an internal OpenAI memo dated June 2019, Microsoft’s investment came with approval rights over “Major Decisions” — including changes to the company’s structure, distributions to partners, and any merger or dissolution.
Microsoft’s $1 billion made it the dominant investor. Under the partnership agreement, major decisions required approval from a majority of limited partners based on how much they had contributed. At 85% of the total, Microsoft had an effective veto, a position of power that would give the company a pivotal role in defining the future of the company.
‘The opposite of open’
In September 2020, Musk responded to reports that Microsoft had exclusively licensed OpenAI’s GPT-3. “This does seem like the opposite of open,” he tweeted. “OpenAI is essentially captured by Microsoft.”
Nadella seemed to take the criticism seriously.
In an October 2020 meeting, according to internal notes cited in a recent court order, Microsoft executives discussed the perception that the company was “effectively owning” OpenAI, with Nadella saying they needed to give thought to Musk’s perspective.
In February 2021, as Microsoft and OpenAI negotiated a new investment, Altman emailed Microsoft’s team: “We want to do everything we can to make you all commercially successful and are happy to move significantly from the term sheet.”
His preference, Altman told the Microsoft execs, was “to make you all a bunch of money as quickly as we can and for you to be enthusiastic about making this additional investment soon.”
They closed the deal in March 2021, for up to $2 billion. This was not disclosed publicly until January 2023, when Microsoft revealed it as part of a larger investment announcement.
By 2022, the pressure to commercialize was explicit.
Mira Murati, left, and Sam Altman at OpenAi DevDay 2023. (GeekWire File Photo / Todd Bishop)
According to a transcript of her deposition, Mira Murati, then OpenAI’s vice president of applied AI and partnerships, had written in contemporaneous notes that the most-cited goal inside the company that year was a $100 million revenue target. Altman had told employees that Nadella and Scott said this needed to be hit to justify the next investment, as much as $10 billion.
Murati testified that Altman told her “it was important to achieve this goal to receive Microsoft’s continued investments.” OpenAI responded by expanding its go-to-market team and building out its enterprise business.
Then everything changed.
The ChatGPT moment
On Nov. 30, 2022, OpenAI announced ChatGPT. The chatbot became the fastest-growing consumer application in history, reaching 100 million users within two months. It was the moment that turned OpenAI from an AI research lab into a household name.
Microsoft’s bet was suddenly looking very different.
OpenAI’s board learned about the launch on Twitter. According to deposition testimony, board members Helen Toner and Tasha McCauley received no advance notice and discovered ChatGPT by seeing screenshots on social media.
McCauley described the fact that a “major release” could happen without the board knowing as “extremely concerning.” Toner testified that she wasn’t surprised — she was “used to the board not being very informed” — but believed it demonstrated that the company’s processes for decisions with “material impact on the mission were inadequate.”
Altman, according to one filing, characterized the release as a “research preview” using existing technology. He said the board “had been talking for months” about building a chat product, but acknowledged that he probably did not send the board an email about the specific release.
As its biggest investor, Microsoft pushed OpenAI to monetize the product’s success.
Microsoft CEO Satya Nadella speaks at OpenAI DevDay in 2023, as Sam Altman looks on. (GeekWire File Photo / Todd Bishop)
In mid-January 2023, Nadella texted Altman asking when they planned to activate a paid subscription.
Altman said they were “hoping to be ready by end of jan, but we can be flexible beyond that. the only real reason for rushing it is we are just so out of capacity and delivering a bad user experience.”
He asked Nadella for his input: “any preference on when we do it?”
“Overall getting this in place sooner is best,” the Microsoft CEO responded, in part.
Two weeks later, Nadella checked in again: “Btw …how many subs have you guys added to chatGPT?”
Altman’s answer revealed what they were dealing with. OpenAI had 6 million daily active users — their capacity limit — and had turned away 50 million people who tried to sign up. “Had to delay charging due to legal issues,” he wrote, “but it should go out this coming week.”
ChatGPT Plus launched on Feb. 1, 2023, at $20 a month.
A week earlier, Microsoft made its landmark $10 billion investment in OpenAI. The companies had begun negotiating the previous summer, when OpenAI was still building ChatGPT. The product’s viral success validated Microsoft’s bet and foreshadowed a new era of demand for its cloud platform.
Ten months later, it nearly collapsed.
‘Run over by a truck’
On Friday afternoon, Nov. 17, 2023, OpenAI’s nonprofit board fired Altman as CEO, issuing a terse statement that he had not been “consistently candid in his communications with the board.” Greg Brockman, the company’s president and cofounder, was removed from the board the same day. He quit hours later.
Microsoft, OpenAI’s largest investor, was not consulted. Murati, then OpenAI’s chief technology officer and the board’s choice for interim CEO, called Nadella and Kevin Scott to warn them just 10 to 15 minutes before Altman himself was told.
“Mira sounded like she had been run over by a truck as she tells me,” Scott wrote in an email to colleagues that weekend.
