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Today’s guest is Caitlin Dewey, creator if Links I Would Gchat You If We Were Friends, a newsletter she started nearly 11 years ago, when she was the social media reporter for the Washington Post. She wrote it for 2 years, taking a 4-year break before bringing it back in 2020; earlier this year, she decided to go all-in and make it her main gig.

We spoke about the particular challenges of being a creator-journalist, how to write an actually good links aggregation newsletter, and choosing to build a lifestyle business instead of a media empire.

00:00 Introducing Caitlin Dewey

03:27 The Origins of the Newsletter

06:16 Taking a Break and the Pressure of a Rebrand

13:36 Building a Community With Readers

17:53 Building a Good Salary From Subscriptions

19:49 The Definition of Creators vs. Journalists

27:42 Bring Back Comfortable Middle Class Lifestyles

32:59 Collaboration in the Newsletter Community

37:37 The Painful Art of Content Planning

43:21 Substack's Shift in Business Model

50:13 The Craft of an Aggregation Newsletter

53:19 Fake News Is Now Just News