Advice Line with Kenneth Cole

July 16, 2026

AI Summary

5 min read

Kenneth Cole built a shoe company from the back of a rented truck during New York Fashion Week, grew it into a global fashion brand, took it public, and later bought it back from shareholders. On this episode of the Advice Line, he fields calls from three early-stage founders and offers a set of operating principles that are less about fashion and more about the fundamentals of brand building in an era of noise, wholesale dependency, and novel product categories.

The real job is selling again, not just selling

When social media arrived, Cole initially worried that competitors now had direct access to his customers. He realized the reverse was also true. "Everybody today can tell a story and everybody today can find an audience. But you have to find a unique narrative and you have to find a voice that distinguishes itself from all the other voices." For Cole, the core insight that shaped his approach was that his goal was never simply to find people to sell to. "I came to realize that my goal really was to sell them again and again because it's not just selling stuff. I have to create a fulfilling experience for our customers and they have to want to come back." That begins with understanding where the customer is emotionally. "My goal is not to tell them what they should wear. It's to understand what they want and give it to them, but not how they expect it. That's the ch

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What you'll learn

1 (02:48) **Episode Introduction & Kenneth Cole Context** - Guy Raz introduces the Advice Line format and his guest, Kenneth Cole, founder of the iconic fashion brand.
2 (08:19) **Call 1: Matt Jacobs - Pedestrian Project (Foot Care Brand)** - Matt Jacobs, co-founder of Pedestrian Project, calls from New York about his modern wellness brand focused on foot care products.
3 (11:44) **Kenneth Cole's Advice on Emotional Connection & Category Growth** - Kenneth advises Matt to focus on the emotional relationship people have with their feet, not just the functional problem.
4 (14:59) **Guy Raz's Advice on Phased Strategy** - Guy suggests Matt should bias towards conversion and education for the existing category first, using retail and Amazon sales.
5 (20:46) **Call 2: Emma Fequadi - Israella Kobla (Fashion Brand)** - Emma Fequadi, a fashion engineer in Toronto, calls about her women's clothing brand that blends minimalism with bold, feminine design.
6 (24:16) **Kenneth Cole's Advice on the Wholesale vs. DTC Trade-off** - Kenneth probes Emma on margins and the challenges of owning inventory for wholesale, which requires forecasting far in advance.
7 (28:18) **Guy Raz's Advice on Using Wholesale as a Marketing Channel** - Guy identifies the core issue: wholesale is acting as a distribution channel, not a marketing channel that builds the brand.

+ Full timestamped outline available in the app

Show Notes

Today’s callers: Matt from New York City unpacks the stigma working against his line of foot wellness products. Then Emefa in Toronto seeks a direct relationship with customers of her fashion brand in the wake of a key retailer going out of business. Finally, Levi in Rhode Island explores new audiences and product lines for his commemorative golf sculpture business.

Plus, Kenneth and Guy discuss how to make social impact a real part of your business model.

Thank you to the founders of Pedestrian Project, ISRAELLA KOBLA, and Swing Sculpt for joining us on the show.

If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.

And be sure to listen to Kenneth Cole’s founding story as told on the show in 2020.

This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley.

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