Every wave of digital media has given marketers a brief window of underpriced attention. Google search ads were like that in the early 2000s, Facebook in the 2010s, TikTok more recently. Each time, those who understood the shift early captured enormous value.

Now, we’re entering the next wave. And it isn’t happening on a social feed or in a search results page. It’s happening inside conversations with AI. This changes everything. A chatbot is not a billboard and not a scrollable feed it’s a dialogue. The ad can’t interrupt, it can’t break trust, it has to feel like a natural extension of the exchange. That means advertising here needs to be conversational, context-aware, and crucially trustworthy.

The opportunity is clear. Users are already in chatbots. Brands are not. That gap won’t last for long. This newsletter is about exploring how to bridge it sharing the experiments, the frameworks, and the early signals of what works and what doesn’t. Because if history has taught us anything, it’s that the first to surf the wave ride it the furthest.

In the next edition, I’ll dig into what it means to make a brand conversational, and why the winners in this new era will be the ones who feel the least like ads at all.