Advice Line with Kenneth Cole

Intro

On this Advice Line episode, Kenneth Cole returns to How I Built This to help three founders solve real business challenges. Drawing on 40+ years of building Kenneth Cole Productions, he shares hard-won wisdom on brand longevity, pricing confidence, and scaling without losing identity.

Caller 1: Matt Jacobs & Pedestrian Project

Matt Jacobs calls from Astoria, New York with a bootstrapped foot care brand that did $500,000 in sales last year. Pedestrian Project sells moisturizers, creams, lotions, pain relief, salt soaks, and accessories through a mix of D2C, Amazon, and Sprouts retail. He still consults part-time and is considering institutional funding. Kenneth's advice centers on the difference between selling products and building a fulfilling experience that makes customers want to come back. He emphasizes understanding customers emotionally rather than telling them what they should want.

Caller 2: Levi Case & Swing Sculpt

Levi Case founded Swing Sculpt, a golf brand that transforms swing data into custom art and jewelry. Each piece is made-to-order from the customer's actual swing motion, making every ring or pendant a one-of-a-kind keepsake. The challenge: how do you price something so personal when the market expects commodity pricing? Kenneth frames the answer around meaning. Swing Sculpt does not compete on price or logo recognition — it competes on the emotional weight of preserving a perfect shot. That narrative justifies premium pricing because the value is not in the metal; it is in the memory.

Caller 3: Emma Fakwade & ISRAELLA KOBLA

Emma Fakwade calls from Toronto with a luxury made-to-order fashion label built on engineering precision. ISRAELLA KOBLA rejects overproduction by crafting each piece on demand, which creates sustainability but complicates scale. Kenneth points to the brand's Nordstrom placement as proof that independent design can coexist with major retail. The challenge now is protecting that independence while meeting the demands of a larger partner. His advice: stay tethered to the atelier process that made the brand distinctive, because that is the asset Nordstrom actually bought.

Final Thought

Kenneth closes by reframing brand identity. The man and the brand are somewhat interchangeable, he says, and that is not a burden — it is a shortcut to trust. When customers know who you are and what you stand for, they do not need a TikTok trend to convince them. They need a reason to return.