In retail media, the biggest wins often come from bold, high-stakes decisions. In this episode, I sit down with a panel of industry leaders who share the risks they took that could have gone either way. From betting on unproven product colors, to pulling the plug on ads during peak hours, these stories will inspire you to rethink what it means to take a chance in retail media.

If you’ve ever wondered whether that big, scary idea is worth pursuing, this episode just might give you the courage to take the leap!

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[1:11] - Josh Clarkson on a strategy that garnered 750M impressions via the world’s largest box of chocolates.
[2:10] - Todd Weagant's gamble on a bold, exclusive headphone color that became an Amazon bestseller.
[3:57] - Neha Gupta Malik’s high-stakes “go dark” search strategy with Walmart and the lessons it revealed.
[5:18] - Why Connected TV (CTV) was a risky but rewarding investment for Mizkan America.
[6:40] - Chris Lowrey's leap from one hero keyword to a diversified retail media strategy.

Links & Resources

• Largest box of chocolates by Russell Stover - Guinness World Records
• Follow Josh Clarkson, Global Lead of Retail Media at Mars, on LinkedIn
• Follow Todd Weagant, Head of Sales at Masimo, on LinkedIn
• Follow Neha Gupta Mallik, Head of Connected Commerce at Mizkan America, on LinkedIn
• Follow Chris Lowrey, Brand Director at Our Home, on LinkedIn
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn

The retail media landscape is booming. But it’s also messy, fragmented, and heavily dominated by just a few players. In this episode, I unpack the challenges that brands face when navigating hundreds of retail media networks and explore whether alliances and federations might hold the key to leveling the playing field.

From eerie parallels with the early days of digital advertising to emerging federations like Rippl, I take a closer look at why cooperation may be the only path forward for smaller players who want to compete with giants like Amazon and Walmart. This is the first episode in a four-part series where I’ll peel back the layers of what it really takes to build sustainable, effective retail media alliances.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[00:00] – How Google’s ad dominance offers a cautionary tale for today’s retail media chaos
[00:57] – Amazon’s commanding market share and the growth gap facing other RMNs
[02:00] – The “doom loop” of retail media networks: revenue vs. investment catch-22
[03:00] – Why brands are frustrated: lack of standardization and the walled garden problem
[04:36] – The case for federations: how alliances could reshape retail media
[05:05] – Rippl: a national consortium offering advertisers scale across regional grocers
[07:03] – Preview of the 4-part series exploring the mechanics, history, and future of RMN alliances

Links & Resources

• Learn more about Yield: How Google Bought, Built, and Bullied its Way to Advertising Dominance by Ari Paparo
• Follow Ari Paparo on LinkedIn
• Article by Grocery Dive about Rippl
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn

The world of advertising is changing faster than many expected and AI is leading the charge. In this episode, I dive into the rise of advertising inside large language models (LLMs) and explore whether eMarketer’s $25 billion projection for AI-driven search ads in the next five years is really as far-fetched as some think.

From Microsoft’s early experiments with sponsored links in Bing Chat, to Amazon’s push into AI-driven recommendations, to Perplexity’s twist on sponsored prompts, the landscape is already evolving in ways that could redefine how brands reach consumers. I also look at the global picture, including China’s AI commerce integration, and dig into why retail media as we know it could face an existential threat as consumers shift more of their research and buying decisions into AI-powered conversations.

We’ll also explore what smart retailers and brands must do to adapt: treating AI agents as VIP customers, rethinking loyalty programs, and preparing for a world where AI dynamically generates ads in real time based on context. This isn’t a distant future, it’s happening right now.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[00:00] - The $25 billion projection for AI search advertising and why it raised eyebrows.

[01:00] - How Microsoft, Amazon, and Perplexity are already monetizing conversational AI.

[03:00] - A look at China’s approach: super apps and commerce-first AI.

[04:00] - Why retail media may lose ground as shoppers shift to LLM-driven research.

[06:17] - Emerging ad formats: showroom ads and dynamic ad generation.

[07:30] - Why conversational ads are proving more effective than traditional search ads.

[08:00] - The playbook for retailers: making it easy for both humans and AI agents to shop.

Links & Resources

• eMarketer article with $25 billion AI ad projections
• My article on this topic on the Retail Media Breakfast Club blog
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn