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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 Short Squeez
- Is AI-written content any different from hiring a ghostwriter?
... and everything else you need to know about the newsletter world.
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About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.
