Jul 16, 2026 · 45m · how-i-built-this
Advice Line with Kenneth Cole
Guy Raz · 15m spoken Kenneth Cole · 10m spoken Emifa Gafe · 5m spoken Levi Case · 5m spoken Matt Jacobs · 3m spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this Advice Line episode of How I Built This Lab, host Guy Raz and fashion pioneer Kenneth Cole mentor three emerging founders on overcoming retail wholesale barriers, destigmatizing niche product categories, and reducing customer acquisition friction.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 40% of the talking time here. How this is scored →
Guy as informed peer 4.4 Guest teaching 2.4 Guest disagreement 1.2 Guy pushing back 1.3
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 35:36 Levi defends capturing imperfect golf swings as authentic art
Levi directly rejects Cole's skeptical premise that customers only want idealized swings, arguing that the flaws in personal swings create the most distinctive sculptures.
Hardest push from Guy ▶ 37:53 Raz pushes Levi out of his golf-only restrictionGuy firmly challenges the founder's narrow golf focus, pressing him to target youth baseball and collegiate sports where parents spend heavily.
Biggest teaching moment ▶ 26:14 Cole explains department store data gatekeepingKenneth Cole educates both Guy and Emifa on retail reality, pointing out that Nordstrom is too sophisticated to let vendors poach their direct customer relationships through packaging hacks.
Guy holds their own ▶ 12:47 Raz breaks down e-commerce funnel priority over narrativeGuy demonstrates deep entrepreneurial expertise by advising the founder to prioritize search conversion and distribution cash flow over premature narrative branding campaigns.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Modern Brand Longevity and Cause-Driven Commerce | 5 | 3 | 1 | 1 | Guy Raz frames the discussion around modern TikTok brand creation versus classic brand longevity. Kenneth Cole expands on the concept, explaining that longevity requires creating emotional resonance and fulfilling experiences rather than just one-off sales. | |
| Kenneth Cole's Social Activism and Mental Health | 4 | 2 | 1 | 1 | Kenneth Cole describes his social purpose coalition work, after which Guy welcomes caller Matt Jacobs of Pedestrian Project, querying him on revenue and market positioning in foot care. | |
| Advising Matt Jacobs: Brand Emotion, Storytelling, and Footwear Partnerships | 6 | 2 | 1 | 2 | Guy Raz demonstrates tactical marketing insight by urging Matt to bias toward Amazon conversion before funding big brand narrative campaigns, while Cole suggests cross-brand synergy with his Gentle Souls line. | |
| Mid-Roll Break and Claude AI Sponsorship | 0 | 0 | 0 | 0 | Solo host mid-roll commercial read for Claude AI sponsorship with zero dialogue interaction. | |
| Caller Emifa Gafe Introduces Israella Kobla | 4 | 2 | 1 | 1 | Caller Emifa Gafe details her fashion label Israella Kobla and explains the challenge of converting her 85% wholesale presence in Nordstrom into direct-to-consumer sales. | |
| Advising Emifa Gafe: Margins, Direct Connections, and Concise Storytelling | 6 | 4 | 2 | 2 | Guy proposes inserting storytelling cards with QR warranty registration inside wholesale orders, but Cole gently schools the group by warning that Nordstrom actively restricts vendors from diverting their shoppers. Cole also pushes Emifa to sharpen and simplify her contradictory brand messaging. | |
| Kenneth Cole on the Strategic Value of Experiential Retail Stores | 4 | 3 | 1 | 1 | Cole outlines why physical retail boutiques must be treated as experiential marketing expenses rather than immediate profit drivers, leading into the introduction of caller Levi Case. | |
| Advising Levi Case: Overcoming Golf Objections and Expanding to Other Sports | 7 | 3 | 3 | 3 | Cole challenges Levi by questioning why amateur golfers would want to immortalize flawed swings. Raz aggressively counters the premise of staying golf-exclusive, pitching Levi on huge monetization opportunities in high school baseball and track. | |
| Kenneth Cole's Retrospective Advice and Archival Retrospective | 4 | 3 | 1 | 1 | Cole reflects on the importance of listening to customers and plays an archival clip illustrating the 1990s department store consolidations that threatened independent fashion brands. |
Statements from this episode (17)
Cole: Brands must deliver what customers want in unexpected ways
“And I also learned early on in my career that 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.”
Cole: Businesses must fill the social gaps left by modern governments
“A government today is, is neither willing or able to service 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.”
Cole: Built a coalition of 50 major mental health providers
“So, I built a coalition of 50 of the nation's largest mental health service providers, mentalhealth.org, if you want to look at it.”
Jacobs: Pedestrian Project generated over $500K in sales last year
“Yes, we did a little over 500,000 dollars last year.”
Jacobs: Foot care is the last personal care category to modernize
“Foot care interestingly is kind of the last category in the personal care world that hasn't gone through a modern brand evolution.”
Cole: Shoes uniquely and disproportionately affect how wearers feel
“I often say in the shoe business, everything you wear affects how you look, but shoes uniquely also affect disproportionately how you feel.”
Gafe: Israella Kobla launched with Hudson's Bay in 2021
“In 2021, we launched with Hudson's Bay through their marketplace, eventually managed to scale that and getting to Three of their stores, including their flagship location.”
Gafe: Nordstrom became Israella Kobla's largest wholesale partner in 2023
“In 2023, we also launched with Nordstrom. And so they right now are our biggest retail wholesale partnership.”
Gafe: Wholesale accounts for 85% of Israella Kobla's revenue
“I'd say a solid 85% is wholesale, and then the remaining 15 D to C.”
Gafe: Israella Kobla generated just under $400K in sales last year
“We were just under about 400 K.”
Gafe: Israella Kobla nets 35% to 50% wholesale margins prior to markup
“Our margins, they vary between 35 and 50%, and then obviously we plan for them to have a 60% markup on top of that, so we are able to make money that way, I think, because of our flexibility.”
Cole: The wholesale retail sector is shrinking rapidly with few growth avenues
“And the wholesale world is getting smaller right now. We're seeing a lot of, you saw what happened with Saks and Hudson Bay to your point. And I don't know if you're going to find a lot of growth opportunities in the short term”
Cole: Nordstrom actively blocks wholesale vendors from poaching its direct customers
“Nordstrom's, by the way, is very sophisticated in that regard. They're very careful. They're not going to build a following and then just hand it off to the vendor. If they can avoid it, they will.”
Cole: Founders must view physical retail stores purely as marketing investments
“You almost have to be prepared to write it off to look at it as a marketing and branding and initiative.”
Cole: Most golf apparel is sold through on-course pro shops
“Most golf apparel, most golf accessories are sold in what they called Greengrass distribution, which is golf shops.”
Case: Swing Sculpt preemptively included figure skating in its patent application
“The plan was always in the future to go into and expand into every sport like tennis, baseball, hockey, basketball. Like when I, we even wrote figure skating into our patent application just because anything with movement can be used in this.”