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.

"Speed of culture" is one of those phrases agencies love to throw around. But when Taylor Swift dropped a surprise album teaser and every brand posted glittery orange logos, it sparked a debate: are brands hopping on trends adding value or just adding noise?

I sat down with Stef Schmit and Josh Rangel from Ogilvy to get into Culture Current, their framework for knowing when to move fast and when to show restraint. We cover the Four S's, why content calendars aren't actually dead, how they turned the Anthony Davis trade into a Woj Bomb moment, and what the Embassy of Japan had to say about Taylor Swift's travel plans.

If you want to learn more about Culture Current, reach out to [email protected]

When 400 brands partner with a single movie (coughwickedcough), most just become noise. So what separates the partnerships that actually work from expensive logo slaps?

I talked with Matt Kessler from Martin Entertainment about their Aspercreme x Spinal Tap II campaign and how brands should be approaching entertainment partnerships. We dug into authenticity, scarcity, and why the barriers to entry are actually the point.

Is your brand building in or bolting on? Listen in to find out.

Huge thanks to Matt Kessler and the team at Martin Entertainment!

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Most agencies treat client approval like a battle to be won. But what if that dynamic is exactly what's killing your best ideas? In this episode, I talk with Chris Colliton, Executive Creative Director at Zulu Alpha Kilo New York, about a completely different approach. One where clients become your partners in crime rather than obstacles to overcome.

We dig into why the ideas that feel most impossible to sell are often the most effective, how to present unprecedented concepts with confidence, and what it takes to build an agency culture where wild ideas can actually thrive.

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For every ad you see on TV, dozens of brilliant ideas were killed along the way. That gut-wrenching feeling of losing a script you loved is a universal part of the creative process.

In this episode, we're going behind the scenes with the creators of the Dead Ad Society, a unique anti-award show where dead ads get a second chance at life.

We'll talk about why great ideas die, how creatives cope with rejection, and the story of one ad that was too good to stay buried.

Big thanks to my special guests:

Caleb Dewart (hungryman)

LJ Johnson (hungryman)

Chad Broude (Highdive)

💀 Enter your favorite dead scripts at deadadsociety.com 💀

Learn more about hungryman.

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Cannes Lions: I went, I saw, I... spent a lot of money.

In this episode, I'm giving you the no-holds-barred recap of my first time at the infamous festival. You'll get my genuine take on the event, a full rundown of what I got up to, and a complete disclosure of my expenses. Most importantly, I'm answering all your burning questions like "Was it worth it?" and "Would you go back again?"