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Kiri Masters and the Duopoly Everyone Pretended Not to See

Inside the Great Retail Media Mirage

Retail media keeps walking around like it just reinvented marketing. Every conference keynote declares it the fastest-growing channel in human history, the future of commerce, the golden child who will save everyone’s margins and maybe even your career.

And yes, it’s a $100B rocket ship if you squint at it the right way. But once you stop inhaling the press releases and actually look at the numbers, the whole thing starts to shimmer like a desert illusion.

Here’s the inconvenient truth hiding under the celebratory LinkedIn carousels: somewhere between 85 and 87 percent of all retail media spend is swallowed whole by exactly two companies. Two. Amazon and Walmart are basically standing at the edge of the buffet with industrial shop-vacs while everyone else is leaning over the table trying to salvage a crouton.

It’s less “ecosystem” and more “Hunger Games with UPC codes.”

Kiri Masters, who somehow manages to observe this circus daily without needing federal witness protection, broke it down for me with the kind of calm you only get from fully accepting the absurdity of your field.

“A good 70–80% of all retail media spend goes to Amazon and Walmart,” she said, in the tone of someone announcing that the sun will continue rising in the east no matter how many retailers insist their loyalty app is a disruptor. “That means the other 250 retailers are fighting over the scraps.”

And by “scraps,” she means oxygen. Attention. Budget lines. Anything to suggest their RMN isn’t just an ambitious side hustle wearing a lanyard.

The Concentration Crush, or Why Everyone Else Is LARPing as a Network

This is the part where retailers try to puff out their chests and talk about “differentiation,” which has come to mean almost nothing. It’s like watching high school seniors explain “relevant experience” on a résumé that includes “babysitting cousin once.”

Amazon didn’t merely set the standard; they welded it into place. Detailed reporting? Check. Real-time measurement? Check. Granular targeting backed by a decade of infrastructure investment? Double check. They built an entire religion around ad performance, and now the congregation expects miracles.

Everyone else is showing up with a PowerPoint deck and a dream.

Kiri sees it plainly: there’s not enough internal buy-in, not enough money, not enough technical talent, and definitely not enough time to reverse-engineer Amazon’s brain. Some retailers are running RMNs with the same energy as someone running a lemonade stand that also promises AI-powered insights. It’s adorable until the CFO asks for actual results.

The Emotional Fragmentation No One Puts on a Slide

People in retail media love the word “fragmented.” Usually they say it with the self-assured confidence of a panelist who knows they’ll be offered sparkling water afterward.

But when Kiri uses it, you can hear the existential dread humming underneath. She’s talking about the human fragmentation — the identity crisis that hits a retailer the moment they realize their brand-new ad network is basically shouting into a canyon while Amazon and Walmart conduct a symphony next door.

The pressure is relentless. The burnout is real. The optimism is mostly caffeine-induced self-preservation. When Kiri admitted she collapses “every five months” from keeping up with the pace, I felt spiritually seen. She wasn’t being dramatic — she was being factual. Retail media is a treadmill set to “inhuman.”

And yet the industry marches on, smiling for the company town hall, pretending everything is scalable and fine, like a houseplant insisting it’s thriving with one dead leaf hanging off the pot.

The Unrealistic Expectation Problem

Amazon’s operational excellence has created a warped gravitational field. Retailers are expected to match a system that took a decade and several billion dollars to build. It’s like handing someone a rusty toolbox and saying, “Great news, you’re doing brain surgery tomorrow.”

Most networks don’t have the infrastructure. They don’t have the unified data. They don’t have executives who even understand what an RMN does beyond “brings in non-traditional revenue.” Kiri summed it up without a hint of melodrama: “They don’t have the buy-in. They don’t have the resources. They don’t have the talent.”

But sure — let’s keep pretending everyone is two quarters away from becoming the next Amazon. Hope springs eternal, delusion springs faster.

Why Readers Need This Series (Beyond Morbid Curiosity)

Retail media feels chaotic because it is chaotic — and that’s before AI shows up with a megaphone and starts asking why humans ever thought they should run the transaction layer of commerce in the first place.

The whole ecosystem runs on ambition, caffeine, and fragile optimism. Beneath the glossy headlines is a category sprinting uphill in flip-flops while insisting everything is fine.

This is the beginning of our series. If this is how the story opens, wait until we get to the part where agentic commerce strolls in and quietly rearranges the furniture.

The Rabbi of ROAS

What You’re Missing in ADOTAT+

If this piece rattled you, wait until you see what’s behind the paywall. The free version gives you the tremors. ADOTAT+ is the full earthquake.

Inside the member edition, I map out the parts nobody else will print:
which RMNs are structurally insolvent, which pillars collapse first, who’s preparing for agentic commerce, who isn’t, and why the measurement layer is about to get rewritten by machines instead of marketers.

It’s the kind of analysis holding companies wish I’d keep to myself.
And the kind indie media can only produce if readers back it.

Support independent reporting, get the unfiltered version, and stay ahead of the herd sleepwalking into the shockwave.

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