The board — Ilya Sutskever, Tasha McCauley, Helen Toner, and Adam D’Angelo — had informed Murati the night before. They had given her less than 24 hours to prepare.
At noon Pacific time, the board delivered the news to Altman. The blog post went live immediately. An all-hands meeting followed at 2 p.m. By Friday night, Brockman had resigned. So had Jakub Pachocki, OpenAI’s head of research, along with a handful of other researchers.
A “whole horde” of employees, Scott wrote, had reached out to Altman and Brockman “expressing loyalty to them, and saying they will resign.”
Microsoft didn’t have a seat on the board. But text messages between Nadella and Altman, revealed in the latest filings, show just how influential it was in the ultimate outcome.
At 7:42 a.m. Pacific on Saturday, Nov. 18, Nadella texted Altman asking if he was free to talk. Altman replied that he was on a board call.
“Good,” Nadella wrote. “Call when done. I have one idea.”
That evening, at 8:25 p.m., Nadella followed up with a detailed message from Brad Smith, Microsoft’s president and top lawyer. In a matter of hours, the trillion-dollar corporation had turned on a dime, establishing a new subsidiary from scratch — legal work done, papers ready to file as soon as the Washington Secretary of State opened Monday morning.
They called it Microsoft RAI Inc., using the acronym for Responsible Artificial Intelligence.
“We can then capitalize the subsidiary and take all the other steps needed to operationalize this and support Sam in whatever way is needed,” Smith wrote. Microsoft was “ready to go if that’s the direction we need to head.”
Altman’s reply: “kk.”
A screenshot of text messages between Microsoft CEO Satya Nadella and OpenAI CEO Sam Altman following Altman’s ouster in 2023.
The company calculated the cost of absorbing the OpenAI team at roughly $25 billion, Nadella later confirmed in a deposition — enough to match the compensation and unvested equity of employees who had been promised stakes in a company that now seemed on the verge of collapse.
By Sunday, Emmett Shear, the Twitch co-founder, had replaced Murati as interim CEO. That night, when the board still hadn’t reinstated Altman, Nadella announced publicly that Microsoft was prepared to hire the OpenAI CEO and key members of his team.
“In a world of bad choices,” Nadella said in his deposition, the move “was definitely not my preferred thing.” But it was preferable to the alternative, he added. “The worst outcome would have been all these people leave and they go to our competition.”
‘Strong strong no’
On Tuesday, Nov. 21, the outcome was still uncertain. Altman messaged Nadella and Scott that morning, “can we talk soon? have a positive update, ish.” Later, he said the situation looked “reasonably positive” for a five-member board. Shear was talking to the remaining directors.
Nadella asked about the composition, according to the newly public transcript of the message thread, which redacts the names of people who ultimately weren’t chosen.
“Is this Larry Summers and [redacted] and you three? Is that still the plan?”
Summers was confirmed, Altman replied. The other slots were “still up in air.”
Altman asked, “would [redacted] be ok with you?”
“No,” Nadella wrote.
Scott was more emphatic, giving one unnamed person a “strong no,” and following up for emphasis: “Strong strong no.”
The vetting continued, as Nadella and Scott offered suggestions, all of them redacted in the public version of the thread.
A screenshot of text messages from Nov. 21, 2023, included as an exhibit in Elon Musk’s lawsuit, shows Microsoft President Brad Smith and CEO Satya Nadella discussing OpenAI board prospects with Sam Altman following his ouster.
Nadella added Smith to the thread. One candidate, the Microsoft president wrote, was “Solid, thoughtful, calm.” Another was “Incredibly smart, firm, practical, while also a good listener.”
At one point, Scott floated a joke: “I can quit for six months and do it.” He added a grinning emoji and commented, “Ready to be downvoted by Satya on this one, and not really serious.”
Nadella gave that a thumbs down.
The back-and-forth reflected a delicate position. Microsoft had no board seat at OpenAI. Nadella had said publicly that the company didn’t want one. But the texts showed something closer to a shadow veto — a real-time screening of the people who would oversee the nonprofit’s mission.
By evening, a framework emerged. Altman proposed Bret Taylor, Larry Summers, and Adam D’Angelo as the board, with himself restored as CEO. Taylor would handle the investigation into his firing.
Smith raised a concern. “Your future would be decided by Larry [Summers],” he wrote. “He’s smart but so mercurial.” He called it “too risky.” (Summers resigned from the OpenAI board in November 2025, following revelations about his correspondence with Jeffrey Epstein.)
Altman wrote, “id accept it given my conversations with him and where we are right now.” He added, “it’s bullshit but i want to save this … can you guys live with it?”
Nadella asked for Summers’ cell number.
At 2:38 p.m., Altman texted the group: “thank you guys for the partnership and trust. excited to get this all sorted to a long-term configuration you can really depend on.”
Nadella loved the message.
Two minutes later, Smith replied: “Thank you! A tough several days. Let’s build on this and regain momentum.”
