What is Unboxed, really? This week, I was in Nashville for Amazon’s signature advertising event — a showcase where the tech giant reveals its latest innovations in retail media, automation, and ad tech. After taking it all in (and chatting with a few familiar faces from the industry), I’m breaking down the key announcements, the unspoken messages, and what they mean for advertisers and partners moving forward.
In this episode, I unpack my biggest takeaways from Unboxed 2025. From Amazon’s relentless reinvention of its ad business to the curious silence around Rufus, and how new “agent” tools could both empower and threaten the partner ecosystem. If you’re navigating Amazon’s retail media landscape, this recap will give you the insights and context you need to understand where the company’s heading next.
This episode is sponsored by Mirakl Ads
Timeline
[00:01:36] - How Amazon keeps evolving its advertising tools, making them simpler, smarter, and more accessible to advertisers of all sizes.
[00:02:42] - Why brands like Advantice Health say Amazon’s ad console outpaces competitors by simplifying data visualization and actionability.
[00:04:10] - A look at Amazon’s “paranoid” culture of continuous innovation, and why that mindset fuels their dominance in retail media.
[00:04:15] - Amazon takes aim at The Trade Desk with lower DSP fees, while still protecting its own walled garden.
[00:06:06] - Why Amazon’s much-hyped AI assistant Rufus went unmentioned during Unboxed, and what that silence might signal about its real-world performance.
[00:08:45] - The return (and rebranding) of agencies and tech vendors as “partners”, and how Amazon’s new AI tools could reshape that dynamic.
[00:12:14] - Reflections on Amazon’s fine line between democratizing ad tools and competing with its own partners.
Links & Resources
In this episode, I share snippets of my recent livestream with Andreas Reiffen, CEO and co-Founder of Pentaleap, to unpack one of the most debated topics in retail media today — Real-Time Bidding (RTB). Once dismissed as a messy, low-quality relic of early programmatic advertising, RTB is now being reimagined as the key to unlocking retail media’s next phase of scalable growth.
Note: I encountered unfortunate technical difficulties during my livestream with Andreas, resulting in choppy video and audio. I've done my best to use palatable snippets in this podcast, but regardless the audio quality is not perfect, please accept my apologies.
Andreas shares why he believes RTB will soon connect fragmented retail media ecosystems, make it easier for brands to access budgets at scale, and even open the door to programmatic innovation in the B2B sector. We cover everything from onsite vs. offsite ad opportunities to how retailers can tap into new revenue streams while maintaining control over their inventory.
This episode is sponsored by Mirakl Ads
Timeline
[00:00:00] – Introducing the debate: Why RTB still carries baggage in retail media
[00:01:00] – How real-time bidding connects platforms like Google and The Trade Desk directly to retailer inventory
[00:02:00] – Andreas’s bold prediction for how much retail media could eventually run through RTB
[00:03:40] – Exploring whether RTB can expand beyond onsite ads to offsite display and video
[00:05:00] – How retailer-led ad networks are evolving with RTB at their core
[00:07:45] – The surprising role RTB could play in B2B commerce and professional buyer targeting
[00:10:00] – Segmenting audiences and optimizing bids for professional vs. consumer shoppers
[00:11:00] – Wrapping up: Why RTB might finally be ready to scale responsibly in retail media
Links & Resources
I’m coming to you fresh from Amazon’s Unboxed event in Nashville, where Amazon dropped a wave of updates that show just how far their advertising ambitions are reaching. Beyond retail, beyond search, and even beyond reality itself!
In this episode, I unpack the biggest product launches and innovations revealed at the event including AI-powered campaign tools, creative automation for Prime Video, and Amazon’s intriguing new “Crystal Box” transparency positioning. I also share my early reactions and what these changes could mean for advertisers, agencies, and third-party software providers.
If you want to stay ahead of what’s next in Amazon Ads — from AI-native analytics to the future of full-funnel campaigns — this recap will bring you right inside the action at Unboxed.
This episode is sponsored by Mirakl Ads
Timeline
[00:00] – Remembering the early days of Amazon Ads and reflecting on how far the platform has come.
[01:11] – Unified Campaign Manager – merging DSP and Sponsored Ads into one seamless platform for cross-format buying and measurement.
[02:30] – Ads Agent – Amazon’s new AI-powered campaign assistant that allows natural language queries, leveling the playing field for advertisers of all sizes.
[04:17] – Creative Agent – generative AI tools for display, audio, and video ads, with outputs now good enough for Prime Video inventory.
[07:30] – “Crystal Box” positioning – Amazon’s transparent alternative to the “black box” automation approach from Meta and Google.
[09:13] – Preview of full-funnel optimization campaigns coming in 2026, closing the loop between awareness and performance.
[10:00] – AI-native analytics – conversational data exploration within Amazon Marketing Cloud, no SQL skills required.
[10:45] – Final thoughts and teaser for my full column in The Drum on Amazon’s “Crystal Box” approach.
Links & Resources
I first met Molly Hjelm, Head of Retail Media at Ace Hardware, during a panel at the RMN Ascendant Event in Silicon Valley, and right away I was struck by her candor and data-driven mindset. In this episode, I share the highlights from our conversation that didn’t make it into my full profile piece for The Drum.
We dive into how Ace Hardware has intentionally taken its time entering retail media, what it means to integrate retail media into a merchant’s P&L, and how Molly’s pragmatic approach to data, partnerships, and culture is helping Ace build Red Vest Media the right way. From leveraging Epsilon as a transparent tech partner, to bringing print back into in-store media, Molly’s perspective challenges a lot of industry assumptions, and offers a refreshing blueprint for sustainable growth in retail media.
This episode is sponsored by Mirakl Ads
Timeline
[01:01] – The #1 theme: retail media should show up in the merchant’s P&L (not as a tax, but as a tool to hit business KPIs).
[02:07] – How data storytelling and reporting shifted internal conversations from “you’re cluttering my site with ads” to “let’s solve this problem together.”
[02:45] – Why Ace Hardware went all-in with Epsilon as a full-stack tech partner (and why transparency and simplicity matter to advertisers).
[04:39] – Red Vest Media’s unconventional start with print-based in-store media, and how independent Ace operators are already innovating locally.
[06:03] – Molly opens up about the toxic dynamic of unrealistic growth projections, and why breathing room to set your own targets is game-changing.
[07:12] – Wrapping up with Molly’s guiding principle: retail media should be a precision tool, not a revenue tax
Links & Resources
A lot of brands are focused on Generative Engine Optimization (GEO) right now — making sure their products surface when consumers ask ChatGPT, Perplexity, or Claude for recommendations. That’s a great first step. But as I explain in this episode, the next frontier isn’t just about being found — it’s about being bought.
We’re entering an era where AI agents won’t just recommend products, they’ll actually complete transactions on behalf of consumers. And that’s where Agent Commerce Optimization (ACO) comes in. I walk through how ACO differs from GEO, what consumer brands need to know to prepare for agent-driven commerce, and what’s in your control (versus what’s in your retail partner’s hands).
If you’re a CPG brand selling primarily through retailers, this episode is for you. I’ll break down the nine-step ACO framework from Retailgentic and share actionable advice for how brands can start these crucial conversations with their retail partners today.
This episode is sponsored by Mirakl Ads
Timeline
[00:00] - The rise of generative engine optimization (GEO) and why it’s only half the story
[01:34] - Introducing Agent Commerce Optimization (ACO) aka preparing for AI agents that buy on behalf of consumers
[02:12] - GEO vs. ACO: discovery versus transaction
[03:15] - Why CPG brands need retailers to open their sites to agent crawlability
[05:00] - The nine-step ACO framework — what’s in your control and what isn’t
[06:00] - Expanded attributes and contextual data: helping AI agents understand how and why products are used
[07:30] - Tracking product cards and digital shelf analytics for AI-driven search
[09:00] - How to collaborate with retailer partners to ensure your products are agent-ready
[09:56] - Where to learn more: Retailgentic ACO framework and other resources
Links & Resources
In this episode, I dive into one of the biggest questions facing retail media leaders today: how can retailers and brands adapt as AI-driven shopping agents and zero-click discovery start reshaping how consumers buy? With sponsored search revenue under pressure and growth slowing across the industry, it’s time to look at creative alternatives to the traditional onsite, offsite, and in-store ad models.
I spotlight three fascinating companies that are doing just that: Rokt, Swish, and Nift. Each of them is monetizing overlooked customer moments in fresh, high-impact ways, from post-purchase offers to AI-driven gifting experiences. These companies are turning everyday customer touchpoints into new opportunities for engagement, brand discovery, and long-term loyalty — proof that innovation still thrives even as the industry shifts beneath our feet.
