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