Oct 22, 2026 · 40 min
Founders learn when to focus, demonstrate and follow demand
Advice Line with Seth Berkowitz of Insomnia Cookies
Three entrepreneurs confront the same growth question: whether to spend scarce resources expanding broadly or deepen what customers already value.
- 1Narrowing a business around proven products and specific customers can make limited marketing budgets work harder.
- 2Experiential selling helps unfamiliar products become understandable, especially when customers need to see and feel them first.
- 3Consumer purchases and enthusiasm offer more reliable strategic signals than a founder’s instinct alone.
Don't miss
Seth recounts cutting his team and going without pay for 18 months when investors stopped funding Insomnia Cookies.
The brief
Seth Berkowitz joins Guy Raz to advise three founders: Kahindo Mateene on rebuilding a fashion brand, Tara Gilman on sauna hats, and Carol Deshawn on collegiate accessories.
The advice converges on disciplined focus: identify the customers and products already showing traction, then build marketing around the occasions and communities where demand is visible.
For Sauna Society, the hosts argue that live demonstrations beat expensive social advertising because customers need to see, feel and understand a sauna hat before buying.
Desden’s next stage raises a different scaling problem: even when parents or grandparents pay, younger fans remain the core users, while managing 90 university licenses may already be too complex.
Seth’s most durable lesson comes from Insomnia Cookies’ difficult early years: follow customer behavior, even after 18 months without pay and painful team cuts.
Books & mentions
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