On Brand with Nick Westergaard

How to Build a Challenger Brand with Prentice Howe


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“A challenger brand is defined by an ethos — a mindset. They have ambitions that outweigh their internal marketing resources. They have to outthink. They can’t outspend.” So how do you punch above your weight class? We talked about this with Door Number 3’s Prentice Howe, author of The Empowered Challenger Playbook.

About Prentice Howe

Prentice Howe has always believed in underdogs. Now, as Owner and Chief Creative Officer of Door Number 3, a full-service advertising agency based in Austin, Texas, he’s helping brands embrace their challenger-ability and topple their giants.

Specializing in challenger brands—rising brands that may not have the resources of the top dogs in their industries but do have the bold ambition to go toe-to-toe with them and steal market share—Door Number 3 is changing the face of marketing and advertising. With features in The New York Times, AdWeek, The Wall Street Journal, Inc., and Communication Arts, as well as recognition from shows like Cannes Lion and the Webby Awards, Prentice has written the book on the challenger space. Literally. An Amazon best-seller, The Empowered Challenger Playbook: How Brands Can Change the Game, Steal Market Share, and Topple Giants describes his strategies in detail and backs them up with case studies.

It helps that Prentice practices what he preaches. He has fire-walked on hot coals at a Tony Robbins event, for one, a feat he credits for shaping his mind-over-matter outlook. In 2015, he made another bold move when he bought Door Number 3 from its founder, and his friend, MP Mueller. Having spent seven years as its Executive Creative Director earlier in his career, he knew the agency inside and out. As a creative person buying the company from a friend, he knew the risks, too. In fact, Door Number 3 is now one of the few agencies in the country owned solely by a creative.

Episode Highlights

What is a challenger brand? It’s not just defined by budget. “It’s an ethos. A mindset. They can’t spend as much as the category leader so they have to do something different.” That can come down to positioning or something innovative with culture or customer service.

Who are Prenctice’s favorite challenger brands? He first pointed to brands like VRBO, Uber, and Tesla. Though they’ve grown they started with the challenger mindset. However, a favorite example of a current upstart is Thinx period panties.

Eric gets it. Prentice told the story of a writer he works with, Eric, who often asks, “What’s safe worth?” In an age of so much digital clutter, standing out is harder than ever. Especially for an upstart. Safe is not an option.

Transfarency. How do you continue to keep your brand and your messaging up to date? As Prentice notes you have to know what your brand is about in “12 words or less.” He then pointed to Southwest Airlines new Transfarency campaign. “It’s a smart way to talk about what’s going on in the industry.”

What brand has made Prentice smile recently? “I love Birddogs.com — the men’s gym shorts. They’re fostering rejection.” This brought us full circle. Birddogs is doing more than just playing it safe. They’re being bold.

To learn more, go to DN3austin.com.


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On Brand with Nick WestergaardBy Nick Westergaard

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