Let’s just say it: most ad agencies are treating AI the same way toddlers treat glitter—smearing it all over everything, hoping it looks fancy, but never once asking if it belongs.

Welcome to Season Four of The ADOTAT Show, where we don't just ask the hard questions—we put people in the hot seat and let the industry feel the heat. And no one better to help us light the match than Jay Friedman, CEO of Goodway Group, the man who scaled a fully remote agency into a media machine while most CMOs were still figuring out how to unjam the office fax.

This season kicks off with something the industry desperately needs: a sharp slap of reality about artificial intelligence.

Jay doesn’t mince words. He told me that yes, AI is going to be used for cost-cutting—and honestly, that’s boring. That’s expected. That’s the table stakes. But what matters, he said, is what happens after the automation. That’s where imagination comes in. The real winners? They're not the ones using AI to make banner ads faster or clean up Excel tabs. They're the ones turning AI into their thinking partner, their creative accomplice, their co-pilot in innovation.

Jay's exact words? “AI should be an imagination partner.” Not a cost-cutting mechanism. Not a glorified proofing assistant. Not another department with a fancy acronym and a license for Midjourney.

He’s walking the talk, too. Jay’s already built seven custom GPTs for himself. One of them is an executive coach, trained on business thinkers, leadership models, and a whole lot of tough love. After a meeting he wasn’t thrilled about, he fed it the transcript and asked what he could’ve done better. The AI replied—straight up—that he should own his mistake, tell his team what he’d do differently, and show up better next time. It even laid out the short-term fix, the behavioral shift, and a long-term habit change to drive growth.

Let me repeat: Jay Friedman has built a robot that holds him accountable in ways most corporate boards can’t.

And while everyone else is debating prompt templates for “increase engagement,” Jay is talking about building auditable, adaptive AI systems that don’t just report metrics—but shape leadership behavior.

But this wasn’t just an AI therapy session. We dug into the industry's pathological need to confuse cheaper with smarter. Jay laid it bare: the obsession with cost-cutting is understandable, but dangerous. "Marketers keep looking at the numerator," he said, referring to cost, "but the real work is growing the denominator.” That’s not just good math—it’s gospel.

He dropped this gem like it was obvious: “Everything in marketing is cost per outcome. Cost per whatever. We need to shrink the numerator and grow the outcome.” But instead, the industry’s been treating AI like a pair of scissors to trim the fat, rather than a scalpel to shape the future.

And if you think this is some abstract executive rambling, Jay’s already applying it. Take Dollar General—yes, the retailer everyone underestimates. Goodway Group supports their retail media network, and unlike the thousands of other RMNs popping up like adtech mushrooms after a rainstorm, this one is built on shared value. Jay told me that they’ve structured the relationship so that Goodway only wins when Dollar General wins. “That kind of value alignment,” he said, “forces both sides to focus on outcomes, not outputs.”

And that retail media narrative? It’s not a tax, it's a takeover. Jay made it clear: “Retail media is the most underrepresented conversation in our industry.” While the rest of the ecosystem is scrambling to duct-tape together identity post-cookiepocalypse, retailers already know their customers. They’ve got the first-party data. They’ve got the checkout receipts. They’ve got what matters.

But still, many brands treat retail media as if it’s some mafia-style shakedown. According to Jay, that’s because too many CPGs are stuck in a mindset that media is either bought by their agency or demanded by their retail partner—and both sides are holding their budgets like Cold War secrets. The truth? Most agencies are afraid of losing control, and retail media threatens their seat at the budget table.

And if you want a Jay Friedman truth bomb? Here you go: he told me that if transparency were mandatory in this industry—if every agency had to actually show where the money went—Goodway would grow five times over. Why? Because he’s convinced a third of agencies wouldn’t survive that level of sunlight. Not because they’re evil. Just because they’ve built entire business models around opacity, inefficiency, and plausible deniability.

The man's not just speculating—he’s betting his growth on it.

We talked about a lot: how AI should be integrated into client-facing pitches—not hidden behind the curtain. How most “strategic planning” today is just recycled performance dashboards. And how if agencies want to stay relevant, they’d better stop feeding AI scraps and start letting it rewrite how they think.

