This episode is a little different.

Instead of talking with a Chief Creative Officer or a Chief Strategy Officer about a recent ad campaign, I sit down with Rebecca Winthrop, senior fellow at The Brookings Institution and co-author of The Disengaged Teen.

Together, we dive into the insights that emerged from her research with over 60,000 students, 25,000 teachers, and 6,000 parents, and we explore what it takes to really engage young people in today’s tech-driven world.

Rebecca’s findings around engagement are fascinating and we talk about different modes of learning (passenger mode vs. resistor mode vs. explorer mode) and the surprising overlaps between the world of branding and the world of education.

In both worlds, you’re dealing with a rich combination of attention, inertia, distraction, and indifference. And in both cases, real engagement only happens when the people you’re talking to connect the experience you’ve created to something meaningful in their own lives.

Some of my favorite aha moments from our conversation include:

• What kids are neurobiologically primed to do in adolescence and the implications for designing more engaging experiences
• The Mattel-OpenAI partnership and why Rebecca is both excited and concerned about its implications
• How repetition and nagging can often shut down executive function in teens (and how brands might accidentally be doing the same thing with their messaging)
• What Minecraft can teach us about learning, rewards, motivation, and flow
• How working for the Fish and Wildlife Department in her 20s led Rebecca to some valuable life lessons about FIO (Figure It Out) jobs
• Why educational innovation starts with rethinking how we measure progress and what that also means for brand strategy

Show Notes:

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

Books:

The Disengaged Teen by Rebecca Winthrop and Jenny Anderson

If I Built a School by Chris Van Dusen

Lies My Teacher Told Me by James W. Lowen

Six of Crows (Crooked Kingdom) by Leigh Bardug

Products

Lego

Clixo Toys

Innovative Alt Education Schools

Big Picture Learning

Templeton Academy

Alpha Schools

Most brands use surface level data to market to superficial stereotypes.

James Addlestone, on the other hand, uses data like a detective, reading between the lines of people’s survey responses and finding innovative ways to get to the truth behind their behaviors.

With a background in behavioral economics and a deep appreciation for detective fiction (we talk quite a bit about Agatha Christie), James brings an exciting approach to data-driven strategy: one that combines quant, qual, and creative curiosity.

During our conversation, James challenges the industry’s overreliance on survey panels, pre-loaded category drivers, and overly-tidy narratives that tend to collapse under real-world scrutiny.

By contrast, James makes the case for embracing those moments when the data doesn’t quite make sense and treating that ambiguity as an invitation to look closer.

In this episode, we explore how James uses data triangulation, not silver bullets, to connect the dots between data points, which leads not only to new campaign directions, but can also result in subtle shifts in operations and product innovation.

Some of my favorite aha moments from our conversation include:

• The “qual sandwich” framework James uses for insight generation
• Why it’s important to challenge company myths every so often with fresh data
• How a surprising spike in tomato sales led to a deeper investigation and a new campaign direction for a major grocer
• How the pet brand, Chewy, focuses on “moments that matter” and why moments-based segmentation matters even more than traditional demographics
• Three reasons why AI won’t replace good analysts anytime soon
• Advice for junior analysts and how to use different AI tools to help with big data projects

Show Notes:

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

Books:

Factfulness: 10 Reasons why You’re Wrong About the World–and Why Things are Better than you Think by Hans Roling

Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are by Steph-Stephens Davidowitz

Algorithms to Live By: The Computer Science of Human Decisions by Tom Griffiths

Stolen Focus: Why You Can’t Pay Attention–and How to Think Deeply Again by Johann Hari

Blueprints: How Mathematics Shapes Creativity by Marcus du Sautoy

Companies

System 1: The World’s Most Predictive Ad Test

Meet the 85: Ethnographic Research Consultancy

Podcasts:

Thinking Inside the Box More Creatively with Dan Cohen, Creative Director at Saatchi New York

Katie Dreke has always been a rough and tumble explorer, ever since she was a kid.

From early childhood days, she wanted to do all the things the boys in her neighborhood were doing - jumping bikes off of ramps, playing in treehouses, reading science fiction - but she quickly realized that the world was always trying to steer her in another direction.

Those childhood experiences led to a lifelong fascination with social constructs and gender norms, which has shaped her groundbreaking work with sports brands, from Arc’teryx to New Balance to Nike’s historic maternity collection.

Katie’s work history has spanned the globe, from Amsterdam to Japan to Australia, and she’s worked at a wide variety of award-winning shops, including Wieden + Kennedy, the Wexley School for Girls, Droga5, and IDEO.

No matter what she’s working on, though, whether it’s a new DTC business model or product innovation, Katie always brings a distinct perspective to every project, one that blends cultural insight and deep empathy for the consumer’s lived experience.

Some of my favorite aha moments from our conversation include:

• How social norms and coded systems still shape women’s experience in sport
• Why many women over 40 were turning to Lululemon and not shopping for themselves at Nike
• How the Nike maternity collection uncovered a blindspot in how athletic potential is defined
• The techniques and strategic questions Katie uses to kick start almost any project
• How working the front desk at a software company in Seattle led her to a global career in strategy

Show Notes:

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

Books:

The Mountain in the Sea by Ray Nayler

Brands & Campagins:

Nike Maternity Collection

The Toughest Athletes - Nike Ad

Houdini Sportswear

Benim Denim - A Start-up Designed to Shut Down

What do David Bowie lyrics, childhood memories of soda, and gut health all have in common?

For Mark Lester, co-founder of the brand consultancy Squint, they’re part of a deeper exploration into how happiness shapes behavior and how brands can use that insight to grow.