Altman loved that one.
Nadella had the last word: “Really looking forward to getting back to building….”
“We are encouraged by the changes to the OpenAI board,” Nadella posted on X. “We believe this is a first essential step on a path to more stable, well-informed, and effective governance.”
The crisis was resolved, but the underlying tensions remained.
‘Project Watershed’
On December 27, 2024, OpenAI announced it would unwind its capped-profit structure. Internally, this initiative was called “Project Watershed,” the documents reveal.
The mechanics played out through 2025. On September 11, Microsoft and OpenAI executed a memorandum of understanding with a 45-day timeline to finalize terms.
Microsoft’s role was straightforward but powerful. Its approval rights over “Major Decisions” including changes to OpenAI’s structure. Asked in a deposition whether those rights covered a recapitalization of OpenAI’s for‑profit entity into a public benefit corporation, Microsoft corporate development executive Michael Wetter testified that they did.
The company had no board seat. “Zero voting rights,” Wetter testified. “We have no role, to be super clear.” But under the 2019 agreement, the conversion couldn’t happen without them.
The timing mattered. A SoftBank-led financing — internally called Project Sakura — was contingent on the recapitalization closing by year-end. Without the conversion, the funding could not proceed. Without Microsoft’s approval, the conversion could not proceed.
Valuation became a key focus of negotiations. Morgan Stanley, working for Microsoft, estimated OpenAI’s value at $122 billion to $177 billion, according to court filings. Goldman Sachs, advising OpenAI, put it at $353 billion. The MOU set Microsoft’s stake at 32.5 percent. By the time the deal closed after the SoftBank round, dilution brought it to 27 percent.
OpenAI’s implied valuation was $500 billion — a record at the time (until it was surpassed in December by Musk’s SpaceX). As Altman put it in his deposition, “That was the willing buyer-willing seller market price, so I won’t argue with it.”
For Microsoft, it was a give-and-take deal: the tech giant lost its right of first refusal on new cloud workloads, even as OpenAI committed to the $250 billion in future Azure purchases.
At the same time, the agreement defused the clause that had loomed over the partnership: under prior terms, a declaration of artificial general intelligence by OpenAI’s board would have cut Microsoft off from future models. Now any such declaration needs to be made by an independent panel, and Microsoft’s IP rights run through 2032 regardless.
The transaction closed on Oct. 28, 2025. The nonprofit remained (renamed the OpenAI Foundation) but as a minority shareholder in the company it had once controlled.
Six days later, OpenAI signed a seven-year, $38 billion infrastructure deal with Amazon Web Services. The company that had “sneaked in there” at the founding, as Nadella put it in 2015, was back — this time as a major cloud provider for Microsoft’s flagship AI partner.
An OpenAI graphic shows its revenue tracking computing consumption.
In a post this weekend, OpenAI CFO Sarah Friar made the shift explicit: “Three years ago, we relied on a single compute provider,” she wrote. “Today, we are working with providers across a diversified ecosystem. That shift gives us resilience and, critically, compute certainty.”
Revenue is up from $2 billion in 2023 to more than $20 billion in 2025. OpenAI is no longer a research lab dependent on Microsoft’s cloud. It’s a platform company with leverage.
In December 2015, Nadella had to ask whether Microsoft had been called to participate in the OpenAI launch. A decade later, nothing could happen without the Redmond tech giant.
Bill Gates says he’s still optimistic about the future overall, with some “footnotes” of caution. (GeekWire File Photo / Kevin Lisota)
Bill Gates had a front-row seat for the rise of AI, from his longtime work at Microsoft to early demonstrations of key breakthroughs from OpenAI that illustrated the technology’s potential. Now he’s urging the rest of us to get ready.
Likening the situation to his pre-COVID warnings about pandemic preparedness, Gates writes in his annual “Year Ahead” letter Friday morning that the world needs to act before AI’s disruptions become unmanageable. But he says that AI’s potential to transform healthcare, climate adaptation, and education remains enormous, if we can navigate the risks.
“There is no upper limit on how intelligent AIs will get or on how good robots will get, and I believe the advances will not plateau before exceeding human levels,” Gates writes.
He acknowledges that missed deadlines for artificial general intelligence, or human-level AI, can “create the impression that these things will never happen.” But he warns against reaching that conclusion, arguing that bigger breakthroughs are coming, even if the timing remains uncertain.
He says he’s still optimistic overall. “As hard as last year was, I don’t believe we will slide back into the Dark Ages,” he writes. “I believe that, within the next decade, we will not only get the world back on track but enter a new era of unprecedented progress.”
But he adds that we’ll need to be “deliberate about how this technology is developed, governed, and deployed” — and that governments, not just markets, will have to lead AI implementation.
More takeaways from the letter:
Job disruption is already here. He says AI makes software developers “at least twice as efficient,” and that disruption is spreading. Warehouse work and phone support are next. He suggests the world use 2026 to prepare, citing the potential for changes like a shorter work week.
