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IT Brew

Microsoft

Brianna Monsanto

itbrew.com

Curiosity may have killed the cat…but for Microsoft veteran Stefan Weitz, it opened a lot of doors.

Curiosity is what led Weitz, who described his younger self as the “prototypical ’80s nerd kid” who loved his computer and 

, to his first gig outside of college with Andersen Consulting, a premier consulting firm.

“I did that because I like the idea of trying different things,” Weitz told IT Brew. “Part of my problem, honestly, is I love to learn different things, which is great, but also from a career perspective, it can be kind of sketchy, because you kind of bounce around.”

His knack for trying new things is what attracted him to Microsoft after Andersen embedded him in the tech giant as a consultant.

“When I was there, I was sitting in RedWest, which was a new building at the time…I looked around as I was having lunch with these people and said, ‘These are all people like me. They’re all just nerds who really just loved the work and loved the puzzles and loved the challenges,’” Weitz recalled.

After six months, a Microsoft recruiter approached Weitz to make his stay permanent with one line: “You can either stay with the Navy or join the pirates” (Microsoft being the pirates in this analogy).

“That was the pitch that got me over,” Weitz said.

Weitz’s time at Microsoft spanned almost two decades, during which he juggled several titles and opportunities.

“I would basically ingratiate myself with different organizations and then they’d say, ‘Well, okay, just come run it then,’” Weitz said.

One of Weitz’s most notable projects as a Microsoftie: helping launch Microsoft’s Bing search engine, which was designed to compete against Google. Part of the challenge of launching a brand-new search engine was not only the need to build something different from the competition, but also persuade people to try it, he said.

“That was literally building a product that nobody said they wanted and then convincing people they actually wanted it,” Weitz said.

The team ended up producing a “decision engine” designed to help users quickly move past “basic” search to find and utilize the information they needed. “So, if you looked at flights to Boston from Seattle, we would give you all the stuff you’d usually see, but we then have a prediction as to whether or not you should buy it now or wait,” Weitz said.

While Bing’s market share was never able to surpass Google’s, the work that Weitz’s team did had a lasting impact.

“It’s helped a lot with the AI efforts because a lot of the work we did in Bing early days…kind of laid the groundwork for a lot of the work in how AI operates today,” Weitz said.

In 2016, Weitz closed his chapter at Microsoft to focus on his love of building. Since then, he has been up to just about everything under the sun, including running the e-commerce fulfillment solution provider Radial for a few years, co-founding a PTSD treatment company, and starting up a music superfans platform.

“I love to go from zero to one,” Weitz said. “I love to have the idea and then get the thing running, and get it all stood up, and then hand it off to somebody to actually really run it. That’s my throughline there, for sure.”

Weitz’s journey after Microsoft hasn’t followed the traditional playbook of ex-Microsofties, but isn’t out of character for Weitz, according to Matt Wallaert, chief experience officer at outsourcing company Oceans and former Microsoft colleague of Weitz, who said Microsoft employees tend to stay with the company long-term or leave the tech giant to chase roles at similar companies.

“You just don't see that many people who go and do something entrepreneurial and do it really well and dive into that with discipline,” Wallaert said. “Stefan is a really shining example of what it looks like to find a second act that is meaningful and thoughtful.”

 These days, Weitz is known for his event-planning skills. Earlier this year, he tried his hand in the conference industry, co-founding the HumanX conference, an AI-centric conference. Inspiration for the conference came after he noticed some industry leaders’ AI investments remained stagnant, as well as a lack of general-purpose AI gatherings.

“I said, ‘Well, shoot, if we’re relying on enterprises to figure their way through this cacophony of innovation that’s happening every single day, we are going to, at best, under-deliver on the promise of what AI can do,” Weitz said.

The conference’s inaugural year went better than Weitz expected, who said the conference industry is not for the “faint of heart.” Even so, he sees room for improvement for year two, including the type of content the conference will focus on.

“It’s very much more focused on the role of the person, not the industry in which they find themselves,” Weitz said. “We’ll have some that are more geared towards that, but the majority is going to be focusing on the people and the job they have to do.”

As a co-founder of one of the largest AI conferences, he advised young AI talent to remain curious and open to challenges, two of the skills that worked in his favor in his own career.

“That curiosity and that lack of determinism is what’s missing in a lot of young people today, but also is the opportunity for those who identify that to thrive.”

A portrait of co-founder and CEO of Human X, an AI conference, Stefan Weitz.