Jay’s doing it. He’s already building AI-driven tools that let clients interact with data in real time—ask questions, explore strategy, challenge assumptions. Not just some demo reel with a hype track. Actual, operational intelligence, not some agency trying to make the same media plan look sexy with a new slide transition.

And then there was the story of the VR bomb.

During a virtual team-building escape room, Jay grabbed a virtual bomb and chucked it into a virtual wormhole while his team yelled “What are you doing?” His answer was perfect. “It was a bomb. I didn’t have time to explain.” That’s leadership in a nutshell—and also maybe the best metaphor for adtech in 2025. We’re all holding bombs. The question is: who’s bold enough to throw it?

So yeah. This isn’t your usual podcast episode. This was a manifesto wrapped in dry humor, served with a side of peanut butter (yes, he’d bring that to a desert island), and topped with a healthy dose of "get your act together."

Because if Jay Friedman’s building GPTs that give better feedback than most CMOs, and your team is still trying to figure out how to prompt “Write ad for shampoo,” it might be time to rethink everything.

Welcome to Season Four.
No fluff. No scripts. Just truth, talent, and tech that doesn’t make excuses.

Jay Friedman’s not here for the theater. He’s here to build.
And if you’re not thinking that big? You’re already obsolete.

🧠🔥 Next up in this issue: Why retail media might actually be sexy (if you rebrand it), why some agencies are afraid of Dollar General, and how throwing bombs in VR might be the best leadership seminar no one’s offering.

Stay bold. Stay curious. And for G-d’s sake, stop asking ChatGPT to write your case studies. You’re embarrassing all of us.

Jay Friedman on GPT therapy, dumb automation, and why agencies need to start thinking again

If your agency is using AI to tweak button colors or autogenerate product descriptions with the personality of a tax return, congratulations—you’re officially part of the problem.

Jay Friedman has thoughts. Big ones. And unlike most AI bandwagon jumpers, he’s not learning about it from LinkedIn slides with rocket ship emojis. He’s building it, using it, and letting it argue with him.

When we got into how AI is showing up across the ad industry, Jay didn’t hesitate. “The cost-cutting stuff? That’s table stakes,” he said. “Procurement’s going to demand it. Finance is going to demand it. But that’s not where the differentiation is going to be.”

What actually matters? According to him, it’s whether AI becomes more than a tool—it becomes an intellectual partner. “The agencies and the tech companies who let AI become an imagination partner, a thinking partner, and something that creates things faster… they’ll win. Full stop.”

And he’s not speaking hypothetically. Jay’s already built seven custom GPTs. “One of them is an executive coach,” he explained. “I had a meeting where I knew I could’ve done better. I literally sat down afterward, typed into the GPT: ‘Here’s what happened. What could I have done differently?’”

It didn’t just give him platitudes—it broke him down. “It came back and said, ‘Recognizing the issue is a good start. When you go back to that team, acknowledge it. Tell them how you’ll do it differently. And then here are things you can work on immediately, and long-term.’ And honestly? It was dead-on.”

Yes. Jay Friedman gets executive coaching advice... from a GPT he built himself.

This isn’t ChatGPT writing copy about cereal. This is AI showing up with receipts and holding the CEO accountable like a no-nonsense board chair.

He told me flatly, “This isn’t about replacing work. It’s about improving how we think.”

And when it comes to how agencies use AI with clients? He’s even more direct: “This can’t be something that sits on our side of the fence. We have to bring it to the client. Let them ask it anything. Make it part of the interaction.”

Jay’s vision is crystal clear. The agency of the future walks into a pitch with AI live in the room. The client doesn’t wait for post-meeting recaps. They ask, “What’s my best performing geo?” or “What channels are underweighted?” and the AI answers right there, on the spot. No hiding. No slides. No post-call Excel.

“Imagine a chatbot with all your dashboards,” he said. “Not just numbers. Strategy. Performance. A tool you actually use, in the meeting. That’s where this goes.”

And don’t mistake him for one of those futurists who wants to automate creativity out of existence. Jay is ruthless about where AI belongs—and where it doesn’t.

“Trafficking? Push-to-platform? Audience loading? That should be automated. That’s the cost-cutting marketers deserve,” he said. “But the value? That’s in thought frameworks, models, and decisions.”

