How I Built This with Guy Raz
How I Built This with Guy Raz

Advice Line with Kenneth Cole

July 16, 2026 • 45m

Summary

⏱️ 7 min read

Overview

In this episode of the How I Built This Lab Advice Line, host Guy Raz is joined by legendary fashion designer Kenneth Cole to help three entrepreneurs navigate business challenges. They advise Matt Jacobs of Pedestrian Project on balancing market share versus category expansion in foot care, Emma Fakwade of Israel Acabla on leveraging wholesale partnerships to build direct-to-consumer relationships, and Levi Case of SwingSculpt on reducing friction for a novel custom product while exploring expansion opportunities beyond golf.

Introduction to Kenneth Cole's Legacy and Modern Brand Building

Kenneth Cole reflects on building his iconic fashion brand from a truck in Manhattan to an enduring empire. He discusses how social media has democratized brand building but emphasizes the importance of creating a unique narrative that distinguishes your voice from the noise. Cole shares his philosophy that success isn't just about selling products once, but creating fulfilling experiences that make customers want to return again and again.

  • Kenneth Cole grew his brand from selling shoes from a 40-foot truck in Midtown Manhattan to an iconic fashion empire
  • Social media gives everyone access to customers worldwide, but you need a unique narrative to stand out
  • The goal isn't just selling stuff once, but creating fulfilling experiences so customers return repeatedly
  • Success comes from understanding what customers want and giving it to them in unexpected ways
  • Kenneth Cole pioneered cause-related marketing with AIDS awareness in the 80s and currently focuses on mental health advocacy
" I used to think when I started my business that my goal was just to find people to sell stuff to. I came to realize that my goal really was to sell them again and again because it's not just selling stuff. "
" I built a business, and the film just came. There's a documentary that just came out that kind of tells a little bit about the story, more of its social impact than about its fashion. It talks about the intersection of cause and commerce and how the two, that together you create something greater than the sum of its parts. "

Kenneth Cole's Philosophy on Customer-Centric Business

Throughout the episode, Kenneth Cole emphasizes his evolved understanding of business success. He shares that the intersection of cause and commerce creates something greater than the sum of its parts, and that businesses should serve customers both in stores and in their lives. His approach focuses on dialogue over monologue, listening over prescribing, and understanding that the brand and the person are interchangeable but neither should be taken too personally.

  • Kenneth Cole views the brand and himself as somewhat interchangeable and doesn't take either too personally
  • All businesses need to serve customers not just when they're in stores, but when they're in their lives
  • The mental health coalition mentalhealth.org represents running non-profits like businesses and businesses with heart
  • Success requires dialogue not monologue—the best salespeople are the best listeners
" A government today is neither willing or able to serve as so many of the social needs that it used to in the past. And I do believe it's incumbent upon us to do a lot of that. "
" It needs to be a dialogue not a monologue so you have to have conversations and you have to feed good listeners. "

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