Remember that Anthropic Super Bowl ad? The one dunking on ChatGPT for putting ads in conversations. Everyone loved it. "Ads are coming to AI. But not to Claude." Standing ovation. We all felt very smart and principled.
Guess what happened while we were clapping.
ChatGPT's ad pilot crossed $100M in revenue. In six weeks. 600+ advertisers signed up. Copilot ads are converting 73% better than traditional search. Users who come through chat ads convert at 1.5x every other channel. The numbers are as subtle as Sam Altman trying to scan your eyeballs.
And here's the fun part: not a single ad tool on the market knows how to write for this format. Everyone's running their Google/Meta copy inside a chat window and hoping for the best. It's like reading a billboard out loud at a dinner party.
Trust me on this: if someone does this right, the whole Anthropic Super Bowl thing is gonna age like milk.
This has happened before by the way. 1952. TV was new. Every respectable ad agency refused to take it seriously. One guy built a simple framework for the new medium, made the most hated commercial in America, and tripled his client's revenue in 18 months. That spot earned more than Gone With the Wind. That legend's name was Rosser Reeves.
The people who mocked the new medium kept their credibility. The guy who built the playbook for it kept their clients.
The playbook for conversational ads doesn't exist yet. Just saying.
Be Rosser Reeves.
This is what happened when CVS installed self-checkout to save on labor:
Sales of condoms went up.
Plan B went up.
Antifungal cream went up.
Double digits across the board. Nothing else changed. They just removed the part where a cashier picks up your item and looks at you.
Turns out a lot of people wanted to buy stuff they just couldn't bring themselves to hand to a stranger.
Meanwhile, Japan has known this for decades.
We call this the embarrassment commerce.
Lots of money to be made here. Many ways to play it.