Monday briefing time!
This week brought some wild stuff. Here’s what caught my attention:
#1
Everyone will hype GPT-5 this week, but you know better…
Marketing gurus are *screaming* about how GPT-5 changes everything forever for all GTM roles.
I spent time where real users are actually testing it. Very different story.
The most upvoted post on r/ChatGPT this week: “GPT-5 is about lowering costs for OpenAI, not pushing boundaries”
Users even tested it with simple tasks. It failed most of them.
I tried it myself for copywriting all weekend - it’s honestly the same as all other AI models. It’s only a question of how you use them.
My take: I’ve learned to ignore AI launch hype. While everyone else chases shiny new tools and rewrites their processes, I double down on getting better results with what already exists.
#2
This bank found a *genius* workaround for trademark law
Banks can’t legally show other companies’ logos in their ads.
TD Bank got creative.
They put ads with HOLES cut out next to Nike, McDonald’s, and Starbucks stores.





The hole frames the logo. Text says “Own a piece of it” (buy their stock).
Brilliant way to reference brands without breaking trademark law.
My take: I love love love when restrictions force creative solutions. Some of the best marketing ideas come from impossible constraints, not unlimited budgets.
#3
Frida made breast milk ice cream (and got free PR)
Ice cream company Frida launched “breast milk-flavored” ice cream.
(Not real breast milk - just the flavor)
Sounds gross? That’s exactly why it works.
Dozens of publications wrote about it. Loads of conversations about it (and if they should do it or not). Zero ad spend.
People hated the concept in threads and comments - but the shock value got Frida massive free coverage.
My take: Most marketers are terrified of negative reactions. Smart marketers know that half the internet hating you is infinitely better than nobody caring about you at all.
#4
This Times Square ad looks like my 4 y/o nephew wrote it
Cluely put up a massive Times Square billboard that says: “hi i’m roy im 21, this was very expensive, pls buy my thing, cluely .com”
The mess is the message.
It looks like Roy texted his friends. That’s why it works.
My take: Sounding human is like a superpower in 2025. While everyone is using AI-generated copy and super-polished designs, the rare marketers who sound human cut through the noise fast.
#5
I got publicly roasted (and it worked perfectly)
I bought a ticket to a tech roast in NYC specifically to get this newsletter exposed to a massive audience.
Raised my hand when the comedians asked. Let them tear me apart for 10 minutes while I slipped in my full domain (“marketing ideas DOT COM”) between the brutal jokes.
They loved laughing at me so much that they brought me back later to give actual marketing advice to another founder. 😅 That second clip exploded even harder!
(Watch the full roast on YouTube)
I stopped buying attention and started earning it.
My take: Look for unconventional stages where your audience gathers. Shows, conferences, even comedy roasts - if your people are there, find a way to get on stage.
🧠 What I learned: The highest ROI marketing happens when you become the content people actually want to see.
See you Thursday ✌️
Tom
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That TD Bank ad is so great!!
Man you’ve got some balls :)
Crazy idea with those roasts