Dive Club Content OS

Ridd hosts one of my absolute favorite industry podcasts: Dive Club. It's been one of the most respected voices in the design community, and genuinely transformational to how I think about my career and skill building since late 2023. In 2025, I got the opportunity to work with Ridd on building out an agentic AI-assisted flow to help produce the written content that goes out with each episode.

The problem was real. After every episode, Ridd needed YouTube show notes, newsletter bullets, social posts, episode hooks, and more. Manual process, slow turnaround, eating into time he could spend on his next episode or his startup, Inflight.

The bigger challenge was the one nobody had solved well yet: making AI-generated writing actually sound like a specific person's voice. I went through three major versions trying to crack it. The breakthrough was adding Ridd's brain dumps -- right after finishing an episode, he'd record his immediate reflections. What stuck out, what felt most compelling, what he wanted the audience to walk away with. That became the guiding light per episode. The AI was tuned to produce content shaped by Ridd's actual writing style, alongside his actual editorial instincts for that specific conversation.

Episode hooks ended up being the hardest deliverable -- AI just had a hard time locking onto what Ridd considered the most compelling theme AND wording it in a way that felt right. Everything else got to about 80% quality where Ridd could tweak and move on.

There's no UI. Claude Code is the entire interface. That's the design decision. The system meets Ridd where he already works. I got it to a solid v1 by the end of Summer '25 and handed it to Ridd to run from there. The thing that made the biggest difference wasn't a better model or a cleverer prompt -- it was 60 seconds of a human talking to himself right after a conversation. I spent weeks trying to engineer my way around the voice problem before realizing the answer was a human one.