Meta launched Muse Wonder Models to power its personal AI assistant. Google dropped Gemini Argon — faster, better at brand guidelines, better at writing. A startup called TypeSafe launched Jev, a model purpose-built for fast decision-making in multiple choice scenarios. And Character AI — once one of the top sources of AI ad inventory on the open web — filed for bankruptcy and is now being acquired by Disney for $20 million. The math of compute cost versus ad revenue caught up with them.
This week, Shiv and Myles welcome Roger Dunn, Chief Commercial Officer at Thrad, joining from Sydney. Roger spent a decade agency side, held a global retail media role at Diageo, and is now on the front lines of one of the most interesting unsolved problems in advertising: what does a good ad actually look like inside a conversational AI environment?
Roger breaks down why the comparison between AI advertising and search undersells the opportunity — with search you’re fighting over a couple of keywords, but with conversational AI you have a full multi-turn dialogue with rich pre-qualification already built in. He also introduces a concept most people haven’t considered: in AI, a well-placed ad doesn’t just respond to a conversation, it can redirect it entirely. His marathon runner and supplements example makes it immediately concrete. And he gives the clearest map of where AI ad inventory actually exists beyond ChatGPT — browsers, companion apps, social platforms, vertical agents, publishers with AI interfaces, and retail.
They also get into why Character AI was burning $8–10 million a month on compute and why the ad math simply never worked, why polling ads — a sponsored question with answer options — might be the most native format anyone has found so far, and why the $60 CPM that OpenAI launched with was never going to hold.
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