Here is a delightful little parlor trick for your next industry mixer, assuming you still go to those, assuming anyone still does without first checking LinkedIn to see who's had a title change since Tuesday: find someone who has spent two decades wiring the exact machinery that follows you around the internet whispering buy this, buy that, also have you considered these running shoes you glanced at once in 2022, and ask them how surveilled they feel.

Mark Donahue, GM of retail media at Placements.io, will tell you he feels great about it.

Great. About it.

And you know what? I kind of love him for it.

Because here is the thing about Donahue, and here is the thing that made this conversation genuinely worth having: he is not doing the industry two-step. He is not pretending to be scandalized by a system he helped build. He is not showing up to a podcast in 2026 clutching pearls he himself manufactured and sold wholesale. The man has spent two decades building media networks inside one of the world's largest online auction marketplaces, a legacy American apparel brand that still haunts every mall in America like the Ghost of Khakis Past, and a money-transfer giant whose entire customer base is people wiring cash across borders to family. And when asked on a scale of one-to-my-browser-just-served-me-an-ad-for-the-thing-I-was-thinking-about how surveilled he felt, he gave the rarest answer in ad tech:

An honest one.

He wants his experience tailored. He quoted Doc Searls without irony, which, let's be clear, is the ad tech equivalent of a cardinal quoting Spinoza. He said, and I swear on my grandmother's brisket, "give them what they want."

Reader. He is them. And he knows. And he's fine with it. And that, I submit, is more useful than a hundred LinkedIn posts about privacy.

Donahue's philosophical frame is coherent, charming, and almost entirely aspirational. He invoked Searls's intention economy, the lovely notion that consumers raise their hands, signal what they want, and relevant offers come to them. You need a rental car? Terrific. Tell the universe. The rental car people pitch you. Clean. Consensual. Almost romantic.

The delightful thing is that Donahue does not pretend this is how the internet works. He names the gap out loud. "I put information out into the universe," he said, "it comes back to me in various other forms from other parties, meaning that that information is flowing across hands. And I feel that's a little suboptimal."

Suboptimal.

God, I love that word choice. A man who has wired these pipes for twenty years just described the output as suboptimal, which is the corporate equivalent of calling a house fire "a thermal event" or describing the Hindenburg as "a rough landing." It is the most restrained burn I have heard from inside the industry in a long time, and restraint, in 2026, is basically a form of honesty. He is not yelling. He is not grandstanding. He is just noting, with the tired affection of a mechanic looking at a car he has personally rebuilt six times, that the thing doesn't quite run right. And he would like to fix it.

This is better than outrage. Outrage is cheap. Diagnosis is rare.

Now let me pause on a number Donahue tossed out with the casual energy of a man mentioning the weather.

On average, he said, we each hand explicit permission to eighty different vendors to gather information about us.

Eighty.

Sit with that. Roll it around. Eighty companies that you have, in some legally enforceable sense, nodded at. Your airline. Your grocery app. The app that tracks your period. The app that tracks the bus. The coffee place loyalty program. The other coffee place loyalty program. The shoe brand you gave your email to in 2019 for a 15 percent coupon and have since forgotten about entirely, but which I promise you remembers you in loving detail.

Here is what I love about Donahue naming the eighty: he is not doing it to scare you. He is doing it to respect you. The whole industry has spent a decade trying to make this number invisible, buried under the cookie banner, hidden three menus deep in your settings, and Donahue just walked on a podcast and said the number out loud, conversationally, like it's a fact worth knowing.

That is the move of a man who thinks users can handle the truth. Which, frankly, is a more generous posture than most of ad tech has taken toward its own customers since roughly 2012.

The moment that made me genuinely sit up came when Donahue described his run at the money transfer company. The customer base, he said, was "overwhelmingly non-English first language." Sending money across borders. Typically to family. And the question his team had to wrestle, in his own exact phrasing, was this:

If you are targeting based on information you know about me, do I want to be known? Are you revealing you know something about me that I don't want known about me?

Stop. Read that again. Slower.

This is a man who has sat in conference rooms, at enterprise scale, with P&Ls and dashboards and ops teams, and seriously grappled with whether showing a targeted ad to a migrant sending money home is the kind of thing that should be done at all. That is not a whitepaper concern. That is a real-world, kitchen-table, who-knows-where-I-live concern. And Donahue, instead of waving it away with the usual value exchange hand-puppetry, calls it what it is: a gauntlet. Appropriateness. Context. Language. Consent.

He does not pretend it was solved. He does not pretend the industry has it figured out. He describes the work as closer to triage than strategy, and I submit to you that this is the most honest and most humane thing anyone in ad tech has said into a microphone all year. This is a man who has looked at his own customers, seen them as whole people with real stakes, and tried to build accordingly.

You know how rare that is? It is so rare that I want to laminate it.

Here is the thing I cannot quite square, and here is where Part II will pick it up and run.

Donahue's superpower wish, the thing he'd snap his fingers for, was perfect identity resolution. Knowing exactly who a person is across every device, every channel, every touchpoint. He threw in flight as the fun one. Identity resolution was the real answer.

This is a man who, in the same conversation, expressed genuine discomfort about his own data flowing across eighty vendors. Who worried about what the money transfer company was signaling to its customers. Who quoted a privacy philosopher with real affection.

And whose professional dream is essentially the surveillance singularity.

Now, a lesser interviewee, and frankly a lesser human, would try to paper this over. Donahue doesn't. He names it. He calls it the two sides of my personality, the work self and the citizen self, and he lets them sit in the room together without pretending they agree. Which is, I'd argue, exactly how most thoughtful people in this industry actually feel, and almost nobody has the nerve to say on the record.

The contradiction isn't a flaw. The contradiction is the job. And Donahue, bless him, is one of maybe a dozen people I've talked to who will say so on a microphone without first running it past four layers of comms.

Next in The Donahue Files, Part II: We get into the walled gardens, the retail media explosion, why the industry's favorite new darling is quietly turning into fifteen new monopolies in a trench coat, and whether the man who ran media networks inside Gap and a money transfer giant thinks anyone can actually buy across all of them without losing their mind. Spoiler: he has thoughts. Delicious ones.

Part I was the version I can publish on the open web without getting a phone call. Parts II and III are the version I wrote for the people who actually do this work.

Part II is the insider briefing. The "two is the limit" problem that top CPG buyers will only admit on background, the organizational choke point that kills every mid-tier RMN build before it ships, the math that explains why the retail media landscape will not consolidate in the next four years no matter what the consultants are telling your CEO, and the payments-layer disruption scenario Donohue did not laugh at when I pitched it.

Part III is the one I could not stop thinking about for two weeks. It is built around a single sentence from Donohue's Western Union years, the question almost nobody in this industry asks out loud, and why the absence of that question is the reason retail media keeps drifting toward surveillance when it was supposed to be drifting toward relevance.

If you work in retail media, commerce media, CPG, or any adjacent category, Parts II and III will pay for the subscription by themselves.

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