Why this Microsoft veteran’s next act is AI conferences

The Microsoft veteran recalls what it was like to launch the Bing search engine.

Billy Hurley

Maybe you’re one of those people who wait until the last minute—whether it’s packing for a trip, filing your taxes, or getting your company’s hundreds of Windows 10 machines upgraded to Windows 11.

While many orgs have been budgeting and planning for Microsoft’s Oct. 14 end of support for Windows 10, some have not.

A Q2 global assessment of more than 1 million enterprise Windows devices from desktop-visibility platform ControlUp found that 50% of machines were on Windows 11, and 13% had hardware in need of replacement.

The bottom line for companies still considering their move to Windows 11, according to Anthony Oren, CEO of managed security services provider Nero Consulting: There will be no more security updates.

“Hackers will attack eventually. They don’t need the 

,” he said, referring to never-before-seen exploits. “They’re just going to rely on these organizations failing their deadlines, failing to upgrade a patch, and they’re just going to strike. And that’s really our biggest concern,” Oren said.

We spoke with Oren and other IT professionals about a move from Windows 10 to 11, and four important steps in between.

Microsoft has released minimum hardware requirements for Windows 11 support, including approved CPUs, 4 GB of RAM, and Trusted Platform Module 2.0, a security chip providing cryptographic keys to support device authentication.

Ross Whitmore, owner of the Michigan-based Northern Technology Services, looks for minimum hardware requirements when assisting clients with the 11 upgrade: 500 GB drive, 16 GB of RAM, and no less than an Intel i5 or i7 processor. Whitmore uses asset management tools like CloudRadial to track machines and their updates throughout the process, as well as remote-monitoring software like NinjaOne to understand warranties and other health-specific attributes of individual devices.

Amit Patel, SVP at Consulting Solutions, recommends that companies perform an inventory to determine which devices will be upgraded or refreshed.

“They probably need to replace certain hardware, at least even components within their devices, but it’s usually underestimated,” Patel said. “Not just from a cost perspective, but also the time perspective of acquiring those new components or new devices.”

Patel advises orgs to make a list of mission-critical applications—and get ready to test them on a Windows 11 device. He also recommends reaching out to vendors as early as possible to see if their customers have experienced specific challenges related to the OS transition.

Whitmore adds that downtime during upgrades is often linked to “wonky” line-of-business applications. To avoid the wonk, he advises customers to check devices, and maybe even reinstall a device’s operating system, to ensure firmware and OS updates have been made.

Also, check in with your users. Whitmore told us; even if specs look correct, “it might still take them 30 seconds or two minutes from the moment they try to open a file to the moment the file actually fully opens,” he said.

Make sure a user’s profile and documents are backed up, Patel said, before an upgrade to avoid any unexpected upgrade-related disruptions. Meanwhile, Whitmore loves to encourage clients to use the sync capabilities of OneDrive, Microsoft’s cloud-storage option.

Patel prefers an incremental deployment approach—one that begins with a few tech-savvy, cross-department early adopters. “That way, if you need to pause…you’re not impacting every user across the board,” he said. Patel also recommends documenting any troubleshooting problems encountered along the way.

“You have that for future reference as well when you need to do the next upgrade,” he said.

An illustration of a white window with blue paned glass in front of a yellow background. The top four panes are made to look like Microsoft's slanted, rectangular Windows logo, and peeping out through the open part of the window is a swirly blue background.

Four considerations as you move from Windows 10 to 11

IT pros break down the upgrade gameplan. 

 in the Microsoft Authenticator app should get ready to say their goodbyes as the beloved feature counts its days.

 earlier this year it would discontinue autofill in Microsoft Authenticator in July in a bid to consolidate its credential management features in Microsoft Edge, the company’s AI-powered browser. The suspension is set to occur in three phrases:

Starting this month, Microsoft said users will be unable to add or import new passwords in the Microsoft Authenticator app. It noted that users could continue to save passwords in autofull until the next phase in its transition.

In July, autofill will be discontinued in Microsoft Authenticator.

In August, saved passwords will no longer be accessible in Microsoft Authenticator.

 To all the hardcore autofill fans out there, all is not lost. Microsoft said the functionality will continue to be accessible through Edge. Users can also use alternative password managers, such as Google Password Manager or iCloud Keychain, by setting them as their default autofill provider in their phone settings.

Microsoft said Authenticator will still continue to support passkeys. Passkeys set up through Authenticator will need the app to remain enabled as a passkey provider in order for them to work.

