Editor’s note (April 2025): This article is part of Blog Herald’s editorial archive. Originally published in November 2009, it has been reviewed and updated to ensure accuracy and relevance for today’s readers.
In November 2009, something happened at Microsoft’s Professional Developers Conference in Los Angeles that stopped a lot of people in the tech world cold. Matt Mullenweg — the co-creator of WordPress, the face of open-source publishing, a man who had built his entire reputation on the idea that software should be free and open — walked onto a Microsoft stage alongside Ray Ozzie, the company’s Chief Software Architect, to help launch Windows Azure.
The reaction was immediate. Confusion. Suspicion. Speculation. And underneath it all, a genuine question that pointed toward something much larger than one conference appearance: what does it mean when the boundaries between open and closed, between the scrappy independent web and the corporate platform economy, start to blur?
That question has only grown more relevant in the years since.
What actually happened at PDC 2009
The original Blog Herald coverage treated the appearance as something of a mystery — a question mark hanging over Mullenweg’s allegiances. But the full picture was a little more nuanced than the initial headlines suggested.
Mullenweg took the PDC stage to demonstrate that Windows Azure could support MySQL, PHP, and Apache — the open-source stack that powers WordPress. Automattic, his company, was announced as one of Azure’s early production customers. The specific project was a new site called OddlySpecific.com, built on SQL Azure. WordPress.com itself wasn’t moving anywhere; the existing infrastructure stayed put.
Mullenweg addressed the tension directly on the WordPress VIP blog shortly after: the partnership wasn’t a contradiction of open-source values, he argued, but an extension of them. Getting the open web stack deeper into Microsoft’s cloud infrastructure meant more developers could use familiar, free tools in a new environment. As he put it at the time, once you get a taste of freedom, it’s hard to go back.
That didn’t stop the speculation. German-language tech commentary at the time captured the mood well. Observers noted the conspicuous silence around the financial details of the arrangement, and floated the idea that a WordPress acquisition by Microsoft might be in play — a migration first, then a full buyout. After the conference, the question circulating among observers was blunt: “Is Matt a customer or an employee? Neither seems to fit.”
It was a reasonable thing to wonder. The appearance was a marketing coup for Microsoft — the open-source community’s most visible figure, standing on the proprietary platform stage. Whether Mullenweg fully appreciated how it would read to his community at the time is a separate question.
The bigger shift nobody was naming yet
Looking back, the PDC 2009 moment was an early signal of something the tech industry would spend the next fifteen years working through: Microsoft’s gradual, then accelerating, pivot toward open source.
The company had previously been openly hostile to the movement — its executives had used words like “un-American” and “cancer” to describe open-source software. By 2009, that position was already softening. Azure’s support for PHP, MySQL, and Apache was part of a deliberate strategy to reach developers wherever they were, not just those inside the Microsoft ecosystem.
The transformation continued well beyond that conference. Microsoft acquired GitHub in 2018 for $7.5 billion. It became one of the largest contributors to the Linux kernel. Today it sits alongside Google, Meta, and Amazon as a foundational force in open-source infrastructure. The company that once treated open source as a threat now depends on it.
For Mullenweg, the Azure appearance looks in retrospect like an early expression of a philosophy he would articulate more explicitly later: that open-source software is strengthened, not weakened, by running on proprietary infrastructure. The goal is reach. The goal is ubiquity. The platform underneath matters less than the freedom of the code on top.
What the moment reveals about platform relationships
There’s a quieter lesson here for bloggers and independent publishers, one that doesn’t require taking sides in a decade-old corporate alliance.
Every creator who publishes on the open web is already navigating a version of this tension. You might write on WordPress — open-source software — but you’re probably hosting on AWS, Cloudflare, or a managed provider with its own terms of service.
You’re distributing through Google Search, which operates its own ranking systems. You might monetise through ad networks that run on proprietary stacks. The open web and the platform economy are not two separate things. They’re deeply entangled.
Mullenweg’s PDC appearance made this visible in a way that was hard to ignore. An open-source advocate on a Microsoft stage isn’t a contradiction — it’s a snapshot of how the web actually works. The question worth sitting with isn’t whether to engage with proprietary platforms. It’s how to do so without losing the independence that makes your work worth anything in the first place.
That’s a question Mullenweg himself has continued to wrestle with publicly, most visibly in the ongoing disputes over WordPress governance, contributor obligations, and the relationship between commercial hosting providers and the open-source project they profit from.
The PDC moment was an early chapter in a longer story about what it means to steward something open in a world that rewards scale and extraction.
What bloggers can take from this
The 2009 conference appearance is worth revisiting not for the gossip value — whether Microsoft was secretly angling to buy WordPress — but for what it illustrates about strategic pragmatism in the independent web.
Building on open-source principles doesn’t require ideological purity about which infrastructure you run on. What it requires is clarity about what you’re protecting: your ability to own your content, move it freely, publish without asking permission, and serve your audience without a platform intermediary being able to take that away.
WordPress still powers more than 40 percent of the web. That scale was built partly through exactly the kind of pragmatic platform engagement that raised eyebrows in 2009. The lesson isn’t that principle doesn’t matter. It’s that principle has to be held at the level of the work itself — in the code, in the license, in the community — not in a refusal to ever share a stage with someone whose values differ from yours.
The open web isn’t fragile. But it does require attention.
