This local newsletter is rebuilding an entire town

About this episode

Apply to the Letterland Live Social Media Manager role now: https://drive.google.com/file/d/1hOfhf3DPUJa-BTtZqxJW7f0fnCSMa9BV/view?usp=sharing This week on Letterland LIVE we're joined by Jack Westerkamp, co-founder of Breaking & Entering, and Michael Kauffmann, founder of Catskill Crew. Jack runs a daily live show about the ad industry and recently revamped B&E's newsletter. He breaks down why a camera-first media company needs email, how he turns a social following into subscribers, and what he'd do differently on day one if he were starting Breaking & Entering for a different industry today. Michael is monetizing a local newsletter in ways most operators have never dreamed of (think: literally rebuilding an entire town). He also walks through the network of local newsletters he's assembling to sell to national advertisers. We'll also get into: - Sam Parr is back in the newsletter game - Heatmap's revenue is up 115% year-to-date thanks to AI data centers - Tech journalist Alex Heath joins Sound Ventures as a VC partner - Ted Williams' plan to buy the Charlotte Observer back from hedge fund ownership for $5M - Media kits that actually close: Bay Area Times, TLDR, CFO Dive and