In this episode I’m digging into a question I’ve been thinking about for months: If ads inevitably show up inside AI interfaces… do they actually have to suck? With billions invested into AI infrastructure and only modest subscription revenue to offset it, advertising is the most likely economic engine powering the next wave of AI platforms. But I’m not convinced it has to lead us down the same messy, cluttered path that search and marketplaces took.

Drawing from an op-ed I recently wrote for The Drum, I explore why AI ads spark so much anxiety, how agentic advertising offers a fundamentally different model from surveillance-era targeting, and what all of this means for retailers, advertisers, and the future of trust online. This is a nuanced conversation about economics, ethics, innovation, and why this moment might actually give us a chance to rebuild advertising on better foundations.

This episode is sponsored by Mirakl Ads

Timeline

[00:15] – Why subscription revenue alone can’t support the massive cost of AI infrastructure
[01:23] – How AI is intercepting retail search behavior before shoppers ever reach a retailer’s site
[03:04] – The trust problem: what we fear when ads enter our most intimate digital spaces
[05:17] – The real economics of the internet and why advertising keeps it freely accessible
[07:00] – What “agentic advertising” actually is, and how it flips the traditional targeting model
[09:31] – Why conversational advertising could be more relevant (and less creepy) than legacy ad formats
[10:20] – The high-stakes implications for retail media when AI captures intent upstream

Links & Resources

• This article originally appeared in my column for The Drum on November 6, 2025 as Why the arrival of advertising in AI Search may not be the catastrophe many fear
• Brian O’Kelley, co-founder and CEO at Scope3, outlined the Ad Context Protocol (AdCP) in a Fast Company op-ed 
• Read my article Real Time Bidding: Retail Media's Savior Or Saboteur?
• Read my article How an RMN's tech stack impacts your advertising results
• Are you based in Atlanta or be in the ATL area on Weds Dec 3rd? Join me and a couple dozen of your new retail media industry besties for a festive happy hour! Register here
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