This episode is sponsored by Mirakl Ads
Timeline
[00:00] – Retail media’s new threat: how AI shopping agents and zero-click search are changing ad revenue dynamics.
[02:16] – Why 200+ retail media networks are all fighting for just 16% of ad dollars, and why differentiation is key.
[02:45] – Company #1: Rokt – Turning post-purchase moments into premium ad inventory.
[05:00] – Company #2: Swish – Treating the product itself as media through full-size sample placements in online grocery orders.
[06:45] – Company #3: Nift – “Gifting as acquisition” by using AI to match consumers with brand gifts after key customer actions.
[07:54] – Why these innovations could be more “AI-proof” than traditional retail media strategies.
[08:45] – My closing thoughts on the importance of thinking beyond ad slots to build meaningful brand-retailer partnerships.
Links & Resources
How many times have you not hit publish, not applied, or not shared your achievements because of fear of what others might think? In this episode, I’m diving into the concept of Tall Poppy Syndrome - a cultural tendency to cut down those who stand out - and how it feeds into FOPO, the fear of other people’s opinions.
After being named one of the National Retail Federation’s 2026 Top Retail Voices, I found myself wrestling with the same insecurities so many of us face: “Will people think I’m full of myself if I share this?” This episode is a candid, honest look at why it’s so hard to own our success, and why we need to do it anyway. Whether it’s hitting publish on your next blog post, launching your podcast, or applying for that award, I’m here to remind you: apply for the damn award!
This episode is sponsored by Mirakl Ads
Timeline
[00:00] – Reflecting on imposter syndrome after being named a National Retail Federation 2026 Top Retail Voice.
[01:00] – Introducing Tall Poppy Syndrome and how it affects ambitious professionals.
[02:15] – Understanding FOPO: the fear of other people’s opinions.
[03:05] – Why applying for awards feels uncomfortable—and how to reframe it.
[04:30] – My five practical steps for getting past FOPO and putting yourself out there:
[06:00] – Access my Notion database of retail media industry awards to help plan your 2026 goals.
[06:30] – Closing reflections and what’s coming next on the podcast.
Links & Resources
In this 'Snips' episode, I’m adding commentary to clips of one of my favorite ecommerce podcasts: Cocktails & Commerce with Brian Walker and Bill Friend. These two industry veterans bring on some of the sharpest minds in digital commerce, and in this snippet, they’re joined by John Andrews, co-founder and CEO of Cimulate, a generative AI company focused on commerce platforms.
If you’ve been seeing the term 'CommerceGPT' floating around and wondering what it actually means (like I was), this is the perfect primer. John breaks down the idea behind CommerceGPTs: what they are, how they might transform the way brands connect with customers, and why they could soon become the “brains” behind future retail experiences. We also hear fascinating insights into the rise of “answer engines” like ChatGPT and Perplexity, how they’ll change product discoverability, and what brands can do right now to stay visible in this new era of AI-driven commerce.
This episode is sponsored by Mirakl Ads
Timeline
[01:00] – John Andrews explains the concept of a CommerceGPT and how it represents a new layer in the commerce technology stack.
[02:15] – What it means for a model to truly “understand” customer behavior and use that knowledge to enhance shopping experiences.
[03:00] – Imagining a focused AI model that knows everything about a product category or retailer (and uses it to drive smarter engagement).
[05:00] – The rise of answer engines like ChatGPT and Perplexity, and what that means for product discoverability.
[06:15] – How brands can position themselves to be seen by these AI systems, and why visibility will require new kinds of data accessibility.
[08:05] – The future of “agent-to-agent commerce” — where AIs talk directly to each other to fulfill transactions.
[09:30] – Brian Walker’s perspective on consumer trust, behavioral change, and how long it may take for AI-powered commerce to go mainstream.
[11:15] – My takeaway: perfection isn’t the goal. Brands that experiment now will be best positioned for what’s next.
Links & Resources
Despite the buzz surrounding in-store retail media, most retailers are still struggling to move beyond the pilot phase. But Sam’s Club? They’ve done it, and done it well. After touring one of their clubs in Murfreesboro, Tennessee, with Harvey Ma, Head of Sam’s Club’s Member Access Platform, I witnessed firsthand how they’ve turned what’s typically a complex, fragmented endeavor into a well-oiled, data-driven ecosystem.
