Let’s be honest, Microsoft is the richest overachieving underdog in tech history. If tech companies were people, Microsoft would be the guy who trips over his shoelaces, spills coffee on his shirt, forgets his lines at the meeting and still gets promoted to CEO. No one knows how, but we all nod and cheer.
Take Clippy, for example. That overly enthusiastic paperclip who popped up at the worst times with terrible advice. “It looks like you’re writing a letter,” it would chirp, as you screamed internally and clicked “X” for the tenth time. Clippy became a meme before memes were cool. And yet, while Clippy retired to the nostalgic land of corporate shame, Microsoft just kept cashing checks.
Remember the Zune? Of course you don’t. Microsoft’s noble but doomed attempt to dethrone the iPod arrived fashionably late to a party that had already ended. It was brown. It had buttons. It made you question whether music really mattered after all. While Apple was selling sleek innovation, Microsoft was out there peddling a digital potato. And still—still—they somehow made billions elsewhere.
Then came Windows Vista, the operating system that looked nice but functioned like a caffeinated jellyfish. Every action prompted a pop-up asking for your permission, like a paranoid butler double-checking if you really wanted to breathe. Vista was so widely disliked it became a verb. “Don’t Vista this project,” people would say. Microsoft simply shrugged and moved on.
And who could forget Internet Explorer, the browser everyone used once, just long enough to download a better browser. Developers didn’t just stop supporting it; they actively sabotaged it. Still, Microsoft laughed all the way to the bank, probably using Edge (which is basically Internet Explorer after therapy and a wardrobe upgrade).
Let’s not skip over the Windows Phone, though. Microsoft saw Apple and Android dominating and said, “Us too!” The world responded, “No thanks.” It was a sleek device with no apps and no future. It was like showing up to a Formula 1 race on a Segway. But again, Microsoft wasn’t fazed. They buried it and built something else.
That something was Azure. While most of us were distracted by gadgets and gadgets-that-want-to-be-gadgets, Microsoft quietly turned cloud computing into a gold mine. Azure now powers everything from major corporations to the AI models that are probably helping your fridge talk back to you. It’s not the coolest technology product, but it prints money.
Then came the partnership with OpenAI. Suddenly Microsoft was cool again. Like, really cool. Their investment gave them a stake in the future of artificial intelligence—and in some ways, control over it. It’s as if your grandpa bought shares in TikTok and now he’s on the board of directors.
Speaking of surprise power moves, Microsoft also bought GitHub. That’s right, they acquired the platform beloved by the same developers who used to roll their eyes at anything remotely Microsoft. It was a classic strategy, if you can’t win their love, just buy the neighborhood.
And what about Teams? The collaboration tool that installs itself faster than a teenager dodging chores. You didn’t ask for it. You didn’t want it. And now it opens every time you blink. Somehow, Teams became the de facto way office workers yell at each other over webcams.
Then there’s Microsoft Office, which now lives on a subscription model. Yes, they found a way to make you pay for Word every single month. And we do it. Willingly. We hand over our credit cards to edit documents that still somehow lose formatting when you paste in a photo.
Even Xbox, which once caught fire both literally and figuratively, is now a gaming juggernaut. Microsoft turned it into a Game Pass service that rivals Netflix, except instead of canceling shows, it just lets you replay Skyrim until the end of time.
So how does Microsoft do it? Simple. They fail often, fail publicly, and then succeed even harder. They don’t chase trends, they quietly become the infrastructure those trends need. While Apple is busy making titanium phones and Google’s off in its AI lab reinventing email for the fifth time, Microsoft is over here running your office, your cloud, your code, and now your chatbot.
In the end, Microsoft is proof that you can trip, crash, reboot, and update—and still end up leading the market. They are the Rocky Balboa of tech, knocked down repeatedly, but still standing when the final bell rings. You don’t have to be perfect. You just have to be persistent, and maybe own half the world’s productivity software.