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[Kenneth Cole on Building a Lasting Brand: Advice for Modern Entrepreneurs]-[Advice Line with Kenneth Cole]

How I Built This with Guy Raz · B2 · 2026-07-16

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📋 Summary

Cultivating a Brand Beyond the Product

In this episode of How I Built This, legendary fashion entrepreneur Kenneth Cole joins Guy Raz to discuss the evolution of brand building in the digital age. Reflecting on his own journey—which famously began in the back of a 40-foot truck—Cole emphasizes that while the tools for distribution have changed, the fundamental requirement for a lasting business remains the same: the ability to foster an emotional connection with the customer. Cole notes, "I used to think my goal was just to find people to sell stuff to. I came to realize my goal really was to sell them again and again." He argues that in an era of social media "noise," brands must move beyond mere transactions to create a "fulfilling experience."

The Intersection of Cause and Commerce

One of the most defining pillars of the Kenneth Cole brand is its social activism. Cole explains that businesses today have a responsibility to address social needs that governments may no longer be able to manage. By embedding causes—such as AIDS research in the 80s and more recently, mental health—directly into the business model, the brand creates a value proposition that is "greater than the sum of its parts." He advises that social impact should not be a marketing tool but a genuine commitment that is "truly embedded in the business model."

Advice for Emerging Founders

1. Pedestrian Project: Navigating Category Education

Matt Jacobs, founder of Pedestrian Project, sought advice on how to grow the foot care category from a reactive "problem-solution" model to a proactive "wellness" routine. Cole suggests focusing on the emotional resonance of the product, noting that shoes and foot care "uniquely affect you disproportionately how you feel." He cautions against trying to do too much too soon, recommending that Matt prioritize conversion-heavy channels like Amazon and retail partnerships before layering in the broader narrative and influencer-led storytelling.

2. Israelia Kobla: Distribution vs. Brand Building

Emifa Fuquade, founder of Israelia Kobla, discussed the struggle of scaling through wholesale partnerships like Nordstrom without losing the brand's direct connection to consumers. Cole offers a sobering reality check: "The wholesale side is not performing as much as a marketing channel as you’d hoped. It’s more of a distribution channel." He advises Emifa to use storytelling tools—such as including brand narratives in packaging—to capture the customer, while warning that retailers like Nordstrom are "very careful" about not handing off their hard-earned following to vendors.

3. Swing Sculpt: Expanding the Market

Levi Case, founder of Swing Sculpt, asked how to reduce friction for his bespoke golf-swing sculptures. Cole and Raz suggest that the business should lean into the "emotional use cases" like gift-giving for Father’s Day or retirement. Furthermore, they challenge Levi to expand beyond the niche of golf into high school sports, where parents are often willing to spend on unique, sentimental items. Cole encourages a bold approach: "Just send them [the pros] gifts. One of them likely may call you back."

Conclusion: The Art of Listening

Ultimately, Cole’s philosophy for success is anchored in humility and deep observation. He stresses that entrepreneurs should not try to dictate what consumers want but rather "understand what they want and give it to them, but not how they expect it." He concludes that the best salespeople are, first and foremost, the best listeners, reinforcing that a brand is a dialogue, not a monologue.

🎯Key Sentences

1
I don't take either very personally.
2
It's not a marketing tool.
3
Careful what they ask for.
4
I'm only as good as you know me to be.
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📝Key Phrases

1
make sense of a lot of moving pieces
2
turn over in your head
3
came into its own
4
greater than the sum of its parts
5
incumbent upon us
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📖 Transcript

Before we get into the episode, thanks to our presenting sponsor, Anthropic.
They make Claude an AI built for the problems that take real thinking research, strategy planning and making sense of a lot of moving pieces.
Give it a try for the next thing you can't quite stop turning over in your head.
For problems worth solving, get started with Claude at claude.ai.
Hello and welcome to the advice line on how I built this lab.
I'm Guy Raz.

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