In this episode, I break down exactly how Sam’s Club is scaling its in-store retail media efforts, uniting their teams, and rethinking the shopper experience. From tech-powered measurement to their innovative “Retail Experience Network,” Sam’s Club is setting a new benchmark for what in-store retail media can achieve. If you’ve been curious about how physical retail can deliver digital-level insights and measurable sales impact then this episode is for you.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[01:12] – Why most in-store retail media programs get stuck in pilot purgatory.
[02:20] – The massive infrastructure and organizational hurdles that make scaling so tough.
[02:43] – Sam’s Club’s early investment and the simple principle guiding their approach: advertising exists to sell more things.
[03:07] – Introducing the “Retail Experience Network” and how it redefines in-store activations.
[04:00] – Behind-the-scenes of Sam’s Club’s IndyCar sponsorship and what made it a success.
[05:11] – How everyday tech like floor scrubbers and Scan & Go contribute to measurement and personalization.
[07:00] – Rethinking Joint Business Planning (JBP): how Sam’s Club integrates media and merchandising conversations.
[08:22] – A reality check on in-store media spend projections and why Sam’s Club’s model stands out.
Links & Resources
I’m a total podcast junkie, and today I’m bringing you another episode in my 'Snips' series, where I share bite-sized highlights from fascinating conversations and add my personal commentary. This one’s a crossover between Commerce Media Matters and Mind the Model, a newer podcast that’s quickly made its way into my regular rotation (find both shows under 'Links & Resources' below).
The snips I’m sharing today tackle a fascinating and urgent question for our industry: What happens to a retailer’s data advantage when AI platforms like ChatGPT start processing transactions? Spoiler alert: the answer might not be as bleak as you think.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[01:07] – Who owns transaction data in an AI-driven world?
[03:28] – Retailers gaining new data signals
[04:15] – Losing exclusivity vs. gaining context
[06:38] – Content as a competitive advantage
[09:01] – Owning content, audience, and data
[09:45] – Not all doom and gloom
Links & Resources
Last week, I got a first look at groundbreaking new research from EMARKETER and Bain that flips the retail media conversation on its head. Instead of surveying brands and media buyers, this study goes straight to the source, the leaders of Retail Media Networks (RMNs), to uncover their honest perspectives on what’s working, what’s not, and where the industry is headed next.
In this episode, I unpack some of my personal highlights from the preview webinar. From the surprising honesty RMN leaders are showing about their measurement challenges, to their quiet anxiety about the impact of agentic AI on the retail media landscape. Simply put; we’re entering what I like to call the “awkward teenage years” of retail media. Plus, I draw a parallel between retail media’s growing pains and the iconic babyccino!
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[00:00] – A first look at new Bain & EMARKETER research that shifts the lens to RMN leaders.
[01:00] – What the humble babyccino can teach us about growing up (and retail media’s maturing phase).
[02:30] – Public confidence vs. private reality: the top challenges RMN leaders admit to behind the scenes.
[03:00] – Measurement and attribution: why nearly half of RMNs say it’s their biggest hurdle.
[03:30] – The “Retail Media Doom Loop” and how tech and talent gaps are keeping networks stuck.
[05:00] – Agentic AI and GenAI search: the top disruptive forces worrying retail leaders.
[06:00] – Bain’s Stephen Mewborn hints at new partnership models.
[06:30] – Retail media growing up, facing scrutiny, and learning to move beyond trade dollars.
Links & Resources
In my recent LinkedIn Live with Andreas Reiffen, co-founder and CEO of adtech company Pentaleap, we dove into one of the most intriguing shifts happening in retail media right now: the rise of multi-retailer ad networks. This isn’t just about another layer of technology, it’s about simplifying one of the biggest pain points for brands and media buyers: the crushing complexity of managing ad spend across dozens of disconnected retailer systems.
We explored how these syndicated and programmatic retail media models are reshaping the landscape. From Amazon’s new retail ad service with Macy’s, to Instacart’s Carrot Ads and Best Buy’s ambitions to become a true ad network. Andreas and I discussed the historical irony of retail media returning to its ad network roots (just with more sophisticated tech and better use of first-party retail data).