, the company emphasized its commitment to 

, stating it had joined the FIDO Alliance in recognizing the industry holiday as World Passkey Day and that new Microsoft accounts would be “passwordless by default” moving forward.

“Although passwords have been around for centuries, we hope their reign over our online world is ending,” the company wrote in the 

Text bubble with starred passwords and arrows clicking copy and paste.

Microsoft Authenticator’s autofill feature is coming to an end. Now what?

Starting in August, saved passwords in Microsoft Authenticator will no longer be accessible. 

The sky is the limit—unless you’re Microsoft, in which case, it is a booming business line that has solidified its place as a top cloud giant over the years.

When talking about cloud hyperscalers in the industry, Azure is a name that is hard to ignore. According to 

, Azure had a global market share of 22% in Q1 2025. In the same period, AWS had a global market share of 29%, while Google Cloud had 12%.

To understand how Azure secured a spot as one of the 

, IT Brew caught up with cloud computing experts to learn about some of the core decisions made in the cloud giant’s early days that positioned it for success.

Mark Russinovich, Azure CTO and technical fellow, told IT Brew that the story behind Azure began in 2006 when Dave Cutler, known for his key role in the development of Windows NT, set off on a project to create a platform for the emerging “software-plus-service era.” The internal project was known as Project Red Dog.

“This team with Dave, under [then Microsoft Chief Software Architect] Ray Ozzie, started to look around the company and talk to different teams that had services, including teams like Hotmail and the Windows Live team, about what they needed to make it easier for them to run services,” Russinovich said.

Azure, formerly Windows Azure, was officially announced in 2008 at the Professional Developers Conference and made its commercial debut in 2010. Brand-naming agency Lexicon claims to have come up with the name Azure, which means sky blue, to reflect Microsoft’s “new attitude” and the “open-ended and flexible nature” of the platform.

“As far as the name Azure, marketing picked that,” Russinovich said. “I thought it was an odd pick at the time because Azure is the color of the sky with no clouds in it, which is the opposite of cloud.”

Wade Wegner, a director of technical evangelism for Azure from 2010 to 2012, told IT Brew that Azure was immediately attractive to Microsoft’s “loyal base,” which included .NET developers. However, outside of that, things looked slightly different, partly because of Amazon Web Services’s (AWS) 

“The broader developer ecosystem actually was centered and flocking around what AWS was doing and it was hard for us, especially early days, given we had such a very specific platform as a service approach to building for the cloud,” Wegner, now a chief ecosystem and growth officer at DigitalOcean, said.

Karthik Ranganathan, founder and co-CEO of Yugabyte, an open-source distributed SQL database company, added that Microsoft’s later entrance into the cloud market ultimately became a focal point for industry onlookers in Azure’s early days. Ranganathan worked as a software design engineer at Microsoft between 2005 and 2007.

“The critics would point out that this gap is going to be very tough to bridge because Amazon’s running away with it, or so to speak,” he said.

Still, several decisions made along the years helped propel the cloud giant as a serious contender in the cloud race. For starters, Russinovich said the company’s move to release Azure Virtual Machines, an infrastructure-as-a-service (IaaS) offering, in 2012 “unlocked a lot of business.”

“What we found was, there were customers that wanted that kind of convenience of what the platform could do for them but a lot of enterprises had existing software that they wanted to just migrate into a cloud platform, and not having an IaaS capability meant that they couldn’t use Azure,” Russinovich said.

Russinovich added that Microsoft’s growing support of open-source, 2018 acquisition of 

, and strong relationship with enterprises also shaped Azure’s trajectory.

“We had this long history of relationships and understanding what enterprises wanted,” Russinovich said. “So, we could bring that to the design of our platform from a security, reliability, operation, [and] support perspective.”

Others, like Cockroach Labs Senior Director of Global Alliances Cassie Zimmerman, credit current Microsoft CEO Satya Nadella, who took on the role in 2014, as another big driver behind Azure’s trajectory. (Cockroach Labs is an Azure database partner.)

“He was really the one who came in and declared Microsoft as this cloud-first, mobile-first company,” Zimmerman said. She pointed to Azure’s rebrand from Windows Azure to Microsoft Azure shortly after Nadella took the reins as a reflection of that shift.

Today, Russinovich said Azure is in the “AI era.” Recent decisions at the company actively reflect this. Microsoft has partnered with OpenAI since 2019 and has pumped 

, the tech company announced that it recently added xAI’s Grok 3 models to the Azure AI Foundry, along with several updates to the unified application platform.

