How do you help strategists transform boring briefs into better briefs so that creatives can do what they do best?

That’s just one of many questions I ask Ashley Rutstein during our interview.

Ashley is a copywriter-creative director, an Adweek Creative 100, and the founder of Stuff About Advertising - a multiplatform channel with hundreds of thousands of followers, where Ashley covers a wide range of topics, including insights, effective brainstorming techniques, and brilliant movie marketing activations.

I first discovered Ashley because of her Weekly Advertising Roundup videos, where she highlights and dissects advertising wins and fails from the week in advertising. She’s been doing these roundups every week (or almost every week) for the past four years, so I thought it would interesting to learn what patterns she’s discovered about great (and bad) advertising, and how it has helped her with her own creative work.

Some of my favorite aha moments from our conversation include:

• The awkward middle school moment that led to Ashley’s fascination with blind spots
• The insight that led to a refreshingly honest addiction recovery campaign
• How Ashley and her team helped Zespri yellow kiwis get more attention in the US
• The Discover Card commercial that has made Ashley consider getting a tattoo
• The methods and questions behind her “unhinged concept” videos for brands like Crocs and Poppi
• Ashley’s advice for brands who are trying to gain more traction on TikTok and YouTube

Show Notes:

Below are links to inspiring ideas that came up during our conversation.

Books:

Fourth Wing by Rebecca Yarros

The Way of Kings by Brandon Sanderson

Videos:

Unhinged Concepts: Ideas for Poppi

Dr. Barlow: Intro to African American Studies

Sinners Trailer

Campaigns:

Face it Together (Addiction Recovery Center): Day One

Dr. Barlow: Netflix Black History Month

Discover Card: Frog Protection

Surreal Cereal: Fake Celebrity

What’s the difference between a good observation and a real insight? According to Mark Pollard, one of the most sought-after strategy consultants and trainers in the industry, it often comes down to whether someone’s willing to confess something they’ve never said out loud before.

As an Australian strategist, Mark brings a different voice to the podcast - literally and figuratively. You’ll notice from his very first line, he doesn’t mince words and he’s not afraid to call a spade a spade. Maybe it’s the Aussie accent that allows him to be so bold. Or maybe it’s because he’s been doing strategy for so long that he just knows how to cut through all the bullshit and get to the heart of a situation.

Mark has been in the agency world since he was 19 and he’s worked with a wide variety of agencies, including Big Spaceship, Leo Burnett NY, Edelman NY, and Ogilvy, just to name a few. His client roster is equally as impressive, working with brands like Audi, Hilton, Netflix, The Economist, Facebook, Electronic Arts, and more.

In this episode, Mark takes a break from his global strategy training tour to talk about the messy, awkward, and deeply human side of strategy.

Some of my favorite aha moments from our conversation include:

• The difference between loud and quiet questions when interviewing people
• How to highlight problems and challenge assumptions without pissing people off
• Why studying a language might actually be better than therapy
• The many marketing riddles that are built into US corporate culture
• Figuring out which people in the organization are the most useful to talk to
• Some of Mark’s favorite comedians and what he’s learned from them

Show Notes:

Below are links to inspiring ideas that came up during our conversation.

Books:

The Innovators Dilemma by Clayton M. Christensen

Campaigns:

Steal Banksy: An Australian Hotel Chain Challenges Guests to Steal Art

Comedians:

Anthony Jeselnik Comedy Special - Caligula

Jim Jeffries - The Jim Jeffries Show

Sebastian Maniscalco - Aren’t You Embarrassed?

Videos & Shows:

Why The Loudest Caribbean City Is Also The Most Creative - Santo Domingo, The Dominican Republic 🇩🇴

Weak Hero Trailer (Netflix)

Friends & Neighbors Trailer (Apple TV)

Where do the best insights come from?

For Kate Rush Sheehy, Chief Strategy Officer at GSD&M, it’s not always based on what people say or even what they do. Sometimes, it’s about what they don’t say or what they don’t do in certain situations.

Sometimes, it’s about having a sixth sense or some feral intelligence.

In this episode, Kate shares her unique approach to uncovering brand-defining insights, from analyzing who shows up to a focus group (and who doesn’t), to asking clients the kinds of questions most agencies shy away from.

We explore the social-first strategy that helped Crocs become a Gen Z phenomenon and the cultural nuance behind Corona’s “La Playa Awaits.”

Some of my favorite aha moments from our conversation include:

• How Kate builds bridges between performance and brand marketing
• The social-first shift that helped Crocs go from cringe to cultural icon
• The difference between Jibbitz, Fibbitz, and “ugly shoe” theory
• How a deep dive into Mexican X (aka Twitter) led to Corona’s new creative direction
• The AI technique Kate’s team uses to pressure-test strategic ideas before they present strategic and creative work
• Some valuable lessons Kate learned about human nature by working in restaurants and retail

Show Notes:

Below are links to inspiring ideas that came up during our conversation.

Books:

Fourth Wing by Rebecca Yarros

Who Knew? by Barry Diller

Campaigns & Videos:

Dept. of Veterans Affairs (work in partnership with the Ad Council: The Question)

Southwest Airlines: That’s a Big Flex

Corona: La Playa Awaits