If you’ve been wondering where retail media is heading next, this conversation is a must-listen.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[0:15] - The problem with fragmented retail media and the promise of multi-retailer networks
[1:20] - Revisiting pre-Amazon ad network models and why they might be making a comeback
[2:15] - Andreas on how programmatic buying could transform retail media
[4:40] - Why even large CPGs hesitate to expand across multiple RMNs
[6:45] - Amazon’s partnership with Macy’s and the emergence of three network models
[7:23] - Instacart’s Carrot Ads and other players joining the race
[8:35] - The irony of Amazon fixing the fragmentation problem it helped create
[10:15] - How programmatic networks and direct retail relationships will likely coexist
Links & Resources
We all know the usual suspects — ROAS, impressions, clicks — but what if the real indicators of retail media success are hiding in plain sight? In this episode, I ask four leading brand-side retail media experts a simple but revealing question: What’s the metric you’re obsessed with that everyone else seems to ignore?
You’ll hear why one leader swapped vanity metrics for incrementality and household penetration. Another reveals an underrated email metric that shows exactly what’s resonating with customers. We’ll also explore how branded search volume can be a crystal ball for future growth, and why new-to-brand might just be your most important indicator of scalable success.
If you’re ready to move beyond the same old KPIs and start measuring what really matters, this episode will broaden your perspective about retail media performance.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[0:00] – Why the most important retail media metrics might not be the ones you’re tracking
[1:00] – The power of “Revenue Per Recipient” in email campaigns
[2:00] – Turning influencers into brand ambassadors through “Posts Per Influencer”
[2:39] – Why branded search volume is a powerful leading indicator of brand strength
[4:25] – Why “New-to-Brand” reveals true growth, not just recycled buyers
[5:30] – Measuring incrementality, household penetration, and long-term brand salience
Links & Resources
A few weeks ago, I sat down with Brian Monahan of Albertsons Media Collective, for a profile in The Drum. And let me tell you, Brian isn’t your typical corporate executive. He’s unfiltered, entrepreneurial, and not afraid to say what everyone else in retail media is only thinking.
In this 'Snips' episode, I dive into some of the biggest insights from Brian’s recent appearance on The Snarketing Podcast, where he expanded on themes from our original conversation. Find links to my profile in The Drum and the full Snarketing episode under 'Links & Resources' below.
I explore Brian's bold takes on where retail media really stands, why alignment between advertisers and retailers matters more than ever, and how Albertsons is experimenting with ideas that most leaders wouldn’t dare to pitch in their first 60 days. If you think you know what retail media looks like, Brian might just convince you to think again.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[1:12] - Brian’s bold claim: Retail media is the only medium where buyers and sellers share the same goal.
[2:00] - Beyond ads: How gamified scavenger hunts and shoppable recipes could redefine in-store engagement.
[3:26] - The big money challenge: Why most retail media networks are still living off trade and shopper budgets.
[4:30] - The “do or die” moment: How retailers can tap into national brand dollars by integrating workflow and data.
[6:00] - Rethinking brand equity: What retailers like Safeway and Acme can teach us about customer loyalty and trust.
[7:27] - A bold experiment: Albertsons’ “BOGO for retail media” program that proves alignment with advertisers.
[8:30] - Looking ahead: Why Brian Monahan is just getting started.
Links & Resources
The retail world is buzzing over OpenAI’s new Instant Checkout. But here’s the big question: is it truly agentic commerce, or just another slick integration?
In this episode, I break down the debate between definition purists and pragmatists, unpack what 'agentic' really means in the context of AI-assisted shopping, and explore why this conversation might be missing the real story.
While the industry argues over semantics, I share why the ground beneath retail media’s most profitable foundation (its data) may already be shifting. From Walmart’s partnership with OpenAI, to new research showing that 78% of consumers have used AI for shopping in the past three months, the future of retail media is evolving fast. The real disruption might not come from autonomy definitions but from who owns the transaction data.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[0:12] – The new retail debate: what 'agentic commerce' really means and why everyone’s arguing about it.
[1:28] – Mastercard’s definition of agentic commerce and why some analysts say ChatGPT’s checkout doesn’t qualify.
[2:32] – The pragmatists’ view: seeing agentic commerce as a continuum of autonomy, not a binary state.
[3:00] – Why the Instant Checkout still matters, and how it’s quietly reshaping data ownership between AI platforms and retailers.
[4:30] – A refresher on the three pillars of retail media revenue: onsite, offsite, and in-store.
[6:57] – Why offsite retail media might be the first domino to fall in an agentic commerce world.
