Ep. 30: Lifestyle over empire ft. Caitlin Dewey

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