This week: An episode inspired by our 2025 guests - there were over 25 of them! This wasn’t a typical Watson Weekend. There was no singular guest, no straight narrative arc, no gentle warm-up.
Instead we turned the lights up, the madness on, and ran a full Jeopardy board across the entire year of retail.
A quiz show. Here are some notes from our producer Vinny O’Brien.
Some humming, then hawwing..
A retrospective.
Beneath the jokes, the nostalgia, and Rick’s increasingly violent attempts to control the scoring system, something unexpected happened:
we extracted the clearest lessons of the year by turning them into questions.
Retail is a riddle.
So why not answer it in question form?
We Came for the Fun. We Left With the Truth.
We prepped a silly recap.
We left with a sociological autopsy of the industry.
What follows are the real takeaways the insights disguised as punchlines.
Retail is a Memory Game Everyone Pretends to Be Good At
The moment the “Marketplace Mayhem” category dropped, everyone collectively groaned because every question was a flashback to something we still haven’t emotionally processed.
Amazon rule changes.
Walmart’s acceleration.
Temu’s physics-defying growth.
The year the entire industry finally admitted:
The gravitational pull of the modern marketplace. Not all are created equal.
Retail in 2025 punishes amnesia.
The operators who win aren’t the smartest they’re the ones who actually remember what happened last quarter and adapt.
Retail Media Is Still a Beautiful Disaster
Under the “Retail Media” and “AI Illuminati” categories, the jokes wrote themselves.
The industry has collectively agreed to pretend:
attribution is solved.
the dashboards are accurate.
offsite equals “don’t ask questions”.
every impression has spiritual meaning.
Retail media is now so big that no one understands it including the people building it.
It’s not a channel.
It’s a tax.
A very profitable tax.
And we’re all still arguing over who’s actually paying it.
But you know, we all do.
Culture Beat Strategy Every Day of the Week
“Culture Club” ended up being the most revealing category because it was the only one where the room got quiet. The quotes that surfaced were human:
“Empathy scales performance.”
“Unclear expectations kill more teams than bad data.”
“The COO is the real CMO now.”
In a year where everyone chased optimization, culture kept the lights on.
And what the game reminded us is painfully simple: you can’t out-smart a team you haven’t stabilized. Leaders, you have been warned.
AI Is Getting Better, But the Humans Are Getting Funnier
The AI category contained some of the best lines of the show:
“Half of AI exists to rewrite LinkedIn posts.”
“Agentic AI is great, but who’s teaching it not to burn the house down?”
“Your brand voice isn’t a prompt it’s a personality disorder.”
And beneath the humor, the lesson here was clear:
AI isn’t here to replace operators maybe it’s here to expose who never had a process to begin with.
The future is conversational we are told, but, as ever, the chaos is human.
Ecommerce Fatigue Is Real — Laughter Is the Only Known Antidote
Every question triggered a shared trauma response: This was visual, not something they said. Whether it was Kaplan fumbling in the dark or Rick openly admitting it.
“Oh god, I forgot that happened.”
The industry is exhausted and this episode proved something important:
Humor is how operators metabolize change. This is the human we speak of.
What We Learned (The Real List)
Retail is a pattern recognition sport.
If you can’t remember the year, you can’t navigate the next one.Retail Media is a coordination problem, not a media problem.
If merch, ops, and marketing don’t align, the spend is wasted.AI will collapse the funnel but elevate the operator. Again, this has to play out but some good signals to process. Automate the predictable; humanize the rest.
Marketplace gravity is now stronger than brand strategy. Ignore it at your peril.Remember your customer is hiding in plain sight.
Culture will determine survival. Talent, clarity, and psychological stability beat cleverness.
Humor keeps teams alive. A business that laughs together lasts longer. That’s our motto and we are sticking to it.
This wasn’t a standard episode because this isn’t a standard industry anymore. And to be fair to our team, they came in blind. Remembering all of our guests, all of our conversations is now an easy ask. They handled this capably.
Thinking About Me, Thinking About You
This Jeopardy episode reminded me of the same theme I touched on in my Substack piece,
“It Once Rained for Two Million Years on Earth.”
Long, slow, unstoppable change.
That’s retail today:
not a storm,
not a crisis,
not an apocalypse —
a climate. Are we in an age or an era? I will shut up now.
Everything is moving at once.
Everything is unstable.
Everything is possible.
You can’t stop the weather.
You can only build the right clothing.
From the Backlot (Producers’ Meanderings)
We trialled this format with some of our partners this year. We turned content into games. We expect to do alot more of this next year. It is a fun, simple way to distribute a message. It challenges us too. Game shows we choose are those that have draw on muscle memory and take you back, connect you in an instant with all of their visual assets.
Fast.
Chaotic.
Unpredictable.
And defined entirely by how quickly you can recall what you learned last time things fell apart.
Right now and for the foreseeable volatility is the environment, operators must become the climate-resilient species.
And if you can’t fix the chaos? At least learn to enjoy the buzzers.
This Week - NRF Edition
Friday November 21st Noon Eastern Time. Beer o Clock on GMT.
Credits - where due
Produced by my good self, Kaylea Sepulvado and Libby Dallis
Music by RYAL - the creation of the wonderful Jacquelyn Laufer and Aaron Nevezie
Show Sponsor Rithum
