Today, Microsoft turns 50.

I’m sitting in the middle of the celebration here in Redmond, watching Brenda (no last name needed—she owns the stage) walk us through a timeline of Microsoft logos. We’re talking everything from the funky, retro 1975 original to the slightly metal, vaguely aggressive version, all the way to the clean, modern four-square logo we know today.

It’s not just a history lesson—it’s a full-on nostalgia trip. And as someone who’s been here for a touch over 18 years, I’ve seen a few of these logos fly by in real time.

From BASIC to Copilot: The Microsoft Tech Journey

1975 – BASIC for the Altair 8800
Microsoft’s first product was a version of BASIC. It ran on the Altair 8800, which looked more like a piece of lab equipment than a computer. But hey—it worked. It also helped kick off the personal computing revolution.

1980s – MS-DOS, Windows, and Big Hair Energy
We licensed MS-DOS to IBM and the rest was history. Windows 1.0 showed up in ’85 and brought the mouse and GUI into the mix. Suddenly, we were all clicking on stuff and pretending we were fancy.

1990s – Windows 95, Office, and a Little Thing Called the Internet
Windows 95 dropped like a bomb. The Start button! Plug and play! And that launch video with the Friends theme? Chef’s kiss. Office became the gold standard for productivity, and Internet Explorer… well, let’s just say it made some waves.

2000s – Enterprise Time and the Xbox Move
.NET Framework showed up. Windows Server and Active Directory became the backbone of IT departments everywhere. And then we launched Xbox and crashed into the gaming world like we meant it.

2010s – Cloud, GitHub, and Cross-Platform Hugs
Azure matured into a cloud powerhouse. Office 365 changed how businesses worked. GitHub joined the family, and Microsoft leaned into open source like never before. I may or may not have said, “Told you so,” a few times.

2020s – Copilot Everything and AI Everywhere
We’re now living in the age of AI copilots. GitHub Copilot. Microsoft 365 Copilot. Copilot in Windows, in Azure, in Security, in the kitchen (okay, not yet). All powered by Azure OpenAI. We went from BASIC to building language models that write code, documents, and poems—sometimes all at once.

My 18-Year Tour Through the Chaos

Let me rewind a bit. I joined Microsoft back in 2006 as an Architect Evangelist in Michigan. Great role, great people. But I realized pretty quickly that I had more fun—and got more traction—talking to the folks who really didn’t like Microsoft. So, naturally, I leaned into that.

By 2008, I was full-time open source—PHP, Rails, Node.js. Yep, Microsoft was doing open source back then. And yep, people were skeptical. It was a fun time to be in those conversations.

In 2010, I moved to Ireland to be the technical evangelist for all of Microsoft tech. One person, all tech, the whole country. You learn to juggle fast in roles like that.

In 2013, I came to Redmond to join the IE dev marketing team. I was part of the effort to modernize a browser with a bit of… reputation baggage. Let’s just say we had to do a lot of convincing.

After 10 months, I joined TED (Technical Evangelism and Development). That team was full of big ideas, even bigger personalities, and we helped push the boundaries of what developers could do with Microsoft’s tech stack. I stuck with TED until 2018.

Then I made the jump to the Edge browser product team—just in time for the browser reboot. I became the acting Group Product Manager for Developer Experiences, and yes, I was one of the eight people who voted to move to Chromium. That was a big deal. You’re welcome. 😎

In 2019, I moved to CSE (Commercial Software Engineering), which eventually evolved into ISE (Industry Software Engineering), where I still hang out. These days, I help companies solve gnarly problems with cutting-edge tech. The tech keeps changing, but the gnarliness remains beautifully consistent.

Cheers to the Next 50

Watching the logo timeline roll by today, I’m thinking less about the tech and more about the people—folks I’ve worked with, battled bugs with, defended tab spacing preferences with.

Microsoft isn’t perfect, but it’s constantly evolving. And if the last 50 years are any sign, the next 50 will be even weirder, wilder, and more fun.

I’m here for it.