Using AI to Repurpose Long-Form

Jay shares his workflow automating short-form extraction from long transcripts while grappling with guilt about outsourcing.

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Episode notes

This week I'm joined by my good friend Chenell Basilio, creator of Growth in Reverse and one of the most thorough newsletter analysts in the space. We spent over an hour diving deep into what's really working in email right now — from the death of newsletter hype to the opportunity hiding in recommendation networks. Chenell shared her framework of "insanely valuable content" (the one thing that matters more than any growth hack), and we got surprisingly honest about using AI to create short-form content from our long-form work.

We also tackled the big question: how do you grow an email list if you refuse to use social media? Turns out there are more options than you think — from public homework challenges to old-school guest posting making a comeback. Plus, I introduced a new segment called "Unhinged Questions" where we played kiss, marry, kill with email platforms.