Stuff About Advertising

Across India, Brazil, and the UAE, people already shop by chatting with businesses on WhatsApp. But in the US, most of us have never thought about buying anything inside a messaging app. This episode digs into why.
I traveled to Meta's Conversations event in London to understand the rise of conversational commerce: why messaging became a storefront, the psychology of why a conversation sells better than a landing page, what actually changes for advertisers when an ad opens a chat, and Meta's big new Business Agent.
Plus an honest look at the trade-off of building your business inside someone else's ecosystem.

Featuring:
Natsumi Tomishige, Creative Strategist at Meta
Karishma Shah, Head of Marketing at Loco Bear

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This was my second time attending advertising's biggest event of the year, and just like last year, I have mixed feelings.

In this ad-libbed debrief, I'm giving you the honest details on:
What I did all week
How the festival has changed
What the activations were like
The separation between industry and creators
AI everything
What I'd do differently next time
If I'd recommend it for advertisers and creators

Airlines used to have personalities. They sold aspiration and exploration. A feeling. Now, they sell...credit cards. And bonus loyalty points.
In this episode, I trace the full arc of airline advertising — from the golden age, when airlines couldn't compete on price so they competed on image, through deregulation and the death of Pan Am, to Southwest's personable brand and the investor that completely dismantled it in under a year.
Note: Since this episode was recorded, Spirit Airlines has ceased operations. On May 2, 2026, Spirit shut down after failing to secure a federal bailout, becoming the first major U.S. airline to go out of business since the September 11 attacks. In the episode, I mention that Spirit could be forced to liquidate. That has now happened. 😬

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For some reason, tech companies cannot figure out mascots. They keep trying, and they keep getting it wrong. Or they get it right for about five minutes before it falls apart.
This episode is the history of that problem, from Microsoft Bob to Clippy to Bonzi Buddy to Ask Jeeves. Plus, Apple's Lil' Finder Guy is the internet's new obsession, but Apple hasn't said a single word about him.

Learn more about my creative thinking course, Big Idea Bootcamp here.

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What happens when the same tools we use to sell chips and shoes get pointed at a war?
From the War Advertising Council in the 1940s to the post-9/11 rebrand of America to a $729 million Israeli influence machine — the advertising industry has never been a neutral party in wartime. This episode traces 80 years of marketers putting their most powerful tools in the service of governments waging wars.