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

Did you know that while 70% of shoppers have experimented with AI tools to help them shop, fewer than 15% have actually used a retailer’s AI shopping assistant? In this episode, I unpack fresh shopper research from Acosta Group that reveals which retail AI tools are getting traction (and which are still invisible to most consumers).

We’ll dive into surprising adoption numbers for tools like Amazon’s Rufus, Walmart’s Sparky, and category-specific assistants like Kroger’s Chefbot and Ulta’s GLAMlab. I share what this data tells us about placement, awareness, and how retailers can make AI assistants an integrated part of the shopping experience rather than a hidden gimmick. Plus, I explore what all of this means for brands trying to win in the evolving AI-enabled shopping landscape.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[00:00] - The surprising gap between general AI use and retailer AI assistant adoption
[01:00] - Usage stats for Amazon Rufus, Walmart Sparky, Kroger Chefbot, and Ulta GLAMlab
[02:45] - Why launch timing isn’t the key to AI assistant success
[03:30] - The “front door always wins” rule: why placement beats features
[05:00] - How reach and frequency shape awareness and adoption
[06:15] - Why category retailers should double down on specialization
[07:45] - Three takeaways retailers need to accept about AI assistant success
[08:45] - What brands must prepare for in the fragmented retail AI landscape

Links & Resources

• Acosta Group's Shopper Insights
• Supermarket News article on Kroger Chefbot
• My article Walmart Reveals AI Roadmap That Points To A World Without Search Bars
• My article Why Agentic Shopping Poses an Existential Threat to Retail Media (Part 1)
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn

Remember the Amazon FBA boom? When all you needed was an Alibaba find, a seller account and a dream? Between 2012 and 2020, thousands of entrepreneurs built entire businesses inside Amazon’s walls. And for a while, it was a gold rush. But like all gold rushes, the music eventually stopped. Costs went up, competition flooded in, and only a select few brands broke free.

Today, we’re standing at the edge of a similar moment — this time, powered by AI marketplaces. Imagine AI agents that don’t just recommend products, but handle the entire transaction right inside the conversation. The opportunity is huge… but the window will be even shorter.

In this episode, I unpack the striking parallels between Amazon’s FBA era and the coming wave of AI-powered commerce, explore what AI-native brands might look like, and explain why the gold rush could be over in months, not years.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[00:00] – Looking back at the Amazon FBA boom and how it created a new business model for entrepreneurial suburbanites.
[02:13] – The simplicity and early profitability of FBA for first movers.
[04:02] – The predictable shift from organic discovery to pay-to-play on Amazon.
[05:23] – How AI marketplaces could compress the same cycle into months.
[07:14] – The rise of AI-native brands and how small teams could scale to $100M+.
[09:15] – The risk of losing control over customer relationships in an AI-driven shopping world.
[10:12] – Why the AI marketplace gold rush will close much faster than Amazon’s.

Links & Resources

• Marketplace Pulse article Amazon Takes a 50% Cut of Sellers' Revenue
• Retail Media Breakfast Club article Mary Meeker Is So Back: My Notes From Her 340-Page AI Futurecast
• Karl Haller episode of Retailgentic podcast The AI-Native Brand Revolution: A Conversation with IBM’s Karl Haller
• Follow Karl Haller on LinkedIn
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn

When your own tech partners start publicly celebrating your struggles, you know the game has changed. In this episode, I unpack the fascinating shake-up happening in retail media, sparked by Criteo’s recent challenges — from high-profile client losses to a wave of nimble competitors seizing their moment.

What’s even more intriguing? Many of these challengers once relied on Criteo’s own infrastructure to get started.

We’ll dive into the irony of Criteo facing the very playbook it once used to disrupt the adtech giants of the past, the role of real-time bidding in eroding their moat, and the strategic crossroads they face today. Will they acquire their way back into the lead, or will a consolidation of challengers rewrite the rules entirely?

