Ben Thompson: belief

Transcript context

…I want to go forward to your leaving Microsoft. Give me the emotional moment where you're like, it feels like it could work. I think there's something here, I think I have content/market fit. To go to the back of the Hawaii trip, there was an aspect about going to Microsoft. It's like, well, I should go to a place that is directly oppositional to everything I believe in. Can I make changes at Microsoft? Very sort of arrogant. Really, I learned a lot from Microsoft as opposed to the other way around. I signed up for it knowing this is probably not where I was going to be long-term. After that trip is when I did Stratechery. I wanted to figure out a way to get back to Taiwan at some point. My wife is from Taiwan, and we enjoyed living here. Also, again, I just felt like there was this whole opportunity. I looked at Gruber as someone that was like, well, he did it, but it was also pretty clear that an advertising-based model was probably not going to work. That was obviously a regular theme of mine about the centralization of advertising under Google and Facebook. That world of starting a blog and throwing up some Google Ads was not going to be a viable one. What made you think that? To my mind, at least, there is a very viable and robust alternative history where Stratechery is an advertising business model.…

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