How I Spent the Gold Medal Hockey Game.
The only ad newsletter that wants you to go ahead and make better Olympic content than the official sponsors, that'd be great.
How do you say, “Aahh, now, are you going to go ahead and have those TPS reports for us this afternoon?” in Italian?
By now, everyone knows Canada lost the men’s hockey gold medal in overtime on Sunday morning. If you watched it, you know.
If you didn’t, it wasn’t the 3-on-3 overtime, or the silver medal that broke Canada. It was that the players were handed a stuffed animal and looked at it the way you look when someone says "we've brought snacks" and then put down a stupid tray of baby carrots.
I think my first idea for today’s newsletter was outlining some brand winners and losers of the Olympics. As thrilling as writing about the boxes of Puffs that surrounded the figure skaters as they awaited their scores might be (what did the deck say? We want to be associated with complete heartache and crying, let’s call it “The Kiss and Cry Area”).
That sounded like Ad Age content. Not Drink Cart content. Sure enough they were talking about all the Gold medalists you’ll want to be partnering with. (Spoiler alert: this whole idea is also something that really clicked with me). They have added how Olympic Memes are our last shared language. Although I do quite like this: “The meme is the stadium.” Ironically the article shows none of the great memes.
I was pretty much on X the entire game, enjoy-scrolling the reactions on both sides of the border and honestly wishing that we could pass a bill that forbids politicians from posting on social around major cultural events.
In the last period and the moments after overtime in what became collective Canadian grief, something clicked.
In the second period I’d seen another round of commentary about Wayne Gretzky from The Globe and Mail (How are we still talking about this?) and was thinking about how to reply to some of the posts in a fun way.
It hit me: Could I turn Wayne Gretzky into the Ben Affleck smoking meme? Would that be funny?
I tried Grok - surely it was crazy enough for the challenge. It was not.
I tried Gemini - Not even close.
I had been experimenting with Hedra, more for video, but its interface seemed geared to this idea of remixing memes.
It did it in one shot. Exasperated Wayne. Only issue? I think I was the only person that thought this was remotely funny.
Then the stuffies happened.
Here’s the actual process, because I think there’s something sort of useful in it:
Step 1: Find the feeling everyone’s already having.
X told me everything I needed to know. The mascot handout was the moment. Not the overtime goal. Not the celebration. The indignity of players like Marchand and MacKinnon standing there after losing holding a ridiculous little white stuffed animal.
My first output didn’t really land. It was smoking Affleck holding the mascot. Funny, but not that funny.
It didn’t capture the real story. There was too much Affleck. Sorry Ben. That and how merciless people were to the poor mascots. So on two fronts I was making sad and exasperated memes into stuffy gold.
Step 2: Have your tools warm before the moment arrives.
I’d already been in Hedra for the “Gretzky Afflecking”. Already understood what it could do. So when the image hit, I wasn’t scrambling to figure out a new tool — I just pointed it at the new moment. Feed in the Ben Affleck meme, the mascot, used Claude to sharpen the prompt. The output: Tina exasperated, smoking. Then Tina crying like Michael Scott.
Nothing is sadder.
Step 3: Borrow the format that’s already working.
Then Topps Now started posting gold medal cards for Team USA in real time — clean, official, beautiful. I took their format, the aesthetic, then flipped it to the Canadian silver and put Marchand and MacKinnon on the card with the caption: “The indignity of getting a stuffed animal after losing a hockey game.”
That made me laugh so hard (it’s also still racking up likes, saves and impressions). Then I made a relic patch card with an “Authentic Olympic Mascot Plush Swatch.” Like Marchand had ceremoniously sliced up poor Tina to put in a limited edition batch of commemorative cards. Cruel and hilarious.
Only one small text anomaly on this one - but more than good to ship. One day I want to share about my battle with Claude on creating a prompt for a funny but absolutely tasteless Prince Andrew English Pub sign. Claude said the idea was beyond satire. We disagreed.
Joke’s on Claude. Turns out you can trick it and then get Hedra to do the dirty work. It will be our little secret. Suffice to say that whole ordeal while writing this newsletter is something Ricky Gervais would have burned Claude to the ground over like it was the Golden Globes.
Here’s the actual ad industry lesson hiding inside this ridiculous story.
Cutting through is about arriving at the right moment, in the right format, with the right instinct behind it.
AI wasn’t sitting around thinking of remixing Tina and Ben Affleck or making Topps Now cards. But I was there to figure it out and get into posting mode in 90 seconds or less.
To throw in a remixed meme that utilizes the real moment context is so much better than posting the same old memes could ever be.
You just need some warm hands, the taste to make something completely outrageous, the fearlessness to post and the right AI tools to let you cook in real time.
Thank you Tina and whoever at the Olympic games who thought giving out plush toys to people who just lost gold medals was a good idea. Silver really is the worst.
Drink Cart Approved™ agency discussion topics
Are you ready for Sailingcore?
Are you ready for Dr. Pepper Sausages?
Am I the only one depressed that in 10-years we’ve gone from Conan O’Brien to someone called “the kombucha girl” as Vanity Fair’s The New Late Night. Or just old?
I fail to see who this content is designed for? Sunny the mascot from Raisin Brain making terrible fiber memes.
Breaking: Being chronically online is gauche now since tech bros have discovered “taste”.
Last Call: The Silver Bullet
Canada came for gold and went home with silver and a stuffed animal.
That feels like a drink is warranted.
The original Silver Bullet is gin, kümmel and lemon juice — and it’s been in the Savoy Cocktail Book since 1930, which means Harry Craddock was making it for Prohibition-era Americans who’d crossed the Atlantic just to legally have a drink. Nobody knows who actually invented it. Classic cocktail history move. The original is basically a “kümmelised gin sour.” I can see why only weird old golfers are interested.
Kümmel really is the weird part. It’s a caraway and fennel liqueur that started in Latvia, became Peter the Great’s favourite drink after he snuck into Holland disguised as a shipbuilder, then somehow ended up as the official nerve-calmer of Scottish golf clubs, where it’s still called “putting mixture.” It is allegedly also Prince Philip’s favourite cocktail. The Silver Bullet has a type.
The gin-and-scotch version of the same drink once went by the name “Poor Man’s Champagne”. Both feel right for a Sunday morning hockey loss. Both feel right for a Wednesday newsletter.
The Silver Bullet
2 1/2 oz gin
1/4 oz Scotch (a rinse, really — just enough to hurt)
Stir with ice, strain into a chilled coupe. Lemon twist. This one is terrible idea.
The Drink Cart is the newsletter version of sitting at a really good bar with someone who thinks too much about advertising and won't shut up about it.