Bioterrorism is his top AI concern. Gates warns that “an even greater risk than a naturally caused pandemic is that a non-government group will use open source AI tools to design a bioterrorism weapon.”
Climate will cause “enormous suffering” without action. Gates cautions that if we don’t limit climate change, it will join poverty and infectious disease in hitting the world’s poorest people hardest, and even in the best case, temperatures will keep rising.
Child mortality went backward in 2025. Stepping outside AI, Gates calls this the thing he’s “most upset about.” Deaths for children under 5 years old rose from 4.6 million in 2024 to 4.8 million in 2025, the first increase this century, which he traced to cuts in aid from rich countries.
AI could leapfrog rich-world farming. Gates predicts AI will soon give poor farmers “better advice about weather, prices, crop diseases, and soil than even the richest farmers get today.” The Gates Foundation has committed $1.4 billion to help farmers facing extreme weather.
Gates is using AI for his own health. He says he uses AI “to better understand my own health,” and sees a future where high-quality medical advice is available to every patient and provider around the clock.
AI is now the Gates Foundation’s biggest bet in education. Personalized learning powered by AI is “now the biggest focus of the Gates Foundation’s spending on education.” Gates says he’s seen it working firsthand in New Jersey and believes it will be “game changing” at scale.
Bill Gates and Melinda French Gates. (GeekWire File Photo, left, and Jason Bell Photo)
Microsoft co-founder Bill Gates paid his ex-wife Melinda French Gates nearly $8 billion as part of the settlement from the former couple’s 2021 divorce.
The money shows up as a 2024 donation to French Gates’ Pivotal Philanthropies Foundation and is called “one of the largest charitable contributions ever publicly recorded” by the Times.
French Gates announced in May 2024 that she was resigning as co-chair of the Seattle-based Bill & Melinda Gates Foundation (now just Gates Foundation). She left the philanthropic organization with $12.5 billion for her own initiatives as part of her divorce agreement with Gates, and said at the time that she would commit that money to her work “on behalf of women and families.”
Pivotal Philanthropies Foundation was established in 2022, a year after the divorce. Between 2022-2024, the foundation gave more than $540 million in charitable grants.
The Times noted that the balance of the agreement — about $4.6 billion — could still be coming and would show up in 2025 tax filings later this year. It’s also possible that the missing amount “was not given to a charitable foundation, but to an entity, such as French Gates’s limited-liability company, Pivotal Ventures, that does not file a tax return,” the Times reported.
Pivotal confirmed to GeekWire that the $12.5 billion agreement has been fulfilled.
GeekWire reached out to representatives for Gates and will update when we hear back.
Gates and French Gates announced the decision to end their 27-year marriage in May 2021. The Microsoft co-founder began dating Melinda French after she started at Microsoft in 1987. The two married on Jan. 1, 1994, raised three children together and grew into one of the world’s richest and most influential pairings.
Gates is 13th on the Forbes Billionaire List with a net worth of $108 billion. French Gates is No. 77 on the list with a net worth of $29.4 billion.
An illustration by ChatGPT based on its interpretation of our year-end GeekWire Podcast discussion.
The past year may go down as one of the most consequential in technology history, in both the Seattle tech community and the world. But in some ways, it’s not without precedent.
As we sat down to reflect on the past year, we rewound all the way back to January — when, as part of a larger discussion with Bill Gates, we asked the Microsoft co-founder to compare the early days of the PC with these early years of AI.
Gates reflected on the PC era as a moment of computing becoming free, effectively.
“Now what’s happening is intelligence is becoming free,” he said, “and that’s even more profound than computing becoming free.”
As we looked through GeekWire’s top stories of the year, almost every one felt like a subplot to that larger narrative. On this special year-end episode of the GeekWire Podcast, we reviewed the articles that resonated most with readers, and compared notes to make sense of it all.
Listen below, and continue reading for episode notes and links.
Enigma of success: ‘Brutal reality’ of tech cycles
The unexpected way AI is affecting jobs — not by replacing workers directly, but by pressuring companies to cut costs as they pour money into infrastructure.
MIT study: 95% of projects using generative AI have failed or produced no return.
Worker stress: Mandates to use AI, but no playbook on how.
One tech veteran’s take: “The enigma of success is a polite way of describing the brutal reality of tech cycles. … The challenge, and opportunity for leadership, is whether the bets actually compound into something durable, or just become another slide deck for next year’s reorg.”
Bill Radke on KUOW: “The tech industry had quite a year. Amazon ordered their workers back to the office. You must come back to the office. Are you here? Good. You’re laid off. Not all of you. Just the humans.“
A pivotal year for Amazon
Andy Jassy’s explanation: Not financially driven, not even really AI driven — it’s culture.
After rapid growth, Amazon trying to get back to operating like “the world’s largest startup.”
The new motto seems to be: Get small and nimble, faster.
Can Amazon find that next pillar of business, as Jeff Bezos used to say?
