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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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On this episode of AI: Machine-Made Marketing, we sit down with Dennis Kirschner, Co-Founder & CMO of ShowHeroes Group, for an unfiltered look at the escalating content crisis inside the walled gardens — and what it means for advertisers navigating an AI-accelerated media ecosystem.
Dennis breaks down why AI-generated content is exploding at unprecedented scale across major platforms, creating volatile new risks around brand safety, misinformation, and transparency. Instead of suggesting brands pull out of the walled gardens, he explains how to invest smarter, ask harder questions, and reclaim clarity in environments that are becoming increasingly opaque.
He also maps out what he sees as the antidote:
A multiscreen strategy anchored in premium publishers
The open web as a counterweight to fraud-ridden feeds
And AI-powered tools that elevate targeting precision, content suitability, and performance across trusted environments
Looking ahead, Dennis shares his perspective on how AI will re-balance power between the walled gardens and the open web — and what advertisers and publishers need to prepare for as machine-generated media continues to reshape attention, authenticity, and trust.
5 episodes
