What Running Windows at Microsoft Taught Steven Sinofsky About Apple
The a16z Show
a16z
4.2 • 1.2K Ratings
🗓️ 10 April 2026
⏱️ 31 minutes
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| 0:00.0 | I think that Steve created a culture of artists, and they thought of themselves that way. |
| 0:06.0 | And in many ways, Microsoft was a culture of technologists solving technology problems. |
| 0:11.0 | And it led to very, very different products, but also very, very different scale, at least until the iPhone came out. |
| 0:19.0 | People will say that the circus hardware was the only time Apple |
| 0:22.6 | really paid attention to something Microsoft did |
| 0:25.6 | and that they really actually thought we had done a good job on the surface hardware, |
| 0:29.6 | which was quite the high praise at the time. |
| 0:32.6 | Windows is really caught in this conundrum of the value that corporations and enterprises see in Windows |
| 0:38.9 | is compatibility. And the levels of compatibility that Windows has are legendary. It was just |
| 0:45.4 | sort of speculating what would Apple be like if Steve Jobs were still running it. |
| 0:51.1 | In 2007, Bill Gates sat on stage with Steve Jobs at the All Things D conference. |
| 0:57.4 | Asked what he saw as the biggest difference between their companies, Gates looked at jobs and said, |
| 1:03.0 | I wish we had your taste. It was a rare concession from the most dominant technology company on Earth. |
| 1:10.0 | A decade earlier, Apple had nearly gone bankrupt. |
| 1:13.6 | Microsoft held the PC market so completely that Apple's share had fallen below 3%. |
| 1:19.6 | 50 years after its founding, Apple has not only survived, |
| 1:23.6 | but reshaped entire categories of computing. |
| 1:26.6 | From phones to watches to a $600 laptop, the PC industry cannot match. |
| 1:32.3 | The question is how, and whether taste alone explains it. |
| 1:37.3 | Steven Sinovsky, board partner at A16Z and former president of the Windows Division at Microsoft, speaks to A16Z research partner, Theo Jaffe. |
| 1:50.1 | We have a very special guest. We have Steven Sinovsky, who is a legendary software warrior in the industry. |
| 1:58.2 | According to his LinkedIn, he's a board partner at 816Z. He wrote |
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