Magdalena Balazinska, director of the Paul G. Allen School: “Coding, or the translation of a precise design into software instructions, is dead. AI can do that. We have never graduated coders. We have always graduated software engineers.”
The issue was explored by the New York Times in its Daily podcast on Code.org and the shifting landscape for coding education. See the response from Hadi Partovi of Code.org.
Complex alchemy of interest rates, regulation, and market conditions.
AI becomes real
Brad Smith at Microsoft’s annual meeting: Asked Copilot’s researcher agent to produce a report on an issue from seven or eight years ago. Fifteen minutes later: 25-page report with 100 citations.
What’s happening now: the shift from individual productivity to team productivity, from people using AI to organizations figuring it out.
As companies implement AI agents, we move from desktop/individual applications to true enterprise services, playing to Seattle’s strengths.
Quote of the Year
“We look forward to joining Matt on his private island next year.” — Kiana Ehsani, CEO of Vercept, after her co-founder Matt Deitke left to join Meta for a reported hundreds of millions of dollars.
Stickler of the Year
Proud Seattleite and grammarian Ken Jennings on Jeopardy!, correcting a contestant: “Sorry, Dan, we are sticklers in Seattle. It’s Pike Place — no s.”
Feel-Good Moment of the Year
Ambika Singh, CEO and founder of Armoire, accepting the Workplace of the Year award at the GeekWire Awards: “It is not a surprise to any of you that we are losing community outside of these walls in this country. But here, it feels alive and well.”
Members of the Windows 1.0 team at their 40-year reunion this week. L-R, kneeling/sitting: Joe Barello, Ed Mills, Tandy Trower, Mark Cliggett, Steve Ballmer (holding a Windows 1.0 screenshot) and Don Hasson. Standing: Walt Moore, Mark Taylor, Rao Remala, Dan McCabe, Joe King, Scott Ludwig, Neil Konzen, Marlin Eller, Lin Shaw, Steve Wood, and Debbie Hill. (GeekWire Photo / Kevin Lisota)
Tracking down a far-flung team for a 40-year reunion isn’t easy. But the people who worked on Windows 1.0 got some help from their younger selves: a mischievous Easter egg they hid long ago in the software that would become the foundation of the world’s dominant PC platform.
Back in the mid-1980s, before the product launched, they secretly inserted credits in the code, listing their names, to be revealed through a specific combination of keystrokes.
As the story goes, Bill Gates inadvertently found the list by slamming his fists on the keyboard in frustration over the system’s sluggishness, a discovery that only made things worse. The fix: make the sequence more obscure. It worked. The credits went unnoticed by the public until 2022, when a researcher who was reverse-engineering old Windows binaries found them.
When members of the Windows 1.0 team decided to hold a 40th anniversary reunion this year, that roster became their starting point. It was a time capsule that doubled as a guest list.
A core group from that original Windows team reunited over dinner at Steve Ballmer’s offices in Bellevue on Tuesday evening — trading memories, correcting the historical record, and marveling at what they accomplished back then under nearly impossible circumstances.
“Today, developers have all these tools, drag and drop,” said Rao Remala, an early Windows developer, adding that he would challenge anyone today to build a functioning PC operating environment under the 64K segment limits and other technical constraints of the era.
“Have you tried it in ChatGPT?” Ballmer joked from across the room.
This year has been filled with commemorative milestones for the tech giant, from Microsoft’s 50th to Excel’s 40th to the 30th anniversary of the company’s internet pivot. But this one is different. It’s a glimpse into one of Microsoft’s scrappiest projects, from a moment in its history when key resources — including budget and computing power — were far more scarce.
Microsoft’s landmark platform
Windows 1.0, which shipped on a set of 5.25-inch floppy disks, was technically considered an operating environment, not an operating system, because it ran on MS-DOS 2.0.
Microsoft announced it was developing Windows in November 1983. The release was delayed as the team worked through leadership turnover, technical challenges, and user-interface debates (i.e., tiled vs. overlapping windows), giving rise to industry accusations of peddling “vaporware.” Windows 1.0 finally debuted on Nov. 20, 1985.
Boxed copy of Microsoft Windows 1.0, introduced in 1985 as an operating environment for IBM PCs and compatibles. This example comes from the Computer History Museum’s collection. (Computer History Museum Photo)
By the time it launched, Apple’s Macintosh had set the standard with its elegant interface (at least by 1980s standards). Other DOS-based alternatives were also on the market. Critics favored the Mac’s polish, but Microsoft bet on broad PC compatibility, and that approach ultimately paid off.
Microsoft would later get sidetracked temporarily by its ill-fated OS/2 partnership with IBM, before Windows 3.1 became a breakout hit and Windows 95 set the global standard.
But none of it would have been possible without Windows 1.0. The intense, multi-year project was the foundation for the platform that ultimately turned Microsoft into one of the world’s most valuable companies, launching careers that would reshape the tech industry.