Ranganathan said Microsoft’s early wager on AI has ultimately paid off.

“I’m sure they diversified into a lot of bets and this was the bet that really started taking off in the market,” Ranganathan said.

Beyond AI, Ranganathan said industry onlookers may be waiting for the cloud giant to “round out” its offering for those that fall outside of its enterprise audience.

“Its origins were so much in the enterprise stack…that some of the workflows and some of the ways that developers consume it, it’s complicated,” Ranganathan said. “It works great for large enterprises. It’s difficult for a startup sometimes.”

A Microsoft building peeking through trees.

How Azure rose to the ranks as a cloud giant

“I thought it was an odd pick at the time because Azure is the color of the sky with no clouds in it, which is the opposite of cloud,” Microsoft Azure CTO and technical fellow tells IT Brew.

Eoin Higgins

The year was 2006, and Microsoft was hoping for a big splash with its Windows Vista operating system—but the rollout had the opposite effect.

“I thought, ‘This stuff is really bad,’” Peter Gutmann, a computer scientist at the University of Auckland, New Zealand, and early Vista critic, told IT Brew of the operating system’s debut. “It’s just not going to work. You can’t do it like this.”

He wasn’t the only one. Wes Miller, a former Microsoft product manager, told IT Brew that the concerns he had with Vista, developed under the code name Longhorn, led to his parting ways with the corporation.

“The fundamental reason I left was because Longhorn was not going to work in the enterprise,” Miller, who today works as a research analyst with independent IT planning firm Directions on Microsoft, said.

Steve Ballmer, Microsoft CEO from 2000 to 2014, 

 his “biggest regret” in an interview with ZDNet around the time he was leaving the company.

“The thing I regret most is the, what shall I call it, the loopedy-loo that we did that was sort of Longhorn to Vista,” Ballmer said. “I would say that's probably the thing I regret most. And you know, there are side effects of that when you tie up a big team to do something that doesn’t prove to be as valuable.”

Development of Vista was a tricky process. In a 

 on the platform’s release, Ben Fathi, who was Microsoft’s corporate VP of the security technology unit when Vista was released, wrote that the company’s disorganization was part of the problem.

“At the time, the Windows development environment was a mishmash of tools stitched together over many years,” Fathi wrote. “Teams couldn’t simply build and test their own component without having to spend many hours compiling the universe from scratch to make sure they hadn’t missed an undetected header file dependency.”

For Robert Scoble, a former “evangelist” at Microsoft whose job it was during the run up to Vista to hype the new platform, the development process led to a lot of on-the-fly backing off of prior promises of what would be delivered.

“It went on for months—oh, this feature is disappearing, oh, this feature is disappearing,” Scoble told IT Brew.

 With the wildly successful Windows already acting as the dominant operating system in both consumer and enterprise environments, innovation wasn’t considered a priority. Rather, the company added to the existing infrastructure incrementally—a process that meant there was added complexity to the system and made it “harder to leapfrog the competition,” Fathi wrote.

Further, the new software was asking a lot of older hardware, and needed newer, up-to-date machines to run properly. This introduced a major issue for consumers who were less than enthusiastic about purchasing new computers for the newer operating system, as former Microsoft CVP for Office Development Terry Crowley 

“An important part of what was happening here was a deeper problem — the basic sufficiency of the desktop form factor for the jobs it was being asked to do,” Crowley explained. “The basic use cases — productivity (mostly Office), communications, browsing (including search, websites, and web applications), custom internal line-of-business applications, front ends to custom devices (think of your dentist’s X-ray machine) had mostly stabilized by 2000 and have not changed much since then.”

What did this mean for Vista? Well, most existing hardware—not the newest computers and laptops, but the older ones that were still ubiquitous—was built for software that the new platform would largely render obsolete. And that meant that while Vista would run on older devices, 

“To be fair to Vista, when you install it on a new PC, it actually had a pretty good experience,” Miller said. “The problem for people like me who were in the enterprise space was we’d already just asked people to get new PCs for XP a few years prior. So, companies in particular were not enthusiastic.”

Miller, looking back on the release, said that while the company may have exposed its issues in the rollout and development, it also provided the space for firms like Winternals—where he went after leaving Microsoft in 2004—to innovate.

“I’m not sure the right lessons were learned, I would say [from] my perspective, looking in from the outside, was that it was kind of depressing,” Miller said. “But at the same time, it created an opportunity, because at Winternals, we created software that could make XP last longer.”

