Best Kiri Masters Podcasts (2025)

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The Man Who Tried to Escape Retail (and Failed) - Watson Weekend Episode 91 58:47

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8h ago58:47

58:47

This week on Watson Weekend, we’re closing out our guest interviews for the year with James Lang, the leader behind Ulta Beauty’s fast-growing marketplace platform. James has spent more than 20 years building marketplace and dropship programs across Belk, ChannelAdvisor, Rithum, and now Ulta. He calls himself a “builder of asset-light strategies” b…

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Why Amazon Can’t Stop Agentic Commerce — And Why Other Retailers Must Lean In 13:16

3d ago13:16

13:16

Agentic commerce continues to spark tension across the industry. Today, I’m diving straight into one of the biggest debates: whether Amazon’s refusal to embrace open agent interoperability means agentic shopping is doomed. This conversation was inspired by ad industry analyst Eric Seufert, whose skepticism about agentic commerce I genuinely value. …

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5 Big Marketing Lessons Retail Media Must Steal From Venture Capital 9:59

4d ago9:59

9:59

In this episode of the Retail Media Breakfast Club, I reflect on a recent conversation from the a16z Podcast and the surprisingly relevant lessons that venture capital can teach retail media networks. Listening to Marc Andreessen, Ben Horowitz, and Margit Wennmachers talk about how a16z deliberately broke VC’s long-standing “code of silence” remind…

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Amazon’s Sea of Ads: Why 25+ Sponsored Products Per Page Still Works 9:01

5d ago9:01

9:01

In this episode, I expand on my latest column in The Drum, where I unpack new data showing that Amazon now averages 25+ sponsored products per page load—far more than Walmart or Home Depot. Despite fears that ad overload would harm the customer experience, Amazon maintains near-universal ad coverage while keeping relevance high, even on complex lon…

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The Retail Media Civil War Is Ending: How “Fluid” Sponsored Products Are Reshaping Search 11:43

6d ago11:43

11:43

In today’s episode, I dig into one of the biggest internal conflicts inside retail organizations—the clash between merchant teams and retail media teams. One side is incentivized to fill every available ad slot, the other is responsible for driving product sales, and shoppers are the ones caught in the crossfire. As Charlie Munger said, “Show me th…

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The Marketing Industry Does Not Want You To Hear This With Trevor Testwuide 1:01:57

1d ago1:01:57

1:01:57

Watson Weekend host Rick Watson is joined by Nick Kaplan for the week's retail and e-commerce news. The headline hangover contains results from Black Friday and Cyber Monday, and Amazon is testing 30-minute deliveries. The company's AI assistant Rufus continues to make headlines. There is also a discussion on the closing of Omnicom's IPG acquisitio…

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AI vs. Retail Media: The Platform Shift No One Is Ready For 12:03

10d ago12:03

12:03

In this 'Snips' episode, I unpack some of the most thought-provoking ideas from tech analyst Benedict Evans’ recent interview on The Knowledge Project, specifically his comparison of AI to the invention of the iPhone. Not electricity. Not the Industrial Revolution. The iPhone. And the second-order effects of that comparison are much more relevant t…

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Inside Costco’s Secretive Retail Media Strategy: What Mark Williamson Revealed 13:50

11d ago13:50

13:50

Costco has always been the effortlessly cool kid of the retail media world: unbothered by hype, quietly confident, and doing things entirely on its own terms. In this episode, I unpack what makes Costco’s retail media approach so different from the 80+ U.S. retail media networks vying for attention, and why their “member-first, margin-second” philo…

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AI Shopping Hype? My Black Friday to Cyber Monday Halftime Breakdown 7:54

12d ago7:54

7:54

In this halftime recap of Black Friday — Cyber Monday, I unpack the avalanche of headlines claiming that AI shopping has finally arrived. Everywhere you look, analysts are touting explosive growth — 805% spikes, billions in generative AI-influenced sales, and a surge in chatbot-assisted shopping sessions. But as I dig into the data, I’m asking a mu…

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Why Retail Media’s Metrics Are Failing — And What Actually Drives Brand Growth 11:10

13d ago11:10

11:10

This week, I’m digging into a fiery debate that lit up LinkedIn — one that questions whether retail media is measuring the right things at all. After reading a thought-provoking post from Steve Gray, I found myself going down a rabbit hole of insights, rebuttals, and philosophical clashes about how brands actually grow—and what retail media should …

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Why Long-Tail Advertisers Are Becoming Retail Media’s Biggest Growth Engine 8:29

18d ago8:29

8:29

In today’s episode I dig into a surprising and quietly powerful engine of growth for retail media networks: long-tail advertisers. While major CPG brands continue to cap their RMN partnerships at around six networks, retailers are pouring investment into Amazon and Walmart-level capabilities, hoping to win those national budgets. But the ceiling is…

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How RMNs Can Finally Win Over Media Agencies 10:01

