What Running Windows at Microsoft Taught Steven Sinofsky About Apple
Episode publishedPodcast: The a16z ShowThe a16z Show
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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 v
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 que
We have a very special guest. We have Steven Sunovsky, 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 quite the claim to fame.
He's dressed up as Clippy.
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 think are the most important, most salient cultural differences between Apple and Microsoft?
Well, Apple and Microsoft, there's a very famous moment late in both Bill Gates' career and in Steve Jobs' career where they were being interviewed on stage at a conference together, and it was the first time they'd ever been interviewed on stage, which is kind of bookend to one of the very earliest times they were together was on an Apple PR event that was called the PC dating game. There was Bill and Steve and a bunch of other original OG PC people, and they were asked all these trivia questions about the industry, and that was I think in 1982 or 'eighty one. Unbelievable. And then you fast
So do you think this distinction still captures it twenty years after this Gates Jobs interview? Is Apple still artists and indeed Absolutely. Happy
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