Why Microsoft Sucks —And Other Things I Learned from the Cool Kids

In the world of software development, success is optional. But looking cool? That’s mission critical.

And nothing ruins your street cred faster than uttering the words "Microsoft." Trust me—I’ve been there. I've worked at software companies where the mere mention of .NET or Azure would make developers wince like you’d just suggested replacing their MacBooks with fax machines.

You see, Microsoft technologies aren’t cool. They’re stable, scalable, secure, and—brace yourself—designed for businesses that want to make money. Gross.

Why use a mature, battle-tested platform when you can spin up a dozen microservices in a framework that’s still in beta and maintained by a 17-year-old in Luxembourg? That’s how real innovation happens. Right before everything breaks in production.

But the real fun begins when you let your dev team build everything from scratch. Because when you have a team whose experience is limited to a very narrow set of tools and open-source dogma, the obvious next step is to over-engineer every product into oblivion.

Need a simple CRM? Great—we’ll architect a distributed, containerized, quantum-ready, blockchain-adjacent solution with 74 microservices, two front-end frameworks, and a custom-built CI/CD pipeline that no one understands. Think of it like building a Boeing 767 to get to the gas station two blocks away. Is it practical? No. But it feels good.

And sure, you could have delivered something useful to customers in three weeks using Power Apps or Dynamics, but where’s the romance in that? How will your devs brag about their handmade event-driven architecture on Reddit?

At my previous companies, we embraced this philosophy. Our developers vetoed anything Microsoft-related not because it didn’t work, but because it worked too well. How were we supposed to stay edgy if we weren’t spending half our sprint debugging YAML configs and reinventing user authentication from scratch?

We burned through investor money like it was a bonfire at Burning Man, but at least we didn’t sell out to something as “corporate” as SQL Server. And don't even get me started on SharePoint—what are we, accountants?

Here’s the thing: small business owners, if your goal is to build something reliable, efficient, and profitable… don’t listen to us. We’re here for vibes, not viability.

Ignore the fact that Microsoft has decades of enterprise experience, global support, and tools that integrate seamlessly. That stuff’s for boomers. Stick with what’s trendy—because nothing impresses your customers like a half-working app with a sick dark mode.

Remember, it’s not about what helps your business succeed. It’s about what looks cool in a Medium blog post or a poorly-lit TikTok.

So go ahead—ditch the tools that work. Keep chasing the next hot JavaScript framework of the month. After all, if your product crashes but your GitHub repo has 10k stars, did you even fail?