[8:19] – The Amazon vs. Barnes & Noble story from 1997 and what it teaches us about getting stuck in semantic debates.
[9:15] – What retailers need to start doing now to prepare for AI intermediaries owning transaction data.
[10:00] – Instant checkout may not be 'truly agentic,' but it’s already changing retail media forever.
Links & Resources
Today I’m doing something a little different! Instead of my usual trends and insights, I’m sharing a clip from my recent guest appearance on Scot Wingo’s podcast, Retailgentech. Scott flipped the script and let me ask him about his career journey, his perspective on where retail is headed, and one of the biggest questions in e-commerce right now: How will large language models (LLMs) like ChatGPT make their money in the future?
Will they follow the traditional ad-based route we’ve seen from Google and Facebook? Or will they build marketplaces and take a cut from transactions, as we’re starting to see with new initiatives from Walmart, Instacart, and DoorDash?
In this conversation, we dive into how AI-driven commerce could reshape loyalty, customer ownership, and what it means to be a “merchant of record” in the next era of retail. Find the link to the full Retailgentic podcast below under 'Links & Resources'.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[1:01] – Will LLMs make money through ads, or through marketplaces?
[1:30] – Scot breaks down ChatGPT’s “checkout” model and why he views it as a marketplace, not an affiliate system.
[2:50] – How Google’s AI agent checkout experience compares and what that means for merchants.
[3:00] – The retailer concern: will AI intermediaries cause commoditization?
[4:00] – Why Scott believes this new wave of AI players won’t repeat the mistakes of Facebook–Google–Amazon.
[6:00] – What it means for retailers to be the “merchant of record” and how that unlocks loyalty opportunities.
[7:30] – The comeback of loyalty programs and non-price differentiators in retail.
[8:30] – How omnichannel experiences and brand identity will help retailers stay relevant in the AI-driven marketplace era.
[9:00] – Wrapping up: why the fundamentals of loyalty, differentiation, and customer connection still matter more than ever.
Links & Resources
In this episode, I start with a trip back to 1916, when Clarence Saunders launched the first self-service supermarket, Piggly Wiggly, and everyone thought it was a ridiculous idea. Customers serving themselves? Paying cash instead of running a tab? Madness. Yet, it reshaped retail forever.
I use that story as a lens to explore today’s 'crazy-sounding' innovation: agentic shopping (AI agents shopping on our behalf). Drawing from retail analyst Andrew Lipsman’s critiques, I unpack why skepticism toward new retail tech is healthy, but can also blind us to early versions of world-changing ideas. From Webvan to Amazon to TikTok, I show how many 'failed' technologies weren’t wrong — they were just early.
Then, I dig into what needs to align for AI-driven shopping to go mainstream: better tech, real consumer pain points, frictionless distribution, sustainable economics, and cultural trust.
Will agentic shopping become the next self-service revolution, or just another voice commerce flop? Let’s find out.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[00:00] – The wild story of Clarence Saunders and how Piggly Wiggly reinvented grocery shopping.
[02:05] – The lesson: the future doesn’t arrive by request, it’s created by those who rethink inefficiencies.
[02:32] – Introducing today’s topic: why agentic shopping feels 'too weird' and why that’s familiar.
[03:13] – Andrew Lipsman’s skeptical take: retail tech hype cycles and a graveyard of failed innovations.
[04:17] – Why some 'failures' (like Webvan) were just early, not wrong — lessons from timing and execution.
[05:12] – Amazon’s early struggles: when buying books online seemed absurd until it wasn’t.
[07:24] – The TikTok lesson: from lip-syncing app to global phenomenon, how tech evolves beyond its first use case.
[08:14] – My firsthand experiment: buying a lavender candle through ChatGPT’s instant checkout (clunky but promising!).
[09:00] – What needs to align for agentic commerce to succeed: technology, pain, distribution, economics, and trust.
[12:33] – Back to Piggly Wiggly: irrational innovations often look crazy, until they become inevitable.
[13:28] – Final takeaway: better to prepare for possibility than assume limits based on early imperfections.
Links & Resources
When you think about retail media, you probably picture shoppers scrolling through Instacart or Walmart’s app. But what about the millions of Americans living far from big-box stores? That’s exactly where Dollar General sees its biggest opportunity. And Austin Leonard, just three months into leading the Dollar General Media Network (DGMN), is on a mission to redefine what 'the last mile' really means.