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[0:12] – Adweek article reveals Criteo’s client losses and competitive pressures
[0:51] – Competitors’ cheeky LinkedIn reactions and what they signal about the market
[2:00] – The irony: Criteo once played this disruptor role in adtech!
[3:18] – How real-time bidding is dismantling Criteo’s pricing power
[4:47] – The 'frenemy' effect: why partners are now becoming rivals
[6:05] – Two scenarios for how this standoff could end
[8:21] – The ticking clock: looming shifts toward AI-driven shopping

Links & Resources

• Kathryn Lundstrom's Criteo article on Adweek
• LinkedIn thread featuring Jon Flugstad from Moloco, Andreas Reiffen from Pentaleap, and Drew Cashmore from Vantage reacting to the Adweek Criteo article on LinkedIn
• AdExchanger article from 2015 that discusses Criteo's former ad tech disruptor status
• Retail Media Breakfast Club's real-time bidding visual explainer
• Kiri Masters' Forbes article DSPs Promise To Unlock Retail Media Demand. What’s Holding Retailers Back?
• Pentaleap and TEADS partnership announcement
• Skai and Koddi partnership announcement
• Retail Media Breakfast Club article Why Agentic Shopping Poses an Existential Threat to Retail Media (Part 1)
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn

Let’s be real: retail media is full of shiny, headline-grabbing metrics that come and go with the latest trends. But in today, I’m digging into the metrics that brand leaders swear by day in and day out AKA the workhorses that drive real business decisions. I asked three brand-side leaders to share that one metric they come back to time and again, even when the industry is distracted by the 'next big thing'.

We’ll hear why TACoS is the daily go-to for navigating the quirks of Amazon vendor revenue, how market share keeps your brand grounded in a sea of competitive noise, and why new-to-brand is the holy grail for understanding true discovery. If you're ready to cut through the fluff and focus on what actually moves the needle, this one’s for you.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[1:28] – Luiz Antunes on why TACoS remains his north star for budget tracking, especially around events like Prime Day.
[3:04] – Danny Silverman explains how market share reveals the truth about performance in a turbulent category landscape.
[4:33] – Elizabeth Rivas shares how new-to-brand metrics fuel AlgaCal’s discovery-driven strategy and guide ad creative planning.
[5:30] – Exploring which ad formats are actually pulling in new customers using AMC insights.
[6:03] – Wrap-up and a reminder that these foundational metrics keep us anchored, no matter the trends.

Links & Resources

• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn
• Follow Luiz Antunes on LinkedIn
• Follow Danny Silverman on LinkedIn
• Follow Elizabeth Rivas on LinkedIn

In part two of my conversation with Scott Wingo, we dive deeper into how AI-powered agentic shopping could reshape - and potentially upend - the current retail media landscape. We explore what happens when AI becomes the primary interface for shopping leaving behind the traditional retailer website. Who stands to lose the most? Who has a shot at staying relevant?

We also question whether retail media's dominance is as secure as it seems, especially for players heavily invested in e-commerce and ad revenue. Scott and I touch on intriguing strategic differences between Amazon and Walmart’s AI integration philosophies, and how loyalty programs could become a retailer’s secret weapon in this evolving game. If you’ve been wondering where brands should place their bets in an AI-powered future, this is the episode for you.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[00:01:15] - Why we’re skeptical about a future without ads in generative AI
[00:02:45] - Will in-store trade budgets become the safest media investment?
[00:03:29] - Agentic shopping's potential market share by 2030 and what that really means
[00:04:10] - Which retailers are most vulnerable to losing their retail media advantage
[00:05:48] - Is Instacart in trouble? The challenges agents pose to their ad business
[00:06:53] - The untapped potential of loyalty programs in an AI-driven world
[00:08:15] - How retailers can still win with differentiation—speed, returns, and selection
[00:08:45] - Walmart vs. Amazon: Two radically different approaches to AI agents

Links & Resources

• Watch full Retailgentic episode with Kiri Masters on YouTube
• Listen to full Retailgentic episode with Kiri Masters on Spotify
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn
• Subscribe to Retailgentic on YouTube
• Subscribe to Retailgentic on Apple Podcasts
• Subscribe to Retailgentic on Spotify
• Explore the Retailgentic website
• Follow Scot Wingo on LinkedIn