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