Ben Gilbert: belief

Transcript context

…We had an editorial board, but it basically ended up me writing an editorial every single day. It's what it came down to do. Not every day for the vast majority. It's interesting because there's an echo of what I ended up doing with my career. This daily hitting points, having to generate content. But it was, (1) just from a practical perspective, it was fun and interesting. It's something I definitely enjoyed, and (2) it worked. Of our five things, we had goals. We accomplished four of them. 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.…

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