For Ballmer, who was tapped to get Windows 1.0 across the finish line long before he became Microsoft’s CEO, the 40-year reunion stirred up old memories and emotions.
“Of all the things I worked on at Microsoft, in a way, I have the most pride about this project,” he told the group, explaining that he truly felt part of the team.
Figuring things out on the fly
As the night went on, the stories came out, some of them for the first time.
Working out of Microsoft’s Bellevue offices, before the company moved to Redmond, the team was largely in their 20s and even their teens in some cases. (Ballmer, in his late 20s at the time, was one of the older people in the office.) That helps to explain the culture at the time.
“Work and social life — there was no difference. It all sort of blended together,” said Scott Ludwig, who worked on the Windows 1.0 window manager, the core system that handled windows, input, events, menus, and dialog boxes.
They were often figuring things out as they went. For example, when Lin Shaw started in August 1984, months before the original ship date, not a single printer driver existed. She built the banding architecture — a way of imaging one strip of a page at a time to work within memory constraints — that would last through Windows 95.
She routinely stayed up all night and considered it the best job in the world. “It was just like college,” she told the group during the reunion dinner, “except I got paid really well.”
Rao Remala leads a toast to the Windows 1.0 team. (GeekWire Photo / Kevin Lisota)
Gates got involved — at times down to the smallest details. Mark Taylor, who wrote the calculator and other early Windows apps, recalled Gates asking him to remove a timer delay in the Reversi game — not to make it faster, but to make Windows look faster. Years later, chips got so fast that the move flashed by too quickly to see, turning the fix into a bug.
Joe King, who worked on the Windows Control Panel, had an office across the hall from Ballmer with remarkably thin walls. He watched a parade of people come for their “SteveB meeting.” The pattern was always the same: quiet conversation at first, then Ballmer would start pacing, getting louder, gesturing emphatically, and reaching a crescendo before it was over.
“The door would open, a guy would sheepishly walk out, and Steve would greet the next person with full energy and enthusiasm,” King recalled. “I would see that all day long.”
Tandy Trower reminisced about joining the team in 1985 despite being warned that it was a dead end by another product manager, Rob Glaser, later of RealNetworks fame.
“I came to Microsoft with this vision of bringing software to the people,” Trower said, explaining that Ballmer pitched the Windows project to him as a way of accomplishing that goal.
He took the job, only to discover the head development manager was already gone. Ballmer offered reassurances that the product was “virtually done.” It wasn’t.
When Trower suggested changes — overlapping windows, proportional fonts — he got the same response: “You want to ship this year?” The answer was yes. Trower ended up working on Windows through Windows 95, part of a Microsoft career that ultimately spanned 28 years.
Marlin Eller, a programmer and musician, was interested in building a music notation editor. At the end of his first year, Gates asked what he wanted to work on. Eller pitched his idea. Gates engaged enthusiastically, then asked: “How big is the market?” Eller realized it was very small.
Gates had another idea. For music notation, Eller would need to build a graphics package — lines, ovals, curves, etc. An operating system needed that foundational technology to support spreadsheets and charts. And that’s how Eller ended up working on Windows.
“The thing the world does not know,” Eller joked before the dinner, “is that Windows was written so I could do music notation. All those other people were working for me.”
Pulling pranks and checking facts
And then there were the pranks. A month or two before Windows 1.0 shipped, for example, developer Mark Cliggett decided to have some fun. He wrote a program that gradually turned off bits on a computer screen, and installed it on Ballmer’s machine when he wasn’t there.
“Multiple bad decisions right there,” Cliggett acknowledged: putting malware on a colleague’s computer, giving it to the future CEO, and missing the irony given the security challenges that would consume the industry years later. Marlin Eller wasted an hour debugging the problem before realizing what had happened. Ballmer, to his credit, didn’t hold a grudge.
GeekWire was invited to cover the Windows 1.0 reunion and document all this history. To prepare, I pulled together a 16-page report using Google’s NotebookLM to mine for information about Windows 1.0 in a variety of historical documents, books, and articles.
After I mentioned this to Ballmer, he suggested I open the evening by reading some colorful anecdotes from the research. It turned into an impromptu fact-checking exercise.
Did Ballmer really call a meeting at 9 a.m. on Easter Sunday 1985 and take down the names of anyone who didn’t show? Yes, he called the meeting. No, he didn’t take names. “I wouldn’t call it exactly a loyalty test,” Ballmer explained, saying it was more about setting a tone.
Did the team really blow off steam by making bombs and rockets with sugar and saltpeter, drawing police to the building when a security guard smelled explosives? Actually, that happened when making a later Windows version, according to someone who was there. The security guard joined them to blow up traffic cones in the parking garage. The police came later, when they were hiding in the library. (The details are a little fuzzy, but you get the idea.)
And finally, turning to a canonical story about the Windows 1.0 project: was the pivotal 1983 Comdex demo really just a videotape flashing graphics on the screen — classic smoke and mirrors to freeze the market? No. “This was real code,” Remala insisted.