19d ago10:01

10:01

In today’s 'Snips' episode, I’m diving into one of the biggest unlocks for retail media networks right now: earning the trust (and the budgets) of media agencies. As retail media growth slows and retailers look beyond performance budgets, everyone suddenly wants a slice of those top-of-funnel brand-building dollars. But as I unpack the insights fro…

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AI-Fueled Shopping for The Holidays 10:49

20d ago10:49

10:49

This week, I’m breaking down a fascinating shift I’ve been watching closely: the moment AI-enabled commerce finally tips from novelty to norm, just in time for the holiday shopping rush. After a near-disaster of traveling without my wallet (which somehow wasn’t a disaster at all), I couldn’t help but notice how quickly behavior changes when technol…

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A Standard For Commerce Operations, A Non-Profit and Jeoparty Part Deux with Kelly Goetsch 40:37

16d ago40:37

40:37

Rick Watson, Jessica Lesesky, and Nick Kaplan warm up the show with jokes about last week’s performance and introduce the episode’s segments. They highlight Jeoparty, Headline Hangover, and the week's special guest, Kelly Goetsch. Headline Hangover: The team guesses blacked-out words from recent retail and e-commerce headlines. * Levi’s chooses Mic…

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Will Ads Ruin AI? Why Agentic Advertising Might Save the Internet 10:59

24d ago10:59

10:59

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’…

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Get on the Damn Stage: Why 2026 Is Your Year to Step Into the Spotlight 11:32

25d ago11:32

11:32

In this reprise episode, I’m bringing back one of the most timely conversations we can have as we gear up for 2026 conference season: getting on the damn stage. After so many of you resonated with my encouragement to apply for the damn award despite imposter syndrome, it felt like the perfect moment to revisit this message. Because the truth is no …

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Inside Mars’s Retail Media Investment Matrix — Why Only the Top 6 Retail Media Networks Win 10:23

26d ago10:23

10:23

Last week at the Path to Purchase Institute LIVE conference, I heard something that most retail media networks probably don’t want to hear out loud: Mars has built a structured, data-driven investment matrix that decides exactly who gets budget and who doesn’t. In today’s episode, I’m breaking down what Mars revealed, why scorecards are becoming st…

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AI Shopping Agents vs. Retailers: Who Owns Discovery Now? 10:06

27d ago10:06

10:06

In today’s 'Snips' episode, I’m diving into one of the conversations that has been rattling around in my head for a while now. While listening to the Unpacking the Digital Shelf podcast with my friends Lauren Livak Gilbert, and Peter Crosby, I found myself nodding as their guest Natalija Pavic from Kibo Commerce unpacked the rise of agentic AI and …

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The End of Instacart? Airbnb’s Grocery Solution Announced 43:12

19d ago43:12

43:12

The Watson Weekend hosts, Rick Watson and Jessica Lasesky, and guest Nick Kaplan discuss retail and commerce trends for Q4 and 2025. This week’s headline hangover includes the resurgence of Toys R Us, Airbnb's pilot kitchen stocking service with Instacart, and the integration of AI to enhance efficiency rather than replace humans. The Big 2025 “Jeo…

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Unfiltered Thoughts From Amazon Unboxed 2025 13:52

1M ago13:52

13:52

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, …

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Developments in RTB (Real-Time Bidding) for Retail Media 11:35

1M ago11:35

11:35

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 …

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Amazon Unboxed 2025 - Fresh Off The Press Announcements from Nashville 11:17

1M ago11:17

11:17

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 camp…

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"Late By Design" - Molly Hjelm from Ace Hardware's RedVest Media Shares her Retail Media Gameplan 8:00

1M ago8:00

8:00

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 in…

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How an 18-Year-Old Outsmarted Big Tech and Raised $1.4M 59:02

1M ago59:02

59:02

The Watson Weekend hosts Rick Watson and Jessica Lesesky discuss the most important retail and e-commerce news from the past week. In the Headline Hangover, they discuss retail's Q4 challenges, AI's impact on brick-and-mortar stores, and retail media trends. They highlight Amazon CEO Andy Jassy's view that AI will accelerate the decline of physical…

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Combating Margin Erosion on Amazon 25:58

28d ago25:58

25:58

Amazon brands are facing record-tight margins—and it’s not just ad spend. From hidden FBA fees and rising inbound costs to shifting tariffs and competitive pricing pressures, profitability is under attack. In this episode, Jasim Eisa, CEO of Voadera, joins Sreenath Reddy, CEO of Intentwise, to unpack the real causes of margin erosion and share acti…

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What CPG Brands Actually Control with Agentic Commerce Optimization (ACO) 10:21

1M ago10:21

10:21

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 A…

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AI Search to Disrupt Discovery for Retailers — Here's 3 Companies Thinking Outside The Box 8:58

1M ago8:58

8:58

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 th…

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Apply For The Damn Award & Conquer Your FOPO (Fear Of Other People's Opinions) 6:37

1M ago6:37

6:37

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 Na…

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What is a 'CommerceGPT'? ['Snips' from Cocktails & Commerce] 11:37