He’s building systems that help marketers model emotional resonance, simulate customer journeys, and think beyond KPIs. “Everything in marketing is cost-per-whatever. Shrink the numerator, grow the denominator. That’s it. That’s the job.”

And yet, he says, most agencies are still focused entirely on the numerator—on slicing pennies off CPMs instead of building value worth paying for.

So if you’re still using AI to write ad copy for shampoo, Jay’s already ten steps ahead—coaching himself with GPTs, building client-facing AI interfaces, and asking questions no one else dares to put into a dashboard.

He’s not automating for efficiency.
He’s automating for clarity, creativity, and control.

And he’s not quietly testing. He’s shipping. Thinking. Leading. While most of the industry is still writing prompts like it’s Mad Libs for marketers.

The bottom line? Jay doesn’t want AI to do the work for him. He wants it to make the work better.

If yours isn’t doing that… then what, exactly, are you paying for?

Jay Friedman on why retail media isn’t a tax—it’s the future of identity and results

If you still think retail media is just a new name for co-op ads and endcap fees, congratulations—you’re officially stuck in 2006, somewhere between faxed IOs and QR codes printed on park benches.

Jay Friedman has a different view. For him, retail media isn’t a distraction—it’s the most under-leveraged, misunderstood, and misbranded opportunity in modern advertising.

“Retail media is the most underrepresented conversation in the industry right now,” he said, not even pretending to hedge it. “If you go to an IAB event, it’s like 2% of the content—if that. But if you’re a CPG? It should be 90% of your strategic planning.”

His frustration is palpable. Despite retail media’s ability to deliver real results, real identity, and real incrementality, it’s still often treated as a budget line item that brands reluctantly check off because Walmart said so. Jay’s done with that narrative.

“It’s not a tax,” he said, “unless you treat it like one.” And that’s exactly what too many agencies and CPGs have been doing—approaching retail media like it’s a forced obligation instead of what it actually is: the most data-rich, signal-strong environment you’re going to get in a post-cookie world.

He explained that the core problem isn’t that retail media lacks value—it’s that it threatens control. “Retailers walk into a brand’s office and say, ‘You’re going to spend $100 million with us this year.’ That’s money the agency no longer controls. And agencies don’t like being told what to do.”

And that’s where the resistance begins. Not with performance. Not with measurement. But with territorial politics and outdated playbooks.

What should be happening, Jay argues, is a total rethinking of how retail data gets integrated into brand strategy. “Retailers know more about their customers than anyone else. They have purchase history. They have loyalty behavior. They have location. And they can activate that without relying on shaky third-party ID graphs.”

But many CPGs? They’re still clinging to the idea that brand equity is something built only through national TV and clever storytelling. Jay’s not against branding—but he sees the false binary being drawn between “brand” and “performance” as lazy thinking.

“You can prove incrementality through retail media,” he said. “And if you can do that, then who cares if it came from a banner on a retailer site or a TV ad during the Super Bowl? The denominator matters.”

There it is again—his favorite theme: grow the denominator. The reach, the results, the lift. Retail media, when properly managed, can deliver all of that. But the agencies still dragging their feet? They're not protecting brands—they’re protecting their own fiefdoms.

Jay’s urging marketers to stop fearing Walmart, stop resisting Kroger, and start treating these platforms like the strategic partners they already are. They have the data. They have the access. And they have the customers you can’t find through lookalikes anymore.

So no, retail media isn’t boring. It’s not a tax. It’s not even new. It’s just finally being taken seriously.

If you still don’t get it? You’re not strategic.
You’re just... old.

☕ For Less Than a Dirty Coffee in NYC, You’re Missing This:

💥 Market Share & Margins: The Silent War in Retail Media
Jay Friedman’s pulling the curtain on retail media’s power grab—and let’s just say, it’s not your media agency calling the shots anymore. Walmart’s playing chess. Dollar General’s quietly cleaning up. And agencies? Stuck playing musical chairs on a sinking boat.

📖 Radical Transparency: What If Everyone Had to Open Their Books?
Jay says a third of agencies would spontaneously combust. The markups, the arbitrage, the verification scams—it’s all here, and it’s not pretty. Unless you like watching the house of cards sway.