In this episode, a recap of my recent article for The Drum (find the article link below under 'Links & Resources') I unpack how Dollar General is building the last mile of ecommerce for the last mile of America. I talk about how DGMN is leveraging 90 million shopper profiles, why rural customers are far more digitally engaged than the industry gives them credit for, and how data, delivery partnerships, and rigorous measurement standards are shaping a new kind of retail media network. Whether you’re a media buyer, retailer, or strategist, this conversation will challenge your assumptions about what’s possible outside urban markets.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[00:00] – Setting the stage: why Dollar General’s rural reach presents a massive untapped advertising opportunity.
[01:08] – Austin Leonard’s background across Epsilon, Walmart, and eBay, and how that dual retailer–advertiser experience informs his DGMN strategy.
[01:45] – The surprising data on DoorDash and Uber partnerships driving incremental customer acquisition.
[02:15] – Changing perceptions: how Dollar General’s delivery offerings are attracting new audiences who once saw it as “just a dollar store.”
[02:45] – Busting myths about rural shoppers’ digital habits, and why ad industry bias plays a role.
[04:00] – Inside DGMN’s data infrastructure: building 90 million shopper profiles despite high cash transactions.
[04:38] – A new standard for measurement: DGMN’s test-and-control methodology and push for transparency in retail media.
[05:45] – Austin’s vision for the future: collaboration, standardization, and building the most innovative, shopper-centric retail media network in America.
Links & Resources
Last week, I fell into the hype of Amazon’s Big Deal Days. And as the boxes arrived on my doorstep, I couldn’t shake one uncomfortable thought: "did I actually get a deal?" In this episode, I unpack why online shopping feels less like convenience and more like detective work these days.
From inflated list prices and contradictory product info, to fake reviews and ad overload, I explore the five major ways consumer trust has eroded in ecommerce, and why that’s opening the door for AI shopping agents to step in. Are tools like ChatGPT and Amazon’s Rufus the solution, or are we just trading one layer of trust for another? Tune in as I break down what’s really happening behind the checkout button and what the future of trustworthy shopping might look like.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[00:00] – Asking the uncomfortable question: did I actually get a deal?
[01:00] – Why shopper satisfaction with Amazon’s Prime events is slipping
[02:00] – The five big reasons trust has eroded in eCommerce
[02:30] – Opaque pricing and the lawsuit accusing Amazon of fake discounts
[03:00] – Inconsistent product information and hidden shopping costs
[04:00] – Manipulated reviews and ad overload on retailer websites
[05:00] – How AI shopping tools can handle the “detective work” for consumers
[06:00] – The debate: Are AI shopping agents overhyped or essential?
[07:00] – My frustrating hunt for the perfect winter boots and why trust matters
[08:15] – How AI agents like ChatGPT, Perplexity, and Rufus can rebuild confidence
[09:00] – Amazon vs. Walmart: two very different approaches to AI-assisted shopping
[09:30] – Why AI shopping isn’t a gimmick — it’s a response to real consumer pain
Links & Resources
In today’s episode, I’m diving into one of the biggest challenges facing retail media today: measurement. Retailers may be racing to launch flashy new ad formats and in-store screens, but brands are asking for something far more fundamental — proof that their advertising dollars are working. Enter Cara Pratt, the new President of Global Retail and Media at Circana, who after just 90 days into her role is setting an ambitious agenda to restore trust and bring much-needed consistency to this $60 billion industry.
Cara brings a unique perspective, having previously built Kroger’s retail media network from the inside. Now, with Circana’s acquisitions of Nielsen’s MMM business and NC Solutions, she’s championing a more transparent, faster, and accessible approach to measurement. From bridging the divide between trade and media to introducing real-time optimization through Circana’s Liquid Mix platform, Cara is making the case for why retail media needs a neutral arbiter to guide its future.
This episode is sponsored by Connected Commerce at Acosta Group
Timeline
[00:25] – Introducing Cara Pratt and her new role at Circana
[01:00] – The retail media measurement crisis and why it matters
[02:00] – Circana’s acquisitions and what they mean for comprehensive measurement
[03:30] – Democratizing measurement with Liquid Mix for smaller brands
[05:00] – Bridging the divide between merchant and media teams
[06:00] – Real-time optimization and why speed changes everything
[07:30] – How Circana is positioned to solve retail media’s trust deficit
Links & Resources