You might not know this name, but I recently read about a man named Gary Kildall, someone who could have become as famous and successful as Bill Gates.
Gary wasn’t flashy. He didn’t act like a typical business leader. But he was a quiet kind of genius, the kind who reshapes entire industries without making noise. Back in the 1970s, when most people still didn’t understand what personal computers were for, Gary had already solved one of the biggest problems in computing: how to make software that worked on different machines. His solution was called CP/M, and it became the first widely used operating system for personal computers. Without it, modern software might not exist the way it does.
So, why haven’t most people heard of him? Why isn’t he remembered as a tech pioneer? Because he missed one important meeting. It wasn’t just any meeting. It was “the moment”.
IBM was working on their first personal computer and needed an operating system to run it. They had already spoken to Bill Gates, who was just 25 at the time, and he sent them to Gary. But when IBM arrived at Gary’s office, he wasn’t there. He had gone flying — one of his hobbies. IBM left, unimpressed. That tiny window closed.
Then Microsoft did something.
They paid $75,000 to acquire the rights to a simple operating system called QDOS, short for “Quick and Dirty Operating System.” It wasn’t polished. It wasn’t impressive. But it got the job done. Microsoft rebranded it as MS-DOS and offered it to IBM.
But here’s where they made a genius move: instead of selling it outright, they licensed it. And they didn’t make it exclusive.
IBM thought they had secured a major advantage. But what they really got was a temporary pass. Microsoft, on the other hand, had just made one of the smartest business decisions in tech history. Because as the personal computer market exploded, more companies started building IBM-compatible machines, and every one of them needed an operating system.
Thanks to that licensing deal, each time a company made a PC “clone,” they had to pay Microsoft for MS-DOS. Not IBM. Microsoft. That’s the part that often gets overlooked. Yes, writing the code mattered. But the real breakthrough wasn’t technical; it was legal. The contract changed everything. It may be the greatest business deal the tech world has ever seen.
When I first read this story, I kept thinking about Gary. What it must’ve felt like to be the one who laid the foundation, only to watch others speed past you. To be early, but unprepared. Brilliant, but too hesitant.
Gary died at 52 😭. And while we’ll never know exactly what broke him, I imagine this: when a once-in-a-lifetime opportunity slips through your fingers and the world keeps reminding you of it over and over, it doesn’t just sting. It lingers. It stays with you.
I’ve had my own close calls. Maybe you have too. Chances that showed up quietly, then moved on fast. Times I should’ve said yes. Or no. Sometimes, I still replay those moments in my head, like scenes I wish I could rewrite. But what’s helped me move forward, even grow, is learning to be grateful. And learning to stay present. Waking up each day and reminding myself: Today is also a moment. And this one is still mine to shape.
Yes, Gates was strategic. Yes, Microsoft’s legal team made history. But for those of us outside the boardrooms, maybe the real lesson is this:
Sometimes the biggest wins come down to something simple—being present when it matters.
Because the billion-dollar meeting that never happened? It changed tech forever. But the meetings that do happen—the ones where you show up, stay alert, and choose to act even when it’s messy, those can change you.
So wherever you are right now, starting out, starting over, or just trying again, I hope you remember this: Gary missed his moment. But that doesn’t mean you will.