“It was an example of what not to do,” he told IT Brew.

Reached for comment, Microsoft, through a PR company, asked IT Brew for a detailed list of questions about Vista. They then declined to comment.

Customers try Microsoft’s new operating system “Windows Vista” with some 200 PCs at the WPC computer trade show in Tokyo, October 18, 2006.

Microsoft Vista was a stumble that exposed weakness

“It was an example of what not to do,” one critic tells IT Brew.

Tom McKay

Want security updates for Windows 10 after 

 on October 14, 2025? Prepare to shell out.

 its price list for the extended security updates (ESU) program, The 

—that’s the program under which Windows 10 users can continue to pay for whichever security updates Microsoft chooses to push for the following three years. For the majority of users, Microsoft confirmed each device receiving continued support will cost $61 the first year, doubling annually after that.

Microsoft also clarified the program is “cumulative,” meaning users joining the program in the second or third year will be required to pay retroactively for the previous years. All told, that means users who stick around through all three years of the program will end up paying around $427 per device.

The announcement noted users can receive updates for free under a limited set of circumstances, such as “virtual machines running in Windows 365 or Azure Virtual Desktop.” Microsoft also said it would roll out continued updates to endpoints connected to Windows 365 cloud PCs with current licenses. There’s also a 

Michael Cherry, the Windows analyst at IT information and advisory firm Directions on Microsoft, previously 

“You’re not getting a lot for your money,” he said. “You’re getting the security updates that Microsoft chooses to fix at their discretion, and only the security things.”

However, Cherry also noted many enterprises seeking to avoid the manpower and equipment costs of upgrading to Windows 11 machines may end up paying for ESU.

 shows Windows 11 adoption has increased to 36.6%. That’s a peak for the operating system, but Windows 10 still has a commanding lead with months to go—a little over 60% of users have yet to upgrade, likely 

 due to Trusted Platform Module 2.0 and other hardware requirements that limit native compatibility with older devices.

Microsoft's Greek headquarters with a banner that says "Windows 10 / Do Great Things".

Want extended security updates for Windows 10? It’ll cost you

Receiving security updates past Windows 10’s end-of-life date isn’t cheap.

Python has overtaken JavaScript as the most popular programming language on GitHub, according to the latest edition of GitHub’s annual 

—probably in large part due to a surge of interest in big data and AI.

According to GitHub, 2024 saw nearly double the number of generative AI projects (a 98% increase), with contributions to those projects rising 59% overall. Martin Woodward, VP of developer relations at GitHub, told IT Brew he believes AI “seems to be…helping more and more people actually call themselves developers.”

There are now over 518 million projects on GitHub, according to the Octoverse report, with over 5.2 billion contributions tracked throughout the year. While Python is used for innumerable purposes, it’s particularly useful for 

 projects, both of which are key parts of generative AI.

Throughout 2024, Woodward said, the lion’s share of AI development shifted from building machine learning tools like PyTorch and TensorFlow to projects using the resulting models.

“These GenAI-based tools are so much easier to use when they’re called as a service or as an external API,” he continued. “That’s why I think we’ve seen this massive spike in terms of [the] number of projects building on top of them, and the number of projects using them.”

Woodward also said that might explain some other findings in the report, such as rapid growth in the number of developers in Africa, Latin America, and Asia. For example, open-source projects have helped lower the cost of running AI inferences, which could make generative AI more affordable in those regions.

Woodward also suggested AI is helping those developers jump through language barriers, whether that means human language or programming ones. While he said it’s too early to directly attribute it to AI, he noted “the acceleration in those countries that are linguistically diverse has really stepped up a notch since these tools, like Copilot essentially, has been introduced.”

GitHub also observed a 92% increase in the usage of Jupyter Notebooks, an interactive software tool for developing data science projects. Woodward explained that while Jupyter Notebooks are “incredibly popular amongst the research community and across the data science community,” the findings indicate they’re increasingly using GitHub to share the underlying workings of their research.

The findings dovetail with a recent GitHub 

 that found growth in contributors identifying as minorities, Woodward pointed out.

“Obviously there are still blockers and restrictions for people in different markets, but we’re definitely seeing the energy and the passion in overcoming them,” Woodward added. “We’re seeing huge growth in India as well, where we’ve seen the government there has done a lot of work in terms of helping their next generation of people get into tech.”

Programmers looking at and examining lines of code.