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

Dave Harland LOVES words. Big ones. Little ones. Silly ones. Serious ones.

He has a talent for taking the world’s most boring categories and breathing new life into them with a few flourishes of his pen and some rat-tat-tat-clickety-clacks at his keyboard.

During our conversation, we dig into all kinds of things, including the micro dignities of daily life that are threatened by automation and generative AI, as well as the unmistakable human quirks that make insight building and copywriting an act of creative joy.

We also connect the dots between The Knowledge of London (the rigorous exam that London Cabbies must pass to show they know their way around the city without a map) and the cultural tension between British formality and British humor (e.g. taking the piss).

Some of my favorite aha moments from our conversation include:

• The scrappy, homemade billboard that taught Dave his first big lesson in strategic copywriting
• Dave’s issues with AI shatbots and the limits of AI in copywriting
• How a lackluster acronym led to one of Dave’s favorite brand taglines
• The real-world insights that led to surprisingly punchy (and funny) B2B headlines for a speakerphone brand
• An American phrase that has inexplicably made its way into British business discussions

Show Notes:

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

Dave’s Online Copywriting Course

Write the Funny

Books:

Copywriting Is…:30-or-so thoughts on thinking like a copywriter by Andrew Boulton

Videos:

Bob Mortimor Top Moments | Would I Lie to You?

Monty Python: Ministry of Silly Walks

Life of Brian: Colosseum Scene

Zoe Scaman knows how to rebuild brands and fandoms from the ground up.

Her work with brands like Nike, Netflix, and the NBA has allowed her to dig deep into consumer behavior and organizational structures, resulting in numerous aha moments around community building and how to encourage a culture of co-creation with brand superfans.

Zoe builds a number of beautiful constellations during our conversation as she connects the dots between furries, sports fans, and political communities. We also talk about Lego’s incredibly expanding brand universe and how brands can leverage the flywheel effect to create exponential growth.

Some of my favorite aha moments from our conversation include:

• The provocative question Zoe asked in middle school when she was asked to re-read Lord of the Flies
• The ways Zoe uses AI to help her gut check her own work
• How brands can learn from furries to create a sense of belonging
• The biggest (often invisible) enemy of progress in any organization
• Zoe’s favorite word and why she thinks more people need to use it more often

Show Notes:

Below are links to books, shows, and other inspiring ideas that came up during our conversation.

Musings of a Wandering Mind: Zoe Scaman’s Substack

Hidden Potential: The Science of Achieving Greater Things by Adam Grant

Lord of the Flies by William Golding

The Color Purple by Alice Walker

His Dark Materials by Phillip Pullman

Marilyn Monroe Obituary

Shows & Movies

Mob Land TV Series Trailer

Brands & Campaigns

The Lego Botanical Collection

Adult Fans of Lego (AFOL) - Reddit

Lego Fan Engagement and Programs

Joe Burn has done a LOT of award-winning strategy work, including but not limited to brand strategy, creative strategy, communications strategy, and design strategy.

And it’s these diverse experiences in strategy that have helped Joe connect the dots in the most interesting and unexpected ways for brands like KFC, Heineken, Samsung, Puma, Amnesty International, Benecol, Meta, and more.

But Joe doesn’t just have a passion for strategy and insights. His infatuation with typography, semiotics, and food history helps him become an integral part of the strategic-creative somersault that leads to successful campaigns.

In this episode, Joe shares a lot of ideas and inspiration, including his favorite songs for tapping into his subconscious mind and how a line from Bart Simpson influenced the insight for an entire campaign.

Some of my favorite aha moments from our conversation include:

• An insight for Samsung that led NOT to an ad, but to an awesome music video
• Joe’s unique approach to winning new business pitches
• Why bad ideas are essential to creative success
• How his job as a garbage collector shaped his perspective on advertising
• A piece of advice from Sun Tzu that has influenced his work with clients and creatives

Show Notes:

Below are links to books, shows, and other inspiring ideas that came up during our conversation.

Books:

The Mezzanine by Nicholson Baker

The Art of War by Sun Tzu

Herscht 07769 by László Krasznahorkai

Shows & Movies

The Simpsons - Season 6, Episode 7

Brands & Campaigns

Money Supermarket Ad

Samsung - Samm Henshaw - All Good (Official Video)

For over two decades, Tracy Lovatt has helped brands build transformative insights by challenging assumptions and embracing the chaos of tectonic cultural shifts.

After starting her career at BBDO, where she guided brands like HBO, GE, Bank of America, Hyatt Hotels, PepsiCo and many others, Tracy eventually stepped away from advertising to start Batten & Co, where she now helps brands connect the dots between insights, operations, and the customer experience.

In this episode, Tracy talks about the power of sarcasm to disarm people and she shares her candid approach to uncovering insights that matter.

Some of my favorite aha moments from our conversation include:

• The surprisingly different ways men and women talk about engagement rings
• The power of deprivation studies to get consumers to open up emotionally
• What she’s learned from the Medicis when it comes to inspiration and new ideas
• The surprising impact a British accent can have in American boardrooms
• A memory she had of our first encounter (that made me blush)

Show Notes:

Below are links to books, shows, and other inspiring ideas that came up during our conversation.

Books:

This is what it sounds like: What the music you love says about you (by Susan Rogers)

Musicophilia: Tales of Music and the Brain (by Oliver Sachs)

Shows & Movies

I’m Still Here Trailer

The Last of the Sea Women Trailer (Apple TV)

Brands & Campaigns

GE - Ideas are Scary

Ffern (Fragrance brand)

Ground Up (Nut butter brand)

Great research isn’t just about collecting answers. It’s about knowing which questions to ask and how to observe with all your senses to get to the truth of a situation.

Bob Morais, business anthropologist, ethnographer, and lecturer at Columbia University’s Business School, knows how to read between the lines of what people say and what they actually do, and in this conversation, Bob shares his techniques for consistently finding those aha moments that can help a brand soar.

Over the years, Bob has set up some fascinating research methodologies for a wide variety of emerging and established brands, including Sensodyne, Freshpet, WD-40, and Simply Orange, just to name a few.

And in every case, Bob has helped those brands uncover what their customers really need, not just what they say they want.

Together, we dig into the key differences between a flat-footed finding and an actual insight, and we talk about the importance of “presentation theater.”

Bob also shares his perspective on AI as a research assistant, and why he believes the human element in ethnography is still irreplaceable.

Some of my favorite aha moments from our conversation include:

• Bob’s aha moment that led to a multimillion-dollar product innovation for WD-40
• An unexpected, eye-opening experience during a research project at the Plaza Hotel that helped crystallize the idea of luxury
• The power of research techniques like laddering and guided retrospection
• How to sell ethnography projects to clients who want everything “buttoned up”
• The unexpected ways that playing lead guitar in different rock bands prepared Bob for life in strategy and research

Show Notes:

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

Campaigns & Brand Videos:

Fresh Pet: It’s not dog food. It’s food food.

WD-40 Smart Straw