What Running Windows at Microsoft Taught Steven Sinofsky About Apple

I think that Steve created a culture of artists and they thought of themselves that way. And in in many ways, Microsoft was a culture of technologists solving technology problems. And it led to very, very different products, but also very, very different scale, at least until the iPhone came out. People will say that the Surface hardware was the only time Apple really paid attention to something Microsoft did and that they really actually thought we had done a good job on the the surface hardware, which was quite the high praise at the time. Windows is really caught in this conundrum of the value that corporations enterprises see in Windows is compatibility. And the levels of compatibility that Windows has are legendary. It was just sort of speculating what would Apple be like if Steve Jobs were still running it. In 2007, Bill Gates sat on stage with Steve Jobs at the All Things D Conference. Asked what he saw as the biggest difference between their companies, Gates looked at Jobs and said, I wish we had your taste. It was a rare concession from the most dominant technology company on Earth. A decade earlier, Apple had nearly gone bankrupt. Microsoft held the PC market so completely that Apple's share had fallen below 3%. Fifty years after its founding, Apple has not only survived, but reshaped entire categories of computing. From phones, to watches, to a $600 laptop the PC industry cannot match. The question is how, and whether taste alone explains it. Steven Sinofsky, board partner at a sixteen z and former president of the Windows division at Microsoft, speaks to a sixteen z research partner Theo Jaffe. We have a very special guest. We have Steven Sinofsky, who is a legendary software warrior in the industry. According to his LinkedIn, he's a board partner at a sixteen z. He wrote hardcore software inside the rise and fall of the PC revolution, all about his time at Microsoft, where he was at for forever, starting as a project lead in the eighties and nineties and working his way up to be president of the Windows division. And he worked there at the same time as my dad. So I've heard I've heard many stories about I've heard many stories about, Microsoft from that era in my house. So, Steven I mean, I your dad dressed as clippy at one point, so I think that that's that's, quite the claim to fame. He's dressed up as Clippy. I I might even have a picture of that. That would be so funny. I'll have to ask him about that later. So we're here because this week, April 2026, is the fiftieth anniversary of Apple. Based on your position in the industry over all these years, what do you think are the most important, like, most salient cultural differences between Apple and Microsoft? Well, between Apple and and Microsoft, you know, there were there's a a very famous moment, late …