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

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