Microsoft’s current AI dominance is thrilling the company’s diehard fans

A man holding up two copies of Windows 95 in a crowded store, from August 1995.
Back in 1995, Microsoft’s new operating systems were a big deal. | Torsten Blackwood/AFP via Getty Images

They stayed true through Zunes, Windows Phones, and the original Bing. Now Microsoft’s fans are enjoying its big AI moment.

It’s too early to tell how Microsoft will ultimately fare in the AI search war it started with Google. Both companies have now rolled out their AI-infused search offerings, though Microsoft’s new Bing, the result of its partnership with OpenAI, which made ChatGPT, has gotten the lion’s share of the attention and praise. Google’s Bard chatbot, on the other hand, has so far been a disappointment.

This has put Microsoft in a position that we are used to seeing Google in: on the cutting edge.

It has also put Google on its heels. The search giant currently looks like an also-ran with an inferior product. Microsoft has found itself in that position all too often since Google’s early 2000s rise, which would ultimately allow it to dominate the internet. So now Microsoft’s having a rare moment in the sun, and at Google’s expense.

Microsoft’s fans seem to be enjoying it. Vox asked several of them how they felt about seeing the company at the forefront of what could be potentially world-changing technology for the first time in a very long time. Their answers show how Microsoft’s OpenAI integrations into its consumer products have managed to live up to a lot of the buzz so far, but there’s also a long way to go before anyone can say that they’ll give Microsoft a real edge over competitors.

“Oh, how the turn tables,” Brett Lemoine, an IT worker who lives in Texas, said in an email. “I think, for maybe the first time, Microsoft is ahead of the game on this one. In my opinion, they had better products in the past, but they never stuck because they were released too late and/or never got enough user adoption (Zune, Windows Phone).”

Lemoine calls himself a “Microsoft fanboy” on his Twitter profile, where he’s also posted a photo of his much-faded tattoo of the Windows 7 logo.

Photos of a tattoo of the Windows 7 logo on the back of someone’s left shoulder. One is the brand new version and the other is the faded version 12 years later. Brett Lemoine
Brett Lemoine’s Windows 7 tattoo, then and now.

“I got the tattoo back in college — was my first one,” he explained. “Always wanted a tattoo and I guess Microsoft was my biggest passion at the time.”

Lemoine, who says he is not related to Blake Lemoine, the former Google engineer who thought its chatbot had become sentient, has also passed what may be the truest test of a Microsoft fan: He had a Windows Phone, which was Microsoft’s ill-fated attempt to compete with Apple’s iPhone and Google’s Android ecosystem. Released in 2010 at a cost of billions, the Windows Phone was a relative latecomer to the market and never really caught on. When mobile devices overtook desktop and laptop PCs in terms of usage, Microsoft didn’t have much of a foothold.

Vivian Chandra, who works in education and lives in New Zealand, said in an email that her Windows Phone was “quite awesome,” but she had to give it up. Once developers stopped supporting apps for it, she eventually found herself in an airport needing to use an Air New Zealand app that no longer worked. Chandra is still devoted to the Microsoft hardware that hasn’t been discontinued. When the Surface tablet was first released 10 years ago, she made a special pitstop in the United States on a trip to Canada to pick one up so she wouldn’t have to wait for it to come to her country. She recently bought a Surface Pro 9, too.

“The buzz [over AI] is quite exciting,” Chandra said. “They missed the boat with smartphones, but this might be a new way for them to move ahead of Google.”

Microsoft has indeed missed the boat in the past, but it was doing just fine before OpenAI came along. It’s currently the second-most valuable company in the world, with Apple being the first. Google is fourth, just behind the state-owned Saudi Aramco. So Microsoft’s still beating Google in terms of market cap.

But, aside from its gaming division, it’s been a long time since Microsoft’s consumer offerings got much buzz. Often, the company either enters a market too late, as it did with the Windows Phone, or it loses out to an upstart that offers something better. Google’s search, Chrome, and Gmail are the majority of consumers’ preferred web search, browser, and email providers. Microsoft’s web search, browser, and email offerings are not. Decades ago, people lined up overnight to get their hands on Microsoft’s new Windows operating system; now, Google’s Android mobile operating system has the biggest market share. Microsoft is an enterprise or business services provider, such as Office productivity and server software and cloud computing. Even its social media platform, LinkedIn, is about business. These offerings have been lucrative. They’re also boring.

Microsoft seems to believe that OpenAI will help it recapture that past glory and excitement. OpenAI’s integrations with its consumer products were unveiled at a splashy event in February with a clear message: With generative AI, web search was about to evolve, and Microsoft was going to lead the way. Google was not because it had been playing it too slow and too safe with its AI offerings. Now, Google is forced to scramble to push out its own generative AI products. So far, Bard and Google’s other AI offerings have been met with much less fanfare and had fewer features and more flaws. Even Bing’s missteps have been more interesting than Bard’s.

Google is the boring one now. Microsoft fans who hadn’t used Bing and Edge much before OpenAI — even diehards have their limits — say they’re enjoying the experience now.

Sam Hosea was a “teenage Microsoft groupie” whose earliest memory with Microsoft was “tinkering around with QBasic.” Now 40 years old and living outside DC, where he works as a caregiver, Hosea said in an email that, until recently, he “hadn’t thought about Bing in a very, very, VERY long time.” Lately, he’s been using it quite a bit.

“For the past few weeks, I’ve literally been spending much of my free time chatting with the AI bot on the Bing app!” Hosea said. Meanwhile, he hadn’t even heard of Google’s Bard until he was asked how he thought it compared to Bing.

Lots of other people are trying out Bing, too. Microsoft recently announced that the search engine crossed the 100 million daily user mark (Google, by contrast, does billions of searches per day). Microsoft also said that Edge “continues to grow in usage” without providing a number. It remains to be seen if Microsoft can build on that to become a real competitor to Google, which remains the undisputed leader in search and browsers, or if it will even be able to maintain the excitement around Bing and Edge if and when the AI novelty and hype fades. Even some of Microsoft’s biggest fans aren’t sure of that yet.

Chandra admits that she prefers Chrome and Google search over Edge and Bing now. While she hasn’t noticed a big difference yet in the new offerings, she’s hoping Microsoft will continue its tradition of integrating the Māori language into its products by making it available in AI searches.

And while Hosea is having fun asking Bing deeper questions and having conversations with it, his “go-to for day-to-day searches” is still Google.

Brian Hoyt is the IT director at an elementary and middle school in Washington state, and his Microsoft use dates back to 1984 and MS-DOS. He says he hasn’t used Microsoft’s AI integrations much because they’re not yet available for education customers, but he is wondering if Microsoft will run into issues down the line because it doesn’t own OpenAI outright, while Google’s AI products were either acquired or developed in-house.

“They definitely seem to have the first mover advantage, but it is unclear if that will hold up,” Hoyt said, noting that Microsoft will have to monetize those costly AI offerings at some point and that could cause some pushback.

As for Lemoine, he says he’s considered getting his Windows 7 tattoo refreshed, if not covered up with a newer Windows logo. But he’s not letting Microsoft’s possible renaissance influence that decision.

“OpenAI stuff doesn’t sway me either way,” he said.

A version of this story was first published in the Vox technology newsletter. Sign up here so you don’t miss the next one!


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