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The GitHub Octocat mascot on the floor of the company’s San Francisco headquarters. (Steve Fadden Photo, via Flickr, Creative Commons.)

Will Octocat get along with Ninja Cat?

GitHub co-founder Chris Wanstrath laughed in an interview this week as he pondered the compatibility of his company’s mascot with the flag-waving feline on a fire-breathing unicorn that has become a symbol of Microsoft’s resurgence.

GitHub co-founder Chris Wanstrath. (Dave Fayram Photo, via Flickr, Creative Commons.)

“Time will only tell,” Wanstrath said after thinking for a moment. “Octocat seems to have made a lot of friends in the past. So I’m confident in that relationship.”

The real question, of course, is the compatibility of Microsoft and GitHub, after the tech giant announced a deal Monday to acquire the popular software development platform for $7.5 billion. The third-largest acquisition in Microsoft’s history, it’s part of a broader effort by the company to connect with a new wave of software developers, the influential population of third-party coders who will play a key role in the success or failure of Microsoft’s next generation of products.

With most deals of this size, Microsoft’s toughest audience would have been investors concerned about its ability to pull off another giant acquisition.

But rather than wooing Wall Street, the company spent the past week making its case to the more than 28 million software developers who use GitHub as a critical component of their daily work, relying on the platform to store, share and collaborate on the code that powers technology products around the world.

Microsoft CEO Satya Nadella at the company’s 2015 Imagine Cup student technology competition in Seattle, wearing a Ninja Cat shirt. (GeekWire File Photo / Todd Bishop)

GitHub’s deal with Microsoft is not going over well with developers wary of one company owning a platform that has become so central to their work. And the acquisition is even less popular among those who remember the days when Microsoft was at war with many of the open-source initiatives that use GitHub to collaborate on software projects. The fact that GitHub isn’t a big money-maker is also fueling questions about Microsoft’s ultimate motivations.

In a conference call after the deal was announced, Microsoft CEO Satya Nadella acknowledged that the company has been “on a journey” with the open-source community but said it’s now “all in with open source,” actively participating and contributing to open-source projects, and making many of its key developer tools and technologies open-source themselves.

“When it comes to our commitment to open source, judge us by the actions we have taken in the recent past, our actions today and in the future,” Nadella said.

Charles Fitzgerald, a Seattle-area angel investor and former Microsoft executive, said it’s “a mistake to look at this deal through the lens of Microsoft 10 or 20 years ago.”

“Satya’s Microsoft aligns very well with GitHub,” Fitzgerald said. He added, “The other side of this is GitHub has kind of been going sideways for the last couple years. There is an opportunity here to reaccelerate and make GitHub great again.”

Playing the long game

The fate of the acquisition rests largely in the hands of Nat Friedman, the 40-year-old Microsoft vice president who has been tapped as GitHub’s new CEO. In an joint interview with Wanstrath after the deal was announced, Friedman told GeekWire what Microsoft plans to do with GitHub, and how the Redmond company hopes to benefit … eventually.

GitHub co-founder Chris Wanstrath, future GitHub CEO Nat Friedman, Microsoft CEO Satya Nadella, and Microsoft CFO Amy Hood. (Microsoft Photo)

“Microsoft absolutely intends to be a great steward of GitHub, and not just that, but to make it better,” Friedman said. “And as developers who love GitHub today see that it’s improved under Microsoft, we’ll earn trust with those developers and we’ll earn the right to be considered for the other things that Microsoft does.

He explained, “A developer who says, ‘Microsoft bought GitHub a couple of years ago and yeah, it’s great, it’s gone really well,’ will look to Microsoft’s other developer tools and services with a little more interest.”

In a Reddit AMA online discussion on Thursday, Friedman was peppered with tough questions from GitHub users — including the overlap between GitHub’s Atom text editor and Microsoft’s VS Code, questions about whether there will be advertising on GitHub public repositories, and concerns about the Redmond company’s potential access to competitors’ proprietary code.

“In addition to the most visible public open source repositories, GitHub is home to countless -private- repositories, many of which are owned by companies with offerings that directly compete with Microsoft,” one person asked. “This is a very clear conflict of interest. What steps can Microsoft take to prove private repositories remain private even from Microsoft employees and executives?”

Friedman responded, “Microsoft hosts the confidential information of more than one billion customers today, and this is a responsibility we take extremely seriously. GitHub already has policies and controls in place to limit employee access to private repos, and this will remain as tight as ever under Microsoft.”

Meet the new boss

By designating Friedman as the new CEO, Microsoft is giving GitHub one of its own.

Nat Friedman, designated as the next CEO of GitHub, was previously CEO of Xamarin, a mobile development platform acquired by Microsoft in 2016. (Microsoft Photo)

“My name is Nat and I’ve been a developer since I was six,” he wrote in a “Hello, GitHub” post this week. “I’ve been active in open source since the 90s when I discovered Linux.”

He continued, “I was blown away to discover a free operating system that came with an editor, compiler, and debugger—all of the tools you need to be a developer, and all of the source code! It was an incredible opportunity for a teenager in a small town in Virginia to learn from the best developers in the world. I spent 15 years working with Linux and founded a couple of open source companies. My first commit to GitHub was in 2009, when GitHub was a year old.”

Friedman has also been through his own acquisition process with Microsoft. He and his co-founder Miguel de Icaza sold their cross-platform mobile app development company Xamarin to the Redmond company in 2016, and Friedman is currently Microsoft’s corporate vice president of developer services. He continues to live in San Francisco, where GitHub is based.

“I think I’m just in a good position to know what Chris and the GitHub team are feeling right now, having been myself in exactly that position two years ago,” Friedman said in the interview with GeekWire this week. “Hopefully I’ll be able to be a little bit of a better guide for the team as we go forward because of that experience that I’ve had.”

One major difference between the GitHub and Xamarin acquisitions is that GitHub will continue to operate independently, not just in product development teams but also in sales, marketing and business operations, Friedman said. “The reason that’s important is it gives us the opportunity to work closely together to ensure that we’re giving customers what they want, and that we have an organization which is wholly focused on this developer persona and this developer customer.”

John Connors, the former Microsoft chief financial officer, has a unique perspective on Friedman and the GitHub deal as managing partner at Seattle-based venture capital firm Ignition Partners, which was a key investor in Xamarin prior to the Microsoft acquisition. Even operating independently, GitHub stands to benefit significantly from being part of Microsoft, he said.

“For the GitHub employees and for that team, they will be astounded at what it means to have the go-to-market depth, resources and strategy of a Microsoft,” Connors said.

As Microsoft was negotiating to acquire Xamarin, Connors made a point of identifying Friedman as a promising executive for the company in discussions with Nadella and Scott Guthrie, now the head of Microsoft’s Cloud + AI Group. Connors said he is bullish about Friedman’s ability to lead GitHub, and about the long-term benefits of the acquisition for Microsoft.

“Overnight, Microsoft now has a relationship with almost every developer in the world,” Connors said.

Wanstrath, the GitHub co-founder, announced plans last year to step down as CEO, but the company previously struggled to find his replacement. He will become a technical fellow at Microsoft after the acquisition closes.

In the interview this week, he expressed confidence in Microsoft’s ability to continue operating GitHub as an open platform, and in GitHub’s ability to reach a new level.

“Part of it is just in the air,” he said. “We all know that software is seeping into every part of our lives. We’re seeing more software developers being hired at nontechnical companies than at technical companies. This is really, I think, the start of something big with software. We haven’t even reached the tip of the iceberg yet.”

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