It’s that time of year again: Brand Federation’s Naughty & Nice list is out, and Matt Williams is here to break it down. Matt is President of Brand Federation and former CEO of The Martin Agency, where he led campaigns for GEICO, OREO, UPS, and Walmart. He’s also a visiting professor at William & Mary, sharing decades of brand strategy know-how. On this episode, Matt reveals which brands earned “Nice,” which landed on “Naughty,” and what leaders can learn from both.

What You'll Learn

How brands end up on the Naughty list by ignoring customer context and cultural signals.
How Delta, Starbucks, and others earned their spot on the Nice list through clarity, consistency, and smart leadership.
Why edgy brand moves succeed or fail depending on strategy and self-awareness.
How crisis response can turn a disaster into a win with creativity and cultural savvy.
What Apple’s place on the watch list says about innovation, risk, and the future of tech brands.

Episode Chapters

(00:00) Intro

(00:52) Matt returns to the show

(01:21) Why American Eagle’s “Great Jeans” campaign backfired

(03:52) Cracker Barrel’s tone-deaf rebrand misstep

(06:48) Target’s DEI reversal and the cost of misunderstanding your customer

(09:20) Southwest walks away from its differentiators

(11:52) Meta’s AI avatars go sideways

(12:44) Delta earns a place on the Nice list

(13:55) Starbucks returns to the core

(16:55) How Astronomer turned crisis into comedy

(21:15) Duolingo kills the owl (and nails it)

(24:40) Navigating edgy vs. effective brand moves

(24:51) Apple lands on the watch list

(27:40) The brand that made Matt smile

(29:17) Where to learn more about Brand Federation

(30:08) Closing

Matt Williams is the President of Brand Federation, a brand and marketing consultancy that helps organizations like Harvard, MIT, and Mercy Corps transform their brand strategy for growth and impact. Before that, he spent 26 years at The Martin Agency, rising through strategic planning roles to become CEO. During his tenure, he led strategy and campaigns for GEICO, OREO, UPS, Discover Financial, Benjamin Moore, and Walmart, while guiding the agency to national creative and effectiveness recognition. Matt also teaches as a Visiting Clinical Professor at William & Mary, where he brings decades of brand strategy expertise to future marketers.

Matt lights up when talking about Duolingo, specifically the irreverent, persistent, slightly unhinged owl. The way Duolingo leans hard into its mascot’s attitude — using humor, edge, and cultural relevance — reflects a brand that truly understands both itself and its audience. The owl’s personality, storytelling, and strategic mischief never fail to make Matt smile.

Connect with Matt on LinkedIn.
Check out the Brand Federation, where you can see the full Naughty & Nice List!

On Brand is a part of the Marketing Podcast Network.

Until next week, I’ll see you on the Internet!

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