Prior to starting squint, Mark spent 15 years in the advertising industry, sharing his talents with R/GA, McGarryBowen and Dentsu, working a wide variety of brands, including Samsung, Diageo, and Equinox, just to name a few.

In this episode, Mark shares how Squint’s “Happiness Advantage” approach to brand-building helped turn Olipop into a nearly $2 billion soda brand by leaning into emotional associations, not functional claims.

We also discuss GenZ’s fraying relationship with sport and how an activation at the Olympics was able to help Nike reconnect with a younger generation.

Some of my favorite aha moments from our conversation include:

• Why great brands are built on memories, not just messages
• How a hike in the Hollywood Hills with Olipop’s founder led Mark to some powerful aha moments about himself and the brand
• The consumer research findings that made “soda” a more powerful word than “tonic”
• The evolving nature of competitive sports and the opportunity to be part of the growing movement around collaborative sports
• How being an au pair in France during his gap year after college taught him some valuable life lessons
• Mark’s secret to happiness, both personally and professionally

Show Notes:

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

Books:

The Remains of the Day by Kazuo Ishiguro

Never Let me Go by Kazuo Ishiguro

Campaigns:

Dude Wipes: The Evolution of Wiping

Brands:

Nandos (UK Peri Peri Chicken Restaurant Chain)

Podcasts:

What are the key characteristics of designing a great toy? It turns out, it’s many of the same characteristics that go into building a great brand.

Playfulness. Imagination. A little bit of mischief. And joy.

In this episode, I talk with Assaf Eshet, founder and award-winning toy designer at Clixo Toys.

I met Assaf at the ISTE EdTech conference in San Antonio this summer and I was immediately drawn to the flexible, colorful shapes of Clixo and all the different things you could build with them - robots, animals, vehicles, wearables - you name it.

And when Assaf started telling me about the philosophy behind Clixo - how they blend the best of origami with the best of magnetic building toys - I knew he needed to be a guest on the show. Because he definitely sees the world in a different way compared to most.

I’m glad I met him when I did because since our chance encounter in San Antonio, Clixo has been getting attention just about everywhere. In the past few months Clixo launched nationally in Target, had a huge activation at the MoMA, and was just named one of Time’s Best Inventions of 2025.

In this episode, Assaf and I talk about the principles of great toy design, and how his teaching philosophy helps students embrace failure and experimentation, which are prerequisites for coming up with even better ideas. We also explore the psychology of play and the secret to living as a joyful creature.

Some of my favorite aha moments from our conversation include:

• One of Assaf’s favorite design assignments that he gives to his students each semester
• Why good toy design (like good branding) requires constant testing “in the wild”
• What his grandmother’s hand-sewn Barbie clothing collection taught him about resourcefulness and innovation
• How Italian cinema and Roberto Benigni shaped his outlook on creativity
• The importance of becoming a collector (for whatever you’re passionate about)

Show Notes:

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

Books:

When Nietzsche Wept: A Novel of Obsession by Irvin D. Yalom

Products:

Chomshop: A Kid-Safe Power Tool for Cutting Cardboard

Speeches:

Roberto Benigni Oscar Speech for Life is Beautiful

Tara Lawall has worked at some of the biggest agencies in the world, earned a Cannes Titanium Lion, and her work has even landed a spot in MoMA’s permanent collection, but her sharpest insights might trace back to a comedy class she took at Miami Ad School.

Today, Tara is Chief Creative Officer and Partner at Rethink’s New York office, and in this interview, Tara shares how her team uncovers powerful truths hidden in everyday behavior — something they call cultural sparks at Rethink — and how those truths have led to some of the industry’s most buzzworthy campaigns.

Some of my favorite aha moments from our conversation include:

• The unique “trauma therapy” process Rethink uses to build client relationships that leads to more effective work
• Some aha moments around a spicy but not too spicy Doritos campaign with Walton Goggins
• The creative challenges of finding the perfect soundtrack for different street corners in LA, London, and New York with Epidemic Sound
• The brand love campaign Rethink developed for Mac n’ Cheese
• The Philly slang term that works in literally any sentence
• Important life lessons Tara learned growing up in her dad’s delicatessen and pastry shop

Show Notes:

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

Books:

Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert

A Creative Act: A Way of Being by Rick Rubin

Abundance by Ezra Klein

Campaigns:

Doritos: A Spicy but Not Too Spicy Plumber

Epidemic Sound: A Sound for Every Feeling

Heineken Pub Succession

When Jason Mitchell realized his college professors were still teaching TV-first strategies while every student in the room was glued to Facebook, he saw an opportunity.

That opportunity was the beginning of Movement, a social-first agency that has done award-winning work for brands like the NBA, Netflix, Amazon Prime, and more.

In this episode, Jason shares the early bets and strategic philosophies that have helped Movement grow from a dorm-room idea into one of the most recognized social-first agencies in the industry.

We explore what it means to put social at the center of a campaign rather than treat it as an add-on, and why the best ideas often begin with strategic social listening.

Some of my favorite aha moments from our conversation include:

• How Jason found his way into the journalism and advertising program at University of Colorado despite having terrible grades
• How social listening led to a viral campaign (and a real arrest) for Netflix’s Unsolved Mysteries
• Why Klarna’s biggest brand barrier in the U.S. wasn’t competition, but disbelief over their core value prop
• Jason’s secrets for setting up a great social listening system
• How Jason would rebrand the movie-going experience to help people rekindle their love of cinema in an era of social media

Show Notes:

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

Books:

Turn the Ship Around by L. David Marquet

Campaigns & Videos:

Klarna: What’s the Catch Campaign with Bretman Rock

So Many Dicks Campaign Case Study - e.l.f. Beauty

Unsolved Mysteries Shorty Awards Case Study

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