AI Is the Biggest Change to Email Since the iPhone w/ Dan Oshinsky

Email has only had two truly big moments: the AOL CD in 1998, and the rise of mobile. Dan Oshinsky says the third one is happening right now — and nobody, not even the Gmail team, knows what the inbox looks like on the other side.

Dan ran newsletters at BuzzFeed and The New Yorker before founding Inbox Collective, where he helps newsrooms, nonprofits, and independent newsletters get more readers and make money. I caught his AI talk at the Newsletter Conference in May — it was the conversation everyone kept having in the hallways afterward. So I brought him on the show.

We get into who you should actually be writing for (people, robots, or deliverability), why depth is the new moat, where AI genuinely earns its keep in a newsletter operation, and the one fear keeping publishers up at night: email's stability — the entire foundation of this industry — is being challenged for the first time.

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Inbox Collective: https://inboxcollective.com
LinkedIn: https://www.linkedin.com/in/danoshinsky/

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LinkedIn: https://www.linkedin.com/in/chrismiquel
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