“It was a little more smoky than not,” Ballmer added, “but it was all real code.”
Some notable former members of the Windows 1.0 team were missing from the reunion, including the famously hard-to-reach Gabe Newell, who went on to co-found Valve and build Steam into the dominant PC gaming platform.
Rick Dill and Paul Davis, who led development of the Windows Software Development Kit and organized the first Windows developers conference in Seattle in January 1986, were also unable to attend. Dill later managed Microsoft’s joint OS/2 development with IBM and spent years at Amazon; he is now retired in Redmond.
Scott McGregor, the lead development manager recruited from Xerox PARC, left before Windows 1.0 shipped. McGregor later co-authored the X11 windowing system at DEC and served as CEO of Broadcom.
Members of the Windows 1.0 team have gone on to remarkably varied careers.
For example, user interface developer Neil Konzen worked at Ferrari in Italy and pioneered Formula One telemetry. Ed Mills, who worked on fonts, runs a movement therapy practice in Bellevue and is involved in a nonprofit that operates a roller-skating rink in Issaquah.
Cliggett became a long-distance running coach. Eller (who went on to co-author the book Barbarians Led by Bill Gates) teaches computer science. Trower founded a robotics company and continues to work in the field. Taylor is a Seattle public school teacher.
King still introduces himself in the Seattle tech scene by saying he goes back to Windows 1.0 — sometimes prompting the response: “There was a 1.0?” Yes, there sure was.
For Ballmer, the Windows 1.0 experience led to a management technique he still uses today. On his first day as development manager, he repeated to the team what he’d been told was the schedule for different aspects of the project. He heard laughter in response.
He now calls this the “snicker test” — repeat back what you’ve heard from a project’s leaders, and see how the room reacts. If they laugh, you know you’re not getting the true story.
But the real legacy of Windows is much bigger, he told the group this week. If it had shipped two or three years later, Windows wouldn’t have been a relevant product, he said. The key, he explained, was figuring out how to ship “enough of the right stuff at the right time.”
“You did, and it’s nothing short of amazing,” Ballmer said. “It did change the world.”
On a cold winter’s day in December 1995, Microsoft co-founder Bill Gates shook the tech world with plans to embed internet connectivity into all of Microsoft’s major products, making headlines across the country. Click to enlarge. (GeekWire Graphic / Geof Wheelwright)
December 7 carries historical weight well beyond the tech world, but for those who covered Microsoft in the ’90s, the date has another resonance. Thirty years ago today, Bill Gates gathered more than 200 journalists and analysts at Seattle Center to declare that the company was going “all-in” on the internet.
As managing editor for Microsoft Magazine at the time, I was there, and I remember it well. Three decades later, I can’t help but see the parallels to Microsoft’s current AI push.
The moves that Microsoft kicked off that day to build internet connectivity into all its products would reverberate throughout the next decade, helping to lay the foundation for the dot-com boom years and arguably the eventual rise of cloud computing.
The release of Internet Explorer 2.0 as a free, bundled browser, the internet-enablement of Microsoft Office, the complete revamping of the still-new MSN online service, Microsoft’s licensing of Java from Sun Microsystems and a focus on how the internet might be used commercially were all pieces of the Microsoft plan unveiled that day.
Internet Explorer 2 was a modest, but ambitious, part of Microsoft’s 1995 internet enablement strategy. (GeekWire Screenshot / Geof Wheelwright)
“The internet is the primary driver of all new work we are doing throughout the product line,” Bill Gates told the assembled technology press in 1995. “We are hard core about the internet.”
Substitute the word “AI” for “internet” and you have a statement that current Microsoft CEO Satya Nadella could have made at any moment in the last couple of years.
“Fifty years after our founding, Microsoft is once again at the heart of a generational moment in technology as we find ourselves in the midst of the AI platform shift,” Nadella wrote in his 2025 annual letter to shareholders. “More than any transformation before it, this generation of AI is radically changing every layer of the tech stack, and we are changing with it.”
Whether you are using the Microsoft Azure cloud platform; running a Windows 11 PC, tablet, or laptop; spending time on LinkedIn; or using Microsoft 365, you will find AI baked in.
Comparing then and now, there are insights in both the similarities and the differences, and lessons from Microsoft’s mid-’90s missteps and successes that are still relevant today.
What’s the same?
The challenge of navigating the shift to a new generation of technology in a large, fast-moving company is the biggest similarity between now and 30 years ago.
Bill Gates launches Windows 95 in August 1995, just four months before the company’s massive internet pivot. (Microsoft Photo)
Microsoft was a lot smaller in 1995, but it was still the dominant force in the software industry of its day. When the company launched Windows 95 in August of 1995, it came with the first versions of both Internet Explorer and MSN. Within four months, it had to ship new, better versions of those products alongside a whole lot of other changes.
The push for speedy change grew out of something the company had been telling its senior leaders for several months prior to the launch of Windows 95: It had to move fast and do more if it was going to catch up in a race that it couldn’t afford to lose.