1M ago11:37

11:37

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 fo…

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The Watson Weekend Halloween Special 35:29

1M ago35:29

35:29

The Watson Weekend Halloween Special hosts Rick Watson, Jessica Lesesky, and Nick Kaplan discuss 2025 retail and tech headlines with a Halloween twist. Think of it as the e-commerce and retail news version of Saturday Night Live, but it happened on a Friday. The headline hangover features criticism of Pinterest's AI-powered personalization as a reb…

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Breakdown of How Sam's Club Cracked the Code on In-Store Retail Media 10:08

2M ago10:08

10:08

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…

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How Retailers Can Evolve To Compete With Agentic Shopping ['Snips' from Commerce Media Matters & Mind the Model] 10:06

2M ago10:06

10:06

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 show…

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The Secret Hopes & Dreams of RMN Leaders [New Research Preview] 7:11

2M ago7:11

7:11

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 th…

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Multi-Retailer Networks [Livestream Highlight] 11:07

2M ago11:07

11:07

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 buy…

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How Caddis Uses Mirakl To Service An Underserved Demographic Via Marketplaces With Emma Spagnuolo 1:03:18

2M ago1:03:18

1:03:18

Watson Weekend podcast hosts Rick Watson and Jessica Leseski cover retail industry news, including Target's struggles and layoffs, potential large tariff refunds pending a Supreme Court ruling, and merchandising challenges for Netflix's hit series K-pop Demon Hunters. They discuss Amazon's launch of AWS RTB fabric, a cloud infrastructure for progra…

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Underrated Retail Media Metrics That Fly Under The Radar [Panel Episode] 6:50

2M ago6:50

6:50

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 swa…

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Brian Monahan Is Going Big With Albertsons Media Collective ['Snips' from The Snarketing Podcast] 8:45

2M ago8:45

8:45

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 fr…

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Is ChatGPT's Instant Checkout 'Really' Agentic? And Does It Actually Matter? 10:15

2M ago10:15

10:15

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 conversatio…

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Will LLMS Monetize With Ads or Marketplaces? [Retailgentic Crossover] 9:39

2M ago9:39

9:39

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: H…

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From Spreadsheets to Shipping Label Fraud and Cross-Border e-Commerce with Tommaso Tamburnotti 1:04:03

2M ago1:04:03

1:04:03

Watson Weekend hosts Rick Watson and Nick Kaplan discuss the retail industry's current state, emphasizing AI's integration into shopping experiences, such as Walmart's partnership with OpenAI. They highlight the rapid innovation driven by AI, including new tools like OpenAI's video creation app, and note the proliferation of AI partnerships across …

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Agentic Shopping Looks Crazy. So Did Self-Service Supermarkets. 13:47

2M ago13:47

13:47

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-soundi…

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Live from Amazon Accelerate: Behind the scenes with AMC’s Director, Alan Lewis 21:00

2M ago21:00

21:00

Recorded live at Amazon Accelerate 2025, this special episode of the Intentwise Connect podcast features Alan Lewis, Director of AMC Clean Rooms and one of the first product managers for Amazon Marketing Cloud (AMC). Alan dives into the massive announcement that AMC is now available to anyone using Sponsored Ads without any special setup. He recoun…

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Dollar General’s Austin Leonard Is Bullish On 'Last Mile' Opportunity 7:09

2M ago7:09

7:09

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 …

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I Got Prime Deals. Or Did I? Why Consumer Distrust Is AI Shopping's Real Opening 9:47

2M ago9:47

9:47

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 f…

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The Fairy Godmother Of Retail Media, Cara Pratt, And Her Agenda At Circana 8:15

2M ago8:15

8:15

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 …

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Search Is In An Advantageous Position For AI-based Commerce with John Andrews 1:04:31

2M ago1:04:31

1:04:31

The latest Watson Weekend podcast episode, hosted by Rick Watson and Jessica Lesesky, discusses recent retail developments, including the elimination of the de minimis rule impacting U.S. imports, Starbucks' Taylor Swift-themed in-store experience to regain customers, Instacart 's integration with Tiktok for retail media targeting, and Paypal 's 5%…

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Retail Media's Measurement Problem Isn't Technical — It's Political 11:26

2M ago11:26

11:26

In this episode, I break down some of the key insights from my recent op-ed for WARC on the state of retail media measurement standards. While there’s been progress with guidelines from the IAB and MRC, real adoption is still patchy, and the reasons why might surprise you. I explore why brands and retailers alike are struggling to align on measurem…

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Trade vs. Retail Media: Who's Really Eating Whom? ['Snips' from Particular Audience & The Middlemen] 9:48

2M ago9:48

9:48

In this 'Snips' episode, I dive into one of the biggest debates shaking up the commerce world: is retail media eating trade marketing, or is it the other way around? To unpack this, I analyse commentary from two industry leaders who see the collision from very different vantage points. James Taylor of Particular Audience makes a strong case that tr…