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Hi All, I worked at Microsoft on OS/2 from early 1986 until 1990. I booted one of the first OS/2 builds in 1986. Her is some on OS/2 releases, including OS/2 NT which for a short while was a thing, I have a shirt from MS that has OS/2 NT on it.
Being on the OS/2 team was a great time overall, with smart folks on the Microsoft team who were focused on making a great system. We worked many hours, through weekends without sleep but we stayed positive for the most part even though IBM and Microsoft has such different cultures. It was never easy to create software in this model where every action was aggressively challenged and questioned by IBM, it rolled right up to Steve Balmer who was a great leader for us and he did the best he could to keep us focused on making great software. IBM was used to big systems and the PC was small, so the more IBM pushed the bigger Os/2 got. I remember my boss showing me an expensive memory card, nearly 1 years pay, he was using to test OS/2 on, it held a full 16MB of RAM.
At the same time some of my friends worked on Windows, we did not take them seriously because OS/2 was IBM+Microsoft, clearly the way forward. I am not sure why Bill Gates keep Windows going but he did, backing 2 horses possibly.
At the same time we worked on OS/2 the Windows 3.0 dev team worked on small 386 boxes with a small amount of RAM (possibly 4MB), saying that is what customers had. We had big beefy PCs on the OS/2 team, and IBM sold hardware so the bigger the hardware the better, and the IBM PS/2 with its proprietary bios was on the way, so the future was clear 🙂 OS/2 was already the winner. That version of windows became Windows 95 over time, Windows NT was 100 % different team and code base.
Before Windows 3.0 I had watched the guy across the hall from me write Windows 2.0 all by himself. He as very happy and whistled when he walked around the office. He was very nice and came from a company Microsoft bought that had made a clone of IBM Deskview, but made it small and fast. Had that Deskview clone hit the market Windows and Microsoft would have been at risk in the upcoming post MS DOS world.
I also was friends with the person, the one person, who tested all of MS DOS releases. Just one person, I was always amazed that one person tested a $1B/yr product.
I later was one of 2 devs from the OS/2 team to get invited to the Windows NT team, a great new team MS brought in the Digital Equipment Corp, DEC and DEC West, did not want David Culters new OS. But Bill Gates and Stever Balmer did, they brought the team in and over time NT and OS/2 split, but I do have a shirt with OS/2 NT on it. Windows NT get renamed to Windows 11 but its still the same core.
So in the 80s Microsoft had MS-DOS slowly phases out, and 3 teams working on the next generation, Windows 3.0, OS/2 and Windows NT. For a while all at the same time. Windows NT, my last MS team, was the best horse and it won the race and still lives today, just re named to Windows 11.
Looking back many times on this, the Windows team of course got it right. Keep the teams small and focus on the customer. Sounds obvious. Microsoft also got it right, keep trying different things until you get a win. Fun times then and fun times now.