Gates’ famous “internet tidal wave” memo from May 26, 1995 (which later became an antitrust exhibit) spelled out both the threat and opportunity — calling the internet “the most important single development to come along since the IBM PC was introduced in 1981.”
Later in the memo, Gates acknowledged a significant problem: Microsoft would have to explain why publishers and internet users should use MSN instead of just setting up their own website — and he admitted that the company didn’t have a great answer.
Fast forward to March 2023, a few months after Microsoft partner OpenAI launched ChatGPT, when Satya Nadella made the scale of the AI era clear in a speech on the future of work.
“Today is the start of the next step in this journey, with powerful foundation models and capable copilots accessible via the most universal interface: natural language,” Nadella said. “This will radically transform how computers help us think, plan, and act.”
Of course, Microsoft CEOs have learned a lot over the last 30 years, including the importance of not pointing out the company’s shortcomings in memos that could end up being seen by the rest of the world. Nadella offered nothing like Gates’ MSN admission. But his comments about the size of the AI challenge and opportunity were a direct parallel to the urgency that Gates expressed about the internet 30 years ago.
What’s different?
In the world of PC operating systems and software, Microsoft in the 1990s was king — with few competitors that came even close to the kind of market share it enjoyed. It was arguably late in making a bet-the-company pivot to the internet, but doing so from a very strong position.
Thirty years later, amid the rise of artificial intelligence, Amazon, Google, Nvidia, OpenAI, and Anthropic are part of a more complex network of competitors and partners.
Back in 1995, the big competition was perceived as coming from Netscape and other fast-moving internet startups — and Microsoft was the behemoth battling the insurgents.
The New York Times’ headline about the 1995 event summed up the framing: “Microsoft Seeks Internet Market; Netscape Slides.” As The Seattle Times put it, “Microsoft plays hardball — Game plan for the Internet: Crush the competition.” Many others echoed the theme.
The Seattle Times’ coverage of Microsoft’s internet pivot captured the competitive themes of the day. (Click to enlarge)
I saw that competitive dynamic first-hand at the press event, when by a stroke of luck I ended up sitting beside Bill Gates at lunch. I recall him being a little annoyed by questions about the Java licensing deal with Sun and the broader press interest in the Netscape/Microsoft narrative. He wanted to focus on the broader impact of the day’s announcements.
He stressed, for example, that the licensing by Microsoft of Sun’s Java programming language for use with Microsoft’s Internet Explorer browser was not really a big deal.
“Java you can recreate trivially,” Gates told me, brushing off the licensing deal as a routine business decision, not much different than many others Microsoft made over the years.
The scale is also drastically different. For example, my January 1996 cover story for Microsoft Magazine quoted Gates explaining how the “150 million users of Windows” would benefit from the internet integration it was undertaking across 20 new products and technologies.
In today’s terms, those numbers look tiny. In a blog post earlier this year, Microsoft executive vice president Yusuf Mehdi said Windows now powers more than 1.4 billion monthly active devices. That doesn’t include Microsoft’s massive cloud computing business, Microsoft 365, LinkedIn, Xbox, and its already-significant AI-attributable revenue from Copilot.
The investment gap is more dramatic, even adjusted for inflation. Microsoft poured more than $88 billion into capital expenditures last fiscal year, much of it on AI infrastructure. In 1995, the company’s $220 million deal with NBC to launch MSNBC sounded like a lot of money.
That MSNBC deal, however, highlights another important contrast between the present and the past. In 1995, no one really knew where the internet (and the web) was going to go. Fortunes were made and lost trying to predict which business models would work online.
Tim Bajarin, CEO of the consultancy Creative Strategies and a longtime industry analyst, says Microsoft is better positioned now than it was in 1995. The difference: we already have the underlying architecture for useful AI applications. That wasn’t true with the internet back then.
“We didn’t see the value proposition until we saw the role of applications built on a web-based architecture,” Bajarin said. “That is what is significantly different.”
Lessons for today
Microsoft’s AI push, Bajarin said, will succeed only if it delivers genuine value — implementations that solve real problems and show clear return on investment.
Recent headlines suggest not everyone is convinced. ‘No one asked for this’: Microsoft’s Copilot AI push sparks social media backlash, declared Germany’s PC-WELT magazine. It’s the same question Gates couldn’t answer about MSN in 1995: Why should anyone use this?
Microsoft CEO Satya Nadella speaks at the company’s 50th anniversary event. (GeekWire File Photo / Kevin Lisota)
Perhaps the biggest lesson on the competition front is that there is no guarantee of longevity or relevance in tech. Only one of the competitors listed in the December 1995 New York Times story is still around – IBM – and it is a vastly different company than it was then.
There is one more lesson, about the cost of success. Microsoft’s aggressive internet push worked — but it also triggered a Department of Justice investigation that lasted from 1998 to 2001. Competing hard is essential. Competing too hard has consequences.