He writes about how publishers create, distribute, and monetize their digital content. He and I share the belief that there’s this misconception that the average newsletter reader is clamoring to pay for content, when in reality converting a free reader into a paid subscriber is like pulling teeth. We discuss that, why he’s transparent about the struggles of building a newsletter, alternative tactics that newsletter operators should think more about, building a better paid subscriber experience, where we think Substack is going, and the state of the newsletter business in 2021 and beyond.