Simon Owens covers the media industry for his Substack newsletter and podcast The Business of Content.

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.

If you’re a media operator/publisher/writer/editor/media advertising person/journalism student/C-suite person looking to get more in tune, or you’re just someone who is really really really nerdy about this stuff, today’s episode, like last week’s conversation with Jarrod Dicker from the Washington Post, is for you.

(Some of my favorite pieces Simon has written over the past few years)

Catch up with season 2 of the Office Hours w/me podcast. I want the vibe of this thing to be like a Millennial take on the Charlie Rose show…you know, minus the problematic behavior. So far, season 2 has featured interviews with some big thinkers across cultural industries.

The Office Hours Interview with Folu Akinkuoto of the Unsnackable newsletter and the #HumblebragDiet.

Did you know, that for less than the cost of a bucket of beers, you can support a Black-owned independant media startup? Become a paid supporter of Office Hours with Ernest Wilkins on an ongoing basis today. $7 a month or $75 a year.

Can’t do a paid subscription? Consider showing financial support for my work with a one-time donation!